Easier Said Than Done

On knowing thyself and the things that make thee tick

Sooner or later, we all come face to face with some pretty fundamental questions about what we do with our time. Makes sense, right? Time is, as they say, the only non-renewable resource. It’s only natural that you would eventually have to answer to the treasurer in your head who’s keeping track of how it’s allocated.

For me, that’s why career is such an important area for reflection. I undervalued it in the early years of my working life, until I realized that I spend more time on work than I do... pretty much everything else. The treasurer was pissed. Since then, I’ve been way more intentional about things.

The allure of achievement and its material trappings is persistent, but it only takes a bit of introspection to realize that those highs are temporary, so it would be a shame to not at least enjoy the process of getting there. ‘Unachievement’ isn’t about rejecting success -- it’s about having achievement be the byproduct of doing productive things you can enjoy in the moment, rather than the imaginary justification for wishing away the present.

There’s a tricky part baked in there, though: what the hell are “productive things” that you “enjoy in the moment”? And how often do those two attributes overlap, anyway? These things aren’t obvious as they seem. I mean -- sure, most people’s major life decisions are based on what they think will be enjoyable and productive -- but it can be surprisingly difficult to figure out your own preferences.

My first job out of school was at the big insurance company. I chose it because it seemed like a good job with good prospects for the future. Enjoyable and productive. It took me years to figure out I was wrong on both counts.

I was wrong about enjoying the work, even as I was doing it. I would tell people I liked my job, and I would tell myself the same thing. I wasn’t lying -- I was just… mistaken. After years of tolerating my work, I finally clued in to the fact that tolerance is not the same as enjoyment.

I was also wrong about that career path being productive for me. I didn’t lack for ambition: to climb the hierarchy, get my hands on more money and status -- the usual. Nor did I lack for the potential to achieve those things. But I was wrong about the fact that achieving them would bring any real satisfaction. It’s not that you can’t be satisfied while winning the corporate game -- it’s that you can’t be satisfied by winning the corporate game. Once I recognized that, I began to think a lot harder about the nature of my ambition.

Everyone’s “productive and enjoyable” looks different. The overlap for me is in… drum roll, please… problem-solving. That’s it. Two measly words that took me well more than a decade to discover. If there’s some grand architect of this whole human experiment, s/he’s got some sense of humour.

Turns out I love spending my time and energy on figuring stuff out. Why is that thing like that? What would make it better? How can we do that? The more original the problem, the better. I’ve learned to steer myself toward those kinds of environments, especially in my career. When I do, sure I have my moments of drudgery or frustration like anyone, but on the whole I’m happier than a pig in fertilizer.

The ‘productive’ part of things has a few components. For starters, hopefully the problems I find to work on are interesting, or meaningful, or (ideally). Then there’s the matter of money, lifestyle etc. which -- long story short -- I think is best approached as a matter of “enough” rather than “more”. If I can work on solving problems in a way that checks these boxes, then I’ve met the ‘unachievement’ gold standard.

(Aside: working on startups -- which I’ll define as new/young companies solving original problems -- is my general answer to “what checks all the boxes?” for me. I recently heard someone point out that startups are the ‘inventors’ of today. Once upon a time, the inventor sat in a shed somewhere, tinkering with new ideas or technologies that might change the way the world looks and feels. That role today is filled by startups. The world knows about startups in terms of their tiny potential for massive commercial success, but I don’t think most people recognize what role they play in inventing... well, pretty much everything you use in the process of living life. Look at it through that lens and you’ll see the problem-solving playground that I do.)

Mind you, I want to avoid the mistake of thinking that any of this is permanent. I’m happy that I’ve come to understand what makes me tick for now, but I’ve also been witness to my own evolution over time -- enough to expect that my tastes and sensibilities will probably change again. And then again, until -- oh, forever-ish.

Nonetheless, I’ll take it as a win that I’ve been able to get this far in figuring out my “enjoyable and productive”. If you can relate, you’ll attest to the fact that at a minimum, it makes it way easier to make life decisions. And if you can’t, I’m certain you’re not alone. 

Go figure that one of the hardest things in life to figure out is yourself.