I’m publishing this as I board a flight to Buenos Aires, Argentina, where I’ll be living for the next 4 months. There, I’ll be joined by a few other “digital nomads,” entrepreneurs who have built online businesses that let us travel the world indefinitely.

My income, at this point, is almost completely automated, only spending 2 hours or less a week on work related to how I make money. I’m traveling with just a backpack and duffel, using credit card points to get free business class tickets, staying in Airbnbs, and according to the Runway Calculator have the option of just goofing off and doing whatever I feel like for, well, a long time.

What seemed like a lofty, long-term goal a few years ago has finally come to fruition. I have achieved the 4-Hour Workweek. But… this article isn’t to brag. It’s more a cautionary tale.

For those of you trying to build an automated lifestyle business and work only a few hours a week, it might not turn out quite how you expect.

Getting Here

For the last three years, my primary goal was some form of:

“Build a lifestyle business that can run mostly automated, so I only need to work a few hours a week to have a comfortable living.”

I’d read The 4-Hour Workweek in college, and after a brief stint believing I wanted to be a management consultant, I decided I’d rather put my income on autopilot to travel and learn things and have fun. Not a hard decision.

So, I went to work, trying out a ton of ideas with the goal of creating a passive income. There was the habits blog, meal planner, sleep ebook, Fratboxes, Pillars Playbook, Tailored Fit, a bunch of other projects that never got off the ground, a detour to work at SumoMe, and then a couple ideas that worked: Programming for Marketers, Stamena, and this site.

I think that along the way, I just sort of assumed that once I hit that point where the money was running on autopilot and I didn’t have to work I would “be happy.” That’s not to say I wasn’t happy before, but I didn’t want “a job” and this seemed like the best alternative. If I hated listening to authority and abiding by someone else’s schedule, then clearly working for myself whenever and wherever I wanted was the answer.

So, I kept plugging along, getting closer and closer to hitting that tipping point where I was making more than I was spending, without having to do any freelance or part-time work.

A few weeks ago, I realized I’d hit it. After a month of non-stop traveling, and getting more and more stressed about not working, I poked my head up and noticed that not spending any time on work had led to almost no change in revenue. And, when I looked back on the last few months, I realized it had actually been that way for a while without me ever realizing it. Somehow, I had done it: my income was automated.

And, suddenly, I was depressed. I’d assumed that once I hit that point of income automation and “financial freedom” I’d be happy, but I didn’t feel any different. Worse, that big, motivating goal was suddenly gone. And, since accomplishing it hadn’t made me that happy, I ended up unhappy, since I had to come to grips with the fact that this goal I’d been shooting for over three years wasn’t that life changing.

Or, at least, it wasn’t on its own.

Misplaced Angst

I had originally assumed that my dislike of past jobs stemmed from the restricted freedom and being told what to do, but now I realize there was a bigger problem. It wasn’t so much about working hours or freedom, the bigger problem was what I was working on. I moved away from management consulting because it felt like highly-paid bullshit, and I became dissatisfied with my last job because the world doesn’t need more email popups.

I didn’t realize my frustration with that last job until my passive income started ticking up, though. As long as I needed an income, it was easy to ignore that I wasn’t working on anything important, but once I stopped needing the money, I had to start asking myself more seriously if that was what I wanted to spend my time on.

And while the projects I’ve been working on since then aren’t big, important, life changing things either, I’ve been able to disregard that by focusing on the goal of having enough money to be self-sustaining.

Now that the target of “get to X revenue” is gone, though, there’s no clear goal to take its place. The easy solution would be to set a higher revenue goal, as most lifestyle entrepreneurs would do at this point, but then you get stuck in a cycle of repeatedly upping your revenue goal and you have to ask yourself: “when do I stop?”

I know that constantly making small improvements to my income won’t make me any happier, it’ll just keep extending the runway. And with that, what’s left is the same problem I had at my old jobs: An acute realization that what I’ve been spending time on doesn’t matter that much to me, it doesn’t “move” me philosophically, it’s just been a way to earn a paycheck.

And while having a comfortable living is important, once it’s covered, there’s no longer a motivating force. Instead of relying on that financial outcome to “deliver” happiness, I have to try to figure out what I can spend my time on that does matter, both to me and beyond me, to enjoy the process and avoid this dissatisfaction in the future.

So… what do I do now?

Ikigai

In a study done on some 16,000 Greek workers, retirees were 51% more likely to have died than their counterparts who continued working, and a 5-year increase in the retirement age was linked with a 10% decrease in all-cause mortality. In the Blue Zones research, they saw a similar phenomenon where people who lived the longest had a strong sense of ikigai, or “reason for being.”

The people who live to 100+  spend most of their lives working on something or doing something that gave them a strong sense of meaning. Humans need a clear reason for existing, a purpose to drive us and motivate us to get out of bed every morning.

That purpose, for most people, falls somewhere on the base tiers of Maslow’s hierarchy of needs:

If you’re working a low-income job, then you’ll be focused on making sure you and your family have the basic physiological and safety needs. When you move up the pyramid to the “psychological needs” category, your purpose starts to be about community and esteem. You don’t need more money, per say, but you like the feeling of accomplishment. Or, you were a straight A student, and you never got out of the “I want a shiny gold star” mentality.

But, once you don’t need to worry about your basic needs, have friends, and can get the esteem you need, all you’re left with is the self-actualization tip of the pyramid. And that somehow manages to be both terrifying and incredibly exciting at the same time.

The mistake that I made, and that I imagine many people will make going down this path, is treating the income-automated lifestyle as an end in itself. I assumed it would deliver happiness and self-actualization once it arrived when I should have realized that the only reason to create this much freedom for yourself is as a means to pursue that self-actualization.

What a passive income lifestyle gives you is not complete freedom from work, but the freedom to work on whatever the hell you want. Instead of being driven by the need to not die, or the need to get a gold star, you can spend 100% of your time on pursuing self-actualization and finding the work and focuses that will be meaningful to you.

But… how?

Nat’s Search for Meaning

I have no idea how one goes about self-actualizing. The question of “what’s the point of it all” has been a consistent, underlying theme to philosophy, and I have no illusions about solving it. Well, not today anyway.

But, what I recognize now is that the goal of setting up a lifestyle like this shouldn’t be to opt out of work and life and chill on a beach, but rather, to free up enough time and resources to figure out what you really want to dedicate yourself to. To explore and find what kind of work will be meaningful and self-actualizing, so you don’t get stuck on the “more money” or “shiny gold star” treadmills.

I think that’s what I need to do now. To stop obsessing over the small, incremental improvements on my existing systems, and to instead look at the whole and ask what direction I want to point my life in from here. What high-level goals or ideas I want to focus on next.

While losing some of that sense of purpose and having no idea what to do with myself sucks, it’s also incredibly exciting. I get a clean slate, and Argentina is a great place to try to figure out what to do with it.

This will be the first article in a series on trying to figure out what the hell to do with my life, if you want the future ones, I’ll be sending them to my newsletter which you can join below or here.

Post Script

All of this said, though, I’m super excited about hitting this point. I set the goal of going to Argentina, in particular, two years ago, and now I’m actually on the plane. 

I think this feeling is closest to a kid in front of a massive box of LEGOs with no instructions. You’ve been building according to the sets all your life, but now you have all the pieces you could want, and all the time in the world to play with them. And while that’s a little intimidating, you can’t help but see the potential for something cool to come out of it.