Don’t make me use my California Card

When I started working in online education, I was only 20 years old. It was my first full-time office job.

Since we were a startup division of our parent organization, there were just two of us in the office. And then about 20 contractors who worked remotely.

Thankfully, my boss and I were able to split things pretty evenly down the middle. She liked spreadsheets and systems. I liked marketing and big ideas.

And since, I was slightly less introverted, and since she had seniority, it fell to me to take most of the phone calls.

Especially the nasty ones.

It was a common occurrence for my boss to see the number of a parent come through on her caller ID and shout, “This one is for you!”

So, I’d go down the hall, close my door, pick up the phone, and work my magic.

This often involved using what my boss called my “California Card.”

Here’s the thing about California. For a long time, there were as many homeschoolers living in California as the rest of the U.S.A.

So, since we worked with a lot of homeschoolers, I had a pretty good chance of talking to someone who was living in California, had been to California, or wanted to go to California.

Occasionally, I’d even get someone who wanted California to break off and sink into the ocean. (Et tu, John Donne? Maybe some people do end up as islands unto themselves.)

I could work with that too.

It was kind of like Elvis’ manager selling both “I love Elvis” and “I hate Elvis” pins.

Something for everyone.

I can’t even tell you the number of times I had a parent call and shout at me, lecture me, threaten to sue me, or otherwise complain about our program.

(If you’re wondering why parents would get so upset on the phone, you need to understand that the first wave of homeschoolers were basically people willing to go to jail to teach their kids what they wanted. These moms could have stormed the beaches at Normandy. No one is more punk rock than an 80’s or 90’s era homeschool mom.).

But, most of the time, I was able to get them to calm down, be happy, and often stick with our program rather than demanding a refund.

All it took was a little patience, a little charm, and finding some common ground.

Everything is about belonging. Even this awkward bus ride.

So how did I learn the trick of relating to people?

Well, I worked a few months as a hotel doorman. More on that later, because it’s a Christmas story.

For now, I’ll share that one of my main responsibilities, aside from opening doors and parking cars, was to drive people to and from the airport about 20 minutes away.

When you work for tips, and you only have 5 minutes getting someone’s bag, or you have 20 minutes driving them from the airport, you know that time is of the essence.

The thing is, I had just graduated college as a baby-faced child. I didn’t have any real life experience, or real job experience. And I was incredibly shy.

I really only had one thing in my favor. I’m very curious, and I will learn about anything. I got that from my parents.

If you read widely and get good at asking questions, you can pretty much talk about anything.

When I look back on the few months when I drove that airport shuttle bus, a few conversations stand out to me.

I remember talking to an older woman about socialized medicine, a businessman about surfing in California, a doctor about learning piano, and a party girl about Montessori schools.

Most of the time, I had a really different background from all of the people I drove on the bus. Most of the time, we didn’t agree on our political views, our religious views, or our lifestyle.

But, I learned pretty quickly that people are people everywhere, and everyone just wants to belong.

So, all you really need to do is show them that you have the tiniest bit in common, and that’s enough to build that sense of belonging.

That’s why all the best sales frameworks include listening as one of the first steps.

Listening first. Not selling.

You don’t make money by groveling for tips. You build connections by making people feel less alone.

Meet people where they are. Don’t forget the details.

When it comes to making people feel less alone, it all comes down to the details.

Nothing makes someone feel more appreciated than when someone else notices something small and decides to care about it.

While I refined my customer service skills working as a doorman, I learned the art of paying attention to details from my dad.

My dad is a very private person. I’ve had this essay sitting on the back burner since January 2026, because I wasn’t sure exactly what to write about him.

But I’ll share what I can.

I think what I like most about my dad is his ability to relate to basically anyone.

He’s held his own at fancy dinners with lawyers and $1,000 bills. He and my mom have met more Hollywood celebrities than anyone else I know. (This was a lot easier to do if you lived in California a long time ago).

But as much as it’s cool that he knows how to hold his own in posh environments, that’s not my favorite thing about him.

My favorite thing about my dad is that he treats no one like they’re beneath him.

I remember one time about a decade ago, we went to Wal-Mart late at night, and he greeted the employee by name. The employee could only speak broken English, but she smiled. Clearly, she knew my dad.

I asked him, “Dad, why do you know the name of the greeter at Wal-Mart?”

He just said, “I know everybody.”

And he kind of does. In another life, I think my dad would have made a good mayor of a small town.

All throughout my life, my dad remembered things about people and made a big deal of those small things. He’d save newspaper clippings and articles for people and then give them a folder of ideas he thought they’d like. Or, if one of my friends told him they liked a certain topic, he’d go to the thrift store and buy them a book about that topic.

There was a time I ordered pizza for one of my friends and added on cheesy bread on the side. He asked why, and I said, “A few months ago, you said it was your favorite.” He was completely shocked I remembered that.

But to me it felt totally normal. I’d seen my dad do things like that a hundred times.

My very favorite story about my dad comes from when I played soccer as a little kid.

One year, my dad was the team coach. I played in a local community league, and there was a kid on my team whose mom was a single mom. To help her out, my dad would sometimes give her son a ride to practice.

At the end of the year, we all got medals. Just for participation. You know, the American way. Well, this kid didn’t show up to get his medal.

No problem. My dad got his medal and said he’d drop it off at the kid’s house. Well, for whatever reason, that kid and his mom moved away suddenly. No explanation why. And my dad didn’t actually have her phone number.

So, he just drove around for years with that kid’s medal in the glove box of his car, hoping that one day he’d run into them.

I remember my 8 or 10 year old self thinking, Who cares? It’s just a participation trophy. What’s the point of keeping it in your car? That kid probably doesn’t even miss it!

My dad never did run into them again.

But I was proud of him for caring about the small things.

Yes, you can stay true to yourself while changing how you connect with others.

I think the best example of relating to people on a deep, fundamental level comes from a 1st-century legal scholar.

You may have heard of Saul of Tarsus. Or, as he later became known, St. Paul.

Paul was essentially a legal scholar who became a street preacher and was responsible for spreading Christianity across the Mediterranean around 30 to 60 A.D.

No matter your religious views, I think we all can learn a little from Paul about how to relate to people. The guy had top tier communication skills.

You see, Paul was known for being a Jewish legal scholar. But he also was known for being a Roman citizen and an expert on Roman laws, Greek philosophy, and pop culture.

If you study him hard enough, you realize his writing is full of references to Greek stoicism, the Olympic games, weird Turkish cults (shoutout to the historian Tom Holland!), Roman cultural practices, Jewish scriptures, and all kinds of other topics.

The dude knew a lot. And he knew exactly when to pull out that knowledge to relate to his audience.

Paul was a bit of a chameleon. But I don’t think that’s a bad thing.

Nobody likes a hypocrite. But Paul wasn’t a hypocrite. He didn’t actually change his beliefs for anyone. In that sense, he was remarkably consistent.

But he changed his approach for everyone.

And whether you’re taking customer service calls, driving a bus to the airport, or simply trying to be a better friend, I think there’s a lesson here.

You can be authentic and relatable at the same time.

I think a lot of times modern society makes it seem like that’s not true. In the name of being authentic, we often give ourselves permission to be abrasive and cut off anyone who doesn’t agree with us.

Modern society makes this pretty easy.

We can use Spotify to listen to our own weird music instead of the Top 40 on the radio. We can befriend only liberals or conservatives on Facebook so that we never have to hear anyone else’s opinions. We can live in the wealthy neighborhood and pretend there aren’t people down the street trying to figure out how to feed their kids tonight.

We tell ourselves that sticking to our inner circle of comrades isn’t selfish. It’s self care.

Sounds lonely.

Humanity is beautiful. Humans are annoying.

Last weekend, I stayed up late at night listening to David Foster Wallace’s 2005 graduation speech at Kenyon College. I wonder sometimes if he knew it would one day become a famous speech.

In it, he describes two young fishes who come across an older fish.

The older fish says “How’s the water today, boys?”

After he swims away, one of the young fishes asks his friend “What the hell is water?”

DFW’s point was that most of us go through life stuck in our default mode. In short, most of us don’t pay attention to our environment or the people around us.

We go through life being, as he says, “imperially selfish.”

He describes what it’s like to sit in traffic or walk through the grocery store and think something like this.

“The point is that petty, frustrating crap like this is exactly where the work of choosing is gonna come in. Because the traffic jams and crowded aisles and long checkout lines give me time to think, and if I don’t make a conscious decision about how to think and what to pay attention to, I’m gonna be pissed and miserable every time I have to shop.

Because my natural default setting is the certainty that situations like this are really all about me. About MY hungriness and MY fatigue and MY desire to just get home, and it’s going to seem for all the world like everybody else is just in my way.

And who are all these people in my way? And look at how repulsive most of them are, and how stupid and cow-like and dead-eyed and nonhuman they seem in the checkout line, or at how annoying and rude it is that people are talking loudly on cell phones in the middle of the line. And look at how deeply and personally unfair this is.”

His point is that you have two main jobs as a human being.

First, pay attention. Then, care.

You either swim in the ocean with the other fishes. Or, you drown in a shallow puddle of self-centered cynicism.

Cut negative people out of your life. Ruthlessly protect your calendar. Say no to anything that’s not a paid opportunity.

Sure, man. At least you have the puddle all to yourself.

By all means, I’m not saying you should keep terrible, abusive people in your life. I’m just saying, haven’t we had enough self-help books telling us we’re the center of the universe?

I already act like I’m the center of the universe. I don’t need a book to encourage me.

Wallace closes out his speech with a reminder that we shouldn’t be striving for the freedom that will get us more money, power, and fame.

He says this,

“The really important kind of freedom involves attention and awareness and discipline, and being able truly to care about other people and to sacrifice for them over and over in myriad petty, unsexy ways every day…

That is real freedom. That is being educated, and understanding how to think.

The alternative is unconsciousness, the default setting, the rat race, the constant gnawing sense of having had, and lost, some infinite thing.”

I don’t know about you, but I don’t want to lose that infinite thing.

That’s why Wallace says you have to keep reminding yourself:

“This is water.”

Let’s pretend.

When I was younger, I was so shy that I had to literally teach myself how to relate to people. I treated getting to know music, books, and other topics like a research project just so I could have something to talk about.

All my friends consider me to be a huge music lover now. I’m the concert guy among a lot of my friends. But, I mostly got into music to start with so that I could relate to people. It was only through that process that I came to really love it.

It’s funny, when you work for tips, or when you take customer service calls, you are essentially pretending to relate to people and care about them so you can make some extra cash.

And on its face, that may sound terrible.

But maybe pretending gets a bad rap. Sometimes, pretending is the only place to start.

I’ve always appreciated C.S. Lewis’s advice that if you want to start believing in something, you should act like you believe in it. As a result of the action, you may end up actually believing.

So, maybe it’s a good time for us all to start pretending to care a bit more.

It might be something small, like smiling at strangers more. Or, actually listening when they talk. Paying attention to details. Remembering things they told you. Finding common ground in talking about California. Keeping a soccer medal in your car glove box for a few years.

Or, maybe it’s something bigger, like Paul learning about the cultures around him so he could relate to them better, right up until the point of his execution.

The thing is, everything we have is going to disappear eventually. So, that little kingdom you built for yourself isn’t going to matter much.

All you really own is your attention.

All you control is what you decide to care about.

And, hey, even if you have to pretend to care about people in order to actually care…

Well, there are worse ways to spend your time.

Want to read more like this?

Here’s a few of my favorites.

To learn more and see my essay archive, visit my Start Here page.

Never meet your heroes.

10 years ago, I read an article in a dentist’s office, and it’s been bothering me ever since.

Now you get to hear about it.

In 2016, the American roots rock duo Dan Auerbach and Patrick Carney of The Black Keys inducted Steve Miller into the Rock and Roll Hall of Fame.

If you don’t know Steve Miller, you may remember him from the time he took the money and ran, presumably while smoking the green.

Steve Miller is a legend.

Yet, the guys from The Black Keys said they had one regret from the ceremony.

Steve Miller was rude to them.

They were so excited to meet one of their heroes and tell him how he helped inspire their own musical journey. In response, Miller basically said he had no idea who they were. He was completely dismissive.

Now, The Black Keys aren’t as famous as Steve Miller, but they’ve won some fame, including 6 Grammys. They aren’t nobodies.

After accepting his award, Miller launched into a rant backstage. Later, in other interviews, he said the Rock and Roll Hall of Fame was just a bunch of “crooks and gangsters.”

After the event, Auerbach and Carney said they deeply regretted participating and that Miller had ruined the experience for them.

I’m not saying that Steve Miller is a bad guy. Maybe it just wasn’t his best moment. I have no idea what he’s like in real life. So, I can’t comment on whether this was just his typical personality or a low moment.

But I do know, there’s nothing like meeting someone in real life and realizing they don’t live up to the expectations in your head.

And it’s even worse when that person is the one looking at you in the mirror.

The hero with two faces.

How many faces do you have? Does anyone know your real one?

When I managed an online education startup, I was known for being extremely calm, almost unreasonably calm.

People would call us and yell at us. People would threaten to sue us. Students would make threatening jokes to their teachers. Students would make each other uncomfortable with the messages they sent.

It was everything you’d expect would happen at a school, just online.

And my staff would oscillate between being unnerved by or laughing at how stoic I seemed.

I had to be. The buck stopped with me.

But at night, I’d go home and be a bit different.

I’d lie awake from 2:00 a.m. to 5:00 a.m. almost every night for years. I’d get into fights with my family. In short, I wasn’t easy to be around.

To be honest, I’m still not easy to be around.

I’d like to think I’m working on it.

It’s not easy to be the same person at work as you are at home.

It’s even more difficult to be the same person in real life that people think you are on paper.

Imperfect class acts.

Perhaps other people struggle with this.

I think maybe a lot of leaders know how to be calm in front of their subordinates and struggle in private moments. Two of my favorite examples of this are William Sherman and Ulysses Grant in the American Civil War.

Now, if you’re from the South, you may remember these two gentlemen as the guys who ordered the burning of many of the farms in Georgia and the Shenandoah Valley.

Or, if you’re from the North, you might remember them as the two generals who helped finally put an end to slavery in the U.S. and preserved the nation.

As a native Californian, that’s what I like to remember. But wars are complicated.

Just like people.

Though I spent my childhood obsessively studying the American Civil War, it’s not always the battles and heroic exploits that first come to mind when I think of these men.

It’s their character and their inner life.

You see, Sherman struggled with crippling depression and suicidal thoughts. Grant struggled with alcohol.

Grant’s officers knew that after an especially brutal battle, even if his army won, Grant would disappear for 2 or 3 days. He’d keep it together and stay stone-cold sober during the lead-up and the fight itself. Then, he’d go off on his own and get drunk for a couple of days.

Or at least, that’s the rumor.

It’s difficult to know the truth. Maybe it was something his critics said to make him look bad.

But we do know Grant struggled with drinking, so the truth is likely that Grant was something like this:

A hero in public. A struggling man in private.

Despite their struggles, Sherman and Grant were both strong colleagues and fast friends. Sherman himself is quoted as saying,

“Grant stood by me when I was crazy, and I stood by him when he was drunk, and now we stand by each other.”

To his credit, though Grant was known for his unrelenting energy and uncompromising approach to war, he was a gentleman when it came to the important moments.

For example, when Lee’s army of Northern Virginia finally surrendered to Grant in the spring of 1865, some people claimed that Lee’s soldiers were living on 1 tablespoon of rice or flour a day.

Whether this figure is exaggerated, it’s clear Lee’s army was in bad shape.

So, when Grant accepted this surrender, he fed Lee’s army, ordering 25,000 rations to be sent to Lee’s men.

I’m not condoning the South or slavery. It was a good thing that the Confederacy lost. And I like my states united.

But I appreciate that Grant understood that your enemies are still human beings, and you don’t let people starve.

Like I said, war is complicated. Being a leader is tough. But Grant was a class act.

All filters are half-off between 4:00 and 6:00.

In my own life, I’ve had a range of leaders with varying levels of authenticity.

I’ve had bosses who were unashamed about their Christian faith and their love of motorcycles.

I’ve had bosses who told me in our first meeting how they came out to their parents as teenagers.

I’ve had bosses who admitted their own mistakes and stood up for me when I made mistakes.

And I’ve had bosses who lied to me about little things, like whether or not they liked doing PowerPoint decks.

In all of these cases, I found that I cared a lot less about whether I agreed with my bosses on everything and a lot more about whether they were trustworthy and consistent.

Find me a boss who’s honest, and I’ll follow that person through a hurricane.

When I think about one of my old bosses from the bank, I appreciate the fact that I saw him in so many contexts. Zoom calls, team meetings, mini-conferences, one-on-one lunches, long Uber rides through NYC, and group happy hours. Though we didn’t agree on much of anything personally, I was so grateful that he was the same in every context and always treated me with respect.

Mixing alcohol and work relationships can be an odd thing. But maybe it’s useful to be able to assess your coworkers in multiple contexts. If your boss treats you with respect at both work and the bar, that’s probably a good sign they’re a decent person.

In other words, the fewer faces someone has, the better.

The first rule of book club.

But enough about bosses. We started with heroes, and I think we should end with that.

I’ve had the chance to meet a few of my heroes over the years. I haven’t met anyone too big. Mostly a few authors and musicians. But I’m happy to say that for the few heroes I’ve met, I felt like I saw the real deal.

One moment that stands out in particular was back in 2022. On a cool April evening in D.C., my sister and I got to meet Mikel Jollett, the founder and lead singer of The Airborne Toxic Event.

Mikel’s an interesting guy.

He grew up in a real, no-joke cult called Synanon in California and was then later raised by his dad, who was both an ex-heroin addict and an ex-jailbird.

Then, he went to Stanford and was a state champion runner. Things were looking up.

But, as life would have it, he chose the wrong career. Upon graduation, he pursued the well-worn path of corporate business. Over the next few years, as he describes it, he got fat, old before his time, and miserable.

After years of feeling like he was losing himself, he finally had an awakening.

You might find what happens next a bit juvenile, but it’s a true story. And I like it.

Mikel spent a week watching Fight Club multiple nights in a row at a movie theater. After this, he quit his job, began running and working out obsessively, started working construction, wrote for a music magazine, and slogged his way through a winding 10-year path to becoming a musician.

It’s a wild story filled with moments like Mikel and Robert Smith of The Cure wandering drunk around NYC’s Central Park, a conversation that finally tipped Mikel over the edge and inspired him to start a band.

Sixteen years after this, and a decade after seeing him in concert for the first time, I finally met Mikel Jollett at a small book signing for his memoir Hollywood Park.

Having seen him in concert so many times, I thought I knew what to expect.

