041 | The Happiness of Pursuit

having things isn't fun, getting things are

Jimmy Carr said: it’s not the pursuit of happiness — it’s the happiness of pursuit.

I heard this after about ten years in my career, and it clicked immediately — because I had already learned the lesson the hard way.

Back in 2020, I joined my company one level lower than I wanted due to an interview hiccup. So I chased the Senior title as hard as I could. I got there. And when I did, it was just... depressing. The goalpost moved immediately — Staff Engineer became my new reality overnight. I felt like I’d already exhausted everything I had and yet I was on this new marathon right away. I’m still behind because of that setback. I can’t rest or waste any time.

My life had centered around just that one immediate goal. I’d given up travel, given up exercise. After a 14-day war room stretch in late 2022, I tried to go for a run and my whole body hurt — I couldn’t breathe. Am I not supposed to chase after ambitious goals? Or am I just doing something wrong along the way?

I didn’t figure out the answer then. But I knew I didn’t want this to happen again. So when I started chasing my next career goal, I changed one thing: I set my goal to be two levels ahead instead of one. Staff became a milestone I knew I’d get to. When I did get to Staff, this strategy proved itself. I celebrated for about fifteen minutes, and moved on. No depression. No huge celebration. Just a milestone — I was perhaps 10k into the marathon. I took my water and energy gel, and kept going.

It was about three or four years after that first depressing promotion when I saw that reel on Instagram: “it’s not the pursuit of happiness — it’s the happiness of pursuit.” And I thought: of course. How else could this be? “Enjoy the process,” right? People had been telling me that since I was a child. But it had always been meaningless because it was framed as a consolation for losers. It’s okay if you lose the match but you enjoyed the process. I didn’t buy it. I wanted to win the prize, not just “enjoy the process.”

Now I understand it was just over-simplified framing. It’s not about winning or losing. It’s about the type of person you become going through the challenges, and the type of strength you gain on the journey. I care about everything I cared about five years ago, not any bit less. I just aim further.

Occasionally peers at work ask me — should I go for this next thing? I never have a smart answer in the moment, but I keep landing on the same thing: if you have to be there for 40 hours a week, you might as well make it something fun to chase after. Go after the next goal. You’ll become stronger through the chase whether you get there or not.