Lessons from One Year of Nomadic Passive Income

in Life

It’s now been almost exactly a year since my last real job ended and I started working for myself while traveling.

In that time, I’ve lived in Austin, Paris, NYC, Buenos Aires, and San Francisco, while also visiting Boston, Minneapolis, Chicago, Napa Valley, Wallingford, DC, Pittsburgh, Medellin, Los Cabos, Puerta Vallarta, Florence, Tuscany, Ushuaia, and Antarctica.

Antarctica National Geographic landscape

Antarctica was by far my favorite

This site grew from ~120,000 monthly visits to ~450,000. I launched an app, a course, and a book. I took on my first marketing consulting client. I wrote some 400,000 words across all of my projects, and read somewhere around 60-80 books.

It’s been amazing, and I’m extremely grateful that I’ve been able to live this lifestyle. I know it’s one that many readers of this site are going after as well, and now that it’s been a year, I want to share how some of my thinking has evolved around it.

I don’t think I need to explain all of the great parts. I only worked 20 hours for three months. I get to work for myself, when I want, where I want. If I want to go completely offline for two weeks, I can. If I want to pick up and go to a new country tomorrow, I can. If I want to quit one project and start a new one, I can. There’s no boss, no schedule, no limitations, just total freedom as a 100% certified organic free range human.

But there are also some not-so-great parts, and for anyone else considering doing the digital nomad passive income 4-hour workweek life (I only barfed a little writing that sentence), there are some psychological aspects that don’t get talked about as much. And many of those have manifested into a few important realizations I’ve had over the last year, which I want to walk you through here.

Let’s start with the void.

The Void

“The wise use of leisure, it must be conceded, is a product of civilization and education. A man who has worked long hours all his life will be bored if he becomes suddenly idle. But without a considerable amount of leisure a man is cut off from many of the best things.” – In Praise of Idleness, Bertrand Russell

There’s a weird dissatisfaction that comes with finally making this lifestyle work, something I talked about at more length in my “I Built a 4-Hour Workweek, What Do I Do Now?” article.

You may not realize it, but you’ve spent most of your time in your life up to this point on other-driven work. First from school, then from your job. Even freelancers and entrepreneurs haven’t escaped it since they too have bosses, just significantly more of them.

It’s easy to fall into the belief that once that obligation to do work for others is lifted, even if it’s temporary, that you’ll suddenly be euphorically happy and filled with meaning and excitement. It’s the belief that keeps so many people working long hours into their 60s, telling themselves “It’ll all be worth it once I retire. Then I’ll be happy and free.”

Sadly, it doesn’t work like that. As soon as you get that freedom, you realize that a fundamental part of being human is doing things, and once you have no things you need to do you can get listless and depressed. It’s the depression that causes recent retirees to be much more likely to die than their peers who haven’t retired yet. They lost the sense of ikigai, or meaning, and their body shut down.

Assuming you don’t roll over and die when you’re faced with that void, you’ll naturally try to find something to fill it with. And unfortunately, the same drive that can make this lifestyle possible might make it impossible to fully enjoy it.

Malicious Productivity

“It starts with this: put your desk in the corner, and every time you sit down there to write, remind yourself why it isn’t in the middle of the room. Life isn’t a support system for art. It’s the other way around.” – On Writing, Stephen King

One downside of pursuing this lifestyle is that I lost many of the hobbies I had. When you work for yourself, free time becomes an opportunity to do more work, and when your idea of leisure is “learning programming” or “starting side projects” it’s easy to get sucked in and lose the ability to just play and goof off. Even reading, the closest thing I had to a hobby, was at least half productive.

There are so many people hopped up on one too many Gary Vaynerchuk videos who believe the answer to happiness and success is to hustle harder, sleep less, crank out that extra bit of productivity, but for what? Treating productivity as an end in itself is dangerous: you can always work harder, work longer, pile on more to do, and if you don’t have a clear reason for why that’s worth doing then you’ll treat it as tautological and keep taking on work because it’s the only thing that gives you any sense of meaning.

This malicious productivity also introduces its own brand of FOMO. You could be working on one thing, but then your friend has a side hustle that’s making some money so you start something similar. Everyone else’s success becomes something you should try to emulate, and every free moment must be harnessed in pursuit of more or of hitting your goals faster.