I was really happy to find out my expectations were right.

He was exactly the same at a book signing event attended by 30 people as he was at the rock concert later that night attended by 2,000. Ok, slightly quieter. But still, he wore the same face.

I remember telling him, “Hey, that essay you wrote about watching Fight Club and quitting your job is what inspired me to go to grad school.”

Instead of acting self-important or snobbish at all about it, he just quietly said something to the effect of…

“Oh wow. That’s super cool. Did you know some people have told me their professors used that essay to teach narrative nonfiction writing at their colleges? Isn’t that crazy?”

Remember, this was a guy with a niche but decently successful band, who had just published a bestselling memoir. When his book first came out, Oprah listed it as one of the 30 most anticipated books of 2020.

Yet, here he was, totally humble and surprised about the fact that a college professor might use an old magazine essay of his as an example.

He’s not a perfect guy. I’ve read about his low moments.

But the man on paper matched the man in reality. And that was really cool.

The hero with one (imperfect) face.

Nobody is perfect. Not Grant. Not Sherman. Not Steve Miller. Not Mikel Jollett. Not my old bosses. Not me.

None of us can live up to our ideals perfectly. And really, none of us will ever be as kind, calm, or likeable in person as we may seem on paper.

But, we can try.

My sister once said that only people with ideals can be hypocrites. What she meant by this is that you can only really fall short of a standard if you actually take a stand. When someone has no standards at all, it’s pretty hard to criticize them for not living up to them.

I think my sister has a good point, but maybe it’s not quite the right wording.

Maybe what makes people hypocritical is not when they fail, but when they hold their own values in contempt. When they have two faces and know it.

In short, when they stop trying at all.

I think we’ve all seen enough charlatans on TV to come up with a few examples on our own.

As we wind this down, I don’t want to make anyone feel bad about themselves. I’m not perfect, and I don’t expect anyone else to be either. But I think the key is that you can’t stop trying to live up to your standards, even if you don’t really do it very well.

To quote John Steinbeck,

“Now that you don’t have to be perfect, you can be good.”

We can’t share every aspect of our personalities in every situation. There will always be different sides we show when we’re at work, hanging out with friends, or spending time with family.

But, ideally, when it comes to faces, I think we should all just have one.

There’s an old saying that you should never meet your heroes. To that I say, maybe you should just get better ones.

But let’s not be too quick to judge. Maybe the problem isn’t our heroes after all. Maybe it’s us.

Perhaps we all have those moments when we look in the mirror and don’t feel like we can live up to our own standards.

Maybe like Grant and Sherman, we can stick with each other through that too.

Want to read more like this?

Here’s a few of my favorites.

• Stop Trying So Hard

• I Don’t Have Time for an Intervention

• Don’t Quit

To learn more and see my essay archive, visit my Start Here page.

Glad you dropped by. This is an intervention.

The Minnesota-based punk band Banner Pilot can teach you a thing or two about work-life balance.

Their song Intervention details a guy fighting with his girlfriend and trying to deal with his crippling alcohol addiction. Fair warning. There’s some language.

In the song, our main character knows he has a problem. He knows he’s screwed up his life. But as he sobers up, all his hopes and dreams become an impassable mountain range in his mind. He doesn’t even want to try, because he just expects to be met with disappointment.

What struck me was one particular line.

Toward the end of the song, our protagonist repeats over and over these words:

“I don’t have time for an intervention.”

This isn’t an essay about addiction, though I do think addiction is far more related to everyday, normal issues than we’d like to admit.

This is actually an essay about time. It’s also about emotional burnout, work, and what to do when everything feels stacked against you.

I may not have resisted a traditional intervention, but I’ve found myself saying similar words to our hero in the song.

“I’ll go see a therapist when life is less hectic.”

“I’ll get organized when work slows down.”

“I’ll take a break when I’m not so stressed.”

“I’ll look for a better job once I get this one under control.”

I can’t be the only one who’s said things like this, right?

I think we all do this sometimes. It’s far too easy to get caught up in whatever busyness or stress is keeping us down, only to find out another 6 months have passed, and you still haven’t made that doctor’s appointment, started that podcast, or applied to that job.

If there’s one thing my own experience has borne out, and one thing history suggests, it’s that you need to find time for that intervention.

Take a break before you break.

“How could I possibly be expected to handle school on a day like this?”

–Ferris Bueller’s Day Off (1986)

This is your body on burnout.

When it comes to burnout and rest, two examples stand out in my mind.

The first comes from Lottie Unwin. She runs Up World, a group of 1,200 entrepreneurs and marketing leaders who meet up and collaborate on various cool projects. This all started from a small supper club called Copy Club, just a few friends getting dinner and chatting.

She’s quite open about her mental health journey, and she talks about how for several years she’d work super hard for 6 weeks and then completely crash. Her business partners joked about it and called it her “quarterly burnout.”

In an interview with Dan Pope, she talked about how in April 2021 this got so bad, she couldn’t speak. She lay in bed and just texted her friends a number, on a scale of 1 to 10, of how she was doing.

This lasted for 3 weeks.

She’s not the only entrepreneur facing this challenge. Chris Williamson, the host of the Modern Wisdom podcast, talks about how he used to suffer from severe depression. Or so he thought.

Prior to hosting the podcast, he ran nightclubs in the northeast of England. After staying up until 4 a.m. for days on end, he’d end up stuck in bed for a few days, sleeping and ordering takeout.

Looking back, he says that what he thought was severe depression was just a severe lack of balance in his life. Extreme tiredness and extreme depression look pretty similar sometimes.

I’ve never faced anything quite like this in my life. But, I’ve had smaller versions of the same thing. In grad school, I often would get sick at the end of every finals season.

Or, when I was stuck for several years in a job I disliked, my stress would get so bad that I’d end up needing to take a random day off when my immune system crashed.

I think we often feel guilty taking a day off. Or, our bosses make us feel guilty.

Whether the tyrant in your life is an internal or external one (or both), the outcome is the same.

If you don’t end up taking some rest just for fun, your body and mind will force you to.

If you remember the classic 80s film Ferris Bueller’s Day Off, you’ll remember that you have two options when you hit that emotional and physical wall.

Be like Cameron and lie in bed, too sick and depressed to do anything.

Or, be like Ferris. Pretend to be sick, and go have an adventure instead.

But neither of these options is very sustainable.

Maybe it’s better to find a healthier alternative before you hit that breaking point. Instead of playing hooky from work and gallivanting off to Chicago, maybe just take more breaks.

If only there were one or two days set aside per week to get some rest…

“Rest is not idleness, and to lie sometimes on the grass under trees on a summer’s day, listening to the murmur of the water, or watching the clouds float across the sky, is by no means a waste of time.”

–Sir John Lubbock, the founder of the British bank holiday movement, in his 1894 book The Use of Life

Thank God it’s Friday.

Have you ever wondered how we got the weekend?

The modern 5-day workweek was popularized by Henry Ford. He wanted his employees to have a day off (Saturday) to buy cars. Sunday was for church, and stores were closed.

But why the weekend at all? Why the rest on Sunday?

According to the Judeo-Christian tradition, God created the world in 6 days and then rested on the 7th. Now, whatever you believe about God, you have to admit, it’s an interesting story.

Why does an all-powerful God who just created the universe need to take a day off to rest?

Did He get tired? Doesn’t that mean He’s not all-powerful?

Early scriptural texts provide more context, but I think the clearest answer comes from Jesus of Nazareth, thousands of years later.

There’s a story where Jesus and the 12 disciples are walking through a field on a Saturday (the Jewish Sabbath), and they pick some grain to eat while they walk.

A group of conservative religious leaders observe this and criticize Jesus. According to their moral tradition, picking grain, even in a casual manner like this, is work.

And doing work on the Sabbath is totally forbidden.

In response, Jesus tells them “Man was not made for the Sabbath, but the Sabbath for man.”

Here’s where it comes full circle.

God didn’t rest because He was tired. He didn’t require people to take a day off just for arbitrary reasons. No, He set the example of taking a day to rest, because it would be good for humans.

In this tradition, the Sabbath is a day to re-align with God, take a break, and revisit what’s important in life.

From this same tradition, we get the concept of leaving land fallow every 7 years. Turns out, modern science has verified that soil really does need time to rest to restore its nutrients.

Much like humans.

I think we can all agree. Whether you take a Sabbath on Saturday or Sunday, and whether you take it for religious or practical reasons, more rest is probably a good idea.

But when you have a full-time job (or a family to take care of!), this is easier said than done.

“You may drive out nature with a pitchfork, yet she will always come running back.”

–Horace, Epistles, written around 20 B.C.

This is a letter from management. You have to work this weekend.

Humanity hasn’t always had a 7-day week.

But, man, do we seem to need it.

The ancient Egyptians had a 10-day week, including 2 days of rest. The Romans had an 8-day market cycle, though this wasn’t quite the same as a true workweek.

While the lengths of the weeks differed, the important thing was that both cultures took some time for rest.

Here’s where it gets interesting.

Humans have tried to ditch tradition, use pure reason to redesign the week, and get rid of all that useless downtime.

It didn’t go well.

During the French Revolution in the 1790s, rational thinkers tried to organize the calendar from the top down. There would be twelve 30-day months, split up into 10-day weeks.

Work 9 days. Rest on the 10th.

As you might imagine, this was extremely unpopular and resulted in a lot of people unofficially taking off Sundays or slacking off at work.

Wow. Turns out Gen Z didn’t invent “quiet quitting.” Those pesky young people.

Napoleon eventually killed the 10-day week. This was in part to get the Catholic Church on his side, and partly to keep the people from rebelling against him. Pretty good thinking on his part.

When you take away someone’s ability to rest, spend time with their family, or invest in meaningful community activities and faith traditions… well, bad things happen.

Even though both the French and the Egyptians tried 10-day weeks, it seems like the Egyptians were onto something with that 2-day weekend.

As a more recent example, in 1929, the Soviet Union spent 2 years trying to implement a continuous, revolving workweek. Everyone worked for 4 days and got a 5th day off, but everyone was on a different schedule.

Oddly enough, 1 day off in 5 might seem better than 1 day off in 7. But no one had the same schedule, so families rarely saw each other, community meetings were difficult to schedule, and people felt hurried and exhausted.

The system gradually broke down and was replaced with a 6-day work week. Finally, right before entering WWII, the Soviet Union changed its schedule to align with the rest of the world.

If there’s a principle we can learn from this historical walkthrough, it’s that random schedules, a lack of time for community, and overly long weeks don’t work.

Pure rationalism, separated from the natural human rhythms of life, doesn’t really work.

Humans need structure. But that structure needs to include real rest.

Festina lente.

“Hasten slowly.”

–Emperor Augustus of Rome, on leadership and rash behavior (as recorded by Suetonius in the 2nd century.)

You’re only as busy as you feel.

I’m not always great about going slow and taking rest.

When I managed a team for the online high school program where I worked in my early 20s, I often talked about the importance of rest. I’d encourage my team to go on walks, take breaks, or leave early if they were completely burned out.

But, at the same time, I was notorious for working at night, working on weekends, or having strict vacation policies around certain points in the school year.

I even came to work one day right after having minor dental surgery. My face was totally swollen, and I’m not sure exactly what I was trying to prove… except, “I’m still the boss, and I won’t let this stop me.”

But, good business practices have to come from the top down. If God took a rest, maybe I should have too. Dental surgery is a pretty good excuse, right?

People follow examples a lot more than they follow words.

Things really started to come to a boil the year before I left the team. We were absolutely drowning in work, the phones were ringing off the hook, and we had a team of mostly new people.

Everyone said they were too busy.

They were busy. There’s absolutely no doubt about that.

But the real issue is that they felt busy.

Perception shapes our reality.

I made a few changes that helped. We had a more clear structure of who would answer phones. We also tried to implement a rule that there’d be no meetings for at least 2-4 hours every morning.

These measures helped, but it wasn’t until after I left the team altogether that I finally started to get a clearer picture of all this in my mind.

One year later, in the summer of 2019, I was doing digital marketing work in Wilmington, Delaware. By chance, I stumbled across a New York Times article about how procrastination was an emotional problem, not a time-management problem.

Dr. Timothy Pychyl & Dr. Fuschia Sirois started studying this issue back in the 1990s and early 2000s, but their collaborative paper in 2013 really made the connection.

Here’s what they found: Procrastination isn’t really about laziness. We procrastinate because we’re tired, scared, anxious, burned out, or just don’t feel like doing the work right now.

It’s typically not because we don’t have the time.

I think burnout and procrastination might be cousins. Obviously, some people are just bad at time management. But, more importantly, a lot of us are bad at emotional management.

Sometimes when things feel like they’re moving too fast, like you’d absolutely lose control if you slowed down or took a break, that’s exactly when you need to take a break.

If you don’t go for that walk, you’ll probably just end up scrolling on your phone between meetings. In the end, you just feel worse.

“A stitch in time saves nine.”

–18th century English proverb, recorded first by Thomas Fuller and later attributed to the American Ben Franklin

Take a cue from punks in white collar dress shirts.

I looked up the band Banner Pilot to find out more details.

Turns out, none of them are addicts. It’s all just made up stories based on other people.

In fact, none of them are even full-time musicians. They’re guys with white-collar jobs who play shows on the weekend.

I’m dead serious. The band members work in investment banking, mortgages, healthcare administration, and theater operations. They use their corporate vacation time to do small tours and play shows on the weekend.

Not bad for a 21-year career and 4 studio albums.

So, I guess these guys really do know about work-life balance.

I could give you a long list of things you could do to find more balance, but I think you and I both already know the answer.

Obviously, if you have a serious problem, go see a doctor. Go see a counselor. Go to the AA meeting. Find a better job with a boss who likes you.

But, for a lot of life, it’s the simple solutions that hold the best answers.

It seems fitting that at the end of the song Intervention, the guy says all he wants is a ride home and a couple days of sleep.

Maybe mom was right. Good food, sunshine, and sleep do cure a multitude of ills.

Beyond taking care of yourself, if you’re a manager at work, I think part of your job is to take care of your team too.

Obviously, you can’t (and shouldn’t) micromanage every aspect of your employees’ lives. But, you can make sure they’re not on the brink of burnout or a breakdown. And if they are, you can take real steps to come up with a better plan.

Having an Employee Assistance Program or a wellness program doesn’t make up for being a bad manager. That’s just neglect dressed up with an HR name badge.

It’s not easy to find balance. It’s not easy to provide it for your team.

But let’s put it this way. If a bunch of white-collar guys from Minnesota can find the time to do full-time jobs and play some punk rock shows on the weekends…

I think you and I can figure it out too.

Let’s go find some balance in our lives. Or, at least go for a walk and get some sleep.

Don’t wait until you actually do need an intervention.

Want to read more like this?

Here’s a few of my favorites.

• If You Win the Rat Race, You’re Still a Rat

• Don’t Quit

• You Can’t Win Everyone Over

To learn more and see my essay archive, visit my Start Here page.

In this essay (11 min. read)

• The worst hiring decision I ever made and how I recovered from it

• Why you should let your employees eat ice cream while taking calls

• Why everyone should hire more like a bean company in the U.K.

• An unconventional question to find out if a candidate is kind

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The worst mistake I ever made hiring.

Picture this.

You’re 24 years old, managing an online high school program with 1600 students and nearly 100 teachers.

You hired someone who looks incredible on paper. Stellar credentials. Has a portfolio of real work posted online. Kind, easy-to-get along with, seems like a good guy.

The only problem?

It’s a few weeks before classes start, and this guy’s basically suckered you out of thousands of dollars. The product he delivered is absolute garbage, only half-done. And he’s not answering your calls or emails.

The only way you’re going to fix this is to go back to your second choice, the person you wanted to hire for his position but for some reason didn’t.

Hat in hand. No excuses. Beg for help.

What do you do?

This is what I learned about hiring from doing roughly 500 job interviews.

Let’s get this out of the way first. The credibility issue.

You might be asking yourself, how is it possible to do 500 job interviews? Are you the most rejected candidate of all time?

No, but thanks for asking.

I did roughly 325 interviews hiring teachers for an online education program that I used to run. Those were just the ones I counted in my last year or so of 3 years of hiring, so I think the number is a bit higher.

Then, I did roughly 90 interviews or informal interview networking calls in connection to grad school or my time in banking. That’s between applying for jobs in grad school, looking for roles at the bank, or interviewing candidates who wanted to work at the bank.

Plus roughly 75 practice consulting case interviews in grad school.

And then all the other random interviews I’ve done applying for other jobs.

So do those all count? And is it really 500?

Who knows? I say close enough.

For now, I’m going to focus on the perspective of hiring managers. But I’m sure I’ll do another piece sometime from the perspective of interviewees.

Ok, enough preamble. Let’s dive in.

Lesson 1: Find out who the candidate admires. That’s who they’ll be.

When I hired teachers, I’d always ask two things. Who their favorite teachers were. And how they’d help a struggling student.

The answers always corresponded. And while the questions may seem obvious, the answers never were.

The truth is, of course I didn’t actually care about their favorite 4th grade math teacher Mrs. Johnson. What I cared about was what kind of person Mrs. Johnson was.

Because that’s who the candidate wanted to be. And that’s exactly who they would be toward their students.

Whenever teachers answered this question, I’d learn what they really thought made a good teacher. I’d learn if they were strict and mainly valued the rules. I’d also learn if they were kind and compassionate toward students who were struggling.

It sounds so simple, but I can’t tell you how many teachers looked excellent on paper and were rejected because of their answers to these two questions.

Job candidates can fake their way through almost anything.

But most people don’t think about faking their heroes.

Lesson 2: Hire for character and personality. You can train skills.

One of the best people I ever hired is my friend Joseph (name changed). He’s now a highly regarded professor and a well-liked writer on Substack.

I’ll always remember two things about him.

First, he used to take customer service calls in a broken desk chair that allowed him to recline almost flat on his back. He’d sit there, reclined all the way, eating Chick-fil-A ice cream he got at lunch.

How he did this without spilling, I’ll never know. How he did this while still sounding completely professional on the phone was an even greater mystery.

But he was great on the phone, so I wasn’t too worried. Parents and students loved him, and everyone in the office thought he was a joy to work with.

What made Joseph such a nice guy? Well, partly I think that’s just his personality.

But I think it’s also important that he worked at a McDonald’s located at a rest stop on a busy interstate highway in Tennessee. There’s something about working in a crazy, busy, fast-paced environment that just makes you good with people.

The second thing I remember about him was that on his first week of the job, I needed help working at the office until about 10 p.m. on an incredibly boring, tedious project. Printing out and mailing every student’s final grades.

Later we decided this was utterly ridiculous. Students could just look at their grades online.

