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.

This isn’t your traditional business newsletter.

This is about how to thrive in business and keep your soul while doing it.

I’ll be sharing insights from business, history, and culture, along with stories from my time in online education and banking.

If you're just starting out, looking for a new career path, or trying to build a more purposeful life, this newsletter is for you.

I publish every other week on Thursdays.

Table of Contents

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

Decision-Making, Judgement, & Risk

• Cut It Off or Drown

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

• Fortune Favors the Bold

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

Marketing:

• What Fashion Taught Me about Trust

• Your Best Customers Haven’t Bought Anything Yet

Perspective & Meaning:

• When Was the Last Time You Saw Something Sublime?

• Reflections from That Time I Got Kicked Out of a Meditation Garden

Interviews and Substack Live Sessions:

• Episode 1 of Jason Steven’s The Selfish Podcast

Here are a few of my favorite posts.

Why I Write

I’ve always enjoyed writing, but aside from a brief stint at an email newsletter to a small group of friends back in 2009, this is the first time I’ve written publicly.

I was inspired to write this newsletter, because I had a hard time reconciling the experience I had in a small, mission-driven online education business with the experience I had working at the largest bank in the world.

I’m writing to merge the lessons I learned in both environments.

I’m convinced that it’s possible to do world-class business in kind, ethical, deeply human way. This newsletter is my way of presenting a better path forward.

I can’t say enough how grateful I am that you’re here.

From the bottom of my heart, thank you. It means a lot.

About Me

I grew up in Southern California and have lived in the Midwest and Northeast. Now, I live in Virginia, about an hour from D.C.

I spent 6 years in online education, where I took an online high school program from a 10% annual deficit to a 12% annual profit. Then, I got my MBA from the University of Notre Dame and spent another 5 years working at JPMorgan Chase.

Now I work as a consultant and write about business.

I’m a Christian, and that’s the core of my life and my worldview. You’ll see Christian themes pop up from time to time in my writing. However, this is not a Christian newsletter. This is for everyone interested in living well and doing meaningful work.

I hope that the lessons I’ve learned and knowledge I’ve accumulated over the years will be helpful to you on your journey.

In my free time, I love studying history, reading classic literature, going to rock concerts, and spending time in nature.

To learn more, check out my full About page. You can also find me on LinkedIn.

© 2026 Colin Black

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.

“Can you jump on a call? I’m meeting with legal in 5 minutes, and I really hate them.”

This was a message I received from a coworker a week or two into my summer internship at one of the largest banks in the world.

Lest you think that sounds a bit exaggerated or unprofessional, I’ll assure you it’s 100% real. You have to understand… I was working with mostly New Yorkers and a fiery Australian whose favorite words were all four letters.

My job that summer was designing a content creation process for a new education center for the bank. What no one told me was that this project had already failed once because the teams involved didn’t get along.

So that was my job. Cleaning up the mess.

With only 10 weeks to do it.

When I joined that call, I realized I was going to have to fall back on some old training.

Without further ado, this is what being a narc in high school taught me about conflict resolution.

Back in Southern California, when I was 14 years old, I did what any overachiever (or at least a disorganized overachiever) might do. I signed up for basically every class, every sport, and every club possible. I really didn’t have a plan. I just signed up for anything that sounded remotely interesting.

I signed up for a volunteer drug counseling program called PAL: Peer Assisted Leadership.

We were the narcs on campus.

Or, at least that’s probably how our classmates felt about us.

The idea was that if a student was struggling with drugs or alcohol, by the time a parent or teacher observed the problem, it was probably too late. So the goal was to train students to recognize the signs of addiction and become adept at supporting their fellow students by observing, listening to the needs of their friends, and bringing in adults when necessary.

The truth is, it wasn’t really about policing behavior. We were just trying to notice when something felt off, so we could help our friends.

I don’t have any scientific data behind whether this worked, but I think the idea made sense. Plus, the woman who ran the program had a genuine heart of care for the students.

The most useful takeaway I got from the program was from a training session we did on a crisp Saturday morning.

We were put into pairs of students and given a fake conflict to reenact. Each student took a side and began to argue with each other. What surprised me most was how committed people get to an idea they think they’re supposed to support. Even though it was a reenactment, students got genuinely heated and defensive.

The fake conflicts started to feel like real conflicts.

So here’s what we were told to do. Once the argument got heated, one of the students was supposed to take a pause, think about what the other person was saying, and then repeat it back to their partner.

Now that I’m an adult, I know that’s called active listening.

