What if I yeeted myself to Bali, Lisbon, Medellín, or Mexico City to re-experience the luxurious nomadic life? What if I took on two remote-first jobs to double my income automatically? What if I pursued freelancing? What if I started my own company while soaking in the New York City serendipity? What if I plunged head-first into a full-time creative career? What does passive income look like?
. . .
These are the questions drifting through my fractaled mind as I situate myself in a very strange working world, by any objective standard. I look back at the past two years and can't help but chuckle at my own shenanigans when I realize how the nature of “work” has changed so drastically.
What I mean: In January 2021 I was balancing ~9 extracurricular activities with my full-time job. In January 2022, I was hopping from country to country every few weeks while taking meetings at airports and on nature walks. In January 2023... who knows what wacky arrangement I'll be playing with?
The common threads here are two-fold: living a remote life and embracing the pathless path. Coincidentally, I recently finished reading The Pathless Path by Paul Millerd, which was extremely helpful to ground my reality in some legible pattern language that I could relate to. He speaks to the cognitive trap of mental rigidity and the importance of being open to reinvention:
Moving abroad, running my own business, and living in more than 20 places in only a few years have made me much more resilient to change and more aware of my own default to become rigid in my thinking. I’ve become more capable of proactively embracing change, but I’d be lying if I said I am excited about every new shift in my environment, schedule, and work. Nonetheless, I’ve come to see reinvention as one of the most valuable meta‐skills worth developing, and on the other side of these experiments, I am often much more relaxed and confident than before.
Paul's experience points to an interesting insight: the role of experimentation in a long-term career. I've realized there's a main reason why the Growth role in tech is centered around experiments. If you don't test, you don't grow. There's a kind of compounding forward momentum the more you mix it up. The more you embrace the chaos and change, the greater the potential for upside in your personal and professional pursuits.
In the same vein, this isn't necessarily a jab at people who are “career lifers” (where they stay at the same cushy firm and advance in a linear way). This is more of a cautionary tale that reminds us that the concept of “work” and “career” isn't isolated to what we grow up knowing or what we see most people doing around us. In my world, there's always possibility at every corner, new scenarios waiting to be played with. A career where you curate and create, the way you want to. A career where you can feel free.
So what exactly makes this dreamy career? There are an endless sea of articles and posts on this, so I won't regurgitate the basics. My ideal career includes:
Being paid to learn
Being paid to build
Being paid to connect
If my current career track hits all three targets to some extent, then we're in a good happy place. They represent a layer of yellow caution tape in my mind: if I sense that a role or function is going to deviate too much from these fundamental properties of work, then we have a problem. The so-called “email jobs” where you're glued to your inbox most of the day might be most criminal.
Let's take a close-to-home example: project management as a part of your sexy Product Manager gig. In this case, project management violates my very sacred internal commandments (along with any derivative: firefighting, babysitting, corporatized forensic investigating — no offence to actual practitioners of these fields). You're not necessarily learning too much assuming you've seen the Xth development cycle or product launch. You're literally not building anything except maybe custom glue for the broken shit you see. You are in fact connecting with people, but in such an adverse unfriendly way because you're trying to get folks to move faster or persuade them to give you something.
I think what I'm trying to say is that we might need to expand our view on work, in the broadest sense. Career is what we do for a living; work includes effort in all other areas of our life — creative work, inner work, interpersonal work, etc. As I stare down the barrel of another calendar year older, my attention will be laser-focused on figuring out what work means to me. Naturally this makes sense as I experiment with my day jobs, but extends to higher-level thoughts — the role of community, the role of passion, the role of intuition. Stay tuned.
Taken from Flywheel of Focus 2022:
[Personal] I want to end the year with one capstone creative project
[Professional] I want to align on one clear direction for my career
[Existential] I want to articulate a one-line vision statement for my life
. . .