But, at the time, that’s what we did. And what I remember is that Joseph was the only employee who volunteered to do it. Everyone else refused.

I had other employees who would watch the website crash at 5 p.m. and say “Well, that’s not my problem. I’m heading home.”

Not Joseph.

You can train someone to do calls. You can train them to do Google Ads. You can train them to write marketing emails

You can’t train someone to go the extra mile.

You have to hire for that.

Lesson 3: Treat your job candidates like real people. They are.

Earlier this year, I had two interviews to run marketing for one of the biggest authors in the world. I’m serious. This person has written many books and is a well-known public figure.

I was told I was in the top 4 candidates.

The day after I had my second interview, everyone on the team re-posted the job on LinkedIn. (Yes, I admit I looked them all up!)

Then, I got ghosted. Even after I sent a follow-up email to ask about next steps… nothing.

I used to be a huge fan, but honestly, it will be difficult to listen to or read that author again.

Contrast this with another experience I had.

When I was first out of college, I was rejected to be a legal assistant at an education-focused law firm.

Later, I applied to work for that law firm’s online education program. The lawyer who rejected me put in a good word for me. He didn’t think I was the right fit to work for him, but he thought I’d be a good fit for this role instead.

Not every door needs to shut at once.

Or, just this week, I heard about a famous brand doing a great job of following up.

Amelia Christie-Miller has gained some fame in the UK food market for her company Bold Bean Co. Against all odds, she’s found a way to make beans seem a lot cooler, through clever branding, marketing collaborations, and unique cookbooks.

The brand went viral on LinkedIn for sending a thank-you note along with a gift of gourmet beans to job candidates who made it to the final round but weren’t hired.

It’s a simple gesture. But who really thinks of doing that level of expensive follow-up with rejected candidates?

It’s easy to think that once a candidate is out of the hiring process, that person no longer has a relationship with your company. But that’s not true. They could be a potential future customer, a fan, or a future collaborator.

Hiring managers have the power to create their own fans or their own brand’s worst critics.

A rejection doesn’t have to be a burned bridge.

Lesson 4: Consider the data. Go with your gut.

As we start to wind down, I want to get back to the opening story.

What happened with that guy I hired? And did he actually rip me off?

Well, we were trying to hire a course developer and 4 teachers for an online chemistry course. If you think teaching online is tough, trying teaching online and including science labs.

I think we went through at least 50 interviews just in the first round of hiring.

Candidate 1 was a guy who had great experience teaching, had his own science channel on YouTube, and who had even done scientific research for the U.S. government.

Candidate 2 was a qualified scientist but had only about 2 years of teaching experience and had never taught online.

I asked the whole team, and they said hire Candidate 1.

Pretty obvious decision, right?

The problem is that I liked Candidate 2 better.

I just couldn’t really explain why. She just seemed like who I’d choose to teach my own kids. She was a bit more humble and easy to get along with.

Candidate 1 seemed fantastic, but somehow I just knew he was the wrong choice. He seemed too good to be true. And those kinds of situations bother me.

But it was all so subtle, it was difficult to put into words.

I spent about a week spiraling and overthinking.

After too much deliberation, I hired Candidate 1 to develop the course. Candidate 2 would be one of the 4 teachers.

Well, the months kept slipping by and I kept checking in on the course development. He kept turning in subpar work (or no work!) but continued asking for his next check.

Instead of just standing up to him, I kept mailing the check.

I figured he’d get it together eventually! I’d seen what he could do! He was just having family troubles this summer!

I think in part I was overwhelmed. We were developing 10 new courses that year, hiring dozens of people, and revamping both our internal and external websites.

This guy was a professional. Why did I have to hold his hand? He’d get it done eventually.

Or so I thought.

About 2 or 3 weeks before the classes started, none of the other teachers had heard from him. I couldn’t reach him either. And he wasn’t done developing the course.

Finally, I got a hold of him on the phone.

I told him, “This isn’t working out. I’m going to have to let you go.”

Oddly enough, he seemed kind of surprised.

He asked, “Have you ever had to fire someone before? I know that must be hard…”

Internally, I was thinking, what the heck is wrong with you, you condescending jerk?! Did you really just ask me that?

Here I was as the manager, and I’d never felt like more of a child.

Even worse, I was out somewhere between $6,000 to $8,000.

He was great on paper. Everyone liked him. There seemed to be no red flags.

Except that weird feeling that I was making a mistake.

I went with the data, but I ignored my gut.

Maybe the best way is to combine intuition with data. I suppose that’s what 90-day probation periods are for.

Podcaster Dan Pope likes to talk about 2-D lessons and 3-D lessons. You learn a 2-D lesson when you read a principle in a book. You learn a 3-D lesson when you live through it.

Like when you lose thousands of dollars over a bad hire.

I guess this was a 3-D lesson.

Lesson 5: Protect your brand. Be honest in the hiring process.

After I got off the phone call, I had only one option. I had to go back to Candidate 2.

There simply was not enough time to find anyone else.

I had to tell her everything. How I wanted to hire her, but he was more qualified on paper. How I’d made a mistake and I needed her help cleaning up the mess.

She wasn’t going to be teaching a pre-developed Chemistry course. Easy peasy.

No, she was going to be building the airplane while flying.

She was going to have to learn teaching online for the first time, manage two other teachers, teach an extra class section, and develop a course from scratch, a week or two ahead of the actual class. Meaning, as we were on week 3 of the class, she’d be writing the material for week 4 and 5.

In short, it was going to be an absolute nightmare.

I told her, “This is going to be an awful year, and you’re going to have to work really hard. But I have no other options, or I have to refund all these students. I really need your help.”

She said yes.

Talk about eating humble pie.

I was right. The year was a nightmare.

The next spring, she told me she wasn’t coming back. I don’t blame her.

Then, I had to hire for Chemistry all over again. Another 40 or 50 interviews.

We did hire again. We found two excellent course developers who tag-teamed to redevelop the course and knocked it out of the park. It just cost us 2-3x as much to develop Chemistry as it should have.

There was a silver lining. I’m pretty sure a year or two later, Candidate 2 actually came back and taught again for another year. So, at least she didn’t hate us.

Midway through that school year, I remember her telling me something important.

“If you’d lied about how hard it was going to be, I wouldn’t have accepted. I’m glad you told me it was going to be awful.”

The moral of the story? If you want someone to walk through a storm for you, tell them about that storm that’s coming. Never hire under false pretenses.

Or simply, in the words of David Beckham, “Be honest.”

Concluding thoughts

I’m writing all this down about a decade after it happened. Hopefully, a little older and wiser.

There’s so many other things I could share, but I thought I’d start with these five.

A lot of them may seem like obvious takeaways, but I’m a big believer in 3-D lessons, so I’m hoping the stories help.

To recap the 5 lessons:

• Find out who someone’s heroes are. That’s who they’ll become.

• Hire for character over skillset. Skills can be developed.

• Treat your job candidates like human beings. Even when you reject them.

• Use the data, but trust your gut. Better yet, use both.

• Never hire under false pretenses. Hire people who will willingly walk into a storm.

If you’re not a hiring manager, a lot of this may not seem applicable to you. Don’t worry! I’ll probably write a follow-up piece for job seekers too.

But I think it’s helpful for all of us to remember that hiring managers are real people trying to solve real problems. And a lot of the time, they don’t get it right.

Then again, employees don’t always get it right either.

If I had to choose one principle for both employees and managers, it would be this:

Remember to be human. Forgive people for when they are.

. . .

But seriously, if the website crashes at 5:00 p.m., please don’t just go home.

Want to read more like this?

Here’s a few of my favorites.

• Fortune Favors the Bold

• Business for Humans: The Principles of Hospitality

• 80% Reliable. 20% Weird. The Recipe for a Memorable Brand.

To learn more and see my essay archive, visit my Start Here page.

When I was a senior in college, I got 9 credits of C’s.

I’d never gotten a C before in college. It was all A’s and B’s for me.

This is going to sound counterintuitive, but here’s some advice I learned the hard way.

You need to stop trying so hard.

Never back down.

Ever since I was a little kid, I always wanted to prove myself. Most of the time, it worked out really well.

A few times, it burned me badly.

Since I was homeschooled, I begged my mom to start school when I was 4. Then, I begged her to let me do the same schoolwork as my older sister.

All throughout high school and college, if there was a challenge no one wanted, I signed up.

Give a presentation on a difficult topic? Sure. Take golf lessons when I was already doing cross country? Why not? Sign up for academic decathlon when I was already doing 7 honors and AP classes? No problem.

When I started college, I was 16 years old. Technically, I was a dually-enrolled high school student, but from that point onward, it was just 4 years of full-time college classes. That said, to officially finish high school, I still needed 3 years of a foreign language. Since I’d only done Latin 1 and 2 at the Catholic high school I attended for 2 years, I needed to test into Latin 3.

That meant I’d have to finish all the remaining chapters I hadn’t finished for Latin 2. So, with the help of my very generous college Latin professor, I went through the last 7 or 8 chapters. One chapter a day.

While everyone else was having fun during freshman orientation, I was in the library, studying.

It was brutal. But I had a point to make. Yeah, I might be young, but I belong here.

This time, it worked.

I crushed the Latin entrance exam and ended up earning a small scholarship for languages.

But it didn’t work every time.

If it scares you, you should try it. Sometimes.

And so college went. I was often studying hard, writing things at the last minute, and feeling like I was just getting by. But I got pretty good grades and made it through.

I decided to be a history major.

Partly because I love history. Partly because I was young and had no idea what else to study. And partly because senior history majors had to write a 100 page thesis.

It terrified me. So I had to do it.

I don’t like backing down from a challenge.

The problem is that I kind of set myself up to fail.

As a junior, I had to write a 35 page paper on ancient history. I got an A- on it from a professor I liked. For my senior thesis, I should have just expanded on that paper and chosen that professor as my advisor.

Instead, I chose a professor who had only given me one A- in college. Aside from that, I’d never received higher than a B.

Why did I choose this advisor? Well, I was scared of having to write about ancient history and potentially translate Latin (even though I was good at that… and most sources I’d need would have already been translated anyway). Also, modern history seemed more relevant to current life.

And lastly, this time, I was going to get an A no matter what.

Well, that year I ended up working a few jobs on campus, from custodial, to events, to working for the Director of Distance Learning. I had my first girlfriend. I lived on campus for the first time. And I took an absolutely brutal courseload.

Cut to me at the end of senior year.

No girlfriend, because we broke up around Christmas. Goofing around too much living on campus. Wasting time on all the wrong things. And working my tail off trying to write for a professor who really didn’t like me much.

Maybe it’s not just about the challenges you take on. It’s about how many you take on at once.

That May, when we walked across the stage at graduation, I had a placeholder document in my diploma. Basically the equivalent of a restaurant opening banner that said “coming soon!”

Classmates who’d used my notes to study got awards and ribbons. I got nothing.

Walking across the stage of my college graduation at the age of 19 felt like one of the most meaningless events in my life.

Somehow, I just couldn’t shake the sense of burnout. Summer turned to fall, and finally I cranked out a really terrible thesis in October. 100 pages written in about a week.

It might sound like I worked hard, but the truth is I really did a pretty bad job of it.

All C’s. And it was deserved.

And this wasn’t the last time I’d make that mistake.

Older, not wiser.

8 years later, when I was starting full time in corporate at a bank, I was told by my first boss that she didn’t want me on her team. She only wanted expert coders. Never mind the fact that I was in a rotational learning development program. Or that she herself had come from that program.

I complained to the program manager and was given the opportunity to switch teams. For whatever reason, I said no. I was going to make this work.

Right, yeah.

A year and a half later I did the same thing. Took a hard role in finance at a time when we were supposed to be taking easy roles and looking for a full-time placement. I didn’t even want to do finance. I just thought I needed to face my fears and do it.

If I hadn’t been semi-guaranteed a final placement, I probably would have been fired.

I found a full-time placement on a team I liked, with bosses I liked. But I started to realize slowly that I was on a sinking ship. My wonderful boss got sick and had to stop working full-time, and I was stuck with a new boss who again didn’t like me. I knew I needed to leave, but for some reason I stayed. I was going to turn things around.

I stayed long enough to see my team get dissolved one by one. Including me.

When that happened, I thought about the conversation I had with my friend on the streets of Morristown, New Jersey, 6 months earlier.

As we wandered around looking at shops in the cold February air, she asked me “Colin, why do you always choose the hardest path? I feel like you’re constantly setting yourself up for a struggle, even at things you don’t like, just because it’s hard.”

She was right.

She’d said it many times before.

Why indeed.

Turns out, there’s a formula for the optimal challenge. I just wasn’t ready to accept it.

The Formula for the Optimal Challenge

You may have seen a meme floating around the internet. A simple circle with the words “your comfort zone” written on the inside, along with “where the magic happens” on the outside.

There’s some truth in that. But I don’t think it tells the whole story.

I think the magic happens right on the line.

I wish I could say I came up with that myself. But I got it from Jordan Peterson, the Canadian psychology professor. He writes about the distinction between order and chaos.

Perfect order is the totalitarian state, or the totally rule-bound mind. It offers stability but stifles creativity. Pure chaos is where new ideas run free. It allows for new birth and renaissance, but it’s also a destructive force.

You don’t want either. You want to be right on the line between order and chaos.

Enough rules, tradition, and stability to keep you grounded. Enough chaos, creativity, and regenerative potential to create new life and new order.

Malcolm Gladwell presents a good example of how to put this into practice. Specifically, his advice for choosing a college.

He said you should try to attend a college where you can be solidly in the middle of the pack.

Don’t go to a college where you’re easily at the top, because that probably means you didn’t challenge yourself. Also, don’t go to a college where you’re just barely scraping by. That’s too stressful, and you won’t learn much anyway.

In other words, it’s better to be a solid A or B student at a big state school than a C or D student at Harvard.

And I think that was one thing I didn’t learn fast enough at the bank. In some ways I pushed myself too much. In other ways, I pushed myself too much in the wrong environment.

That said, I’m grateful I did one thing right. I went to the University of Notre Dame for grad school. For someone who’d never studied business before, it was pretty tough. But it wasn’t backbreaking. I was challenged, but not crushed.

The magic happens right on the border.

That border is the key to success and happiness

I was listening to the Hungry podcast recently, which features entrepreneurs from food and drink brands. Max Halley, considered the UK’s King of Sandwiches, had this advice:

“The key to having a happy life is having achievable goals.”

That’s a tough lesson to learn. And frankly, I don’t think I’ve completely sorted it out in my mind.

The problem with dreamers is that they often choose unrealistic goals. Yet, the problem with realistic people is that they often don’t do anything interesting at all.

Peterson, Gladwell, and Halley aren’t quite saying the same thing. But I think they’re all onto something similar. There’s a fine line between order and chaos, challenging environments and bad ones, and ambitious goals and unrealistic ones.

In short, you need to dream. But you need a dose of reality too.

So how do you actually walk that line? How do you choose the right challenges?

Maybe it’s a constant struggle, with slipping on or off the line on either side.

Why is it that I could test into Latin 3 at 16 but not write a decent senior thesis at 19? Why could I get into the biggest bank in the world but not succeed on the finance team?

I don’t have all the answers, but I guess it’s about knowing when to quit.

There’s a difference between challenging your strengths and challenging your weaknesses.

I knew I was good at Latin, and I had a supportive professor. It was a challenge, but it was one I knew I could handle.

At the same time, I also knew I wasn’t great at coding and had little interest in finance. I had unsupportive bosses. And I knew that professor was never going to give me an A on my thesis.

But I did it anyway.

Maybe that’s not grit. Maybe that’s just ego.

I’m not advocating for laziness. I think most of us actually need to try harder. But if you’re like me, maybe you need to be a bit more discerning.

When you’re in the gym, you can feel the difference between stressing your muscles in a good way and straining your tendons. Learn this too late, and you might feel a pain in your elbow for the rest of your life. Trust me, I know.

Signing up for challenges you know might break you isn’t brave. It’s just dumb.

The goal isn’t to break yourself. It’s to grow.

Stop trying so hard.

Or, at least stop trying so hard at the wrong things.

Want to read more like this?

Here’s a few of my favorites.

• If You Win the Rat Race, You’re Still a Rat

• Fortune Favors the Bold

• At Least Win at Being Kind

To learn more and see my essay archive, visit my Start Here page.

Most of the time.

Welcome to the Rat Race

The sun was going down.

We’d just had 12 hrs. of meetings back-to-back. 8:30 a.m. to 8:30 p.m.

We’d been on that schedule for about a month. It was summer, but I’d barely been outside.

That’s when my boss’s manager logged into our Zoom call.

And began talking about rats.

I’m dead serious.

Here we were, hours from submitting our 130-page proposal to one of the biggest companies in the world, with mountains of work still to go.

This deal was worth billions.

And then this person logged in and started telling us how the rats ate the wires on their car in New York City.

I remember thinking… Rats? Are you kidding me right now?

Every single person tried to smile through sweaty foreheads, bloodshot eyes, and frayed nerves. I felt like logging off, or at least turning down the volume on my computer.

That night, I finished working at 4:00 a.m. and went to bed.

The sun was coming up.

I woke up around 6:00 a.m. and went for a walk in the hot summer air along the river that flowed a block from my apartment. I had to be logged back on in a few hours.

I felt proud of the work our team had done.

But it was hard to forget about the rats.

Bright Eyes and Bright Futures

I used to work at the largest bank in the world. And for a brief stint, I worked on the deals team.

Prior to this, I made $48k a year managing an online high school program with 1600 students. It was incredibly hard work, with long nights and weekends, but it was also fun, and it was rewarding.

Eventually, I went to grad school at the University of Notre Dame to earn my MBA.

When I joined the bank in 2019, I actually really liked being an intern. It was fun and exciting, the pay was incredible, and I had an amazing boss.

I had made it to the big leagues.

Somehow, between Covid, a mix of bad bosses, and death by PowerPoint presentations (or decks, if you’re a snob), I began to get the sense that this wasn’t for me.

But, the money was good, I hate moving, and I kept thinking things would get better. Somehow, my original plan of two years turned into three. Then it turned into five.

Which begs the question. If you made $48k doing a job that made you happy, would you trade it for a job making $150k a year that made you miserable?

I did.

I just didn’t know it at the time.

If you want a better sense of how much money that is, here’s a few facts for you.

Making $150k a year puts you in the top 5% of America. To be honest, I thought you’d need to make a lot more to clear that hurdle.

For comparison, if you make $30k in America you’re in the top 10% in the world. And if you make $150k in America, you’re in the top 1% globally.

People say money doesn’t buy you happiness.

That’s only partially true.

