How to Tilt the Odds of Career Greatness in Your Favor
The best career move I ever made wasn't moving up. It was admitting I was climbing the wrong ladder.
I started my private equity career in an investing role. I was smart enough to hold my own and competent enough not to get fired. But I never truly loved it. And you could spot the people who did. They were the ones who lit up negotiating legal docs, got weirdly excited about modeling edge cases, and would happily debate EBITDA add-backs at 10 p.m.
Then I got closer to operating roles and portfolio company leadership. And that’s when something clicked. It’s where the juice was for me. Suddenly, the work felt alive. It was messy, human, creative, and high-stakes in a way that got me fired up. And as I gained more exposure to the post-acquisition aspects of PE, I realized: I was never going to be a top-tier investor. Not because I wasn't smart enough (though let's be honest, questionable). But because I didn't love it enough to commit the next 20 years of my life to it.
That realization led me to think differently about what actually drives career success. My working theory:
It’s not always the brightest minds who end up achieving career greatness. It’s the ones who pick a lane and stay in the game long enough for the compounding to kick in.
The career implication is simple but not obvious:
Pick a craft you could see yourself still excitedly doing a few decades from now. If it is greatness you’re after, here’s why this works:
First, if you can see yourself still excited about something decades from now, that almost automatically means you love it. And loving it changes everything. It will make you take it seriously. You’ll go deeper. You’ll practice more. You’ll work harder. You’ll keep tinkering and iterating. You’ll bounce back faster when you fail because you care too much to quit. Dale Carnegie had it right: “You never achieve success unless you like what you are doing.”
Second, the longer you stay with something, the better you become. It’s pretty obvious when you say it out loud, but in a world obsessed with hacks, cheat codes, and immediate results, it's surprisingly easy to forget. It’s tough to be great at something you “kinda like,” in large part because you simply won’t stick with it long enough.
Bestselling author James Patterson spent 21 years waking up at 4 a.m. to write in the dark before heading to his day job in advertising. It took twenty-one years of early mornings and pages no one ever saw before he became a bestselling author.
As Steve Jobs put it: “If you really look closely, most overnight successes took a long time.” James Patterson wasn’t an overnight success. He was just a guy who couldn’t not write. And when you stick with something you love for that long, it’s hard not to get super skilled at it.
Actor Steve Martin tells a story about his banjo side gig that illustrates the same point. When he first took up the banjo decades ago, he was awful. No natural talent, and lots of frustration. "I guarantee you, I had no talent. None," he reflected.
But amidst the early struggle, he made a decision: “I’ll just play for 40 years. Because I can’t imagine anyone who plays for 40 years still sucks at it.” Turns out, it didn’t take 40. Within two decades, he was winning Grammys.
Both are proof of a bigger truth: the power of compounding doesn’t just apply to money. It is about what happens in someone’s career when passion and time work together.
Passion x time = mastery
Subtract either = mediocrity
My “banjo” is teaching and writing. I definitely can’t say I’ve achieved greatness yet, but I know one thing: I can’t imagine not doing them 20 years from now. And because of that, I have full faith that achieving mastery is only a matter of time.
So here’s the question: What’s your banjo? The thing you love enough to still be doing two decades from now?
Don’t stop at the obvious answer. Your first instinct might be something generic like "operations" or "leadership." Fine, but zoom in and get more specific. Is it building teams from scratch? Turning around underperforming divisions? Coaching your next layer of leaders through their first major challenges? What's the part of your job you'd do for free? The thing you'd jump at if you had a spare hour in the week?
Don't limit yourself to what's in your job description today. Your banjo could be a discipline that runs alongside your role—strategy, communication, or inefficient fixing production lines. It could be something totally different and off the beaten path.
Whatever it is, get clear on the thing you can imagine sticking with for decades. Declare it. Commit yourself to it. With enough love and enough time, greatness is inevitable.