I recently spent a weekend with a close friend talking about hopes, dreams, and goals for the future. It was an enlightening and at times an overwhelming challenge! We spent some time working through the Wait But Why guide to picking a career, as well as Julian Shapiro's What to Work On. By Monday morning I had a prioritized list of values to consult when choosing projects to work on:

  1. Human connection
  2. Knowledge
  3. Exercising Talent
  4. Autonomy
  5. Adventure
  6. Money
  7. Power
  8. Fame

I'm planning on fleshing out the reasons for this particular ordering, but first a few high-level observations: human connection was at the top of Julian's list, it was at the top of my friend's list, and it was at the top of my list. This is a reflection of a larger realization I have been having over the past few years: I stress about my career path because it's a primary way of giving meaning to my life. If I could find a way to make meaning that was not related to work, I might not care so much. I don't think there is anything wrong with getting meaning and fulfillment from work, but it is definitely a privilege to be able to arrange so much of my thinking around meaning rather than money. Once you see your career as a key source of meaning, it's pretty easy to prioritize human connection, because our connections to our fellow humans often feel deeply meaningful.

Knowledge came second for me, and this reflects my favorite parts of every job or responsibility I've ever had: learning new things. For me, a few main circumstances have typically resulted in me feeling disconnected from my work:

  • Not being part of a team
  • Not learning anything new

So, for me, it's important to work alongside others, and it's important that the work challenges me to learn new things. That leads into number three: exercising talent. This one is somewhat obvious: it feels good to be good at things. It's been over a decade since I started programming computers, and while I wish that it wasn't such an isolating activity at times, I'm also really sad at the thought of working at a place where I rarely or never get to use all of the random skills I've accumulated during that time. There's an interesting tension between two and three: if I want knowledge, that often requires trying new things which I am almost certainly not good at, but if I want to exercise talent, that might require retreating back into my comfort zone long enough to regain some confidence. Overall, these two things tend to work together rather than against each other. Probably the ideal work for me surfs the wave that runs between these two extremes, much like a human life might surf the wave that runs between a desire for belonging and a desire for freedom and independence. My thinking here is directly drawn from Robert Kegan:

If I were asked to summarize my reading of centuries of wise reflection on what is required of an environment for it to facilitate the growth of its members, I would say this: people grow best when they continuously experience an ingenious blend of support and challenge; the rest is commentary. Environments that are weighted too heavily towards challenge without adequate support are toxic; they promote defensiveness and constriction. Those weighted too heavily towards support without adequate challenge are ultimately boring; they promote devitalization. Both kinds of imbalance lead to withdrawal or dissociation from the context. In contrast, the balance of support and challenge leads to vital engagement.

Autonomy comes next for me. This one is just truly a quirk of my personality and upbringing. I really enjoy being able to pick what I work on, whether that is a particular part of the stack, or a particular problem inside of the larger domain. I have been blessed with some awesome managers during my career, and they have helped me find ways to mesh my working style and interests with the larger organizational mission.

Adventure comes in just behind autonomy, and honestly, I was a little surprised to see it wasn't higher on the list. I'm still tempted to move it, and maybe when the world feels a little more travel-friendly it will get bumped up a few spots. I have left some amazing situations in my life in pursuit of adventure. It's always been a hard choice, but I'm confident that it's always been the right one as well. I can't imagine what my life would be like if I hadn't left my job to hike the Appalachian Trail at 22, or quit my amazing gig at thoughtbot to ride across the country on my bicycle in 2017, or if I had not turned down some big offers in favor of small, remote work in order to do Remote Year, where I met so many kind, inspiring friends.

All of the top five goals had their moment of doubt for me, when I thought "Maybe this should be my number one". Each of them was really hard to place. The only thing that was consistent in every permutation I tried was this: money, power, and fame come last, in that order. Part of the reason money is low is just that I've been very lucky to have a relatively successful career in software. It's pretty easy to find software jobs that pay the bills, even while living in some of the most expensive places in the world. Power and fame simply don't interest me that much. This too fits with my top priorities. To quote Ursula K. LeGuin:

"Having replaced instinct with language, society, and culture, we are the only species that depends on teaching and learning. We aren't human without them. In them is true power. But are they the occupations of the rich and mighty?"

- 3 toasts