Sam Wonders

On playing at work (Dear tiramisu)

Dear tiramisu,

You wrote something in one of your recent posts that really resonated with me:

And I guess therein lies the crux of my career crisis: I'm terrified to do things I enjoy for a living because I don't want obligation to ruin my love for them, yet I can't stand the dreariness of doing something I don't enjoy (at least not for long, anyway).

This is something I’ve been feeling for a while now, but haven’t been able to articulate it into words as succinctly and eloquently as you have.

I’ve been (un)fortunate to experience both sides of this coin in my career thus far.

After graduating college, I found a job in construction tech. My major was in mechanical engineering, but I wanted a job that was more software focused, because I loved building things, and you can build things faster when you have fewer physical constraints. This job didn’t ruin my love for coding, but ultimately I left because the time and cognitive energy commitments were not sustainable for the non-work relationships and adventures I wanted in my life.

I recently (ish) left a software engineering job doing operating systems stuff at a (very) prestigious tech company that was (very) high paying. But I was miserable. It was unequivocally the most difficult work I’ve ever had to do and it was unequivocally the least interesting work I’ve ever had to do. Not a good combination. I left feeling like my career would likely need to go in a direction that wasn’t software for me to be happy.

I just came across this Richard Feynman excerpt on Hacker News, and it reminded me of your comment about both wanting and not wanting to do something you enjoy at work. The excerpt starts with:

Physics disgusts me a little bit now, but I used to enjoy doing physics.

One of the greatest physicists ever experienced something similar to you and me!

Reading this excerpt gave me an interesting moment of realization, and I wanted to share with you because I hope it might be helpful.

I realized that being able to Play At Work is an excellent indicator of how much I’ll enjoy work.

At the construction tech job, there were many opportunities for me to play. While it was preferred to get stuff working as quickly as possible, it was expected that some of the work would have no meaningful result other than building tacit knowledge. I would build mini experiments in Python and ROS for the sake of building intuition of those technologies. I would operate equipment to dig a hole for the sake of learning how best to dig a hole.

But at the operating systems job, it was so hard to play. It would take hours, if not days (or longer!) to even set up any sort of experiment. Everything was so complicated. Everything was so abstract. I wasn’t building anything — I was poring over open source libraries to (possibly) understand the implications of changing a configuration flag. Some of my coworkers genuinely seemed to enjoy this Code Archeology, but boy was it not for me.

So how does someone do something they enjoy for work without letting the work crush that enjoyment?

The takeaway for me from this Feynman excerpt is that you have to make space to Play At Work — in other words, doing the thing for the sake of doing the thing.

Easier said than done, of course. I have thoughts on how to (possibly) do this, but this letter is long enough, so I’ll leave that as a Story For Another Time.

I hope you hear back soon from the roles you’re applying to!

Sincerely,
Sam