When I made this much money, I got to buy a lot of nice gifts for my family. I didn’t have to flinch every time I bought something at a coffee shop. I got to go to Europe twice and Canada once. And I paid off a huge mountain of student debt in only 5 years.

I had a lot to be grateful for.

At the same time, most years I was so busy I didn’t take a vacation until Christmas.

So, I guess there is some truth to the old adage.

Money didn’t fix everything. It didn’t make my ocd or depression better. It didn’t solve all my family’s problems. It didn’t stop me from losing 20 lbs. in a month from a stomach infection. And, It didn’t make me feel less sick every single day working for a string of toxic bosses.

In short, money makes some aspects of life easier. But it doesn’t make life easy.

Finance Bros and Gucci Sneakers

You meet a lot of interesting people climbing up the corporate ladder.

I’ll never forget a coworker I didn’t know well inviting me to get dinner with him. He was a confusing guy. Simultaneously one of the nicest and also most off-putting people I’ve ever met.

It quickly became apparent that dinner was nothing more than an exercise in sizing me up. For what purpose? I never found out.

I remember him asking me, “Want to know what percentage I give that you’ll stay in finance?”

What a weird question. Or, maybe this is just small talk for finance bros.

It wasn’t that it was even that bad a question. It was the way he said it.

Like he was better than me. Like he’d figured me out. Like he was in charge.

Maybe the thing that bothered me the most was how similar it felt to other experiences I’d had.

My first boss telling me on our very first call that she didn’t want me on her team.

My second boss saying, “I don’t give a crap what the name is of the person who works in the dining hall.”

My coworker claiming a beautiful corner office overlooking a river and saying, “I don’t give a shit about the view.”

There were a lot of nice people at the bank. But it seemed like if you wanted to succeed, you had to be a bit cutthroat.

I’m not anti-banking, anti-capitalist, anti-credit card, or anti-ambition.

But you should probably know that somewhere in Delaware, a financial analyst is using Excel to model how many of you will not pay back your debt.

And someone in Philadelphia is talking about how they hate capitalism while wearing $600 Gucci sneakers.

And someone in New York is making boatloads of money deciding your financial future.

I wish I could write this big tell-all piece on what investment banking or stock trading was really like. I can only imagine it was more cutthroat. The truth is, I wasn’t even important. I just did consumer marketing.

Eventually, my position was eliminated, which is fancy talk for “we’re getting rid of you, but in a nice way.”

This came a few months after my boss’s supervisor was fired the day he returned from vacation.

6 months after I left, the guy who replaced me lost his job too.

The Millionaire Socialist

Which brings us to Gary Stevenson.

You might know him from his YouTube channel Gary’s Economics. Or, maybe his acclaimed book The Trading Game.

Or, if none of that means anything to you, you should know two things.

Gary might have been the top stock trader in the world. At least that’s what he claims. Based on the data, at least top 5 of 10. But I think he might be right.

The other thing you should know is that Gary Stevenson is a socialist.

I was never either of those things.

But I did like his book.

Gary grew up poor in East London. So poor they didn’t have a shower. Just a tub with a hose they attached to it.

He didn’t do great in school, but he was great at math. And he was great at reading people. Somehow he made it to the London School of Economics. There, he won a trading simulation put on by Citi Bank: The Trading Game.

Like I said, he was good at reading people. Winning the competition landed him an internship and then a job.

Eventually he became one of the top traders in the world for Citi Bank, if not the top trader. He made millions of dollars, but he wasn’t happy.

Somewhere between the countless drinks, witnessing his friends spiral into drug addiction, and the neverending accumulation of wealth, he started to fade a bit inside.

To Gary at least, he felt like he was getting rich on the backs of poor people. People like his family and neighbors. It’s hard to laugh about your millions when you made them by betting the economy would stay awful.

He tried to leave. Instead, he got transferred to Japan. It was a sort of sabbatical. A chance to reset and see new things.

But it was a punishment too. From one boss to four bosses. Less responsibility. More oversight. And constant threats hanging over his head.

Until I read this book, I didn’t realize that leaving certain banking jobs is a bit like leaving the mafia.

If he quit, they’d say he did something illegal and tie up the next 10 years of his life in court, to make sure he lost all his money.

His health started to decline. He got down to 125 lbs. and spent insomnia-fueled nights running or riding his bike around the city.

He got a months-long sick leave. He got another one. Eventually he wasn’t allowed to take any more time off.

As his depression worsened, he began going to work and sitting there doing nothing. HR wouldn’t fire him, and he couldn’t quit. He just sat there drawing cartoons and slowly whiling away the hours.

I’m not saying Gary was a role model. But I understand the feeling.

Eventually, one fateful day, HR called him down to their office.

He was finally free.

Later, when his friends asked around about him, they asked “Who won? Gary? Or the bank?”

One of his old teammates spoke up.

“It was Gary.”

The American Dream and One-Star Reviews

When I read Gary’s book, I wondered whether it was as bad as he said. You might be wondering that about my story too.

See, there’s a problem with negative reviews.

Comedian and SNL veteran Colin Jost has a bit about this.

Whenever someone writes a one-star review of a restaurant, it’s usually more about them than the restaurant. The reviews almost always have ridiculous personal details like “my boyfriend and I broke up here, so the food was terrible.”

I don’t want to be like that.

When it comes to my experience at the bank, I’ll acknowledge that plenty of the problem was my ego. Stepping down from managing 100 people at a startup to being near the bottom in a company with 100,000 employees is a tough move.

Another major factor was my health. I got incredibly sick from food poisoning, and I haven’t been the same since. At a certain point, it’s difficult to explain to people that you basically feel sick every single day.

Then again, I just read today a quote from Scott Galloway about how sometimes your body tells you things your mind doesn’t want to accept.

Looking back, it wasn’t a completely bad experience. I had a few really good bosses, Eric and Liz to name two. And I had a few really nice friends.

There’s plenty of people who can work in a big, corporate environment and be happy.

I’m just not sure I’m one of them.

Or maybe I don’t have a problem with big, corporate environments. Maybe I just don’t like ruthless, money-worshipping people.

At a certain point, 5 years of working mainly for bosses who treat you like an idiot, in an environment obsessed with the bottom line, working on projects designed to get people deeper in debt…

Well, it gets to you.

To quote the great Jon Foreman of the band Switchfoot, “Maybe we’ve all been caught singing red, white, blue, and green… But that ain’t my American dream.”

That song haunts me.

How are you playing the game?

What does it actually mean to run the rat race?

Some people use that term to refer to all corporate jobs.

I don’t think that’s quite accurate.

Like I said, I don’t have a problem with capitalism. Or jobs in banking. Or ambition.

I don’t think it’s really about the job, or the industry. Or even wanting to make it to the top of the ladder.

I think it’s about how you play the game.

Capitalism without care causes damage. And ambition without virtue creates tyrants.

A Better Path Forward

So, as we come to the close of this story, where is everyone now?

Now that Gary’s no longer at Citi Bank, he talks about economics online and works for nonprofits to try to help the lower classes.

Remember the person with the rats eating their car?

Well, around this same time, the deal team ended up buying a fraudulent company for $175 million dollars. The founder of that company (whom I met on a Zoom call) is currently appealing their 7-year prison sentence. Don’t worry. This is all over the news.

Ironically, as far as I know, no one lost their jobs over that one.

As for me, well, I’m working for an EdTech startup and doing consulting on the side. Plus, I’m getting to interview the coolest people about business, poverty, technology, and what it means to be human.

I think there’s a way to do business that makes the world a better place.

Through my writing and the podcast I’m working on launching, I aim to present that path forward. I know it’s a losing battle. But I think it’s a battle worth fighting anyway.

One year ago today, I found out I would no longer be doing marketing at the bank.

They gave me the opportunity to look for another job at the company, but I decided to move on.

My journey isn’t done yet. This year was just the prologue.

There’s a quote at the end of Gary’s book that really stuck with me:

“So the sun of Japan burnt my shoulders, and I tried to stop thinking at all, and I walked to the sound of cicadas, and I tried to taste the wet heat of the air.

After that, I flew back to London, to try to find a game I couldn’t win.

And I thought, I don’t care if I win anymore, but I should really stop playing alone.”

So, in conclusion, how do you know if you’re playing the wrong game?

Well, look at where you’ll end up if you win. If you don’t like the endgame, you probably won’t like the journey either.

By all means, make what money you can. Enjoy your life and take care of your family.

But on your way up, try to remember the other people climbing the ladder too.

And try to do something good for the world.

Don’t forget.

If you win the rat race, you’re still a rat.

Want to read more like this?

Here’s a few of my favorites.

To learn more and see my essay archive, visit my Start Here page.

In this essay (7 min. read):

• What running a race in the desert can teach you about endurance

• How the British special forces weed out recruits

• Why building your dream may take your entire life

Either way, you’ll live through it.

When I was in high school, I ran cross country.

I started out as a hurdler, and I was remarkably bad at it. Turns out, leaping over hurdles kind of terrifies me, and I’m also not much of a sprinter.

So, I switched from hurdles to long-distance track. From there, I joined cross country.

On the Saturday of the first week of practice, we had to run 9 miles. I have no idea how long it took me. Something like 2 hrs. Before that Monday when I started practice, I’d never done more than 3 miles with my dad (on the same trail, ironically).

It was brutal, but somehow, 6 days after my official debut as a long-distance runner, I did it.

There were a lot of other moments that stand out to me.

Once, my coach had the varsity team run 6 miles from our normal practice location to the race. His rationale was that the race didn’t matter for our rankings, so it was a good chance to practice endurance.

Most of them finished the 3 mile race in the top 10 or 20 runners. At this point, they looked dead tired. I’ll never forget the look on their faces when our coach asked them to run the 6 miles back.

His point: your tank isn’t empty yet. You could have run harder.

I was grateful not to be on the varsity squad.

But, I had my moments like that too.

When I was a sophomore, the most difficult race of the year was Mt. San Antonio College, out in the desert near Pomona, California. Otherwise known as the infamous Mt. SAC race.

3 miles of a totally dirt track. No shade. No grass.

Not nice, packed dirt on an old-school track. Loose dirt on miles of hills, ready to be kicked up into thick brown clouds by the swaths of runners.

Plus, it was over 100 degrees Fahrenheit. 37 degrees Celsius for all the folks overseas.

To prepare, our coach had us run 12 miles of hill repeats. 12 half-mile sprints uphill. 12 half-mile jogs downhill. Start as soon as you get back to the starting line.

It was tough, but in the end, we survived. What was once a long day I dreaded for weeks is now a distant memory from 16 or 17 years ago.

I think that’s true for most of life.

Today’s challenges will either be a faded memory or just a story you tell one day.

Either way, you’ll live through it.

Are you relying on strength or heart?

A more extreme example of this comes from Bear Grylls. If you’re not familiar with him, he became famous doing a number of survival TV shows, where he’d demonstrate survival skills for how to live through difficult situations in the wilderness.

Prior to this, he became famous for hiking Mt. Everest 18 months after breaking his back parachuting, because his chute failed to deploy.

But his first big accomplishment was joining the British Special Air Services, otherwise known as the SAS, widely considered to be one of the top tier military units in the world. They’re known for their grueling mental and physical challenges, in addition to their single-digit pass rate.

At age 19, Edward Michael “Bear” Grylls failed on his first attempt.

Later that year, he tried again and passed.

He tells the story of the final challenge during his 2nd four-month trial period.

In true special forces fashion, candidates were required to march 40 miles through the Breton Beacons mountain range in Wales, without knowing exactly how long the march would be or how much time they had left to complete the 24 hr. challenge.

All this while carrying a 55 lb. rucksack, a rifle, and water.

A common trick used by the instructors was to remove hope and see how the trainees would respond.

Bear describes reaching the end of the march, where he and his teammates saw trucks waiting to pick them up.

As they walked closer, the trucks drove away. They were told to turn around and march back.

Some men quit right on the spot.

Imagine making it through 4 months of brutal training only to quit on the last day. He says the only reason he made it through is because an older recruit simply tightened up the straps on his backpack and started walking.

Not knowing what to do, Bear simply followed suit.

To this day, he says that the main requirement for succeeding in the SAS isn’t strength.

It’s heart.

The path is much longer than you realize.

Resilience in a difficult moment is one thing. Staying the course for two decades is another.

I was listening to a podcast recently with one of my favorite entrepreneurs, David Hieatt, founder of Howie’s, Hiut Denim and The DO Lectures.

His path as an entrepreneur has been a lifelong journey.

When he was 14, he was obsessed with sports brands and began pitching marketing ideas to sportswear companies. Not knowing he was only 14, they’d actually let him come pitch.

When he graduated high school, he delayed college by a year to become an entrepreneur. His dad loaned him 500 British pounds, half of his savings. Unfortunately, David went bankrupt in 6 months.

After David failed, his dad asked him what he learned. David said “I like building a business.”

Rather than harshly judge him for losing the money, his dad replied, “Ok, your next goal is to figure out how to make enough money to keep it going.”

When David finally went to college to learn about marketing, he got kicked out at the age of 19 for having too much fun.

He lived on government welfare for a year and drifted around until he somehow at age 21, landed a copywriting job at Saatchi and Saatchi, one of Britain’s premier ad agencies.

While working as a copywriter, he started a clothing company called Howie’s with his wife. It didn’t make a profit for 6 years. He kept it going on his copywriter salary.

But, eventually the brand became sought after by larger brands, even ones like Gucci. Eventually, he sold it to Timberland for over 3 million pounds.

Despite this success, David felt like he’d quit early. He hadn’t seen a company from beginning to end. So he started over.

In his hometown of Cardigan, Wales, there had been a denim factory. For 40 years, this factory produced 35,000 pairs a week. Most of the town’s residents were employed there, so when it shut down, everyone was suddenly out of work.

David decided to help out. He founded Hiut Denim and rehired many of the old factory workers. Over the next 17 years, he built the company into a premium denim company, making far fewer pairs of jeans, but making them for customers such as the UK’s royal family.

All throughout this time, he had a little side project called The DO Lectures, described as an “encouragement network for entrepreneurs.” It’s an eclectic mix of homely TED talks at a barn in Wales, online courses, in-person retreats, book publishing, and even an old school 24 hr. radio broadcast.

But he couldn’t go all in on it until just this year. He had to keep it small while running the denim company as his main project.

Sometimes creating magic takes a few decades.

Most of us are told to dream bigger, but David said something counterintuitive I’ve been thinking about a lot:

“Sometimes you have to keep your dream small enough to keep it alive for 17 years before you can go all in on it.”

Keeping your dream small is better than quitting.

Overnight success isn’t real.

My friend David McIlRoy recently said, “Many people quit because they didn’t live up to an invisible timeline they had in their head.”

We often want overnight success, and when it doesn’t happen, we get discouraged and quit. Growing a business, becoming a writer, or doing any kind of creative pursuit is daunting because it’s a lifelong game.

Some people quit because it’s hard. But more than that, I think people quit because there’s no end in sight.

It’s not that you have to do a 40 mile march. It’s that the trucks drove away, and you’re not sure how much longer you’ll need to keep walking. Or, on a smaller scale, your coach just told you to run 6 miles home after running a 3 mile race.

I have to remind myself sometimes, the timeline is a lot longer than I think. As the saying goes, every overnight success is 10 years in the making.

It’s not a matter of wondering whether the trucks will drive away. Just assume they will. Life almost never goes according to plan.

Don’t quit.

Want to read more like this?

Here’s a few of my favorites:

• Don’t Worry. They Already Don’t Like You.

• The Year I Skipped Saturday

• At Least Win at Being Kind

To learn more and see my essay archive, visit my Start Here page.

Image Sources:

Mt. SAC. Photo Credit: Kevin Wong. Creative Commons.

Breton Beacon Mountains. Photo Credit: Adrian Pingstone, Public Domain.

Cardigan, Wales. Photo Credit: Michael Garlick, Creative Commons.

• Why being clueless (to a point) might be your secret weapon

• What the zombie apocalypse can teach you about information overload

• Why successful entrepreneurs think like beginners

  ---

One of my favorite quotes comes from the last issue of the Good Earth magazine.

“Stay hungry. Stay foolish.”

Steve Jobs quoted it.

Others have riffed on it.

Like David Hieatt and the motto for his community The DO Lectures:

“Stay Curious.”

Well, I’d like to submit my own take on this.

Stay clueless.

We all start clueless. The trick is how to stay that way.

Sometimes, I’m not sure how I made it through high school.

I went to a Catholic high school for 2 years. When I was a sophomore, I was in 7 classes, 7 clubs, and played two sports at the same time. I got about 4 hrs. of sleep a night.

Believe it or not, the school told all the parents this was pretty normal for their students.

If you asked me about high school, I’d tell you I had a lot of fun, but mostly I spent my time studying. And I was really, really tired. All the time.

Apparently, I was #7 out of 200 in my class. My dad found out somehow.

I didn’t actually know we had class rankings.

It’s fitting my dad found this out, because he’s a big part of the reason I did well in high school. (In addition to the fact that my mom homeschooled me prior to this and did a pretty darn good job).

He figured out my sports’ schedule. Drove me to practices and games. Got me to class at 7:00 a.m. Saved all my awards and records.

I’m glad he did, because I had no idea what was going on.

Every given week, I was so busy, I was just focused on the test at hand.

One example of my lack of awareness still makes me laugh.

I remember winning a bunch of medals for an academic decathlon. One was for art. As a testament to how disorganized and busy I was, I didn’t realize that there was a book of all the artwork, separate from the main study materials. So, I simply memorized descriptions and analyses of paintings, without ever seeing the artwork.

Why didn’t I just Google the artwork? Well… I was pretty new to the internet, and this simply never occurred to me. It was only after the test that I found the book of all the paintings, buried under a stack of other school papers.

In short, I was clueless. A regular Peter Parker.

Over time, I’ve learned to be a bit more organized. (Just a bit). And I’ve realized that a little long-term planning goes a long way.

But I still think there’s a lesson here. Sometimes youthful exuberance, a nose-to-the-grindstone work ethic, and a short-term view of life’s challenges can pay off.

Everyone’s talking about how to be an expert.

But the future belongs to the clueless.

If you’re clueless about how hard it will be, you might actually stick with it until you succeed.

Let me show you. Fast forward to when I was 22.

A few years after college, I ended up overseeing an online high school program. When I started, we had about 400 students and 8 or 9 courses.

We hadn’t made a profit in 6 years, and I was given a year to turn things around. When I left 3 years later, we had 1600 students and about 48 courses.

Looking back, I had no idea what I was doing. Or, at least, it felt like that sometimes.

In those 3 years, I interviewed over 325 teachers. I distinctly remember that first year of hiring new course developers. In particular, I remember hiring for Spanish 1.

