Digital Nomad = Overrated

Settling Down = Underrated

Sup nerds!

Today’s post was sent at hypersonic speed to 10,400+ nerds across cyberspace. Boy do I have got a hot take for you today.

If you’re new here and enjoy what you read, please consider subscribing to get my work in your inbox every Sunday.

When I was 19, I dropped out of college to be a digital nomad.

Over the next year, I’d live the tech bro dream. Thanks to income from an e-commerce business, I’d party in Amsterdam, explore museums in Paris, and eat pasta in Italy. Yet do you wanna know something weird?

I’m happier living in New York getting screamed at by crack addicts, half-naked homeless men, and cranky old ladies than I ever was as a digital nomad jet-setting around Europe. This experience has led me to a central belief:

The digital nomad life is overrated and settling down is underrated.

In the tech world, being a digital nomad is often seen as the ultimate goal: make money on the internet so you can be free and do whatever you want wherever you want. It’s what Tim Ferriss and Mark Manson did. So everyone else wants to do it—except people always forget that when Tim and Mark were digital nomads, they both severely struggled with depression and loneliness. Yeah, you have to read past The Four-Hour Workweek to learn that part. There’s a reason they’d both settle down.

I felt the same way. Sure, I felt freedom working on my laptop from coffee shops. And of course it was fun partying my way across Europe. But damn, those were some of the loneliest times of my life. I missed my real friends, my family, and my dogs. Like sure, I was surrounded by people and “friends” but they were all very weak connections. I don’t talk to any of them anymore. And yeah, it’s fun sleeping with strangers in strange cities until it isn’t fun anymore—it’s just strange.

Fast-forward a few years to present day.

I’m living with my fiancée and my dog. I’ve got a 1-year lease. I can no longer just get up and travel at any point. I’ve got roots. For god’s sake, I’m in a dodgeball league that’s relying on me! Shit, I can’t even leave the house for more than 6 hours at a time because the dog has to go out to pee. And yet I’m 100x happier than when I had all the “freedom” I so desperately craved.

Maximum freedom isn’t a good thing. Maximum freedom means no deep connections, no responsibilities, no one relying on you. You do whatever you want whenever you want and you come first always. You’d think this feels amazing, but it feels empty. It feels good being someone people can rely on. It feels good to see friends and family every week and not just stop by in between flights. It feels good to settle down and be a part of a community bigger than yourself.

You don’t need maximum freedom, you need enough freedom.

Life is a constant balance of freedom and settling down. If you go into the maximum-freedom mode, you’re miserable. And if you go into minimum-freedom mode, you’re miserable. There needs to be balance. You need enough freedom to feel happy, but settle down enough to feel grounded.

Like yes, I’m settled down in NYC, but I still travel out of the city every month either back home to Philly or take a weekend trip to the mountains or beach or wherever. And while I see a lot of the same friends every week, I’m constantly making new friends thanks to Twitter, rec league sports, and all the crazy events NYC has. And of course, it certainly helps I work wherever I want whenever I want from my house to coffee shops to Ubers. I’m settled down and I have freedom. You can have a mix of both.

I always thought that Discipline is Freedom book by Jocko Willinck was bs. How can discipline be freedom? Waking up at 4 AM doesn’t sound free. But I finally get it. A disciplined workout routine is freedom because you’re free to do whatever you want in your unstructured time and not feel guilty that you missed a workout. Well, settling down is freedom in the same way.

Yes, settling down means saying no to other places and constricting yourself to one place. But while you’re tied to one location, your mind is free. Your mind is at peace because you’ve accepted the goods and bads of your location, and you’re not constantly thinking about the next place to live like a fugitive running from yourself. And you’re free to invest in long-term friendships and relationships because people won’t be disappearing in a week to Bali or Croatia or whatever nomad spot is hot these days. The same goes for settling down with a person. While you’re tied to one person, your mind is free and at peace because you’re able to invest in the long-term important things and not spend time worrying about who is liking your Tinder pics.

So before you go chasing the life of a digital nomad, ask yourself are you searching for maximum freedom or maximum happiness—because you can’t have both. While maximum freedom sounds like maximum happiness, it isn’t— it will never give you the real, simple meaningful happiness of settling down and building a life for the long-term surrounded by people you love.

Life is about compromise. Give up some freedom, gain real happiness.

Goal: be the #1 destination for creative cyberpunks

🤖 Cyberpunk writer Steve Flanders published a piece about tech’s groupthink problem. Banger.

🎥 I just watched cyberpunk YouTuber John Coogan’s video on how TikTok tricked America. This is a MUST-WATCH.

🔫 Oops I binged another one of John’s videos. This one was on Microsoft’s Military Empire.


Ngl, I was posting some heat this week.

Thanks for reading nerds.

Create some cool shit this week.

Jason Levin

P.S. Want to really upgrade your content strategy?

🎥 Subscribe on YouTube for weekly videos.

📞 If you want to chat 1-to-1, schedule a call with me.

📘 Check out my book on meme marketing Memes Make Millions

Until next edition, see you on Twitter, LinkedIn, Instagram, and TikTok.