What I’m trying to internalize now is that productivity and output are not ends in themselves. They’re tools and should be used as tools for whatever life you want to create.

For me, that’s meant asking myself the question “why am I working on this?” more. If the answer isn’t “because it’s fun and I’d do it anyway” then I have to cut it out. And if I catch myself feeling guilty for being unproductive, I have to remind myself that the point of working is so that I can have those moments of unproductivity. It’s not that I want to work less hard, just that I want to get better at being okay with not working. That I want to get away from the malicious productivity that is so common among people in this space.

When you try to get all of your meaning in life from your work, life becomes the support system for art. But then as soon as that work goes away, your life suddenly feels meaningless. You can (and should!) be proud of your work and love doing it, but it shouldn’t become your sole source of meaning. It has to be part of a greater whole.

And in the context of nomadism, part of that greater whole is rethinking what travel means.

Unlearning Your Travel Guilt

“He owned a jacket, a book that he could trade for another, and a flock of sheep. But, most important, he was able every day to live out his dream. If he were to tire of the Andalusian fields, he could sell his sheep and go to sea. By the time he had had enough of the sea, he would already have known other cities, other women, and other chances to be happy. I couldn’t have found God in the seminary, he thought, as he looked at the sunrise.” The Alchemist, Paulo Coehlo

My family traveled a lot growing up, but it’s hard to say we really saw any of the places that we visited. For the most part, we blitzed through where we were in pursuit of checking everything off of the list that one “ought to see” in that location.

It’s the style of travel that comes from having only a few free weeks a year and trying to pack as much into that time as possible. And while it’s fun and interesting and has its merits, it’s hard to say you’ve been somewhere. Not just because you’re there for so short a time, but because you haven’t truly seen much of the culture or lifestyle of that area, just the landmarks.

Traveling in this fashion is primarily fueled by Travel Guilt or the sense that you’ll have wasted your trip if you don’t do every single thing available to you in a location. How dare you not stop in every room of the Louvre when you’re in Paris? Do you know how much it cost to get there?

Living more nomadically requires unlearning this impulse to judge yourself for not trying to see every single thing. It requires not feeling guilty for going to the same café every day when you need to get work done. Not feeling guilty for getting take out and watching TV in your apartment. Not feeling guilty for (forgive me) visiting a Starbucks in Paris.

And once you get over that guilt, you get to see what it’s like to truly be somewhere and to try to adopt that lifestyle for yourself. You would get much more out of a trip to Paris by spending an hour or two in the parts of the Louvre you genuinely care about, and then walking around a less touristy area like Le Marais and sitting in cafés for a few days.

When you start to travel this way, and start appreciate places as much as their landmarks, you also get more perspective on how many things there are that you will never see. Part of travel guilt and comes from the notion that you have to see everything, but once you realize and accept that you’re unlikely to see even 1% of the beauty in the world before you die, it’s much easier to relax and enjoy where you are. And if an area is truly so life changing that you must see everything, you can always come back.

That, perhaps, is the ultimate goal of long-term travel: to try to find where you feel most at home.

Taking pictures and seeing sights and trying new foods is great, but if you want to go somewhere for a longer term it should be out of a genuine curiosity about living in that way, and seeing what kinds of environments and lifestyles you thrive in. Not to bring the U.S. with you and talk to Americans while working from your laptops in Prague, but to try to truly be a local.

And when you make that your goal, when you recognize that you’re trying to find where you feel at home instead of constantly trying to find new places to visit, you have to rethink some of the values that started you down this road in the first place.

Freedom is Not The Answer

“What humans need and want isn’t a complete release of tension and responsibility, but the pursuit of a worthwhile goal that they chose freely.” – Man’s Search for Meaning, Viktor Frankl

One month into my stint in Argentina, I was trying to figure out what to do with myself so I picked up a copy of Awaken the Giant Within by Tony Robbins. Halfway though, I found this exercise:

“All you have to do to discover your values is answer one simple question: “What’s most important to me in life?” Brainstorm the answer to this question. Is it peace of mind? Impact? Love? Now put your values in order, from most important to least important. Take a moment and do this now…”

I decided to play along, and when I wrote down my values, these were my top 5:

  1. Freedom
  2. Novelty
  3. Challenge
  4. Learning
  5. Growth

It was immediately a wake-up call. My efforts up to that point had been focused on achieving freedom and pursuing novelty, but now that I had maximized them, I wasn’t any happier. Arguably I was less happy since I’d ditched plenty of amazing things (relationships, communities, cities) out of a sense that they limited my freedom.

