field notes, personal history

Why I left the Real World, and how I’m doing 6 months later

Nearly eight months ago, I left my job in tech, and the world of 9-5 work as a whole (or 10-6 as was more often the case in tech!), to become a wandering writer (producer-of-things, bringer-of-delight, etc etc). On several occasions I have promised to explain the reasoning behind my decision to make that leap. As the 6-month mark passed, it also occurred to me that I should do a 6-month retrospective of what I’ve been up to, plus a snapshot of where I am now. Now I’m late so it’ll have to be a 7.5-month check-in, but I thought I’d include both the backstory and the current story in this here post.


But to properly tell the story of why I left the Real World, I need to tell the story of why I joined the Real World. Why did I become a software engineer in the first place?

Before I ever had anything to do with the tech world, I was in my mid-twenties, I was a part-time tutor helping kids of all ages with standardized tests, school homework, college admissions, and so on. I had time to write on the side. But I was living at my parents’ house, and couldn’t have afforded SF Bay Area rent.

In The downside of staying put, I explained some of the parameters of my decision to become a software engineer, on the more micro level. On the more macro level, which I don’t really go into in that post, some of the assumptions and steps in my thinking were as follows:

What I wanted:

  • Enough money to live on my own. So I could have a cat. (And because living with my parents could be kind of suffocating in some ways.) But I wanted to have a comfortable cushion rather than barely scrape by; I didn’t want to always be worrying about money, because that would make it hard to focus on creative work, too. Oh, and I didn’t want any roommates. No more roommates!

  • Enter the Real World. By and large, the tutors in my company stuck around for a few years, often while in school or some other transitional phase, and then left to join the Real World. Not only for the money, but because there was nowhere to “go” as a tutor, no advancement or growth. You pretty much did the same thing week after week, year after year. And I just had this feeling that the Real World was Out There, this whole other universe, and that was the stuff that the grownups were talking about all the time (“career track,” “thought leadership,” “ROI,” etc), and I wanted to dive in and see for myself what all the fuss was about.

  • Challenge/learning. I’m an ambitious person, and there was only so long that I could keep teaching teenagers the same stuff over and over. I wanted to go into an environment where I would be learning more than I taught, and where I’d be challenged every day.

What I assumed:

  • I should continue to live in the SF Bay Area. There was nowhere in particular that I wanted to live, and I’m from the Bay Area, so it was familiar and felt like home. Plus, I’d had zero luck getting the exact same type of tutoring job in two other major US cities (or any job at all), and in the Bay Area I walked in and got the job. So in my mind, that was the one place where people would give me a chance. And at that point in my life, I had no qualifications in anything; all I wanted/needed in any realm was for somebody to give me a chance. So I just figured I’d live in the Bay forever.

  • I would be able to write and do creative work on the side, alongside a full-time job. It wasn’t a hard and fast assumption, more like I was hopeful, which I had reason to be, as I’d seen other people do it, like my dad, and I’d read about it in books. I knew that creative work was important to me, and if I wouldn’t get to do any at all, then having a “career” in the Real World was probably not going to work out, but the only way to find out was to try it.

Major factor to consider:

  • I had some ability in programming. At this point I was an extremely novice-level self-taught amateur. Like I’d done one of those online courses that has millions of students, and I got through it. I could make things that were useful, even if it took 10x as long as it should have, and even if my code was garbage. But I felt like if somebody would give me a chance to really learn it, I could probably do it for a living. I had no idea what programmers actually did, but I was pretty sure I could do it.

Programming was fun, it was challenging, it was in high demand and short supply and thus lucrative, it was a Real World career, it was one of the easiest fields to break into without a formal background in the field, and it tends to have some of the most reasonable workloads and hours of all the high-paying professions. To live on my own in the Bay Area and not worry about money even at entry level, I pretty much had to work in tech, anyway. I decided to go all in on making it as a software engineer. I didn’t have any plan further out than that, but I’d just see if I could break in, and figure it out from there.

The rest of the decisions in that particular story (as well as the story behind several more decisions I made during my engineering career) are chronicled in The downside of staying put.


Fast-forward 3 years. Suffice it to say, I did make it as an engineer, and more. (Sometimes people ask me if it was as easy as I make it sound. No. No it was not. During those 3 years, I hustled harder than I’ve ever hustled in my life.)

