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What Happens When You’re Living the Digital Nomad Dream and Still Can’t Find the Happy

When I was 23, I lived on a Greek island, worked from a laptop on a balcony, and sunbathed topless on the beach all afternoon. And I was unhappy a lot of the time.

Not with my surroundings — what kind of crazy person hates living here?

But I had just been working for myself for a few months, and I was fucking terrified. I had steadyish work from a couple of clients, and while I wasn’t raking it in by any wild stretch of the imagination, I was doing OK. Rent and grocery money were never an issue.

But I still couldn’t get comfortable with it — I was so scared that the work would dry up, that I’d make a mistake that would turn off my clients forever, that maybe I was already making a huge mistake and should be looking for a “real job.” I knew that things were getting to the point where my traveling around the world and staying out of the traditional job market was going to stop looking like a gap year and start looking like actually committing and really working for myself, for better or worse.

I tried to surround myself with the things that I thought would show that I had made it, thinking that if I surrounded myself with “successful blogger” things, then it would somehow make me feel more comfortable. Greek island! Laying on the beach all afternoon! Drinking fresh orange juice at an open air dockside cafe every morning!

Turns out there are few things more depressing than sitting in an open air dockside cafe drinking freshly pressed orange juice brought to you by a strapping young Greek man as you look out over the azure waves and still thinking “Holy hell. What am I doing with my life?”

This is why you have to do the brain work.

See, though I had done some research about being a digital nomad, I had greatly underestimated the terror factor. I had just assumed that once I started and once money was coming in, then everything would just feel super great. Or even if there wasn’t a lot of money coming in, then I’d still feel great in that painter in the garret way, because dude, my life would be authentic.

So what’s my point? Two things: first, it’s OK to feel constantly freaked out when you’re just starting out (or, you know, any other time). This applies regardless of what your life looks like to other people, and it especially applies if it looks like you’re living the dream and people look at you like you’re a crazy, ungrateful bitch when you say you’re freaked out. It’s really scary when the only thing between you and homelessness is…well, you.

I used to feel really guilty about how worried I felt, because, come on, a lot of people dream of doing what I’m doing for years and most never end up being able to do it. But that just adds another layer of mental suck to the whole thing, so don’t even go there — feel how you feel, and don’t worry about your worrying. And the corollary to this is realize that that person who you think is rocking it may be constantly terrified, despite having an Instagram feed of gorgeous beach shots and apparently being super #blessed!

Second, if you’re going to make the digital nomad thing work, you’ve got to do some soul searching. This means thinking about the things that you really need to be happy, and I’m not talking about the outside things. I mean what your internal landscape needs to look like for you to be OK. What kinds of hangups you have about what work is supposed to look like. Exactly what line your bank account can hit before you start mainlining Oreo milkshakes and stress crying.

And only after you’ve got the internal landscape worked out should you think about the kinds of external things that will really support that. And those things might not look like you think they’re supposed to — if you’re laying on the beach every afternoon because you think that you’re supposed to, or that’s what real bloggers do, then what’s the point?

Your dreams are crazy incredible. But they need all of you on fire and lit up, not halfway really excited but also freaking the fuck out.

So do the brain work — your business needs it. Your success requires it. And your life sure as hell deserves it.

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