It’s great to travel the world and see new places, cultures, people, and to experience all of that, but it has to be done out of a genuine curiosity about wherever you’re going. For many, though, the desire to be nomadic and travel the world is a manifestation of the same freedom-maximizing-FOMO that I’d had.

And when that’s how you’re operating, the solution isn’t more freedom and novelty, it’s resetting your priorities.

When I went through my calendar and reflected on the past year, it was immediately clear what made me happiest. Close relationships, dinners with friends, a sense of community, creating products I’m proud of. They all came from investment and cultivation, not from novelty.

It’s easy to get caught up in the pursuit of greener grass through more money, travel, sex, experiences, people, whatever you believe will bring you to that next level of bliss, but in most cases, the grass is greener where you water it. It’s not about trying to find that 99% perfect city, person, project, lifestyle, but about finding ones that are 80-90% of the way there and then investing in them to make them great.

Freedom can’t be the only goal since it quickly caps out. You want enough to not be obligated to people or work or places you dislike, but not so much that you can’t invest in the good parts of life you want to cultivate. You want enough to not be unhappy, but then you want to reinvest it into things that are already making you happy.

Long-term travel and passive income, despite the incredible appeal, aren’t ends in themselves. They’re tools for something else, because as it turns out…

Wherever You Go, There You Are

“At home I dream that at Naples, at Rome, I can be intoxicated with beauty, and lose my sadness. I pack my trunk, embrace my friends, embark on the sea, and at last wake up in Naples, and there beside me is the stern fact, the sad self, unrelenting, identical, that I fled from.” – Self-Reliance, Ralph Waldo Emerson

If you’re pursuing the lifestyle business digital nomad dream, you have to believe on some level that achieving it will make you happier than you are in your current situation.

And, yes, if your job sucks, you’re working long hours, doing something you hate, and stuck in a boring part of the world, then it will make you happier. But the joy from it isn’t permanent, and you’ll soon settle back into your baseline happiness level, because no matter where you go or how much freedom you accumulate, you can’t escape bringing you along for the ride.

If you’re a paranoid workaholic when you have a job, you’ll be a paranoid workaholic without one. If you can’t spend an afternoon quietly sitting in a café enjoying where you live right now, you won’t be able to do that in Florence either. If you feel the need to constantly check in on social media and email now, you won’t magically stop having that urge when you’re on the other side of the globe. And if you’re pursuing the lifestyle because you believe that freedom is the ultimate end, then you’ll very quickly swing too far in that direction and miss out on the opportunities for cultivating what you already have.

I’m not suggesting you don’t pursue it, quite the contrary. It’s fantastic, and you definitely should. But I think if I were starting over now I’d approach it differently.

It’s not “the end,” or even an end in itself. It’s a way to create more opportunities, a platform for self-discovery and exploration, and if you come at it with that mindset, then you’ll be more able to make the most of it once you reach it.

New Values

“I believe that evolution, which is the natural movement toward better adaptation, is the greatest single force in the universe, and that it is good.” – Principles, Ray Dalio

It took a few days to iron them out, but these were the new top values that I decided I wanted to focus on:

  1. Health
  2. Community
  3. Mastery
  4. Fun
  5. Growth

Health has always been important, but consciously putting it as my top priority helps frame everything else, like not letting work take away from sleep.

Community is my replacement for novelty, by trying to focus more on existing relationships and the environments around them instead of constantly pursuing new ones.

I’ve moved Mastery to pseudo-replace “learning” and “challenge,” because I love writing and want to focus more on that instead of trying to constantly start other side projects.

Fun is obvious: I don’t want to be a boring workaholic, and Growth applies to all of these to push me to not get too complacent.

As for travel, I don’t feel so compelled to do the long-term nomadic moving around so much anymore. I’d much rather live in San Francisco, Austin, or New York and then travel for shorter periods (up to 1-2 months) with people I’m already close to. Visiting new places is great, but not if you’re going to be lonely while doing it.

Freedom is a currency, and I’m much more interested now in spending it.