We didn’t know how to hire a course developer, let alone for a language we didn’t speak. So we came up with a list of questions that took about 2 hrs. to get through.

Literally. The interviews lasted about 2 hrs. long. It was insane.

The funniest part was when we finally found the guy we liked, we knew within 5 minutes he was the right person for the job. But… we still did the full 2 hr. Interview. It didn’t feel right to give different length interviews for all the candidates. So we stuck with the plan.

After this round of hiring, I said enough was enough. We got it down to a list of questions we could get through in 30-60 min. Or 15 min. for particularly bad candidates.

In retrospect, doing 2 hr. interviews was hilarious. So bad it’s almost unthinkable.

I guess that’s what happens when you’re 22 years old and have no idea how to hire people.

But it wasn’t all bad.

You see, the thing is, we had youthful energy and naïveté. And this worked in our favor.

It meant we were too dumb to realize how unlikely it was for us to succeed.

I’m not against planning. When I applied for the job, I spent all weekend in my office writing out a 5 year plan on my whiteboard.

But if I’d known I’d need to hire over a hundred people, write an HR manual from scratch, write legal contracts, fire people I’d known for years, lead a migration to a new learning management system, and help redesign our customer-facing website….

Well, I would have been a lot more scared. Sometimes, it’s better not to know the future.

As Jesus once said, “Sufficient for the day is the evil therein.”

Plan for tomorrow. Focus on today.

To illustrate this point, I’d like to share an example from literature. A few years ago, I gave myself permission to read whatever I wanted, even if it seemed dumb to other people.

So, I decided to read World War Z.

It’s actually a pretty clever book about all the ways humans might respond to a zombie apocalypse, covering journalists, filmmakers, soldiers, and rednecks all trying to survive in different ways.

There’s a scene from the book that has stayed with me for several years, because it’s directly applicable to most things in life.

A group of U.S. marines are given high-tech gear to help them fight, including head’s up displays that feature digital scans showing all the incoming zombies. Much like the speed limit gauge projected on some cars’ windshields.

In the book, the marines are perfectly confident shooting the zombies right in front of them. But when they look at their head’s up displays and see hordes of zombies stretching for miles, they panic. The soldiers break and run.

Sometimes, too much information is a bad thing.

By all means, have a 5 year plan. But don’t try to solve 5 years of problems all at once.

Sometimes it’s better to just worry about the zombie right in front of you.

There’s a fine line between being clueless and being a billionaire.

Before we go, I’d like to share one more story of a high school student for you.

When Richard Branson was 15, he dropped out of school and started Student Magazine, a magazine covering mental and sexual health, education, culture, and all kinds of other issues he thought young people needed to understand.

Before he dropped out, he got the magazine started by selling ads via his school’s payphone to large corporations. Their ad space payments (for a nonexistent magazine) paid for the first issue.

He went on to found the Virgin empire, complete with Virgin Records, Virgin Airlines, Virgin Mobile, and many other brands.

When he founded Virgin Airlines in 1984, he leased a single used 747 for one flight route between London and New York. The terms of the lease agreement with Boeing allowed him to return the plane at the end of the first year if he couldn’t get the business to work.

Clueless, but not stupid.

His attitude of youthful recklessness, clever experimentation, and a sense of naïveté about the world of business fueled him on his path to becoming a billionaire and one of the most recognizable faces in business.

Is dropping out of high school to start a magazine a well-informed move? Not really.

But it’s not the worst move either.

Stay open-minded. Stay a beginner. Stay clueless.

There’s a concept in Zen Buddhism called “The beginner’s mind.”

In the 1970s, Shunryu Suzuki popularized this idea in the West with this book Zen Mind, Beginner’s Mind. It contained this quote:

“In the beginner’s mind there are many possibilities, but in the expert’s there are few.”

The problem with becoming an expert is that as you learn more and grow in wisdom, it’s easy to start closing doors and possibilities. Ideally, you want the wisdom of the old, combined with the openness of the young.

Don’t be like me in high school and memorize descriptions of paintings.

But, as we all grow older and advance in our careers, I hope you don’t give up a small sense of your youthful naïveté, confidence, and exuberance.

Dropping out of high school to start a magazine at 15 is foolhardy.

Running an online high school at 22 is unreasonable.

Yet fortune follows the bold. And there’s something beautiful about the beginner’s mind.

Old sages will sometimes hesitate to go where young warriors will.

But, to quote the first issue of Richard Branson’s Student Magazine… “The brave may not live forever, but the cautious do not live at all.”

Stay curious enough to keep learning.

Stay a beginner long enough to admit you don’t have all the answers.

Stay brave enough to start before you can see the end.

Stay focused on today’s work instead of tomorrow’s problems.

Stay clueless.

Want to read more like this?

Here’s a few of my favorites:

• Genuinely Weird

• Fortune Favors the Bold

• At Least Win at Being Kind

To learn more and see my essay archive, visit my Start Here page.

One of my favorite places in the world is a coffee shop where I got dumped.

It’s in Wilmington, Delaware, where I lived for 5 years.

It’s a semi-forgotten town, famous for banks, shipbuilding, and crime.

It’s where Fight Club is rumored to take place. It’s where the D-Day landing craft were built. It has more crime per capita than Chicago, and its nickname used to be “Murder Town, U.S.A.”

Sometimes I miss it.

One of my favorite things was a chain of local coffee shops called Brew Ha Ha.

They had 9 locations, decorated in an eccentric blend of industrial metal, floral wreaths, and mid-century modern decor. It was a beautiful, quirky staple of the community. And I loved it.

The funny thing is, I only found out about this chain because I got dumped at the nicest location. Sort of. It’s complicated.

Some people wouldn’t go back. But I did.

Eventually I associated the place with peaceful morning walks and family brunch.

I wasn’t going to let a bad start ruin a great place.

How many things from your past haunt you?

For me, it’s a lot.

I’m a nostalgic person, and I tend to romanticize the past, both the good and the bad.

On the one hand, I’ve discovered a lot of beauty this way. On the other hand, sometimes this has caused me to get stuck.

It’s taken me years to get over some relationships.

I wonder if my family ever got over my grandma’s death when I was 8.

I still question whether I was a good manager at the startup I left back in 2016.

Why is it that some memories fade into obscurity and some memories haunt us?

I don’t have all the answers, but I think we all have things we have trouble getting over.

And I firmly believe there’s only one way to do it.

People say we shouldn’t live in the past. But I do think we need to visit it.

It seems fitting that the hero’s journey includes a trip to the underworld.

Odysseus had to visit Achilles in Hades. Harry Potter “died” and came back. And depending on your theology, even Christ descended into hell for 3 days between His death and resurrection.

It seems obvious that death is the enemy we all face.

But maybe it’s more than that.

Maybe you have to visit the dead before you get to return home.

Dead ideas. Past defeats. Old grudges. Emotional scars. Lingering sins.

In The Lord of the Rings_, Faramir tells Frodo and Sam about the decline of his homeland Gondor:

“Kings made tombs more splendid than houses of the living, and counted the names of their descent dearer than the names of sons.”

This isn’t just something fanciful from literature. Humans do this all the time.

When you find out Gondor is based in part on Ancient Egypt, it’s not hard to look at the pyramids and understand how humans build grand houses for the dead at the expense of the living.

A lot of people will tell you to move forward. Never look back. The past is the past.

But I think sometimes when we ignore the past and try to move forward, we’re actually running from it. And by running from it, we’re elevating it, building elaborate tombs that frighten and haunt us.

The problem isn’t revisiting the past. The problem is living in it.

Just ask Jay Gatsby

So how do you revisit the past without trying to relive it?

Sometimes you need to physically go back to a place where you have bad memories.

But for many of us, the trip to the underworld is an internal journey.

Arthur Brooks recommends keeping a failure journal.

Write down a bad thing that happened. Then, in a month write down something you learned from it. In 6 months, write down something good that happened as a result of it. The idea is that eventually, you’ll start looking forward to failures as lessons to be collected.

Jordan Peterson gives similar advice with his self-authoring program, which requires participants to write 15–20 pages about their past life, their present life, and their future goals.

Why is it important to write about the past?

Peterson explains, “What you’re looking for most will be found where you least want to look.”

He attributes it to a principle in alchemy: “In sterquiliniis invenitur.”

“In filth it shall be found.”

Whether it’s physically visiting a coffee shop, tearing down your monuments to past trauma, or simply writing down difficult memories, one thing is clear:

You can’t go home until you visit the dead.

The thing you fear the most holds the answers you seek. In filth it shall be found.

That’s part of why I’m writing on Substack. I’m trying to make sense of the past, but I’m also hoping you can take some lessons from my life with you.

Failures undocumented and unshared become ghosts.

Failures documented and shared become guides and friends.

So where does that leave us?

Back at a coffee shop.

One of my favorite places to write is at a Barnes & Noble café about 20 minutes from my home.

When I go there, I can see the corner where I sat with one of my old girlfriends a week before we broke up. To get there, I have to drive down the streets where I had my last phone call with my most recent ex.

But I don’t mind. Because I have a lot of good memories there too.

It’s where I’ve written many of my essays for Substack. It’s where I shopped for Christmas presents with my sisters before going to Nando’s in the freezing December air. It’s where I’ve spent countless hours wandering around looking at the stacks of books to get ideas.

Before we wrap up, I’d like to ask you something.

What streets are you avoiding? What songs remind you of your ex? What company name makes your stomach churn? What are you too afraid to write about?

You can avoid these things until you die. But avoiding them doesn’t solve anything.

Time alone won’t heal your wounds. In the words of my favorite TV doctor, Gregory House, expertly played by Hugh Laurie,

”They always say time changes things, but you actually have to change them yourself.”

If you build monuments to the dead, you’ll do so at the expense of the living. If you try to run from old haunts, you’ll never run far enough.

So, what to do instead?

Revisit the memories. Write down the past. Go back to the coffee shop.

If your mind and past are full of ghosts, befriend them.

You need to return to the scene of the crime.

Want to read more like this?

Here’s a few of my favorites:

• Cut It Off or Drown

• When Was the Last Time You Saw Something Sublime?

• 10 Reasons Your Son is Trash

To learn more and see my essay archive, visit my Start Here page.

Back in 2017, I skipped Saturday.

Not one Saturday. Almost all of them.

I was winding down my time managing an online high school program, and I was trying to get into grad school. I’d agreed with my team to try to develop 10 new courses, redesign our public website, migrate to a new learning management system, and hire about 40 or 50 new teachers.

I was planning to leave in a year, and so was my second-in-command. Everything had to be done before then.

But beyond work, I needed to figure out the next step for my own life. I had to take the GMAT.

I was a history major, and I hadn’t taken a math course in about 7 years.

It was going to be a long year.

For the first half of that year, this was my typical Saturday.

Wake up. Shower. Get to the office by 8:30.

Take a 4 hour practice test.

Eat a peanut butter and jelly sandwich at my desk.

Look at resumes for a few hours.

Update my application tracking spreadsheet.

Leave around 2:00 or 3:00.

Go to the gym.

Repeat next Saturday.

Between all the new classes, I did around 300 job interviews that year. Somehow, we got everyone hired. We got the new courses developed. We revamped the website. We got a new learning management system.

And somehow, I got into grad school. It just took longer than I expected.

When I took the test in May 2017. I got a pretty unremarkable score. Slightly below average and well below good. Nearly a perfect score in English. Math was another story.

I thought I could enjoy the summer, but instead the process started all over again. This time, I took the GRE in November. Easier test. Not much better score. The clock was ticking. Applications were due in early December.

Sometimes you just have to take the shot.

Then, months of silence. It was torture.

Do I study? Do I give up? Do I apply again next year?

In a last ditch effort, I decided to take the GMAT again. I figured I might just go to a lower-tier school, or maybe wait and apply again the next year.

My test was on March 3, 2018. About 14 months after I started studying.

Then, suddenly, 2 days before the test, I got a phone call. I was in.

My scores didn’t improve much, but they did improve enough to get me a better scholarship.

And finally, I was on my way to the University of Notre Dame.

When I look back at that year, sometimes it doesn’t really seem real. Did I really skip Saturday? Not quite, I calculated it, and I spent around ⅔ to ¾ of my Saturdays in the office that year.

I missed a few social events. I took a lot of math tests. And I slept with a stack of vocabulary flash cards next to my bed.

But it didn’t kill me. And it didn’t even make life that unbearable. Somehow, you learn to adjust.

The most surprising part of it all was that change takes a lot longer than you’d expect. It didn’t really take a year to change my life. It took longer.

On Superbowl Sunday in 2016, I did a phone call with my friend Adam about getting an MBA. I didn’t graduate with my MBA until May 2020. And then I spent the next 5 years working at JP Morgan Chase until fall 2025.

So, how long did it take to change my life?

A year without Saturdays? 4 years of thinking about, applying for, and attending grad school?

Or 10 years of moving from education, to business school, to banking, back to education? (I’m currently doing work for an education startup)

Sometimes life is slow moving forward and fast looking back.

If you’re thinking about changing your life, don’t wait. You don’t know how long it will take.

It might take a year of work. It might take 10 years.

I’m not saying you should give up every Saturday. The world has enough productivity bros telling us to work harder.

But I do know one thing. In 10 years, you probably won’t miss a couple Saturdays.

And you could do a lot worse than a couple of peanut butter and jelly sandwiches at your desk.

Want to read more like this?

Here’s a few of my favorites:

• You Need to Stop Networking

• Fortune Favors the Bold

• All My Best Friends Owe Me Money

To learn more and see my essay archive, visit my Start Here page.

• Why the “shark circle” is a waste of time

• Why you should ignore traditional networking advice

• Why being bad at something might help you get a job

Networking is Awful and Everyone Knows It

When I was getting my MBA at the University of Notre Dame, we had something we called “the shark circle,” or “the circle of death.”

Chances are, you’ve experienced it too.

It’s the circle that forms around a recruiter at a networking event.

Or, if you’ve never been to a formal networking event, you’ve probably been part of this circle at a party. There’s often one person telling a story, and everyone else is either trying to get that person’s attention or trying to jump in with their own addendum to the story.

In the words of Simon and Garfunkel, “people talking without speaking, people hearing without listening.”

Networking is the worst.

You should stop.

Like right now.

Stop Treating Networking Like Climbing a Ladder

During my MBA program, I interned at JP Morgan Chase. It was my first time working in a skyscraper. I’d spent the first 5 years of my career working in an office with only 100 people.

And I didn’t really know how to approach networking.

A lot of the other interns focused on making connections with senior leaders at the bank. They’d organize coffee chats with the heads of prestigious teams and try to find high-level sponsors who could recommend them for a job.

But I had a hunch that this didn’t really matter. The senior leaders didn’t hand out job offers. Your boss did.

Instead of obsessing over coffee chats, I looked for opportunities to work with people.

I did interviews for the internal newsletter. I organized a mini-conference on SEO in NYC. I joined projects involving as many teams as possible.

But the most valuable relationships happened from the quiet moments with my team.

One of my favorite memories involved my teammate and summer mentor, whose last name was Mendoza. Some of the other MBA interns from schools like Penn and NYU gave me flak for going to Notre Dame (even though it’s a top 30 school, cost half the price, and led to the same exact job…).

So, as a joke I asked my coworker to spend an entire networking call with one of these students talking about how great a school Notre Dame was.

He didn’t disappoint. He spent the entire call name dropping Notre Dame, while I sat opposite him trying not to laugh. He nearly said his dad founded the business school, aptly named the Mendoza College of Business. Alas, we didn’t take it that far. But it was still glorious.

It was moments like these that made the summer.

It didn’t feel like networking. It just felt like working with people and getting to know them.

The Best Networking Doesn’t Feel Like Networking

Looking back, many of my opportunities came from relationships rather than networking.

In college, a professor hired me after getting to know me on debate trips and other excursions.

More recently, I was asked to be an advisor for a tech startup, because someone remembered a volunteer project we’d worked on six years earlier.

I even ended up at JP Morgan Chase because I had coffee with a recruiter when I wasn’t particularly interested in working for a bank.

During my summer internship at the bank, I got a full-time offer for a number of reasons. Apparently, I did very well on my summer project, but I’m sure that some of it had to do with social dynamics.

Some notable moments included helping my profanity-loving Australian coworker negotiate with a bunch of hardnosed lawyers, getting beers and watching soccer with my boss at a local dive bar, and showing tenacity by trying hard and still losing 4 or 5 games of table tennis in a row to the internship recruiter.

You still have to do the work. That’s table stakes. (Another horrible bit of MBA-jargon for you).

But the thing is, lots of people can do the work. So, how do you actually stand out?

What people remember are the human moments. The beers, the table tennis, the road trips, and the honest conversations.

It’s the hypothetical airport test played out in real life.

We don’t always actually get stuck with our coworkers at an airport, but we do still get stuck with them at a desk for 8 hours a day.

In other words, it’s not really about networking. It’s about building relationships.

5 Minutes Standing in the Circle. 5 Years Building the Relationship.

Which brings us back to the shark circle. That’s why it feels so icky. It’s just a bunch of people standing around using each other and being used.

I never stayed in that circle very long. I’d always just share one quick chat, make my name known, and set up a 1:1 call with the recruiter at another time.

5 or 10 minutes. Honestly, I don’t think I could have survived much longer than that.

But it’s okay if you can’t stay in the circle very long.

Because time is on your side.

The opportunity doesn’t come in the circle. It comes later in the phone call with the recruiter.

It doesn’t come from the random coffee chat with a senior leader.

It comes from the hours of showing your coworkers that you’re nice to work with and that you genuinely care about them as people.

It’s not about collecting meetings with important people. It’s about making natural connections with people through shared work, shared fun, and shared interests.

So, in the end, I guess maybe the title of this essay doesn’t tell the full story. You can’t totally stop networking.

But you can stop treating it like a transaction. Or a ladder to climb.

Showing a genuine interest in other people won’t necessarily get you a job right away. But it can’t hurt, and it will lead to more opportunities 5 or 10 years down the line.

At the very least, if all else fails, you can always just try losing really badly in table tennis.

Want to read more like this?

Here’s one of my favorites.

To learn more and see my full essay archive, visit my Start Here page.

The Pub Tab Theory of Reciprocity

All my best friends owe me money. And I owe them too.

It’s not exactly the world’s best financial accounting.

But I think it’s the best way to build relationships. It works with friends, and it works in business.

When I was at Notre Dame, my friend Paul and I went out to one of the pubs on campus. (Believe it or not, we actually had two really nice ones). He treated me to some wings.

When I asked him if he wanted money, he said “No, it’s all funny money anyway.”