But, I’d learned at least one new thing with implications for my life strategy: I definitely didn’t want to work full-time in tech until conventional retirement age, in my 60s. Working in tech was fun, it was a great way to pay the bills, but it wasn’t fulfilling me enough to be the main thing to spend the prime decades of my life on. I didn’t know what my purpose in life was. But it wasn’t this.

What’s more, my assumption/hope that I would be able to do creative work on the side turned out to be wrong. Some people can do it. I don’t think I’m one of them. I explain why in my other post I’m not slow, I’m recharging: the EMP energy pattern. TL;DR, the amount of time I need for recovery and rest from work in order to stay sane is very high, and leaves almost no hours for creative thinking. When I tried to do more creative stuff and less recovery, my mental health suffered.

As I also explain in that post, if I’ve decided to do something, I’m ALL in. I can sometimes switch from one kind of thinking to another on a separate day, but I can’t really switch partway through the day. I can’t get home from work and switch to going all in on something else, nor can I do something else in the morning, and then be present at (or on time for) work. If you have my attention, then you have it for a solid 10-12 hours.

All other previous assumptions remained more or less the same. So around 2016 I made a plan: I would put in another 10-15 years full-time in the same line of work, and by the age of 40-45 I would “retire” from full-time work, and from tech, and not need to do stuff for the money ever again. As in, I might or might not work for money, but I wouldn’t need it, so I wouldn’t need to make decisions where money was a major factor. At the rate that I was earning, spending, and saving, the plan was feasible. I decided to run with it until further notice.


Fast-forward another 3 years. By 2019 I was an experienced manager of engineers. This is a very sought-after and even more highly paying position. Unfortunately, for an extremely introverted person such as myself, it also has an even higher energy cost than being an engineer. Plus, deferring deep creative work for years running was taking a heavy toll on me.

Even as THE PLAN was financially more feasible, it became psychologically and emotionally less feasible. I wasn’t sure I could make it another 10 years anymore. Not without becoming a negative person. And I didn’t want to be that person who’s in a job they clearly don’t want to be in, just counting down the years until they can get out. I’m not going to be that person. I won’t do it to myself, and I won’t do it to the people who work with me. Everybody deserves to work with people who want to be there.

The more time passed, the more I thought about shortening the timeline. Could I make something happen in 5 years? What about 3? I actually started a count-up of days in my daily planner. I would just keep counting each day that went by, and as an absolute upper limit, if I hit 3 years (1,096 days) and hadn’t made any plans or changes, I would have to quit my job on the spot and figure it out. I made that pact with myself. But really I was hoping I would figure it out within a year and a half, or 2 years. I set the hard deadline at 3 years to have some breathing room. (Software development trick: just take your best estimate for how long it will take to build something, and double it. It’s always been eerily accurate for me and my teams.)

The count went up for a few months as I continued to not do anything. Then multiple things happened. Friends of mine brought the fire and told me to quit wasting my abilities and get my shit together. (You know who you are. Thank you.) And I read, in Tim Ferriss’ Tools of Titans, this question inspired by Peter Thiel:

So if you’re planning to do something with your life, if you have a 10-year-plan of how to get there, you should ask: Why can’t you do this in 6 months?

Well, good question. Its purpose is to question how long a thing really takes if you’re not bullshitting yourself. And for the first time, I thought: “Could I make a big change this year? How soon could I be doing what I want to be doing, if I started planning this out today?”

So I sat down and revisited all my previous assumptions. And realized that the other major assumption I’d started with was also now defunct: the assumption that I needed to live in the SF Bay Area (or other major city in the US), and thus had to earn enough to live comfortably there. I had already been living abroad, in the Netherlands, for nearly a year (again, see The downside of staying put for more on that decision), and much preferred it to the US. Why live in the US at all?

If I didn’t live in the US, then I could live on much less money. But if I didn’t work full-time in another country, I wouldn’t have residency in another country, and would have to keep moving around every few months according to visa restrictions. Immediately I knew that I was fine with this idea, more than fine.

By SF standards, the savings I had would not get me very far. But as a nomad, even in developed countries which is where I mostly want to be, I could last well over a year on my savings, maybe even two years. That’s a lot of time to figure out what’s next. And nothing beats the clarity of being able to go all in on this question, without worrying about going to work the next day. Every time I had 2 or 3 weeks off from work, I’d turned it into a personal retreat of sorts, and I could see the discrete leaps in clarity that happened with every one of those. What kind of clarity could I reach with a year-long retreat? What would I produce creatively?

