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When I was a senior in college, I got 9 credits of C’s.
I’d never gotten a C before in college. It was all A’s and B’s for me.
This is going to sound counterintuitive, but here’s some advice I learned the hard way.
You need to stop trying so hard.
Never back down.
Ever since I was a little kid, I always wanted to prove myself. Most of the time, it worked out really well.
A few times, it burned me badly.
Since I was homeschooled, I begged my mom to start school when I was 4. Then, I begged her to let me do the same schoolwork as my older sister.
All throughout high school and college, if there was a challenge no one wanted, I signed up.
Give a presentation on a difficult topic? Sure. Take golf lessons when I was already doing cross country? Why not? Sign up for academic decathlon when I was already doing 7 honors and AP classes? No problem.
When I started college, I was 16 years old. Technically, I was a dually-enrolled high school student, but from that point onward, it was just 4 years of full-time college classes. That said, to officially finish high school, I still needed 3 years of a foreign language. Since I’d only done Latin 1 and 2 at the Catholic high school I attended for 2 years, I needed to test into Latin 3.
That meant I’d have to finish all the remaining chapters I hadn’t finished for Latin 2. So, with the help of my very generous college Latin professor, I went through the last 7 or 8 chapters. One chapter a day.
While everyone else was having fun during freshman orientation, I was in the library, studying.
It was brutal. But I had a point to make. Yeah, I might be young, but I belong here.
This time, it worked.
I crushed the Latin entrance exam and ended up earning a small scholarship for languages.
But it didn’t work every time.
If it scares you, you should try it. Sometimes.
And so college went. I was often studying hard, writing things at the last minute, and feeling like I was just getting by. But I got pretty good grades and made it through.
I decided to be a history major.
Partly because I love history. Partly because I was young and had no idea what else to study. And partly because senior history majors had to write a 100 page thesis.
It terrified me. So I had to do it.
I don’t like backing down from a challenge.
The problem is that I kind of set myself up to fail.
As a junior, I had to write a 35 page paper on ancient history. I got an A- on it from a professor I liked. For my senior thesis, I should have just expanded on that paper and chosen that professor as my advisor.
Instead, I chose a professor who had only given me one A- in college. Aside from that, I’d never received higher than a B.
Why did I choose this advisor? Well, I was scared of having to write about ancient history and potentially translate Latin (even though I was good at that… and most sources I’d need would have already been translated anyway). Also, modern history seemed more relevant to current life.
And lastly, this time, I was going to get an A no matter what.
Well, that year I ended up working a few jobs on campus, from custodial, to events, to working for the Director of Distance Learning. I had my first girlfriend. I lived on campus for the first time. And I took an absolutely brutal courseload.
Cut to me at the end of senior year.
No girlfriend, because we broke up around Christmas. Goofing around too much living on campus. Wasting time on all the wrong things. And working my tail off trying to write for a professor who really didn’t like me much.
Maybe it’s not just about the challenges you take on. It’s about how many you take on at once.
That May, when we walked across the stage at graduation, I had a placeholder document in my diploma. Basically the equivalent of a restaurant opening banner that said “coming soon!”
Classmates who’d used my notes to study got awards and ribbons. I got nothing.
Walking across the stage of my college graduation at the age of 19 felt like one of the most meaningless events in my life.
Somehow, I just couldn’t shake the sense of burnout. Summer turned to fall, and finally I cranked out a really terrible thesis in October. 100 pages written in about a week.
It might sound like I worked hard, but the truth is I really did a pretty bad job of it.
All C’s. And it was deserved.
And this wasn’t the last time I’d make that mistake.
Older, not wiser.
8 years later, when I was starting full time in corporate at a bank, I was told by my first boss that she didn’t want me on her team. She only wanted expert coders. Never mind the fact that I was in a rotational learning development program. Or that she herself had come from that program.
I complained to the program manager and was given the opportunity to switch teams. For whatever reason, I said no. I was going to make this work.
Right, yeah.
A year and a half later I did the same thing. Took a hard role in finance at a time when we were supposed to be taking easy roles and looking for a full-time placement. I didn’t even want to do finance. I just thought I needed to face my fears and do it.
If I hadn’t been semi-guaranteed a final placement, I probably would have been fired.
I found a full-time placement on a team I liked, with bosses I liked. But I started to realize slowly that I was on a sinking ship. My wonderful boss got sick and had to stop working full-time, and I was stuck with a new boss who again didn’t like me. I knew I needed to leave, but for some reason I stayed. I was going to turn things around.