Last week I attended a very interesting French-salon style event at The Sophia Club that tackled this topic head-on ("What work is"). I found the concept especially interesting: “live philosophy”, where a classic speaker session is combined with an unexpected artistic performance as interlude. What does an anthropological study of Indonesian hunter-gatherer societies have to do with a sensual half-naked, half-silent dance performance by two New York artists? Hardly anything, but it was weird, and I enjoyed it.
In any case, I thought researcher Manvir's Singh's insights were salient and relevant to what I had been pondering earlier in this piece. Why do we shun leisure as unimportant during our formative professional years? The hunter-gatherer socieities typically worked on a task-oriented schedule: there would be a list of action items and you would work for as long as you needed to, at whatever time you felt comfortable with. This typically amounted to 2-3 hours per day. Their means are modest, but so are their needs. The rest of the time would be for social activities, relaxation time, or other creative tasks that they would do out of their own volition.
The task-oriented vs. time-oriented model is a key thread to follow in our investigation of what work means. Let's imagine an even more extreme world whereby your work is stripped of all social activity, your work is completely detached from products of the labour, and you have no control of/over your work. Sounds like a completely nightmarish situation, but not too far from some of the corporate arrangements we‘re all too keen to subscribe to in our early career. Why then do we stay? Why don’t we take the leaps of faith more often?
To close the loop on this sticky issue, I wanted to compare the learnings from this talk with a super fascinating article I came across recently: Quit Your Job.
Author Wolf Tivy reminisces about their experience quitting a high-paying, high-status career. In what he calls “active unemployment”, or more simply leisure time, that's where the special thought space of Other Possibilities opens.
I wanted to pull out three parts of his essay that struck a strong chord with me; the commentary feels personal, urgent, and essential as my adulthood reaches a local inflection point. First on novelty and curiosity:
You cannot pursue interesting novelty—things that no one else is doing or which you have never seen before, or the little threads of nagging curiosity or doubt—by chasing along known direct value gradients. But that’s where the treasure is. That’s how you will find the place where you need to build. To get the biggest and most interesting payoffs, you have to start by chasing merely interesting novelty in an open-ended way.
On the surface, this sounds somewhat obvious: if you're stuck in rigid work that drains your TEA (time, energy, attention), then you won't have the space to even think about interesting strands of potential. But if we dig one level deeper, we notice that even if we freed up the TEA, it takes a certain type of individual to really sit with this mindset and delve into the unknown gold mines of creativity.
Working even a good job cramps your sense of possibility, imposes narrow objectives, and eats away at the little things that could grow into big things if they weren’t so oppressed by the rigors of existing structure. The world is full of ideas and opportunities to explore, but it takes time outside of structure to even adjust your eyes to the landscape of possibility.
This echoes back to Paul Millerd's point about reinvention. Imagine being whisked from your ivory tower in some grandiose megacity and then being dropped in some random desert in the Middle East, stripped of any sense of order and structure (note to self: sound familiar?). Chances are that you'll be okay, but you're overwhlemed with shock and fear at the outset. Your eyes are literally blinded by the sun of a brand new world, a world where you can write the rules instead of slaving away for someone else's rulebook.
Transform your perspective thus: rather than seeing the job as carrying out someone else’s will in exchange for money, see it as itself your sacred cosmic duty. What important task do you do for the project you work for? How does that project fit into creating a more glorious future? How is that future pleasing to God, the proper order of things, and your own felt value instincts?
The most intriguing part of Wolf's piece is the added suggestion of spirituality. While defining work above has mainly been a mental and emotional exercise, the hidden cosmic qualities are such a refreshing spin on an overplayed topic.
I'm not sure if I'm ready to declare my work as some sacred cosmic duty, but this language makes me think of people trying to find “their calling”. Some greater force that compels us to create, to go further, to explore our inner possibility frontier. What I am ready for is the never-ending voyage — finding new treasures in the distance, finding temporary shores to dock in, finding other similar sailors to share with, and finding ways to build our growing fleet.
Here's to work, work, work, work :)
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