That was the last piece I needed: the financial and logistical assurance that if I made a big change sooner rather than later, I’d have enough runway to get massive value out of it, to get something out of it that I wouldn’t otherwise see for at least 10 years–or maybe would never see, as I wouldn’t think the same thoughts or create the same stuff at 40 as I would at 30. What I didn’t want was to quit my job, worry about money the whole time, and then just come back a couple of months later without having learned anything I couldn’t have learned by staying.

The assurance of giving myself one year without worrying about money was this: No matter what happens, I’ll be a completely different person by the end of that year. And then it was a no-brainer. Give up one year’s salary, and–best case–possibly transform into a new person, understand what to do next, and thus save myself the next 10 years? And worst case, have 1 year off and just come back to tech, fully rested? Yes. Done and done. This is what’s known in investing as an asymmetric bet, heavily in my favor: it’s almost all upside, with very little risk. I’d take that deal every time.

There is nothing more important in life than living it. There’s nothing more worth your time. It sounds like kind of a pointless thing to say. But it’s a sign of our strange, upside-down society, that that statement has any meaning at all, that it also sounds like a kind of stake in the ground.


All of the above thoughts had been developing during a 2-week vacation. On my last full day before I returned home, I wrote out an RFC (Request for Comments) of my life strategy, a document that outlined all the points I’ve mentioned here: my previous assumptions and why my thinking had changed; my previous plan and why it wasn’t working; my new assumptions; my new plan; but also, what a successful change would look like, and what an unsuccessful change would look like (in other words, a change that would be basically no change, or which would leave me worse off than I was before).

The point of writing all this out was first of all to make all of it clear to myself, to my current self as well as my future self who might be at risk of forgetting my priorities or the purpose of what I was doing; and secondly so that I could share it with a few friends, and get some feedback.

If I take a look back at the list of things I wanted when I set out to become an engineer, almost none of them still held true:

  • Enough money to live on my own. This one still holds, but in a somewhat adjusted way. I still want to be able to live alone for the majority of the year, but I don’t mind spending parts of the year with my parents, because our dynamic has evolved over time, and because it’s different when it’s not the only option I have. The other change is that my conception of what it means to “live” has changed completely. It no longer automatically means holding a lease on an apartment, owning furniture and household things, or any of those markers of being a grownup. That’s not to say I’ll never return to those things. But for the foreseeable future I’m content to be a drifter, without a permanent residence, without my own household, and without Stuff.

  • Enter the Real World. Well, I finally got to spend time in the Real World. (“Real” loosely meaning “corporate,” by my definition. The world of legitimacy, which usually means money or at least prestige.) Not only did I learn about “career tracks,” “thought leadership,” “ROI,” and so much more, I ended up in positions where I influenced such things and taught other people about them. I made it to a level where I could see how it all worked, from the entry level to the executives. And once you see how it works, it’s always only going to be more of the same. Unless you can change it. But if you’re convinced you can’t change it (so I told myself), or that changing it isn’t what you want to do with your life, then it’s time to go. There’s nothing more for you to learn, and there’s nothing more for you to give.

  • Challenge/learning. See the point above. I didn’t see any further learning or challenge of the kind that I was interested in, in the world of tech. In any game, the first thing is you learn how to play the game, so that people will let you join them and play alongside them. Later, you learn the game as a construct: how the rules got to be what they are, how you might change them, change the game itself. And with that understanding, you can use it as an advantage to win at the game; or you can decide, this isn’t the game you want to play at all. For me, it was the latter.

The new plan was simple: leave my job within 4-6 months; leave the Netherlands 3 months after that and become nomadic; go at least 6-12 months without working for pay; after that, pick up paying work as needed (in compliance with the strategy doc, in which I specified which kinds of work I would and would not be willing to take, and how much I would take). Continue indefinitely. Live simply. Survive.

I sent the doc to a 3-4 friends, who challenged some of the statements, asked for clarification, suggested ideas they’d seen other people do before, and who were all supportive and agreed that the plan was feasible. With my new strategy set, I was ready to make it happen.


I’d written the plan in late spring of 2019, and I left my job within 4 months of that. (By the way, according to my count-up, my last day was on Day 255.)

