As I type these words, I don’t have a sales pitch for you for why you should read what I’m writing. I’m more or less writing this to prove to myself that I have something to say. I don’t have any real ambitions of having a newsletter, but in a world with so much noise, I think it would help me to solidify my own thoughts, in my own head, by writing them down. In order to set myself down a somewhat coherent path, this first entry will be about myself and why at 31, I find myself at a bit of a crossroads in my career. So here’s a little bit about me…

Jumping back to my days as a student in high school and through college, when I pictured what my career would be like, I imagined I would study something promising, get a good paying job, stable job, and for lack of a better term, kick things into cruise control. Throughout school, from elementary through college, I was never a particularly motivated individual. In high school I enrolled in advanced classes and always did well enough to keep my loving mother from getting on my case, but never more. I only did the harder courses because I was capable of it and it’s what my parents asked of me. So when I imagined a career, I pictured school, continued. So when it was time for graduation, I did interviews I qualified for and took the first offer I got. It was a decent paying job at a small consulting company. Everything was going according to plan.

Walking into the door on my first day of full time employment with a salary, 401k, PTO, health benefits, etc… I was walking into the last step of any real life plan I had. Up until that point, there was a pretty simple path to follow. Coming from a middle class family, I was doing what other people around me did. Go to school, study, get a job, work, but I had never really thought about what work would be like. It wasn’t long after starting my job that I started to ask myself, “ok now what?”.

At 21, I wasn’t asking myself things like ”am I making a difference in the world?” I was driven. But driven in the sense that I feel like I should have a goal, which meant my goal would be the next thing in front of me. Looking back, I was lucky to be hired into a small company that was growing because it meant as the company grew, I had the opportunity to grow with it. That also ensured I had a next career goal to aim for: Software Engineer II, Senior Software Engineer, Team Lead, etc. And that’s how it went. Looking back at it, it went a lot like school went for me, doing enough to get that carrot out in front of me.

To keep things short, I’ll fast forward to covid. For most people, covid became a time of a lot of change. For me, it was mostly boring. Boring to the point that I needed a change. A big one. Thanks to the perfect mix of remote work, getting dumped, social distancing pushing me to go crazy in my one bedroom apartment, I got the courage to put my stuff in storage and test the digital nomad lifestyle. When I started I planned to drive around the country and see some cities before deciding where I might want to live next. I went south (Arizona was my first stop) because that’s where covid rules were more lax (or non existent). My digital nomad chapter is important to the story not because I’m turning this into a travel blog, but because that was the turning point for me. That’s when I started experiencing a level of freedom I had never had before.

That freedom comes with it’s own challenges. However, being in different places and meeting so many different people opened my eyes to all these other ways people live their lives.

“The limits of my language mean the limits of my world.” — Ludwig Wittgenstein

If you don’t have the vocabulary to explain something, can you really understanding what that something truly is? If you haven’t experienced something for yourself, do you really understand what that experience would mean for other people? I hadn’t really thought of what else was possible because I hadn’t seen it. This realization clicked for me when I decided to dip my foot in being an international nomad. The kind that has their backpack and their laptop and eats overpriced acai bowls by the beach. The first place I remote worked outside of the US was Playa del Carmen, Mexico. To be fair, it’s not far enough from the US to give a real culture shock and it is geared at tourists, but because Playa is a “nomad hotspot”, I got to see how my new “community” lived. For those of us who are fortunate enough to: have no responsibilities tying us to a specific location, with disposable income (or enough for a plane ticket and a room), with a skillset that can be done from a computer, while lucky enough (for some of us) to have all those things when COVID struck, the way of seeing the world is drastically different that how the average person sees the world. And once you get a taste of freedom, it turns out to be a taste that’s hard to not want more of.

Fast forward to today and my life is centered around maximizing my freedom. I moved to freelance work so I could pick my own schedule and now I’m living across the world in Seoul. If I were to describe my current life to pre-covid me, I think it would be such a foreign concept that he would think I was just a crazy guy off the street.

All this has been great and I wouldn’t change a single thing in my life up until this point, but while maximizing for freedom, I think I’ve left out an important ingredient of a “happy life” as I see it.

“The hardest part is not doing what you want — it’s knowing what you want to do.”
- The Almanack of Naval Ravikant

While listening to a podcast episode from the Naval Ravikant (quoted above) , he explained perfectly what I’ve been missing lately. To summarize, what ambitious people want is to be on a stag hunt with people they trust. To be with like minded people in a high-trust situation going after a goal together. This is obviously skewed for the startup world he lives in, but I think the core of what he’s saying is true. The only difference for me, is my dream has been to do this alone. To dedicate myself to something intrinsically rewarding and provide for my family while I do it. When I picture how my life could be, I picture people like Pieter Levels. Travel, work on what one finds interesting, and make a lot of money while doing it. How does it get better than that?

Do different stuff, meet different people, become different and see different problems.
- Pieter Levels

The older I get, the more I realize life is cyclical. We’re a bunch of people experiencing the same problems people before us had to face. We just dress up a little different and so do our problems. For some (most, all?) of us, the same is true within our lifetime as well. We go through seasons of growth, good times, bad times, and transitions. I think that’s where I am now, in a transition just like when I was first out of school ten years ago. So as I come into my last decade before I hit my peak earnings, or my peak productivity, I get to choose the type of person I’ll be in my work life (personal life too, but that’s not what we’re talking about here). The consensus I’ve landed on is I agree with the quote from Peter above. Interesting people doing interesting shit and if I get to choose, I’d like to be one of the interesting ones.

Which brings me to my dilemma today. Over my career I’ve become pretty good at a lot of different skills in my field, however I find myself as a master of none. Changing that is the core of this whole manifesto.

I want to find my singular pursuit that I can dedicate my life to. Without that, I feel like I can’t find my footing… to base myself in something. These days, without that thing, I have misguided ambition. That takes away from the small joys in life. Instead of being able to go to the movies and just enjoy the evening, I find myself comparing myself to the lead (”It is a leap of faith you haven’t yet made, Odysseus.”). I find myself reaching for every little possible direction for my life and spread myself too thin. Great men throughout history tend to pursue a single pursuit until they’ve reached their end. At this point in my life I likely won’t be one of them, but why not try.

So that leaves me with the hardest question, “what am I looking for?”. I read So Good They Can’t Ignore You by Cal Newport my first year or two after graduating. A lot of his ideas have stuck with me since, but the most relevant right now is the introduction of the Self Determination Theory. The idea is that all of us (and this may be skewed for the Western world, which is fine for my purposes) have three psychological needs: autonomy, competence, and relatedness. And we need these things to be intrinsically motivated. When I think about what I want to do with the remainder of my life, my wants all fall into one of those categories: freedom, to perform the best work I’m capable of, and to be a positive in my loved ones’ lives. But it’s the competence category I’m currently lacking.

The thing about humans is we’re programmed to keep evolving. That’s why we have tech billionaires starting space companies for fun. We just can’t stop. So while I would say I’m extremely competent in the exact job I do to pay the bills, there’s room for challenge and I’m looking to find what that means for me. And there’s no time like the present to do so. Like a wise man once said…

“Life’s barely long enough to get good at one thing. So be careful what you get good at.”
- Matthew McConaughey