Fair point. When you live off student loans for two years, money feels pretty abstract.

On another occasion, Paul and I spent hundreds of dollars at Costco planning a party to watch a UFC fight at his house. Despite the fact that I don’t really like parties, and I barely drink, I wanted to plan something fun for our classmates.

In the end, the party ballooned so much we started getting invited by random people. I’m not saying random people showed up. I’m saying we got invited by random people, even though we were the hosts. The fight itself lasted about 16 seconds. And we realized that we’d spent way too much at Costco.

But I don’t look back at the giant bill, the short fight, or the party that could have gotten out of control. I think about my friend Paul, and how he’s one of the most generous people I know.

That memory brings to mind what I like to call the “pub tab theory of reciprocity.”

(Actually, it turns out Simon Sinek came up with this. Apparently, I heard it and remembered it later. So much for brilliant, original shower thoughts.)

I should say now, this is a theory of social behavior. Not necessarily financial advice. Please don’t ask me for help with your taxes.

Good friends treat each other to rounds at a pub.

They don’t spend wildly different amounts and then split the bill evenly, causing some people to get financially raked over the coals.

Nor do they take out their phone calculator and do everything 50/50, including the tip. They just operate from a general sense of what’s fair.

It may not end up being exactly equal in terms of dollars spent. But it’s close enough. It works.

Real friends don’t keep score.

Unfortunately, not everyone plays by those rules. Especially not at work.

How to Survive in a World of Matchers and Takers

In the first 7 weeks of the MBA program at Notre Dame, we read Adam Grant’s book Give and Take in our ethics class. In this book, Grant argues that people can be divided into three groups: givers, matchers, and takers.

The names are fairly intuitive, but I’ll break it down for you.

Givers tend to give without expectation of receiving anything back. They’re kind and empathetic but also vulnerable to being taken advantage of by others.

Takers tend to look out for themselves first and view the world through the lens of how others can help them on their way up.

Matchers are an interesting bunch. They’re harder to spot. Sometimes they give. Sometimes they take. But, they always expect something back.

Givers are somewhat obvious, but how do you know if someone is a matcher or a taker?

Simple. You just disappoint them.

That’s how I found out with one of my coworkers.

We were doing marketing at one of the biggest banks in the world. We had to get about 7 or 8 approvals on all our projects, including approvals from peers on our team. It had a purpose, but it was still a huge pain. (Did I mention we worked at a bank?)

So, this guy and I decided to make a deal that we’d approve and review each other’s forms whenever we had time, because it was tough to find a teammate with enough free time.

The thing is, I didn’t realize that I’d be submitting one form every few weeks. He’d be submitting several forms each week. Also, he was part of a group of 4 or 5 people. I was a one-man show.

One week when I was drowning in deadlines, he asked for help at the last minute. I told him I’d get it done before 1:00 p.m. One fire after another came up, and I finally had time to look at it around 12:40. Cutting it close, but enough time for a quick review.

I’m not saying I was right to wait until the last minute. But I remember it as one of the few times someone really got mad at me at that job.

Even more wild, I don’t think he ever asked for my help again. Not once.

Not in the next year and a half of working together.

I hate to say it, but I was a little relieved. What I hate to say even more is that I think subconsciously I’d decided to disappoint him once, so that he’d maybe stop taking advantage of me so much. And as much as I felt like a bit of a jerk, it worked.

So what’s the solution?

Well, for starters, it’s probably better to set boundaries before you have to burn some bridges.

According to Grant’s theory, givers are others-focused to the point that it often becomes a problem. They get taken advantage of, or they have a hard time saying no.

His solution is to become an “otherish giver.”

In other words, in the event of a crash, put on your own air mask first.

Don’t stop being generous. Just be smart about it.

Humans aren’t rational creatures. They’re relational.

It doesn’t matter whether you’re talking about friendships, businesses, or society as a whole, it all comes down to this:

Are you keeping score, or are you building relationships?

I’ll leave you with one last work story.

About midway through that marketing job, I visited some coworkers in New York and Chicago, mainly on my own dime.

I remember my boss saying, “Does it really matter if you buy these people lunch or visit them? They’re supposed to help you. It’s their job.”

I get what she meant. I mean, after all, we were paying the agencies, and the in-house teams were supposed to help us.

But here’s a question for you.

When you’re submitting 100+ content production tickets a year, or when you need an extension on an invoice, or when you need to get your work prioritized over other projects, who do you think your coworkers will help first?

I can guarantee you from experience… it’s not the people they’ve only met on Zoom calls.

It’s the person they’ve had matcha with on Madison Avenue. Or the person who treated them to pizza in Tribeca. Or the person who randomly took a gangsters and ghosts tour with them in Chicago on a slow Friday afternoon after work.

I hate to break it to you, former boss. Pizza wins. Every time.

It’s silly. But it’s true.

Unlike what most economists think, there isn’t actually a homo economicus. Most people aren’t optimizing every part of their lives, or trying to rationally find maximum utility in every scenario.

Being homo economicus means you always want the fastest route. Being human means sometimes you want the scenic route instead. Just ask Rory Sutherland.

Or, as you may remember from my essay on hospitality, the famous Indian restaurant Dishoom could offer every customer a 16% discount. Instead, they let their lunch customers roll a 6-sided die for a chance to get a free meal.

Math says it’s the same result. Human experience says something different.

I’m about to launch a new project soon, and one of my former coworkers is going to help with part of it, even though until last week I hadn’t talked to her for 3 years.

You see, we got coffee in New York with her team back in 2021 or so. Then, we grabbed beers in London in late 2023.

It wasn’t convenient. I’m sure she would have rather gone straight home to her family after work. And I had more sightseeing I wanted to do that day. I’d promised my mom’s friend that I’d go see a garden in Richmond that night, and I wanted to see where Ted Lasso was filmed.

Sometimes grabbing drinks outside in the freezing cold in London in December isn’t rational. For that matter, taking an hour-long train out to Richmond Green alone at night in the dark probably isn’t rational either.

Spending too much on a party at Costco isn’t rational.

Treating your friends to wings and beers without wanting to be paid back isn’t rational.

Buying pizza for coworkers you’ll never see again in person isn’t rational.

But it is human.

Want to read more like this?

Here’s one of my favorites.

To learn more and see my full essay archive, visit my Start Here page.

This is a story about a letter.

It didn’t actually say “10 Reasons Your Son is Trash.”

It said “10 Reasons Your Son is Shit.”

It was written about an elementary school student.

This is how I heard about the letter.

In 2019, I went to China for about 16 days during spring break for my MBA program. It was an educational trip, complete with visits to historical sites, factories, and cultural institutions.

We spent a week in Beijing, a week in Shanghai, and a few days in Hong Kong.

On one of the first days of the trip, we met with a British entrepreneur named Dominic Johnson-Hill. He arrived in China first as a backpacker and stayed to create Plastered 8, one of the most famous, weird, and controversial t-shirt companies in China.

Plastered 8 became famous for its outlandish marketing, anti-establishment rhetoric, and use of nostalgic Chinese patterns. Think professional fashion shows hosted on busy city streets, a punk rock ethos, and t-shirts featuring classic Chinese comics and designs pulled from kitschy 1950s Chinese lunchboxes and train tickets.

When he was a kid in elementary school, Dominic’s teacher sent him home with a letter for his mom.

It was titled “10 Reasons Your Son is Shit” and included a list of all the ways Dominic was a pain to have in class.

Dominic explained that British families often put up photos of their kids’ accomplishments in the guest bathroom. Much like how an American family might put photos of their kids’ baseball games on the kitchen fridge. The idea was that it’s a subtle way of bragging about your kids. After all, everyone has to use the bathroom.

To her credit, Dominic’s mom framed and hung up this letter in the bathroom.

He was mortified. But she told him to be proud of it, have a laugh, and not care about the teacher’s criticism.

That day in Beijing, Dominic told us that his mom’s attitude toward the letter gave him the courage to start a company in a foreign country.

It’s not just modern entrepreneurs who get devastating letters.

In 1893, Winston Churchill got into a lower-tier military college on his 3rd attempt.

This was his father’s harsh response:

You should be ashamed of your slovenly, happy-go-lucky, harum, scarum style of work.

Do not think that I am going to take the trouble of writing you long letters after every failure you commit and undergo…

If you cannot prevent yourself from leading the idle, useless, unprofitable life you have had during your school days... you will become a mere social wastrel…

You will have to bear all the blame for such misfortunes…

Your mother sends her love.

Brutal.

This wasn’t the only criticism Churchill received in his life. In WWI, he was responsible for one of the more disastrous initiatives in the war. From that point on, he was a political pariah.

But he reinvented himself.

When his political career took a nosedive, he developed himself into a reputable public thinker. Between 1931 and 1939, when he was elected Prime Minister, he published 11 books, wrote 400 articles, and delivered 350 speeches.

The criticism could have destroyed him.

But he didn’t let it define him forever.

In my own life, I’ve been lucky to not have received any letter like this.

But I’ve faced my share of criticism.

I’ve had classmates tell me I was too young, not smart enough, or just didn’t belong. I’ve had bosses quite literally laugh in my face because of my religious and educational background.

So, I’ve never gotten a letter. I’ve never had anything to frame.

But maybe the closest thing would be a failure résumé.

I’ve heard some people recommend doing this as a way to get over your fear of failure. I’ve never created an official one, but here’s some of what would be on there:

• Went from being a straight-A student to getting nine credits of C’s senior year of college. (Turns out, going through your first breakup and working 3 jobs is not a recipe for a winning year.)

• Got fired from the tech helpdesk in college for being uninterested in technology. (Ironically, I’m pretty interested in technology now)

• Was told by a date that she’d been out with over 200 guys, and I was the worst one she’d ever met. (It probably had to do with her abusive ex getting married that weekend. But it still hurt).

• Part of a mass layoff at one of the biggest companies in the world. (Apparently there was a monthly layoff schedule. You have to love corporate America.)

I don’t have a letter to frame. But I have plenty of criticism to reframe. And I have plenty of failures.

Some of the criticism was true. Some of it was ludicrously untrue. But all of it hurt.

Criticism hurts. Failure stings.

You can let it define you and get depressed.

Or you can learn from it and move forward. Do something productive instead.

Go to China and start a company. Write 11 books. Re-enter politics.

Or, do something smaller. Publish essays and share your thoughts publicly even though you’re afraid what your friends and former coworkers think.

In short, if someone sends you a nasty letter reminding you of your flaws…

You have to hang it in the bathroom.

Otherwise, it just hangs around your neck.

The thing is, sometimes criticism is life-changing or world-shaping.

Sometimes it shows up as a dramatic letter.

But usually it just shows up like an ordinary moment.

Later during our time in Beijing, we took a bus trip to the Great Wall of China. It was a two-hour drive, and we had to be on the bus around 8:00 a.m.

One of the students was hungover and missed the bus. He was the only student in the class above ours, so we didn’t know him well. Unfortunately, that made him easy to forget.

When we realized what happened, most people didn’t want to turn around. Like everyone else, I was annoyed at the student, but I felt pretty bad for him too.

What’s the point of flying thousands of miles to China just to miss the Great Wall because you were late for a bus?

About 5 or 10 minutes into the drive, I stood up and walked to the front of the bus. Somehow, I convinced our driver to turn around.

Have you ever annoyed an entire bus full of people?

As I walked back to my seat, I remember everyone shooting daggers at me with their eyes.

It was going to be a long 16 days.

But I knew that today was going to be one of the best days of my life.

Criticism fades. The important things last.

When I got back to my seat, I sat down and smiled to myself.

What did I care what a bus full of my classmates thought?

I was on my way to see the Great Wall of China.

Want to read more like this?

Here are a few of my favorites.

To learn more and see my full essay archive, visit my Start Here page.

One of my favorite bands is the Airborne Toxic Event.

Before becoming a musician, lead singer Mikel Jollett went to Stanford and worked a corporate, white-collar job. An autoimmune diagnosis and the death of his grandma ended up convincing him to leave his corporate job.

Instead, he worked construction, became a magazine writer, and formed a band.

The band is weird. They’re a mix of punk rock, classical music, and electronic beats. The lyrics are sad and thoughtful. Their name comes from the postmodern Don DeLillo novel White Noise.

But their weirdness is what I like about them. It’s also what I like about their fans.

Let’s put it this way: every year they do a multi-day concert series in Palm Springs… complete with both parties and book club meetings.

Punk rock and book clubs?

That’s weird. But it’s also pretty memorable.

It’s not manufactured. It’s just a reflection of their personalities. That’s what makes it special.

It works that way for bands.

It also works that way for brands.

A few months ago, I wrote an essay called 80% Reliable. 20% Weird.

The core idea is that brands need to be dependable and meet their customers’ needs, but they also need to be a little weird. 20% of their energy should go toward off-the-wall ideas.

Think Fallow in London doing a normal menu but also serving a grilled cod’s head. Or Red Rose tea putting china figurines in their boxes of tea. Or In-n-Out’s famous X-crossed palm trees.

These details are weird, but they’re also part of why these brands built a cult following.

This weirdness can’t be faked. It only works if it’s genuine.

And here’s where that comes from.

Unique Brand Identity is Best When It Comes From the Founders

If you read the 80%, 20% piece, you may remember the restaurant Fallow in London. They’re famous for serving weird dishes, emphasizing sustainability, and having a very popular YouTube channel where they show how to make all their recipes.

A lot of Fallow’s unique brand identity comes from founders Jack Croft and Will Murray.

They had their staff t-shirts designed by the artist who made the Grand Theft Auto video game art, simply because they liked playing video games.

In an interview, they mentioned how they started using sustainable ingredients, like using leftovers from local cheesemakers and fishmongers, simply because they liked the challenge. They didn’t have a big agenda. They just naturally found sustainability interesting.

Fallow works because it’s unique to its founders. From the video game art, to the focus on sustainability, to the willingness to share their ideas on YouTube, it’s Jack and Will at the core.

For another example of the importance of founder personality, let’s get back to my roots as a California kid.

In-n-Out Burger doesn’t put Bible verses on their cups just to rile the masses.

Former CEO Rich Snyder started doing it in the 90s before he passed away, simply because his faith was important to him. His niece, current CEO Lynsi Snyder carries on the tradition because it’s meaningful to her too.

And as far as In-n-Out’s X-crossed palm trees go?

According to In-n-Out’s own social media account, they actually come from founder Harry Snyder’s love of the 1963 film It’s a Mad, Mad, Mad, Mad World, which features characters searching for buried treasure underneath palm trees in a W design.

It works because it wasn’t just a gimmicky branding idea. It was a nod to the founder himself.

Unique Brand Identity Works When it Comes From the Customers

Before I read his autobiography, I assumed Paul Van Doren was probably a skateboarder.

I had images in my mind of some rebellious 20-year-old designing shoes in his parents’ garage.

That’s not true.

When he founded Vans shoes, Paul Van Doren was 36 and had 5 kids.

He was a former middle-manager at the Randolph Rubber Company in Massachusetts, where he’d spent the last 20 years learning how to make durable sneakers using vulcanized rubber.

So a middle-aged dad started one of the most iconic punk rock brands of all time?

That’s right.

And he had no intention of making it punk rock.

His customers did.

When he founded the Van Doren Rubber company, Paul just wanted to make regular shoes for regular people.

But another movement was happening in Southern California in 1966.

Skateboarding was starting to take off. In the early 1970s, the Zephyr boys started wearing Vans. Then in the late 1970s and early 80s, the Bones Brigade and Tony Hawk started to come on the scene.

Skateboarders liked Vans because their soft, grippy, waffle-shaped soles could grip boards. They also liked that Vans would allow them to purchase shoes in different colors and replace individual shoes without buying a whole new pair.

If you can imagine how many shoes got torn open skateboarding, this was truly a unique selling point.

Though Vans experimented over time with getting more mainstream or offering dressier clothes, its core audience has long been skateboarders, surfers, punk musicians, and fans of these movements.

Paul Van Doren didn’t decide how to make his brand weird. His customers did.

He was just smart enough to listen.

Unique Brand Identity Only Works if It’s Part of the Culture

Patagonia wasn’t originally supposed to be a company at all.

Yvon Chouinard was a true hippie, spending years sleeping in tents, traveling the country, and hiking or rock climbing whenever he felt like it.

He paid for his vagabond experience by making metal pitons for rock climbing. At the time, pitons couldn’t be removed and reused, and buying new ones was expensive.

His frustration at the lack of reusable equipment led him to create a climbing company focused on recycling and sustainability.

He wasn’t a businessman. He was just a guy who liked to climb and surf.

When Patagonia started, Yvon didn’t always have enough work to give his employees. So he encouraged them to take time off frequently and go surfing, hiking, or climbing. That way they could test equipment and reconnect with outdoor culture.

You can’t write a book called Let My People Go Surfing unless you actually mean it.

And Yvon did.

Unique Brand Identity Has to Cost Something

If you try to please everyone, you won’t please anyone.

The truth is, even the biggest musicians on earth have their haters. Just ask Taylor Swift.

Mikel Jollett could probably be bigger if he ditched the weird literary references and electric violins.

In-n-Out could probably spread faster if they were willing to use frozen, instead of always fresh, meat. They’d also probably be more popular if they stopped putting Bible verses on their cups.

Fallow will probably win a Michelin star one day. But it won’t become a chain, and it probably won’t ever leave London.

The thing is… if anyone of these bands or brands ditched what makes them unique, they’d stop being memorable.

They’d just become another casualty of the sea of sameness.

If a brand wants to be memorable, it needs to lean into the weird quirks of its founders and customers.

It needs to make this unique identity part of the fabric of the company culture.

And it needs to take a stance and accept the costs.

Not everyone wants to go to a rock concert. Some people would rather go to a pop concert and enjoy a little more mass appeal. That’s ok.

I’ve been to see Billie Eilish and Taylor Swift, and I had a great time!

That said, I’ll always have a soft spot for rock shows.

There’s something special about being surrounded by a bunch of misfits wearing ratty band t-shirts and decades-old denim jackets, all singing loudly and awkwardly to the music.

Because for a brief few hours, they weren’t afraid to show the 20% of themselves that is genuinely weird.

They chose to be themselves.

Want to read more like this?

Here are a few of my favorites.

To learn more and see my full essay archive, visit my Start Here page.

Welcome to Notes on Work and Life.

I’m so glad you’re here.

This isn’t your traditional business newsletter.

This is about how to thrive in business and keep your soul while doing it.

Who this is for:

If you’re trying to do business in a more ethical and human way, looking for more meaning at work, or trying to live with more purpose, this newsletter is for you.

What my writing is like:

To help you on your journey, I’ll be sharing insights from business, history, and culture. I’ll also be sharing a lot of stories from my 14 years in online education, banking, and the startup world.