My first order of business was just to complete the transition. There was a lot of stuff that had been accumulating in my mind for years that I needed to address, and a lot of stuff I needed to do to physically move out of the country and become a nomad. Basically the one-time things that needed to get done to let go of my previous life and my previous way of being.

Of course, right after I left my job, I wasn’t thinking of it that way. I was just tired. I slept 10 or 11 hours a day for at least a month or two–sleeping off years of accumulated exhaustion. (I normally need 8-9 hours a day. That’s my average now.)

Recovery involved not only sleeping, but also doing all the relaxing things I’d never had time to do while working. Spend a whole day reading; a whole day watching TV; a whole day writing for this blog; a whole day taking a train to another city and walking around. A month went by before I even started to feel rested. I hadn’t realized how burnt out I was.

While my body and part of my mind had been accumulating exhaustion, another part of my mind had been underutilized, accumulating ideas and the hunger to do something with them. I started to wake up that part of my mind again, and clear it out, by writing out everything I’d been meaning to write about for the past few years, until I ran out of stuff in the attic, so to speak. This took a couple of months.

In the meantime, I took on the large project of preparing to move. I gave away everything I owned, saw my friends as much as I could before I moved, and was out of the country by Christmas–tired all over again, but happy.


Completing that transition took up probably the first 3-4 months of my time as a free person. After that, COVID-19 became increasingly a thing. It drastically changed my travel plans for the year, but for the better, really. Instead of wandering around on adventures, most of this current phase of 3-4+ months has been spent hunkered down in a small studio apartment in Istanbul, Turkey, doing some deep thinking and introspecting, getting inspired again, and laying the foundation of a new self: work I might’ve otherwise put off until much later.

The elements of this new self include:

  • Routine. After I left my job, I started out without a routine, just sleeping and generally being a full-time couch potato, and gradually adding structure from there. Now I’m using this quarantine time as a controlled lab for developing a structure for my days that’s going to keep me active and growing, in the absence of any employer or boss.

  • Rewriting the narrative. Gradually pinpointing beliefs and narratives that have affected my decisions in the past and disempowered or restricted me, and replacing them with ones that are empowering. I mostly do this through the morning pages (google it). One great and hugely consequential example of this is detailed in I’m not slow, I’m recharging. If writing out my creative ideas was like cleaning out the attic, this work is more like cleaning out the basement. It’s dark, it’s not pretty, and there’s some scary stuff in there that’s been there for who knows how long. But there are also some amazing discoveries to be had, of things I had all along but had forgotten about. In this sense, the rewritten narrative isn’t even “new.” It’s more like re-integrating my self with the person I was as a kid–the most important person to re-integrate with, because that’s the last time I was being truly honest.

  • Purpose. If I don’t have a job title, if I don’t have a career track, then who am I, exactly? What do I “do” (as the Americans say)? What have I been put on this earth to work on? How do I prioritize my work accordingly? With my mind starting to get clear (including the attic and the basement!), I have the first inklings of a working understanding of purpose.

  • Community. That’s you! It’s my subscribers, readers, friends, people I text/email and interact with on social media, people I catch up with on Zoom. It’s developing practices around who to keep in touch with, how to keep in touch, what’s important to communicate, and how to keep making new friends and growing my community. The newsletter is one of the best things I have ever done for myself. It gives me a built-in way to fold new friends into my community so that I don’t quickly lose touch with them, as well as a way to regularly remember that people care about me, and to regularly remind people that I care about them.

When I was contemplating the possibility of all this for the first time almost exactly one year ago, I told myself that within a year of getting started, I’d be a completely different person, unrecognizable to myself. And indeed I am already a different person.

Thanks to all of these elements of a new self taking root and beginning to grow, I feel more at peace than I’ve felt since I was a very small child, since I was basically pre-conscious. I know that plenty of people who know me have always thought of me as the calm one, which isn’t untrue, but all my life I’ve also been carrying around some form of depression, anger, frustration, impatience, self-loathing, and shame. Only realizing now that all along, it was just a heavy suit I was trying to walk around in; it wasn’t me. I can unzip it, step out of the suit, and leave it behind.

So that’s the snapshot of where I find myself, just over half a year post-exit from the so-called Real World: well-rested; undergoing a transformation; shedding layers of an earlier self to bring back an even earlier self; feeling lighter than ever before, and full of possibility. As for what I’m doing now and in the near future, perhaps the best way I can describe it is “being full-time curious.” The best job I’ve had so far.