It’s not exactly rocket science, and it wasn’t surprising to me even as a teenager.

At the same time, just because something is simple or obvious doesn’t mean it’s easy.

And it doesn’t mean that people actually do it.

Most people don’t.

In the case of my high school training session, I tried it out and was shocked to find that it worked. My partner got less tense. The muscles in his shoulders relaxed a little. We started to work our way to a common ground.

Maybe this volunteer drug counseling stuff wasn’t so bad after all.

When I joined the Zoom call, I went in with some apprehension. After all, I was just a summer intern, and all I really wanted to do was get a job at the end of the summer.

I didn’t expect to be the mediator between teams of lawyers and senior writers.

The conversation started out heated. I decided to let it play out a little, since I didn’t really understand yet exactly what my project would entail that summer.

After a few minutes of back and forth, I could tell we were getting nowhere.

So finally I asked each side, “If you could get everything you wanted, what would it look like?”

I think they were surprised to be asked that. I’m not sure that the idea they could both get what they wanted had seemed within reach.

Once they spoke, I repeated their answers back.

In this case, it was something simple. Both sides wanted more time to do their work, wanted to feel like they weren’t being micromanaged, and wanted to feel respected.

In the end, we made it work.

When I worked at the bank, I didn’t always feel like I contributed much value.

Seven years later, that program generates roughly a billion dollars in lifetime customer value.

I’m not saying that’s because of me. There were dozens of writers, lawyers, web developers, marketers, and others involved, producing thousands of hours of work.

I just helped get the ball rolling.

And oddly enough, I did that by thinking about something I learned in high school.

People don’t want to be listened to. They want to feel listened to.

The only way to make someone feel listened to is to show them.

The next time you find yourself in a conflict, ask yourself: Am I actually listening? Or do I just want to make myself heard?

There’s a quote attributed to St. Francis (and repeated by Stephen Covey):

“Seek first to understand, then to be understood.”

Once people understand each other, they stop acting like enemies.

They start acting like a team.

Teams solve problems.

And that’s what I learned about conflict resolution from being a narc in high school.

When I was about 23 years old, I managed an online education startup. In this role, I was responsible for leading teams to design a high school curriculum from scratch.

I had the benefit of partnering with college professors and high school teachers, but it was my job to shape the vision of the whole program, understand the books used in each course, and be able to justify our team’s choices.

Our customers were conservative, Christian parents of homeschool and private school students. These parents were very careful about the level of academic rigor and moral backbone of their students’ educational material.

Among our customers, there was a wide range of opinions about what constituted “good educational material.”

One parent might be into classical education, allowing their children to read adult Greek and Roman myths. Another parent might be completely offended by the same stories.

No matter how carefully we worked with our teachers to design a curriculum that was both challenging and relatively kid-friendly, we’d still have parents call and complain.

So, rather than try to sanitize our content perfectly—an impossible task—or ignore the wishes of our customers entirely, we tried a new approach altogether.

We copied a fashion brand.

Around 2010, a new fashion brand opened. A true industry rebel. This brand built a cult following through ethically sourced materials, a transparent production process, fair pricing, and a unique direct-to-consumer sales approach.

That brand was called Everlane.

When I came across this brand, I was impressed by their website. It was nothing like anything I’d seen before. The website included a profile on each of Everlane’s manufacturing facilities, complete with photos of the staff and buildings. There was information on where the fabric came from, how the clothing was made, and how everything was done above board.

The product pages were even more unique. Every product page included the price of the item, along with the true cost. The product descriptions informed customers about everything, from the cost of the materials, to labor, to transportation costs. Customers knew the exact markup.

A $70 shirt is expensive. But when you find out it cost the company $35 to make, the price doesn’t sting quite as much. At least you know you’re not paying $70 for what might be a $10 shirt.

So, in the end, it’s not really about the price at all. It’s about trust.

If trust is important for a clothing company, it’s even more important in the world of education.

With the Everlane playbook in mind, we overhauled our website.

We decided that no matter how many customers we lost through transparency, we’d just be losing the ones who’d be disappointed anyway.

On each of our product listings (in this case, online courses), we included a full description of each book in the curriculum, complete with the major themes covered, the reasons why we chose the book, and a disclaimer about any content we thought parents might find offensive—even if some of the offensive content seemed really minor.

The result?

Our customers loved it.

The complaints got fewer. The angry calls started to fade away.

Instead, parents called and said things like “I wasn’t sure if I was going to sign up for your program, but when I saw how honest you were upfront, I decided you must be a trustworthy company. I knew I could trust you with my kids.”