I have very eclectic interests including classic literature, pop culture, rock music, travel, and fashion and clothing manufacturing.

So, you’ll see quirky references from these areas show up from time to time as well.

What you’ll get when you subscribe:

If you’re looking for short, immediately actionable business frameworks, this may not be your cup of tea. I’m not Alex Hormozi.

But, if you like writers like Malcolm Gladwell, Ryan Holiday, or Rory Sutherland, who share lots of stories and unique ideas to challenge your thinking, you’ve come to the right place.

Expect long, thoughtful essays with creative ideas, personal life anecdotes, and lots of subtle humor. As a plus, I also include a lot of beautiful travel photos.

I publish every other week on Thursday mornings.

What’s my background?

I grew up in Southern California, and now I live in Virginia about an hour from D.C.

I studied history in undergrad and then got an MBA from The University of Notre Dame. My career has taken me from running an online high school program with 1600 students, to marketing at JP Morgan Chase, to now working at an Edtech startup.

I’m also a Christian, and while this is not a Christian publication, you’ll see some elements of my worldview showing up in my writing every now and then.

To learn more, check out my full About page. You can also find me on LinkedIn.

Where should you start?

This publication covers a lot of ground, and I know that the Table of Contents list is quite long!

So here’s where I’d recommend starting if you’re new here.

I write about business and personal development, so here’s a bit of both to help you get the lay of the land.

My favorite essays on branding and marketing:

• Building a Memorable Brand (Part 1): 80% Reliable. 20% Weird.

• Building a Memorable Brand (Part 2): Genuinely Weird

My favorite essays on building character:

• Don’t Quit

• Fortune Favors the Bold

Table of Contents

Develop Character

Courage and Resilience

• Don’t Worry. They Already Don’t Like You

• Fortune Favors the Bold

• 10 Reasons Your Son is Trash

• The Year I Skipped Saturday

• Don’t Quit

Personal Growth

• Cut It Off or Drown

• You Need to Return to the Scene of the Crime

Find Meaning

• When Was the Last Time You Saw Something Sublime?

• Reflections from That Time I Got Kicked Out of a Meditation Garden

Grow Your Business

Brand Building & Customer Experience

• Business for Humans: The Principles of Hospitality

• Building a Memorable Brand (Part 1): 80% Reliable. 20% Weird.

• Building a Memorable Brand (Part 2): Genuinely Weird

• How I Got My First Job by Quoting a Classic Christmas Movie

Hiring

• 5 Lessons I Learned from 500 Job Interviews

Marketing

• What Fashion Taught Me about Trust

• Your Best Customers Haven’t Bought Anything Yet

Strategy

• Stay Clueless

Build Your Career

Choosing the Right Path

• If You Win the Rat Race, You’re Still a Rat

• Stop Trying So Hard

Leadership & Communication

• At Least Win at Being Kind

• What Being a Narc in High School Taught Me About Conflict Resolution

• You Can’t Win Everyone Over

• All My Best Friends Owe Me Money

• You Need to Stop Networking

Work-Life Balance

• I Don’t Have Time for an Intervention

Interviews and Substack Live Sessions

• My interview with Jason Stevens

© Colin Black 2026

My parents met working at Disneyland. Turns out, hospitality runs in my blood.

Hospitality is an art. But it’s also bigger than that. It’s a way of seeing the world as a place not just of transactions, but of people.

When it comes to business, that makes all the difference.

To do hospitality right, you need to know the rules.

Rule 1: Anticipate People’s Needs, Before They Even Articulate Them

Let’s start with my parents.

Back in the 80s, my mom taught hospitality classes at the Disneyland Hotel.

I used to tell people I could see Disneyland from my bedroom window. That wasn’t quite true. I couldn’t see any rides, but I could see the hotel. And I got a free fireworks show every night. So, close enough.

One day, for the first time ever, after my mom finished teaching her three-hour class on hospitality, one of the trainees brought her a glass of water.

That was my dad.

See, one thing my dad is really good at is anticipating people’s needs.

He remembers details about people, like their favorite foods, books, or other interests. Before email, he used to mail people articles they’d find interesting. He’s bought my friend Jon multiple thrift store books about the mafia because one time Jon said he wanted to learn more.

I remember one time I ordered pizza for me and my friend Joseph. I added cheesy breadsticks on the side, his favorite. He asked how I knew.

I said, “You mentioned it once, a few years ago.”

To me, it wasn’t weird. That’s just how I was raised.

And that’s one of the first rules of building a business that actually feels human.

Anticipate the customers’ needs, before they even articulate them.

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Rule 2: Get to Know Your Customers, So You Can Make Their Experience Memorable

Sometimes what customers need isn’t what they order. It’s the experience they came for.

One of the best lessons about hospitality came from a TV show. Or, so I thought.

The Bear tells the story of a young, well-trained chef turning his family’s humble Chicago beef sandwich shop into a fine dining restaurant. In my favorite episode, the head chef sends his main problem employee, Richie, to intern at another restaurant. There he finds his true calling: running the front of house and making people happy.

In one scene, Richie finds out a family missed trying Chicago deep dish, so he goes out and buys them a pizza. The staff transform it into a culinary wonder and serve it to the delighted family.

Turns out, it’s actually a retelling of a true story.

In his book Unreasonable Hospitality, Will Guidara (restaurateur and protege of Danny Meyer) describes a similar moment about serving a family who was leaving NYC to their home overseas.

The father was lamenting the fact that he’d forgotten to try an authentic NY hotdog. You know… the slightly sketchy dirty water dogs you can get on most street corners in midtown.

Funny thing to be lamenting in an upscale restaurant. But it wasn’t about the food. It was about missing part of the NY experience.

So, Guidara had his team go out and buy hotdogs and they served them up exactly how Richie serves up the pizza in The Bear.

Sometimes truth is stranger than fiction.

Guidara became obsessed with hospitality after his restaurant Eleven Madison Park was ranked #50 out of the top 50 restaurants in the world at a prestigious awards ceremony. An honor, but still somewhat humiliating.

He knew he had to turn things around. Not with the best chefs in the world. Not with money. With a strategy. He called it “Unreasonable Hospitality.”

Now Eleven Madison Park has 3 Michelin stars. Not just because of what they serve, but because of how they treat people.

Before every guest comes to the restaurant, the staff stalk them on social media to find out what they look like, so that no one walks into the restaurant and feels unknown or unwelcome. They find out if the guest has a special occasion like an anniversary, or if they’ve been saving up for months for this meal.

One time, they even found out a couple had a falling out with their families the day of their wedding. So their reception got cancelled.

Guidara and his staff transformed the restaurant into a wedding venue and threw an after-hours party with all the staff and the happy couple.

Unreasonable. Memorable.

Rule 3: Pay Attention to Detail

Good memories are built on the details. When something goes well, the details often go unnoticed. It’s only when something goes wrong that people start to see.

Kind of like when you walk into a dirty bathroom.

When I was a senior in college, I had two main jobs. One was working for the Director of Distance Learning. This got me a job at an online education startup.

My other job was working custodial. Slightly less prestigious.

I cleaned toilets, vacuumed, mopped, and collected trash every day for an entire summer and then on Saturday mornings during the school year.

To this day, I hate using public bathrooms because 1) I know how hard they are to clean, and 2) I know all the ways most people don’t do it correctly.

I’ll spare you the details.

Surprisingly, that job cleaning toilets got me my very first job after college, working as a hotel doorman. During the interview, they asked how my past experience related to hospitality.

I didn’t know what to say at first, but I’m pretty good at thinking on the fly.

I remember saying, “Being a hotel doorman is a bit like being a custodial worker.”

You could feel their eyebrows raise.

I continued, “No one really notices a bathroom unless it’s dirty. In the same way, no one really pays attention to a hotel lobby experience until they have a bad one. When someone doesn’t open the door for you, doesn’t smile at you, or doesn’t make you feel welcome, that’s like going into a dirty bathroom.

The goal is to make the experience so good for customers, no one even thinks about it. Just like how you don’t think about a bathroom when it’s clean.”

Apparently, the hotel staff liked my answer, because I spent the next 4 months working there.

I opened doors, carried suitcases, parked cars, and drove guests to the airport. I even parked a $400,000 Rolls Royce. I’ve never been more nervous behind the wheel of a car.

Turns out, in the end, my interview answer was exactly right.

Details make or break the customer experience.

Push a cart the wrong way and it jams against your foot (or the hotel guest’s!). Open the door the wrong way and it looks awkward. Don’t smile, and you don’t get a tip.

Find a way to relate to every single person.

Rack your brain for facts about movies, music, politics, and education so you can always connect with people. Learn the route to the airport. Call down to the hotel lobby to get a new keycard set up when the guest’s door won’t open.

Think hospitality is easy?

Only if you do it wrong.

Every detail matters.

Rule 4: Build Systems, Not Moments

Memorable details only work if there’s a system. Otherwise the customer experience is inconsistent. And no company builds systems quite like Disney.

First, Disney builds hospitality into its physical structures.

There’s a trashcan every 30 feet to ensure cleanliness. They literally measured how far people will carry trash before throwing it on the ground. As another example, the park itself has an entrance that narrows to draw you in. Upon exit, the same path feels short and wide, so guests feel less tired walking to their cars.

Second, Disney instills hospitality into all its employees.

Each employee is a “cast member.” Being in the presence of customers is being “on stage.” No matter what happens backstage, anything in front of customers is a performance.

What does this look like? As one example, costumed characters like Mickey Mouse aren’t allowed to break a hug with a child first. Otherwise, that feels like rejection. And what kid wants to be rejected by Mickey Mouse?

Disney also trains its staff that there are no dumb questions. The book Be Our Guest by the Disney Institute uses the example of the 3:00 parade.

It’s hard not to laugh when a customer asks “What time does the 3:00 parade start?”

But Disney employees are trained to never make a customer feel dumb.

It doesn’t take much imagination to think of the backstory. This family woke up early, spent hundreds of dollars to be here, and has walked miles in 80-degree weather.

So when a customer asks, “When does the 3:00 parade start?”, it might actually mean…

“My kids are on the verge of tears, and my feet hurt. How long do I have to find a good place to sit? Do you guys actually start on time? Once the parade starts, will I get stuck on this side of the park?

Hmm… not such a dumb question after all. And Disney trains for this.

The restaurant industry provides another solid example of hospitality as a system. Danny Meyer, Will Guidara’s mentor, has opened several Michelin-level restaurants in NYC.

But you might know him from his more casual dining option: Shake Shack.

Shake Shack is famous for making its managers work at each restaurant station during training, and managers often work at least one of the stations during each shift.

I first read about this rule when I was 22 and managing an online education startup. It’s why I made all of my staff answer customer service phone calls, no matter how unrelated it seemed to their job.

How can you make decisions about curriculum, teacher bonuses, and software if you don’t talk to students and parents about what they actually want?

You can’t build a good hospitality system without living through the details yourself first.

Rule 5: Make the Ordinary Moments Surprising and Fun

It’s not enough to make everything consistently clean and pleasant. Sometimes, it pays to be surprising, 20% weird, and a little fun.

One time, I waited an hour outside a restaurant in the cold December air. Then, I even had to wait another hour at the bar. Finally, I got to eat.

The restaurant was called Dishoom.

If you don’t know, it’s one of the most famous restaurants in London, and it’s some of the best Indian food you’ll ever eat. (Shoutout to my mom’s friend Debbie Harpe for recommending it!)

They don’t take reservations. They don’t let you put in a phone number and walk away. You wait. Or you don’t eat.

This may not strike you as the most hospitable. But here’s where it gets cool.

At the bar, they have a full alcoholic menu. It’s pretty detailed and has a lot of unique drinks. What’s more unique though… is they have a full non-alcoholic menu too.

Why? Many Indians are sober for religious and cultural reasons. Dishoom’s menu specifically is a nod to Bombay’s (now Mumbai’s) historic ban on alcoholic, which led to the invention of many creative non-alcoholic drinks.

Want to be inclusive? Don’t make people feel weird about being sober.

Design a menu for sober people that’s so fun, long, detailed, and unique, that people drinking alcoholic drinks might actually feel jealous.

Now that’s what I call hospitality.

Another thing they do involves dice. It’s called the Matka game.

Unfortunately, I didn’t get to see this, but I learned about it from Rory Sutherland. (If you’ve ever read anything I’ve written, you’ll know that I think Rory is the marketing G.O.A.T.).

They only do it before 6 p.m. It’s a nice little way to reward your loyal lunch customers, who are more likely to be local business people than tourists.

Here’s how it works. If you roll a 6, your bill is taken care of. Up to 12 people. So, you have a 16.6% chance of getting a free meal.

Why do this?

Well, think of it this way. You either give a 16.6% discount to ALL your customers. Or, you let some customers eat for free.

In the end, the math pretty much works out the same.

But which one do you remember? Which one do you post about on social media? Which one gets you to come back to the restaurant over and over?

Getting a 16% off coupon, or dancing up and down in the restaurant with your party of 12, because you just had one of the greatest dice rolls of your life?

I think you know which one.

If you want people to like your business, you need to make part of the customer experience surprising and memorable.

Most of all, you have to make it fun.

Hospitality is what makes a business go from being just a place where a customer gets something to a place where a customer feels something.

Whether it’s a glass of water at the right moment, a perfectly clean bathroom, a well-timed hot dog, or a lucky roll of the dice… those details are what make an experience memorable.

And that’s why customers come back.

Put simply, hospitality is the art of doing business for humans.

A business needs to make money to survive. But making money is the function of a business. Not the purpose.

The purpose of business is to serve humans.

Hospitality is what makes business feel human.

Want to read more like this?

Here are a few of my favorites.

What do you do when one of your employees tells you they’re unhappy and want to quit?

Do you get defensive?

Do you listen to them and try to change?

Do you accept that they might never be happy and just let them leave?

Do you blame yourself? Do you blame them?

Or, do you accept that the truth probably lies somewhere in the middle?

Back in 2016, I was managing an online high school program. We were sort of a startup and sort of a spinoff of a larger education-focused law firm.

Somehow, by some miracle of networking powers I didn’t know I had, I managed to arrange a two-week trip out to California to go to a conference and meet some of the 80–90 teachers we had working remotely.

At the time, I was in the middle of trying to build a high school curriculum from scratch.

To accomplish this goal, I had a giant spreadsheet of every teacher, listing all the courses they’d previously taught.

The reason?

I had hired some people for one job, hoping to train them and get them to take other jobs 2–3 years later. For example, I hired several people to teach English 1 and 2. But some of them had previously taught multiple higher-level history and English classes.

So, the goal was simple: hire them to teach a lower level class and then ask them to develop or teach the higher level classes once they knew how our company worked.

None of the teachers knew about this spreadsheet. That’s probably a good thing.

Why does this matter?

Well, when I went to California, I had to meet with one teacher named Laura who we’d hired to teach English 1. What I wanted her to do was develop and lead English 2 and 3 courses. She had great camera presence, strong leadership skills, and detailed knowledge of all the relevant subject material.

Plus, I thought we got along really well.

We met for dinner with her husband in Los Olivos, California. I remember the air was cool and the sunlight was hitting the olive trees and oak trees just right. Somehow, even though we weren’t that far from L.A., the town reminded me of a wild west town.

It was picturesque. I wasn’t ready for a difficult conversation.

Sometime about 20 minutes into dinner, Laura told me she wanted to quit.

Cue the gut punch.

She was unhappy with the technology, unhappy with the pay, unhappy with my leadership, and burned out.

Now, obviously, I could have developed the classes without her. I had a pretty deep bench of teachers to choose from.

But she was one of the best.

I had a plan. And this was messing up the plan.

Even worse, I hate people being unhappy with me.

I remember feeling out of my element.

I was 23 years old, managing nearly 100 people. And I felt like I had no idea what I was doing.

Before I resolve that story, I want to share one more similar scenario.

I had another employee, Julie, in the office. I think this was a few years later in early 2018, before I started grad school that August.

Like I said, we had about 90ish teachers who worked remotely, and we had a team of 7 or so in the office, where we worked alongside our parent organization.

When we hired Julie, everyone really liked her. She was fun, smart, and easy to get along with. She ended up working on teacher support projects, like reviewing curriculum, dealing with student discipline issues, and organizing content in our online learning management system.

The year Julie joined was a rough year.

It was my last year in the office, because I was going to grad school. My first hire and right-hand guy, James, was also leaving that year. So we were about to lose a ton of institutional knowledge.

In the meantime, we were trying to develop 10 new courses that year, redesign the website, hire a huge number of teachers, and migrate to a new learning platform.

The issue? Our old learning platform was so antiquated, it had no API plugin to migrate everything automatically to the new platform.

This meant every single quiz question, PDF, video, and link had to be moved by hand. We’re talking thousands and thousands of pieces of content.

It took about 8 or 10 months, while the whole team also worked on everything else involved in running a school.

I remember one of the breaking points.

I asked Julie to review the recordings of our live class sessions and try to find 5 min. clips from each of our main course categories (literature, math, science, etc.) to use on our website as samples.

The idea was that putting more free content online would save us from dozens of repetitive phone calls and emails asking to see examples.

For Julie, this meant spending about an entire week or two watching hours of classes trying to find good clips.

As I’m writing this, I’m painfully aware that now this could be done in minutes or seconds by AI.

But this was back in 2018. AI wasn’t an option.

I remember her asking me if she really had to do this project, and I told her that it would really help the team. I encouraged her to do it in small chunks, take breaks to work on other projects, and do fun things like going on walks to give her brain a rest.

Even so, I could tell she was getting frustrated.

I honestly couldn’t tell you if it was this week, or some other time when the incident happened. But I know if it wasn’t that week, it was definitely sometime around then.

Her boyfriend, who worked on the other side of the building as a legal assistant, came into my office and started chewing me out.

Not quite yelling, but pretty close.

The issue was that Julie was burned out and hated her job, but she didn’t have the heart to tell me. So he took it upon himself to tell me for her.

I remember being pretty concerned but also having a hard time not laughing, just because the situation was so ridiculous and unprofessional.

Some moments are so bizarre, they don’t feel like real life.

I ended up telling him that we’d have this argument in front of HR. (Ah, the benefits of working in a small office). Thankfully, HR took my side and he backed down.

But when I talked to Julie, I learned the truth.

She absolutely hated her job. She thought I was a bad boss, and she was planning to leave in about a month or two.

I asked her if she’d had any intention of telling me how upset she was before she left, and she said no. She was just planning to coast and get by for the next month and never tell me.

I remember saying, “You know, if you’d told me how upset you were months ago, I probably could have changed something to make things better.”

