A dozen lives
The bottoms-up approach to career planning (Stew's Letter #103)
Howdy, welcome to Stew’s Letter.
I’m breaking the usual punchy format this week to share an essay I’ve been working on as part of Foster’s first Season.
For the past three months, 75 of us explored our unexpressed Truths together, digging deep for the things that makes us “us” and working to find the words to express them.
A consistent theme that arose for me is how differently I’ve approached my career than many of my peers.
Today’s essay is an attempt to articulate my career “strategy,” which I hope will feel helpful to anybody whose passions seem to evolve every few years.
As always, hit reply with any feedback.
Let’s get to it.
A dozen lives
The bottoms-up approach to career planning
Picking a single, lifelong career feels like an impossible task for me.
As soon as I’ve gone deep into one domain, I feel compelled to explore another. Stability spawns a desire for novelty. Novelty spawns a desire for stability. The cycle goes on ad infinitum.
This ebb and flow of interest and desire feels natural to me, but totally at odds with my sense of how I “should” live.
After all, the great things in life supposedly come from compounding. A magnificent career awaits any who commits to a lifelong vision and compounds skills for decades. Given enough time, the intern becomes the CEO. The deckhand becomes the captain. The student, the sensei.
In theory, this makes total sense. In practice, long-term planning is not in my genes.
I can’t think more than five years into the future. I am driving a car through the mountains on a foggy night. Some days, I’m driving that bus from Speed – I don’t know where the hell we’re going, but we’ve got to keep this thing moving.
I tend to become obsessed with something for a few short years before I fall in love with something else. Often, the two things are not obviously related. Crucially, what I do day-to-day on each is jarringly different.
In college, for example, I became obsessed with building software – a path that appeared via a random accident. After finding some success as a startup CTO, the passion faded.
As I began to ponder what to do next, I started writing. Writing was something I had always enjoyed but never envisioned building any sort of career around. I became completely obsessed, though (I wrote about why here) eventually launching a few newsletters and co-founding Foster.
At Foster, it would have seemingly made sense for me to lead engineering – as I had done for each startup before. But I had lost the spark for the job. It was clear to me the most impactful thing I could do was help lead our early growth and community development. I knew how to speak to writers because I was one.
And just like that, I was no longer leading sprint planning meetings or triaging bug reports all day; I was planning out new email sequences and writing tweets (it’s real work, damn it).
In the context of my career, it feels like I’m living a new life. I’ve brought elements from my prior lives into it, but my day-to-day feels different enough today to barely be considered the same career “path.”
For the longest time, I’ve struggled to reconcile this approach to life with the “pick a career and stick to it” strategy I’ve been taught. It’s now obvious to me that they are irreconcilable.
Instead, I am going to propose that for many of us, a few things are true:
We change a lot over the course of our lives.
We suck at accurately forecasting what we want.
One of the primary things we optimize for is our personal happiness and well-being.
For people who fall into those buckets, I think the top-down approach to career planning (“I’ll be the CEO of this place one day no matter what it takes!”) is doomed to fail. You are likely to pick a long-term goal that won’t actually make you happy, and your interests will evolve so much along the way that you may not even enjoy the journey getting there.
Instead, what might a more bottoms-up approach look like?
You’d prioritize being present in the moment, paying attention to what you actually like doing, keeping an ear to the ground for opportunities that better fit those desires, and moving towards those opportunities that resonate with you.
You wouldn’t fixate on a 20-year end destination, only doing those things that’d help get you there. Instead, you’d remain open to surprise, optimizing for whatever gives you the most energy in the short to medium term, even if the long-term “story” doesn’t feel cohesive yet.
Sometimes, that may mean continuing to deepen your skills in some area. Other times, it may mean pursuing an idea or space that excites you, even though you’ll need to develop entirely new skills.
We free ourselves of a preconceived notion of what we should be moving towards and pay more attention to what actually excites us right now. I don’t necessarily love how ambiguous this all sounds, but on some level that’s the point.
Here’s another way to think about it:
Anything meaningful takes five years to do, whether that’s getting a company off the ground or mastering a skill.
If we start working at 20, that’s 60 productive years — or 12 five-year blocks to do new things, then move on.
Instead of living one life or career, why not live a dozen instead?
As Derek Sivers put it:
Buridan’s donkey is standing halfway between a pile of hay and a bucket of water. It keeps looking left and right, trying to decide between hay and water. Unable to decide, it eventually dies of hunger and thirst.
A donkey can’t think of the future. If he could, he’d clearly realize that he could first drink the water, then go eat the hay.
Don’t be a donkey. You can do everything you want to do. You just need foresight and patience.
On a more practical note, failing to consistently move towards what lights us up is loaded with subtle risks. The author Robert Greene talks about this frequently:
But eventually our lack of deep connection to the field catches up with us, often in our forties.
We feel increasingly disengaged and not challenged. Our natural creative energies have gone fallow. We fail to pay attention to the changes going on in our field because we are disconnected. People younger, more creative and less expensive quickly replace us. We find that we cannot shift or adapt because we have not built up the proper learning skills or the requisite patience.
It is funny, but the people in life who are primarily motivated by money or security often end up losing whatever they gain, whereas those who follow their passion end up making far more money than they ever desired.
In the case that you have a single, enduring interest in life, congratulations. You get to stay the course for decades.
In the case that you’re an ADHD-type person like myself, I invite you to join me and live a dozen lives.
A special thank you to every Foster member who participated in this Season – each of you helped surface some of the ideas that appear here and many, many more that I’m still processing. Thank you.
🔥 Fire TikToks
Okay, fine. This email wouldn’t be complete without some TikTok action.
I have three for you:
These “Be a man” videos always get me.
How a Princeton undergrad student saved an NYC skyscraper from collapsing.
Until next time,
I'm 'retired' now and on careers 6 and 7: novel-writing, and beekeeping. I'll call the horse riding a hobby. My wife's the same. Curiosity, challenge, and growth have been our guiding principles through several joint businesses and individual adventures. But it took me a long time to reframe this so that instead of thinking I couldn't stick with anything, I feel satisfied that I'm exploring as many opportunities as I can in my time on earth.
Resonate with everything you wrote here - bad at forecasting, quick to boredom and inherently curious. Currently on my third career and now the only career advice I truly believe is to constantly give yourself permission to change your vision of who you are