Even if your customers don’t agree with all your decisions, it goes a long way when they can at least understand those decisions.

Instead of a one-sided sales pitch, the purchasing decision becomes a dialogue. A conversation between you and your customers.

Transparency earns trust.

And trust fuels growth.

“...By the way, before you hang up… I noticed that you’re calling from Singapore. We have about 10 students in Singapore, but we don’t know why. Do you know anything about that?”

“Oh, yeah, they all go to my church group. My children haven’t been old enough to take your classes until now, but I heard about your company a few years ago and have been referring all my friends”

This was a conversation I had on the phone with a customer back around 2015.

Turns out, sometimes your best customers are the ones who haven’t even bought anything yet.

When I worked in online education, I managed an online high school program with students in over 10 countries around the world. Most of our students were from the U.S. but we had a steady minority from military bases, missionary outposts, and private schools in other countries.

Most of the time, we didn’t even know how these pockets emerged, although we knew it had something to do with word of mouth.

In his book The Tipping Point, Malcolm Gladwell explains the importance of network effects. He uses the example of why most Americans have heard of Paul Revere, who warned his fellow patriots about which method the British would use to invade the Massachusetts countryside during the early days of the American Revolution.

In addition to Paul Revere, there was another rider: Richard Dawes. Yet, most of us have never heard of him. Or, if we have, he doesn’t immediately come to mind.

Both men rode similar routes, and yet few people responded to Dawes’ call to arms, or even reported that they remembered talking to him.

Gladwell concluded that the determining variable of their success had nothing to do with that fateful night. It had everything to do with what happened before.

You see, Paul Revere was what Gladwell called a connector.

Networks aren’t linear. They’re more like a bicycle spoke than links in a chain.

Prior to his famous ride, Revere served on a committee to implement Boston’s first streetlights, as health officer during epidemics, and even helped found a fire insurance company. He was known up and down the northeast as a key member of many social groups.

When Revere and Dawes set off on their respective routes, Revere already knew who to warn in order to get the word out to each community. So his messaging was more targeted. He knew how to tap into small, existing networks to get news to travel fast.

When we were trying to grow our online high school program from 400 to 1600 students (and actually make a profit for once!), I realized that we needed to tap into the network effect.

When Facebook started, they specifically targeted colleges. Why? Because colleges already have built-in networks. Once a few students on a college campus had Facebook, other students wanted it too, so they wouldn’t feel left out.

In other words, it’s a lot easier to convince a group of 2,000 friends to do something than it is to convince 2,000 disconnected people.

But when you have a small team, it can be difficult and time-consuming to invent new networks. So, it’s better to use digital and physical channels to connect to networks that already exist.

In our case, it was private schools, church groups, missionary outposts, military bases, and homeschool groups. Basically, any decentralized group looking for quality, online classical Christian education.

Who are the networks for your business?

If you own a coffeeshop, it might be a local church group looking for a place to host a Bible study. It might be students at a local college. It might be employees from a law firm across the street. It might be fans of a musician you asked to come play on Friday night.

If you’re an author, it might be your own online blog community. It might be book clubs, library groups, businesses in need of guest speakers, conference organizations, or other similar groups.

We’ve all seen examples of businesses that struggle because they don’t plug into existing networks. It’s tempting to want to be “self-made” and try to build a business without relying on the help of others. Being self-made is a good story, but it’s also a fool’s errand.

You can use referrals, social media groups, partnerships, and other tactics to leverage the power of communities.

But plugging into networks only works when someone already believes in your product or your mission. In essence, referrals and community building aren’t just about meeting a need or selling a product.

They’re about alignment.

So, don’t sell to disconnected groups of strangers. Get to know communities that already share your values and sell to them.

Remember, sometimes your best customers aren’t the ones who buy consistently, or even buy at all.

Your best customers are the ones who already believe in the same things you do.

I’m not good at making New Year’s resolutions. There’s something about the finality of them that scares me.

But, occasionally I make promises to myself about things I want to change. This was one of those times.

Back in 2016, I had the opportunity to go back to Southern California for the first time in 8 years. My family had moved to the East Coast, and I hadn’t really said goodbye to all the places I missed.

So, when the opportunity arose to work at a conference in Los Angeles and drive up and down the coast for 2 weeks and meet my remote employees, I jumped at the chance.

At the time, I was about 3.5 years into working at an online education startup and about 1.5 years into managing the whole thing. I was in my early twenties, managing people far older than me. I was enjoying the experience, but the stress was also really getting to me. I knew that I needed to make the next career step, but I had no idea what to do.