I stayed long enough to see my team get dissolved one by one. Including me.
When that happened, I thought about the conversation I had with my friend on the streets of Morristown, New Jersey, 6 months earlier.
As we wandered around looking at shops in the cold February air, she asked me “Colin, why do you always choose the hardest path? I feel like you’re constantly setting yourself up for a struggle, even at things you don’t like, just because it’s hard.”
She was right.
She’d said it many times before.
Why indeed.
Turns out, there’s a formula for the optimal challenge. I just wasn’t ready to accept it.
The Formula for the Optimal Challenge
You may have seen a meme floating around the internet. A simple circle with the words “your comfort zone” written on the inside, along with “where the magic happens” on the outside.
There’s some truth in that. But I don’t think it tells the whole story.
I think the magic happens right on the line.
I wish I could say I came up with that myself. But I got it from Jordan Peterson, the Canadian psychology professor. He writes about the distinction between order and chaos.
Perfect order is the totalitarian state, or the totally rule-bound mind. It offers stability but stifles creativity. Pure chaos is where new ideas run free. It allows for new birth and renaissance, but it’s also a destructive force.
You don’t want either. You want to be right on the line between order and chaos.
Enough rules, tradition, and stability to keep you grounded. Enough chaos, creativity, and regenerative potential to create new life and new order.
Malcolm Gladwell presents a good example of how to put this into practice. Specifically, his advice for choosing a college.
He said you should try to attend a college where you can be solidly in the middle of the pack.
Don’t go to a college where you’re easily at the top, because that probably means you didn’t challenge yourself. Also, don’t go to a college where you’re just barely scraping by. That’s too stressful, and you won’t learn much anyway.
In other words, it’s better to be a solid A or B student at a big state school than a C or D student at Harvard.
And I think that was one thing I didn’t learn fast enough at the bank. In some ways I pushed myself too much. In other ways, I pushed myself too much in the wrong environment.
That said, I’m grateful I did one thing right. I went to the University of Notre Dame for grad school. For someone who’d never studied business before, it was pretty tough. But it wasn’t backbreaking. I was challenged, but not crushed.
The magic happens right on the border.
That border is the key to success and happiness
I was listening to the Hungry podcast recently, which features entrepreneurs from food and drink brands. Max Halley, considered the UK’s King of Sandwiches, had this advice:
“The key to having a happy life is having achievable goals.”
That’s a tough lesson to learn. And frankly, I don’t think I’ve completely sorted it out in my mind.
The problem with dreamers is that they often choose unrealistic goals. Yet, the problem with realistic people is that they often don’t do anything interesting at all.
Peterson, Gladwell, and Halley aren’t quite saying the same thing. But I think they’re all onto something similar. There’s a fine line between order and chaos, challenging environments and bad ones, and ambitious goals and unrealistic ones.
In short, you need to dream. But you need a dose of reality too.
So how do you actually walk that line? How do you choose the right challenges?
Maybe it’s a constant struggle, with slipping on or off the line on either side.
Why is it that I could test into Latin 3 at 16 but not write a decent senior thesis at 19? Why could I get into the biggest bank in the world but not succeed on the finance team?
I don’t have all the answers, but I guess it’s about knowing when to quit.
There’s a difference between challenging your strengths and challenging your weaknesses.
I knew I was good at Latin, and I had a supportive professor. It was a challenge, but it was one I knew I could handle.
At the same time, I also knew I wasn’t great at coding and had little interest in finance. I had unsupportive bosses. And I knew that professor was never going to give me an A on my thesis.
But I did it anyway.
Maybe that’s not grit. Maybe that’s just ego.
I’m not advocating for laziness. I think most of us actually need to try harder. But if you’re like me, maybe you need to be a bit more discerning.
When you’re in the gym, you can feel the difference between stressing your muscles in a good way and straining your tendons. Learn this too late, and you might feel a pain in your elbow for the rest of your life. Trust me, I know.
Signing up for challenges you know might break you isn’t brave. It’s just dumb.
The goal isn’t to break yourself. It’s to grow.
Stop trying so hard.
Or, at least stop trying so hard at the wrong things.
Want to read more like this?
Here’s a few of my favorites.
What I liked most is the distinction between grit and ego. Sometimes choosing the hardest path is not courage, it is just refusing to admit that another path might fit us better. “The goal isn’t to break yourself. It’s to grow.” That feels like the heart of the piece.
‘The magic happens on the border’, well said. Enough to challenge you, enough to give the satisfying feeling of progress!