I fell for the promotion trap, then escaped

Nine months into quitting my job, I’ve been battling resentment of my former self.

It's got me thinking: what do you do when you’ve spent years focused on the wrong thing? Does the promotion game damage your ability to learn? Is it possible to look good and get good?
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Right directions, wrong destination

Having the right directions to the wrong destination is a universal problem. After all, you’re asked to make big decisions with limited information: picking a career without real experience, joining a company without working there, launching a product with unknown unknowns.

Luckily, most decisions are reversible or time-boxed. The danger isn’t making a bad turn, it’s sticking with it against your better judgment. But the more you invest, the harder it is to change.  

The cynical voice goes: “You’ve spent so much time on X, how do you just leave and do Y?” Here’s the best visual response I’ve found: 

I’ve spent many restless nights fixating on paths not taken. Not going to medical school, leaving consulting, leaving a startup, not taking an Instagram offer. 

All the what ifs makes it easy to forget a powerful truth: while the time behind you can’t be changed, the time in front of you is completely malleable.

So why is it so hard to switch paths? Perhaps your existing path is an elevator designed to keep you going.
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Trap of “looking good”

I went from new PM to Group PM within 2 years. It was both gratifying and limiting. While recognition was nice, I felt mounting pressure to keep performing at higher levels. This is no accident.  

Once you start riding the corporate elevator, there’s a strong temptation to keep going, hoping the view gets better the higher you go. Sometimes this is a good thing. Pressure and accountability keeps you sharp.  

But pressure to always “look good” also boxes you in. 

Once I learned how the elevator worked, my strategy shifted. I prioritized easy wins over risky bets to secure points on the scoreboard. I skipped learning opportunities to maintain a pristine track record. After all, consistency + points = promotion. And it worked.
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Promotion game

To get promoted, you need to show a track record of “wins” leading up to the decision. This incentivizes more focus on “looking good” than “getting good”. There’s rarely a prize for doing things the hard way. Why work on gnarly problems when you can score a series of layups? 

The shame is not in playing the game. The shame is being so focused on constant validation that you lose the courage to try new things.  

I became trapped in the shadow of my past, afraid to sacrifice what I knew for the unknown. This is true of individuals, and definitely true of organizations. It’s also the first chapter in the book called Stagnation.

The psychology of a promotion, like any form of success, is intoxicating. You unlocked the next level of the game!  

But the truth is more nuanced. Promotion is not the game, it’s just a version played by specific people. What helped you win the last round may backfire in another version with different players.  

Real confidence comes from adaptability, which emerges from exploring and making mistakes. Looking good only matters if it’s the outcome of getting good. And while a promotion is thrilling, it won’t be fulfilling unless you’re keen on the destination.
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Map of possibilities

If you’re anything like me, your idea of a great destination has evolved over time.

Product management, writing a newsletter or starting an online business were nowhere near the map of possibilities 10 years ago! Who knows what will take their place in the future? The map keeps updating at faster speeds. 

To reach new peaks:

• Don’t expect constant, linear growth: be open to venturing down the mountain if it means greater learnings
• Stretch the time horizon you optimize for: when you get good in the near-term, you will look good in the long-term
• Never stop building your talent stack: be a chess player, not a chess piece

A common fear of being a beginner again is having to erase your progress and start over. Having done this a few times, I can assure you your hard-earned experience doesn’t go out the window. You get to keep everything you’ve learned, and apply it in new ways.  

A month ago, I decided to revamp my talent stack. Not knowing how to code has held me back, so I’m now spending most waking hours coding my first project. It’s been a humbling journey filled with mistakes.

Despite my best efforts, I doubt it will make me look good. But here’s what I know for sure: I am getting good — slowly on some days but surely in due time. 

It’s never too late to write a new chapter.