So, over those two weeks, I explored a lot of new places and revisited all the places that meant something to me. My old high school. The Mexican restaurant my family used to go to almost every Sunday. My old house. My grandma’s house. A farm we used to visit every October. The beach.

One place in particular that stands out to me was the meditation garden in Encinitas, just north of San Diego. Though I’d never been here before, it held a special place in my heart for two reasons.

First, my mom had done a weeklong silent retreat there about 40 years earlier, when she was around the same as I was at the time of my story. Second, an author I love, Mark Foreman (father to Jon Foreman, the lead singer of Switchfoot), mentioned that it was his favorite place to go and think.

Even though I’d grown up in California and should have been aware of the traffic, I’d underestimated the 3-4 hours it would take to drive the 70 miles there. So, I arrived right as the gardens were closing.

I wasn’t going to have time to come back, so I did what any red-blooded American would do. As someone was walking out and the gates were closing for the day, I snuck in.

Now, I only ended up having about 10 minutes of blissful reflection enjoying the view of the ocean before someone came and escorted me out.

Was I being disrespectful? Maybe.

But this was a pilgrimage, and I wasn’t about to let something as trivial as opening and closing hours stop me from visiting.

I’d like to say that these promises to myself all came from those 10 minutes in the meditation garden, but the truth is that some came from that moment, and the rest came from a series of peaceful days hiking, driving, and wandering alone over the two weeks that I was there.

When you see this list, you might wonder… why are some of these things even on your list? Eat what you want to eat? Visit the places you want to visit?

Well, yes.

If you’re a classic overthinker and worrier, even little things like what you eat and what you wear can sometimes feel like big decisions.

You also have to be pretty comfortable with yourself to tell your friends that you’re *not* partying it up in Southern California.

Instead, you’re visiting movie sites, the bookstores your favorite band recommended, and going to dive taco joints instead of fancy restaurants.

Sometimes just being yourself is an act of bravery.

So, without any further ado, here’s the list:

• More time in nature

• More time exercising

• More time alone

• Develop more meaningful relationships

• Eat what I want to eat

• Listen to more upbeat music

• Do things I enjoy doing

• Stop caring about what people think

• Be proud of how I dress and how I look

• Be ok with how I act

• Do more new things

• Don’t overthink things

• Don’t think about work off the clock

• Tie up loose ends

• Accomplish what’s on my list

• Don’t look at the clock much

The truth is, when I look back at this list, I’m a bit disappointed. I kept to some of these resolutions, but most of them are still a work in progress.

I don’t spend as much time in nature as I’d like, although for a few years I kept up the habit of walking about 4 miles every Saturday morning.

I still care what people think.

I still don’t accomplish everything on my list.

I still overthink things.

I still like sad music.

But if I’m being honest, even though I haven’t kept these resolutions perfectly, I think they marked a turning point in my life.

It was a time when I started to like myself a little more. It was also a time I decided things needed to change.

It was the beginning of the end of an era.

At the time, I had just started thinking seriously about going to business school. My first conversation about getting an MBA was with my friend Adam in February of that year.

But it would take until the end of the following year for me to send in all my applications, and it would be another eight months after that before I started school.

Sometimes change happens all at once. And sometimes it’s slow.

They say history doesn’t repeat itself, but it does rhyme.

You might say that’s the same for my life. Oddly enough, 2026 seems like it’s going to be about the same as 2016. I’ve come to the end of an era. I left my first major corporate job after grad school, and now I’m working on a plan to launch something of my own.

Between the time I prepped for grad school, went to grad school, and worked my first real corporate job, that’s a 10 year chapter coming to a close.

I don’t know what’s next, but I know that a lot of those promises from that summer in California still remain the same.

I think the reason I don’t like resolutions is that they seem too rigid, and it’s easy to fail them.

I prefer promises.

See, with a resolution, if you miss a certain number of days, you might say you failed your resolution that year. Next year you may get tired of that resolution and choose a new one.

But with a promise that you make to yourself, it’s easier to understand that these aren’t one-and-done goals.

You won’t finish them at the end of the year, and you won’t get to ditch these next year.

It’s a commitment to try to do a little better in these areas every year for the rest of your life.

Some years, I’ll do great at these promises.

Some years, I’ll do terrible.

Some years, I’ll just be glad to make it to the end of the year.

But I can always try again next year.

And so can you.

Can’t believe it’s been 10 years since I wrote down this list in my phone.