She said she knew that, and she didn’t really know why she didn’t say anything.

I guess she was too scared to have that conversation.

Ugh. Another gut punch.

No matter how many books you read on leadership, some lessons you only learn by living them.

So, what happened in the end with Julie and Laura?

Well, Julie stayed true to her word. She left soon after that incident, got married to her boyfriend, and they became farmers. Sounds odd, but that’s what really happened.

Laura stayed.

In fact, she actually stayed about 4 or 5 more years, even after I left. She built English 2 and 3, joined a special committee to choose a new tech platform, and led her teams like a champ.

Same company. Same boss. Different outcomes.

So what was different?

Part of it was timing. Julie told me too late for me to do anything. Laura didn’t.

Part of it was the willingness to communicate. Julie avoided conflict. Laura wanted to have a dialogue.

Part of it was clarity. Julie gave me a general sense of being unhappy. Laura gave me a list of specific things I could fix.

Part of it was the environment. Julie worked with me in the office and saw me every day. Laura worked 3,000 miles away from me. Sometimes distance makes things easier.

Part of it was my leadership.

With Laura, I ate some humble pie, accepted her feedback, and tried hard to change things.

With Julie, it was different.

In the office, she’d seen a year of me being stressed, tense, and defensive.

I was stressed about giving up control and going to grad school.

I was overwhelmed with developing 10 new classes, migrating platforms, redesigning our website, and interviewing 300 potential teachers.

I was anxious about multiple people telling me my program should be cut to save money.

I was young, and I was still learning how to lead.

When you compare how I handled things with Julie and Laura, nearly a decade later, I still don’t know exactly what went wrong or how I could have brought about a different outcome.

I may have simply burned Julie out by assigning too many boring projects that year.

Even though I tried to encourage Julie, and I tried to include her in important conversations about teacher performance and curriculum design, I’m not sure I made her feel enough like an owner.

Looking back, I think the key here is that I didn’t just present a solution to Laura.

I invited her to help build the solution.

I tried to do the same thing with Julie, but somehow it didn’t resonate with her the same way.

Maybe it came too late. Or maybe it just felt like more work, not something meaningful to her.

I still think there’s something to this.

You can’t just make someone feel welcome. You have to make them feel important.

And one of the best ways to do that is by inviting them to build something the company really needs.

But even that doesn’t always work.

I wish I could tell you I was a great boss. I don’t know.

Some people cried when I left. Others just tried to wait me out.

But some people stayed at that company almost 20 years, joining long before me, and staying long after. That gives me hope.

And in the end, we turned around a company making a 10% annual deficit for 6 years and brought it up to a 12% annual profit.

A group of 20-year-olds essentially built a school from scratch.

I’m still proud of that.

All I know is this: the hardest part of being a leader isn’t building a product, a brand, or a business.

It’s building a team.

Sometimes you turn a critic into an ally.

Sometimes you get yelled at by someone’s boyfriend in your office.

Want to read more like this?

Here’s one of my favorites:

Most people know what to change. They just don’t want to do it.

Because letting go hurts.

That’s true in life. It’s true at work too.

I’ve been thinking about this story for a long time.

In 1974, a 22-year-old man from outside London was arrested for armed robbery.

This wasn’t his first infraction, and it wouldn’t be his last.

Joined a gang at 13.
Shoplifting.
Assault.
Grand theft auto.
Property damage.

Early consequences were light: fines and probation.

When he was finally convicted for armed robbery, he was initially sentenced to 7 years in prison.

7 years didn’t stay 7.

During his jail time, he assaulted guards and other prisoners, tried committing suicide, was heavily medicated, and cycled through 120 prisons and psychiatric hospitals.

He’s often referred to as the United Kingdom’s most violent prisoner.

He went by a variety of names, but he’s known for one:

Charles Bronson.

Not the actor.

But this story does actually relate to another actor.

In October 2008, a film about Bronson’s life was released starring an up-and-coming 31-year-old actor named Tom Hardy.

(In case you want to watch this, you should know it’s a great movie, but Bronson was famous for fighting naked and greased up to avoid being caught by prison guards… and the movie’s quite accurate).

While Tom was preparing for the role, he spent hours on the phone talking to Bronson to understand his mindset.

On one of these occasions, Bronson asked Hardy why he seemed depressed, and Hardy explained that he’d recently broken up with his girlfriend.

Bronson then proceeded to remind Hardy about a recent news story.

Earlier that year, a teenage boy near Oxford had died in a flash flood after getting his foot caught in a storm drain. According to Bronson’s telling, no one wanted to cut the boy’s foot off, so he drowned.

Bronson said, “I wouldn’t have drowned. I would have told them to cut it off now!”

His point:

Don’t let it drag you under.

When you look up the details, Bronson’s retelling isn’t quite accurate. The boy drowned because the water rose too fast, not because he or his rescuers refused an amputation.

But whether or not the story was true, the point still holds.

If something is drowning you, cut it off.

We’ll get back to that. But first: the second prisoner.

Our second prisoner was not as notorious, but certainly more famous.
In part, because unlike Bronson with his violent and angry life, this man was innocent.

He was born in a small town in the Middle East. His adoptive father was a working-class man.

This man worked for his father until he was 30, then began a 3-year career doing street ministry.

He challenged the religious norms of his day, and some people even thought that he was going to usher in a rebellion against the government.

Eventually, his habit of getting under the skin of local religious leaders caught up to him. They plotted against him and brought charges of religious dissent. By the time he was brought before the authorities, he was framed as a political threat.

In the end, he was convicted and brutally executed.

That man, you might recognize, was Jesus of Nazareth.

Regardless of what you think about Jesus, he had a way of saying things that stick:

“The first shall be last.”

“Every seed dies before it grows.”

And…

“If your hand or foot causes you to sin, cut it off.”

Sound familiar?

As someone who grew up in the church, I’ve heard these quotes before.

I knew what they meant. But I didn’t feel them in my bones yet.

You need to humble yourself.

You need to give up your old life to gain a new life.

You need to cut bad habits and flaws out of your life.

But it wasn’t until I came across that conversation between Tom Hardy and Charles Bronson that they really hit home.

The problem with changing your life is…

It’s just not fun.

I once heard Richie Stephens, an Irish actor and former gangster, talk about his experience as a drug addict. He said that he would never tell his kids that doing drugs felt awful.

He’d tell them it was fun. But then he’d tell them that drugs also destroyed his life.

Denying the fun keeps the allure.

It’s better to tell the truth.

Something can feel good and still drown you.

When it comes to my own life, I know why I’ve held onto a lot of my flaws.

Because I like them.

I hate them.

I just still like them enough to keep them around.

I like that they bring me comfort when I’m lonely.
I like that they make me feel right when I know I’m wrong.
I like that they give me a sense of control when the world feels like chaos.
I like that they keep me stuck in the past so I can avoid my fear of failing in the future.

I don’t want to drown, but I like being able to walk too. Don’t cut off my legs, man.

It doesn’t work.

Getting over yourself hurts.

But it’s still better than drowning.

So, what happened to old Charlie Bronson?

Sadly, he’s still in jail.

In the last 50 years, he has only been out of prison 121 days. He failed his 9th parole hearing and no release date has been set.

My grandma had a sign in her kitchen, “Take my advice. I’m not using it.”

Maybe Charlie had that in his jail cell too.

See, it wasn’t that Bronson wasn’t smart. He’s written over 10 books while in prison.

It’s not that he wasn’t disciplined.

Bronson was famous for doing 2,000 push-ups a day. Supposedly, he’s been able to do 1,700 in an hour. He’s even written a book called Solitary Fitness detailing how to get strong with just bodyweight exercises.

You might say… well, maybe Bronson had a bad upbringing or mental health issues!

We don’t know for certain, but we know he had a fairly loving, normal middle class life as a child.

Doctors and psychiatrists never landed on a clear diagnosis.

Bronson himself said he found it impossible to understand or relate to other patients in any mental health asylums. He thought they were crazy.

The truth is, despite all his violence and rage, Bronson was a fairly rational guy.

He could be pleasant, kind, charming, and hold a decent conversation.

Just ask Tom Hardy.

In the end, we don’t know.
What his family life was really like.
What was going on in his head.

But what we do know is…

Charlie never got rid of the thing destroying him.

He never cut off his foot, and he’s still drowning. Just slowly, over 50 years.

“If your hand offends you, cut it off.”

Regardless of what you believe about Jesus, the point still rings true.

If you want a better life, part of your old one has to die.

If something is dragging you under, stop protecting it.

I’m writing this trying not to cry in a Barnes & Noble.

I don’t have a problem with drugs or alcohol. I’m not a violent prisoner.

But I do have issues, and I know that where I am in life right now is the direct result of all the things I’ve done, good and bad.

Sometimes, I look back and realize how much time I’ve wasted.

On the outside, my life has gone pretty well.

On the inside, I still know exactly where I get in my own way.

“I’m not in a cell, but all my problems solitary.”
— Machine Gun Kelly

That line feels a little too familiar.

So, where to start?

If your foot is stuck and the water is rising,

you don’t negotiate.

You cut it off.

Easter is coming up. Believe what you want.

It’s still a good day for resurrection.

You already know what’s drowning you.

Want to read more like this?

Here’s one of my favorites:

The Roman poet Virgil once wrote:

Fortuna audaces iuvat — fortune favors the bold.

I learned how true that was in my sophomore year Latin class.

My Latin teacher held a small contest and offered to loan a rare book to whichever student wrote the best essay on why they deserved that book.

We were all dismayed when he mentioned that the 1-page essay had to be handwritten and was due the following day.

Even though I had mountains of homework, and no real need to study yet another Latin book, I wanted to win.

It was a mix of personal pride, wanting to impress the teacher, and being genuinely curious about the book.

Sometime that night, I managed to crank out a couple of subpar paragraphs. It wasn’t amazing, but it seemed decent enough to submit.

When I turned in my essay, I was surprised when he immediately gave me the book.

I asked him why.

He said…

“You were the only one who submitted an essay.”

The same year I was basking in the adolescent anxiety of sunny Southern California, a breakout author was publishing his first book.

In The 4-Hour Work Week, Tim Ferriss talks about how he was teaching a college course and challenged his students to write 3 famous people and try to get a response from at least 1.

All within 48 hours.

The first year?

No students even attempted the challenge.

They were afraid of getting rejected.

Or that other students would outperform them.

The second year?

6 of 17 students accomplished the challenge. One of them even reached Eric Schmidt, the then CEO of Google.

In the end, the task wasn’t really about who the students reached, or what the details of the response entailed. The task was about helping students get over their fear of failure and get a taste for trying absurd, out-of-reach challenges.

About ten years later, I ran into the same lesson again when I applied to business school.

At the time I was managing an online high school program.

As it turned out, just getting into business school was almost harder than school itself.

Here I was, a history major whose only experience was going to an unknown school and working for an unknown company.

I hadn’t taken a math course in 7 years. I didn’t know what a SWOT analysis was. I didn’t know the names of the big 4 consulting firms.

I just knew 3 things:

I liked reading business books.

I needed more money.

And I needed to change my life.

I just didn’t realize how much work it would take to actually get in.

I spent about 3/4 of my Saturdays in the office that year, between reviewing resumes for the many hires we were making that year and taking GMAT practice tests.

Despite all my studying, taking the GMAT twice and the GRE once, my scores were just okay.

Still, I had a solid GPA and experience managing a startup online education program. So, in spite of all my doubts, I applied to 4 schools and got into 2.

I’d had friends who told me to apply for lower-ranked schools, and I myself wasn’t exactly sure how my applications would turn out.

But I knew I’d never forgive myself if I didn’t at least apply for a few schools that I cared about, even if they might be out of my league.

Somehow, with my below-average math scores, terrible grades from senior year of college, and management experience at a tiny, unknown company…

I got into one of my dream schools.

I could hardly believe it.

Looking back, the lesson from all three moments was the same.

Don’t be mistaken, saying “just try” doesn’t mean “just wing it.”

It only took me one night to write that Latin essay, but it took me a year to get into grad school.

No one should run a marathon without training first.

The work is hard. The work is scary.

But the work is necessary.

And the work isn’t as bad as it seems.

Spending every Saturday in an office for nearly a year isn’t fun, but it won’t kill you.

Writing an extra essay for Latin class when your normal homework load already gets you only 4 hrs. of sleep a night (welcome to Catholic school) won’t kill you.

Being embarrassed about starting a Substack or a YouTube channel won’t kill you.

And yet, not that many people are willing to undergo the struggle.

Most people would rather stay in a job they hate

than face the embarrassment of applying for a new job

or starting a company and failing.

But this is to your advantage.

Entrepreneurs like Tim Ferriss or Alex Hormozi will remind you that everyone is afraid of the big things. So not many people try them.

If you have a small goal, everyone might be willing to try for that goal, so you’ll have a lot of competition.

But if you have a big goal, or even a slightly absurd goal, not that many other people will be competing against you.

As Alex Hormozi likes to say, most people give up. So the bar has never been lower.

If there’s something in your life that you want to change, do something about it now.

Don’t die wondering what would have happened if you just put in the effort.

Everyone else is just as busy, scared, and uncertain as you are right now.

Most of them won’t even try.

Don’t worry about them. Submit the essay.

Just try.

You might fail.

But every once in a while, fortune favors the bold.

Want more motivation like this?

Here’s one of my favorites.

Most brands are forgettable.

Rory Sutherland, one of my favorite authors, often talks about how brands need to be a bit more irrational. Here’s why that’s important.

There’s a restaurant in London called Fallow.

It opened as a small bar for burgers and beers during COVID. Now, it’s one of the most popular and famous restaurants in the city.

Why are they so famous?

It probably has something to do with the fact that they’re a bit weird.

Fallow founders and head chefs Jack Croft and Will Murray are a different breed.

They cook whole animals and turn leftover vegetable trimmings and whey into kimchi and cheesecake. They share all their recipes in detail on YouTube to 2M subscribers. They even used the GTA designer to make their staff t-shirts.

Fallow is mostly fancy, slightly strange. Because of that, they have a cult following.

In an interview, the chefs explained their philosophy for designing a menu.

It should be 80% normal. Burgers, pasta, steaks, salads. Things everyone will eat.

Then, it should be 20% weird. Kimchi from kitchen scraps. Baked cod’s heads.

Here’s what that has to do with you.

Designing a brand is a bit like designing a menu.

It should be 80% reliable, 20% weird.

Most brands play it 100% safe.

Want your brand to be memorable? Be creative. Be weird.

The best brands are a little strange. This is why you love them.

Think about why you love your favorite coffeeshop. It probably has good coffee. But so do lots of places. That’s not why it’s your favorite.

It might have good music. It might have lots of big windows and natural light. It might have threadbare couches and antique lamps. It might have plants hanging from the ceiling. It might be modern and serene. It might be pink and decorated with a punk vibe. (Shoutout to 27 Club coffee in Cleveland!)

Whatever the case, there’s a reason why it’s not just “a coffee shop.”

There’s a reason why it’s “my favorite coffee shop.”

No one has a favorite brand that blends in.

The best brands know this. As an example, here’s a few of my favorites.

• The Last Bookstore in downtown Los Angeles has a tunnel of books. It has a rare book room. It has a coffee shop. It has an upstairs filled with small studios where local artists work and sell their wares. It’s not just a bookstore. It’s an experience.

• In-n-Out Burger only sells burgers, fries, sodas, and shakes. Controversially, they put Bible verses on the bottom of their cups. And they have the famous X-crossed palm trees in front of their restaurants.

• Red Rose Tea, my mom’s favorite Canadian tea brand, has included a small china figurine in all of its packages since 1967 in Canada and 1983 in the U.S. Until 2018, they used this loss leader strategy to build loyalty through a sense of whimsy.

• Patagonia launched a New York Times ad saying: ”Don’t Buy This Jacket.” The point was to highlight its commitment to environmentalism and recycling. To this day, Patagonia will repair, replace, or recycle any damaged jacket you bring back. Ironically, this recycling-focused brand positioning increased sales by 30%.

Building creativity into your brand takes work.

Irrational, weird ideas don’t just appear on their own.

Businesses have to cultivate them. Sadly, brands often sacrifice creativity for the sake of efficiency.

From 2004 to 2013, Google famously had a 20% rule for its employees’ time. Every Friday, employees were allowed to work on whatever they wanted, as long as they could show it might benefit the business.

That’s how Gmail was invented.

You can’t build a unique business unless you build time for creativity into the system.

Google didn’t invent this. This principle is actually found in nature.

Rory Sutherland once pointed out that bees have an interesting division of labor. Once bees discover a route of flowers that can reliably support the hive, most of them follow this path and gather as much pollen from it as possible.

The rest of the bees go off the path to find new flowers.

Most exploit. The rest explore.

80% reliable. 20% weird.

To build a weird brand, you need to be weird too.

So, how do you do this?

Learn more. Get more diverse inputs. Study outside your field. Get a little weird.

That cod’s head doesn’t get on the menu by itself.

Dan Pope runs a podcast on food and drink challenger brands in the U.K. called Hungry. To do this, he does what you might expect. He goes to fancy restaurants in London, chats with pub owners, and presumably spends a lot of time in grocery stores.

But he also likes to mix things up, talking to tech entrepreneurs and reading books like Moby Dick to get a fresh perspective.

His newsletters are the most interesting and entertaining business newsletters I’ve read in a long time. In short, reading widely helps.

When I worked in online education, some of my best ideas came from fashion brands, tech startups, and history books. I read traditional business books, but I also read biographies of celebrities, books on the history of fashion, books on .mp3 files and digital music, and a whole range of other topics.

I’m dead serious when I say reading about King Cyrus of Persia helped me figure out how to delegate work and maintain authority as a manager.

If you’re not at least a little embarrassed about your stack of books at the library checkout counter, you’re doing it wrong.

Speaking of which, you can’t just shop online. Amazon recommendations won’t cut it.

The problem with relying on curated algorithms to gain creative ideas is that you’re relying on the masses to give you your ideas.

Creativity requires serendipity.

That’s why browsing the stacks at your local library or bookstore will always beat shopping online. Only you can combine weird ideas in your own unique way from chef’s memoirs, soccer coach biographies, and science books.

Your weird interests are the best thing you have going for you.

They’re the only thing no other person, and no other business, can truly replicate.

You won’t build someone’s favorite brand unless you build something a little weird.

And you won’t do that unless you’re a little weird too.

Build the tunnel of books. Plant the crossed palm trees. Put the figurine in the tea.

Read widely. Travel. Go to rock concerts. Build creativity into your life.

Be reliable. Be memorable.

80%. 20%.

The world doesn’t need another forgettable brand. It needs a weird one.