But I’m looking forward to the next 10.

I’m not sure if this was my last time, but it was a memorable one.

It was Friday, December 6, 2024, in a little coffee shop in Quebec City called the Ma Station café. Sometime around 8:00 a.m.

I was on a much-needed vacation from a job I disliked. My first real vacation that year in fact. In December. Needless to say, I was a little burned out. To paraphrase the great Jon Foreman, “I began to believe that all we are is material.”

I was more body than soul, and it was starting to show.

So, I called up my friend Aaron, and we hung out in Montreal for a couple days before I went on to Quebec City by myself. I’m not really one to sleep in on vacation, due to a profound fear of missing out. So, this particular morning, I was out for a walk in the frigid morning air. The weather was in the teens (fahrenheit, that is), and I was in search of a warm drink to wake me up and clear my head.

On my walk, I stumbled half-awake into the aforementioned coffeeshop. To be honest, it’s the kind of place that might look more at home in California or Miami, with its hot pink mood lighting, minimalistic vibes, and tropical plants. Maybe that was a smart business move in Quebec City, to try to help people forget they lived in a frozen landscape.

But the most important part for this story is that there was a piano.

There I was, sitting and relaxing for a few minutes, when in came a blue-collar worker, complete with a scruffy beard and high-vis stripes on his pants. He sat down at the piano and began to play. I don’t remember what he played, whether it was an original tune or some classical piece I should have recognized. But I do remember the feeling that washed over the coffeeshop. It was as if a sense of peace and serenity had invaded the place, and everyone involuntarily stopped to watch and listen.

The whole experience only lasted about 5 minutes, and when it was over, it was met with a bit of a laugh from the worker and the two men working at the coffee bar. I couldn’t tell whether they knew each other, but I think the reason they laughed is that sometimes you just don’t know how to react to something like that.

How are you supposed to react when something profound, unexpected, and un-asked-for happens in front of you? I think perhaps the only two fitting reactions are laughter or awe.

A year later, I’m still thinking about this moment.

So, back to our original question. When was the last time you saw something profound?

When was the last time you saw something that made you feel a sense of awe or wonder? That made you want to cry? That made you think maybe you’d been spending too long out in the cold and too little time inside listening to the music?

I think there’s a lot of moments like this all around us, but we’re either 1) too busy to notice, or 2) too embarrassed to point it out.

To the first point, it’s pretty easy to be too busy.

Trust me, I understand. I went an entire year only doing a vacation in December (actually 3 years in a row, but that’s another story). It’s pretty easy to go to work, sit down at your computer, crank out emails and presentations all day long, drive home, watch something on Netflix, and go to bed.

At night, you might think to yourself “Did anything good even happen today? Do I even remember what happened, good or bad?”

String enough of these days together and you get a boring, unfulfilling life.

That said, what’s even worse than being busy is becoming so drawn into modern-day materialism that you simply stop looking for the sublime.

Or, that you become too afraid to talk about it.

In his essay on Joseph Frank’s biography of Dostoevsky, David Foster Wallace explains that the prevailing sentiments of modern society are cynicism and skepticism. Modern literature (and movies) have become less sincere. Any moments of sincerity are tongue-in-cheek or ironic.

This feeling has reached beyond art and literature, into the world of business. Profound life lessons are often reduced to a 10 point list of “my top takeaways from x major life event.” Observations and ideas are often reduced to levers that drive bottom-line profit. Lunch conversations revolve around football, reality tv, and credit card points.

Why? Why are we so afraid to just open up to other people? To share about that great sunset we saw, that book quote that really touched our hearts, that childhood memory that makes life meaningful?

Perhaps it’s because profound moments ask something of us. They ask us to stop and notice. They ask us to take stock of our lives. They ask us to live differently.

Stopping to watch a sunset requires us to admit that there’s something bigger than our lives that’s worth watching. Taking the time to actually get to know your coworkers means risking that they’ll learn too much about you, or that you’ll learn too much about them, and now you’ll be obligated to be friends.

Or, in my case, sitting and listening to a construction worker play piano raises the question whether I’ve been living too much for the wrong things.

There’s a quote, often attributed to Dolly Parton, “Don’t be so focused on making a living that you forget to make a life.”

But it’s so easy to do this. There’s always bills to pay, projects to finish, and deadlines to meet. So many that they can make us forget what’s really important.

So how do you avoid this trap?

First, pay attention.

Pay attention to what’s beautiful and sublime.

Pay attention to the everyday moments.

Then, share these moments with someone else.

Don’t let the cynics get you down.

Ok, so if you ask my former boss, she’ll tell you that she hired me because I was the only candidate with relevant work experience. I was just out of college, applying to work at an online high school program, and I’d spent senior year working for my college’s online distance learning program.

That’s the official story.

The unofficial story, the one I like to believe, is this.

I got my first real job out of college by quoting the Christmas classic, Miracle on 34th Street, in my interview. To clarify, we’re talking about the black-and-white 1947 version, not the 1994 version. Please. I do have some class.

If you’re not aware of the plot of this 80 yr. old movie (I think we’re a little late for a spoiler alert), the real Santa Claus comes to NY to observe the state of the world and see whether people still believe in the true Christmas spirit, or whether the holiday has been taken over by crass commercialism. While in NY, he unexpectedly gets roped into the Macy’s Thanksgiving Day Parade and then becomes the official mall Santa for Macy’s on 34th street in Manhattan.

While at Macy’s, he asks children what they want for Christmas and then promises they’ll get the gifts they want. When he is questioned by angry parents who can’t find these gifts anywhere, he points them to the correct store and tells them where they can purchase the present for the least amount of money. The kicker: he starts sending people to other stores.

The Macy’s staff understandably panics, until Mr. Macy himself decides this is a great policy. His rationale is that shoppers will think Macy’s is the “store with a heart” and will consequently spend more money at Macy’s than ever before. So, Santa gets to keep his job, and everyone is happy except for the people who aren’t. But telling you more would definitely spoil the rest of the movie. So you’ll have to see for yourself.

Back to our regularly scheduled programming.

I’m not exactly sure what question I was asked in the interview. Maybe something along the lines of “describe your view of customer service.” Here I was, 20 yrs. old, with no real experience in customer service aside from working as a hotel bellhop, trying to think of something clever. So, I shared this scenario from one of my favorite Christmas movies, and basically said “I think the goal is to be as helpful as possible, even if it means losing an immediate sale, because your long-term reputation as a company is more important.”

Over the next 2.5 years, I learned exactly what this looked like in practice.

I took thousands of phone calls from homeschool parents or high school administrators looking for supplemental classes for their students. I had people cry about family struggles, laugh about jokes I made, yell at me, threaten to sue my company, ask to talk to my boss, beg for discounts, ask me for help choosing a college, and even ask for help ordering textbooks on Amazon.

From all these thousands of calls, I learned one key lesson: serve first, sell second.

Whenever I tried to sell first, it came back to haunt me. I distinctly remember selling about 6 classes to a family with two students. I knew they were a difficult prospect, and I was so excited to tell my boss

“I just made us $3000 over the phone!”

Her response:

“They’re a really difficult family to deal with, so let’s just see what happens. Sometimes when you have to work so hard to get the sale, it’s not worth getting the customer.”

She was right. I spent hours on the phone with the family over the next few weeks, helping with technology, changing their class times, dealing with complaints about the teacher, only to have the family drop all the classes one by one. I’m pretty sure we gave them a refund several weeks after our normal refund window had passed.

I had tried too hard to sell, and I forgot to think about what the customer really needed.

Contrast this to when I did it right.

There were many times when I spent untold hours on the phone, walking customers through their students’ ideas for their college majors and trying to help them determine which classes would provide good preparation. Sometimes this translated into sales worth thousands of dollars. Sometimes this translated to me referring the family to another program that was a better fit.

The best moments were when a parent would use some of my favorite words: “you don’t have the right classes for my student, but you’ve been so kind and helpful, I’m going to tell all my friends about your program.”

Or, better yet, when I heard these words from one of their friends later: “My friend is so-and-so. She’s never signed her student up with you, but she told me how great you were on the phone, so I decided to sign up my student.”

See, the thing is, you need sales now to keep the doors open and the lights on. But you need sales later to keep the business growing.

In my opinion, the best way to get both is this: Serve first. Sell second.

Ask your customers what they need. Truly listen.

Determine whether you can offer it.

If so, great. Sell as hard as you can.

If you can’t, send them to the company that can meet their needs.

And if you can offer what they need in the future, take notes and get to work making changes.

You might not make money doing this.

Or, like me, you might help your company go from a 10% annual deficit to a 12% annual profit.

This Christmas season, ask yourself, what kind of company do I want to work for?

Do I want to work for one that practices kindness and puts customers first, or do I want to work for one that puts the almighty dollar above everything else?

You can make a lot of money just making the sale.

But you might also bring yourself a lot of headaches. And you’re not really helping the customer.

Plus, maybe, just maybe, you can make more money by building a reputation of honesty and service.

Your mileage may vary. Results not guaranteed.

But it will certainly feel better.

And you know what they say.

Good vibes only.

Merry Christmas.

Picture this.

A middle-manager at a large, nearly-trillion-dollar company goes to work every morning where he sees an elderly woman working custodial. Every day for a year and a half, he tries to smile or wave at her, and she ignores him.

Finally, one day, she smiles back. A couple days later, they have a conversation in the break room. Then, a few weeks after that, the man leaves the company and never sees this woman again.

Now I ask you, did this interaction matter?

Did it bring in more money to the company? Did it make the man better at his job? Did it make the elderly woman clean harder?

Did it make the world a little less dark?

There’s no denying, I’ve had a fairly comfortable life. I’ve had a lot of privileges and a lot of opportunities. But, a lot of those opportunities came from generations of hard work.

My maternal grandfather was a handyman. My dad spent quite a bit of time working blue collar jobs (bartender, factory worker, landscaper, cab driver) before he worked his way into a successful white-collar career. His father was a cop, and his forebears worked on the docks and in garbage collection in NYC.

For my own part, I picked up trash and stuffed envelopes to pay for (a tiny amount of) the tuition at my private high school. Then, I briefly worked custodial full-time between my junior and senior years of college. And my very first job out of college was working as a hotel bellhop.

Now, this isn’t to say “I had that one summer job, so I really understand the hard-knock life.”

It’s just to say, I have a soft spot for people with tough jobs.

One moment, or perhaps a series of moments, stands out to me from that summer I worked custodial in college.

After all my bathroom cleaning, one of my daily tasks was to go down the hall through the academic suite and collect everyone’s trash. So, every day I made my way down the hall, feeling a little sheepish about collecting the trash from professors for whom I’d been writing during the previous semester.

One of the first offices in this hallway belonged to a particularly high-ranking person whose job it was to get to know all the students. I collected this person’s trash every day for 3 months, and in all that time, this person never once looked at me, said hello, or thanked me.

This person knew who I was, because I’d been there 3 years. Also, even though this was not my favorite arrangement, I had multiple family members who worked on campus at various times. So, in short, this person knew my whole family.

And yet, not one word of thanks.

I wonder how many muscles it takes to smile? How many calories it takes? How many milliseconds it uses? Remind me to Google this later.

Now for a second story.

Jump ahead 10 years, and I was working on a corporate development team at a large bank where we hashed out multi-million dollar credit card deals. Some of these deals were 130 pages long. Some required all nighters. Not exactly a job for the faint of heart.

I liked the work, but the culture wasn’t the best. It was all ex-consultants, ex-ivy leagues, ex-investment banking people. They were truly the cream of the crop, in terms of raw mental power, writing skills, ambition… and a ruthless drive to win.

In my short stint on the team (an 8 month rotation), I never really got to know my coworkers. We didn’t talk about our personal lives much, even though we worked together (online, because this was during Covid) until 9 p.m. or so most nights. The thing is, no one really cared. When we went to the team Christmas party, I’ve never seen a larger group of more uncomfortable people who had nothing at all to say to each other.

Out of this whole 8 months, one thing that stood out to me was a throwaway comment my boss’s boss made. It was something along the lines of “I don’t give a crap about the name of the person who works in the cafeteria.” (Now that’s not an exact quote, but you get the gist).

It was a comment made in passing for the sake of humor.

You might say it was also a kind of all-American workaholic badge of honor: “I work so hard here I don’t have time to worry about that kind of stuff.”

To be fair, when you’re working on credit card deals that are going to affect millions of customers, this attitude is somewhat understandable.

However, what about when you’ve been working in the same office for 25 years?

Really? You don’t know the names of anyone in the cafeteria? Obviously, this seems like an exaggeration, and it probably was, but I observed my team leader in the cafeteria and realized that he truly, simply didn’t have time for anyone.

All that said, you may be asking yourself, why does any of this matter?

Is smiling at the custodial worker or saying hello to the cafeteria worker going to save money, bring in more customers, or affect our Christmas bonuses?

Work is about making money, right? Or at least, about providing services to people that they need (in order to make money!)?

Obviously, businesses only exist to create value. If we all went to work and simply had fun, every business would shut down pretty quick.

That said, what does it cost? Is it really that hard to be kind?

Will your multi-million-dollar credit card deal fall through because you cracked a smile or asked your teammate about their weekend?

Is saying hello to the cafeteria worker going to make you late on sending that email?

And when we’re all buried in a hole in the ground, will being 5 min. late on that email really matter?

You might not win at every job.

You might be told after all those all-nighters that you should have worked harder. You might have your position eliminated unceremoniously.

You can’t control everything that happens to you. But you can control how you treat people.

Saying hello to that custodial worker probably won’t impact the bottom line. But, not saying hello might make the world a darker place.

I don’t know about you, but that’s not what I signed up for.

Life is tough.

At least win at being kind.

Back in 2012, when I was a senior in college, my friend Adam told me some of the best advice I’ve ever heard:

“People are going to criticize you no matter what you do. So you might as well do what you want.”

And the man really meant it. Shortly after college, he quit a high profile job in political lobbying to work in the oil industry, then took the GMAT 3 times and got into the #1 business school in the U.S., only to turn down the school to accept an offer at Google. Now, he’s the head of product for an AI startup. True to his word, Adam does his own thing.

His words have stuck with me over a decade.

Yet here I am, 13 years later, writing this piece in part to convince myself to let those words sink in. It struck me recently how much I live for the opinions of others. Worse yet, how much I’ve lived for the opinions of people who don’t even like me.

I like to think I don’t care what people think. The truth is, I care a lot.

Like many of us, I still remember mean things people said to me in high school, and I still feel the burn of harsh words from former bosses.

Here are some of things for which I’ve received criticism:

• Being too smart and nerdy

• Not being smart enough

• Being too religious

• Being too worldly

• Being too kind

• Being too mean

• Having an attitude problem

• Not having enough of an attitude / enough backbone

• Going to a fancy school

• Not going to a good enough school

Notice a trend? Well, you can’t please everyone.

No matter how good a life you build for yourself, there will always be someone to tell you it’s not good enough, and there will always be someone to tell you that you’re trying too hard.

No matter how nice you dress, there will always be someone there to tell you that you could have dressed nicer, and there will always be someone who will make fun of you for overdressing.

No matter how smart you are, there will always be someone who will make you feel dumb, and there will always be someone who puts you down for talking about the ideas that excite you.

So, how does this apply to you?

Ask yourself, how many people shape the decisions you make? Most of us are probably mainly influenced by the 5–20 closest people in our lives: family, friends, bosses.

What about the others? Who else influences your decisions, your self worth, your actions?

Former friends? Former college buddies? Random LinkedIn connections you only kind of know? Future children? Future bosses? People who thought you were dumb in high school? That one professor who never liked your writing? That one date who thought you had no potential?

Now ask yourself, how many of these people like me?

Hopefully your friends and family do. But there’s probably a vast cadre of people who think about you in a neutral way, or who just don’t think about you much at all. And there’s probably an even smaller group of people who simply don’t like you, never did, and probably never will.

Now, take it a step further.

How many of these people do you even like?

Do you like your high school bully? Do you like your toxic boss? Do you like your coworkers who will never speak to you again once you leave the job? If not, why would you ever care what they think? And why would you try to get them to approve of you, either in real life, online, or in your mind?

If you don’t even like these people either, ask yourself… how many times have you held yourself back in the past because of their opinions?

How many times have you refrained from sharing about a movie you liked because some people thought it was dumb? How many times have you been afraid of publishing on Substack or LinkedIn because of what former colleagues might think if they saw? How many times have you pursued or stayed in a job because it would sound prestigious to other people, even if you didn’t really like it?

What about now? What are you not doing right now because you’re afraid?

If you have a creative idea, I’m not going to tell you that most people will like it and shower you with praises. Your friends may criticize it. Your parents may doubt it. Your bosses and coworkers may mock it.

So consider, if even the people who love you, such as your friends and family, may have critical words for you, what do you expect from the world at large? What do you expect from the trolls, the naysayers, and the doubters?

You’ll never please these people. So just stop trying.

I hope you have a supportive group of friends and family. I hope you don’t live in fear. I hope you don’t worry about what people say about you at parties. I especially hope you don’t have bullies in your life, toxic bosses, or online trolls. But if you do have doubters in your life, don’t let these people change how you feel or what you do.

Stop worrying about pleasing them. Stop thinking that if you’re successful enough, one day they’ll approve of you. You don’t need their approval, and you don’t really want it either.

And if you’re ready to speak your mind, launch that website, create that video, pursue that grad degree, ask out that person, or follow your dreams… but there’s still that voice inside that asks “yeah, but what if I do it and they don’t like me?”...

Just go for it.

Don’t worry. They already don’t like you.