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Trust-fund baby goes rogue

a guide for the digital nomad

type Humor

time 7 minutes

tl;dr First-world problems.

You’re fresh out of college and a fight with your dad when you decide to be a digital nomad.

No, you say to capitalism, that’s not me.

So you pack up your guitar. You try to lift your suitcase. You repack. Your mom says she’ll keep all your things safe until you get back.

I’m not coming back any time soon, you say with a self-seriousness reserved for the white upper-class.

Where are you going, anyway? she asks, filing her nails.

I’m going to Spain, you say, picking a country at random that you know has a deep appreciation for guitarists. Plus, you took a little Spanish in high school. Enough to get by.

Your first real challenge as a digital nomad comes when the airport wifi cuts out. The work-from-anywhere thing starts to feel strained.

And what work is it you’re doing? your dad had asked.

You hadn’t a good comeback at the time. It was hard to explain to someone like him, with such a rigid mind, that you were going to find yourself and your passion. That anyone could do anything online. It was just a matter of untethering from location, of being able to plug in to self-sufficiency from anywhere. A sort of fiber-optic Walden.

The flight’s long, and you can’t sleep. The lady next to you has been drooling uncontrollably, and her head keeps falling on your shoulder. You push it back, but it seems to have a mind of its own.

It’s okay, though. You use the time to brainstorm. Ideas always flow best when you’re handwriting, so you get out your Apple Pencil. You come up with some plans for work. The trust fund can’t last forever.

Well, maybe it can, but that’s not the point.

It’s muggy when you land in Madrid. There’s less English than you thought there’d be, and even the Uber driver is talking so fast.

You get to the hotel and crash. You know you’ll have to find a real place to live soon, but the Ritz will do in a pinch.

You wash your face, drink some water from the tap. Then, horrified, you realize the water probably isn’t potable. You claw at your phone, trying to connect to the Internet, but the password the concierge gave you isn’t working. You flick the wifi toggle with the madness of a dying man.

You lie on the bed. Try not to move. Slow the poison, you think.

Should I call the front desk?

You wonder how much time you have left. How, at least the headlines will talk about how you died doing what you love. Finding yourself.

There’s a mirror by the bed to watch yourself decay. Heartbeats go by. Other than a few gurgles, your insides seem to be doing fine.

You’re going to have to be stronger than this if you want to be a real digital nomad. You get up, splash your face. Put some clothes on. Order takeout.

After a frankly disappointing burger, you grab the guitar and head out into the afternoon sun.

In the streets of Madrid, there aren’t nearly as many guitarists as you thought there’d be. But no matter. You find a relatively quiet spot and fill the air with sound. One chord, two chord. A risky move to a bridged F. You stick the landing.

After an hour, only one old lady has thrown a coin into your ball-cap, and you’re starting to sweat. As you wander home, you find a small crowd swaying to a guitarist who sounds like they’ve been playing for decades.

You push through, trying to get a look at the musician. Finally, you see her. No more than a teenager.

At the hotel, you realize the single coin you got is an old peseta, which Google tells you hasn’t been legal currency since 2002.

You look for flights to London.

The guitarists of London aren’t nearly as talented, which is a relief. But then again, you’re not really sure busking is for you. There’s a lot of homeless folks who mingle in with the buskers, and you’re not sure how that’s gonna be for your brand.

Your brand which you’ve had the most brilliant idea for. The point of digital nomadship, you’ve realized, is not to stay long in any one place. To leave as soon as the mind or body wills it. The shift to London wasn’t about some failure in Madrid, but rather a move forward, onward.

Maybe there’s more similarities between the homeless of the world and you than you think. Working out of libraries, never sleeping in the same bed for more than a few days. That kind of unwashed hair look.

You’ve started taking some photos for Insta and made a new account. You’ve subscribed to Adobe Creative Cloud. You haven’t posted anything yet, but it’s only a matter of time before you find that perfect first photo.

You need that thing that makes you unique.

Unfortunately, it wasn’t the guitar.

But that doesn’t mean you’ll stop looking.

A couple days into London you realize that the only cafe that consistently lets people sit in all day is Starbucks. You try to ignore that icky American feeling that comes with working out of a Model-T bean factory.

In your new office, you’ve begun to understand the rules:

  • Open bathroom doors so, so, so slowly.
  • There’s a hard, three-adjective limit to drink orders.
  • If someone peeks into the window, they should be barred from entering.
  • And so on.

    You surprise yourself with your rule list. It’s funny, you think. So, you gather up a bunch of London photos and post it as an Insta story, to see how it will do. No post yet—just testing the waters.

    A couple people see it, but nobody reacts. All your followers so far are just people from your main.

    You sigh, world-weary.

    It’s in Amsterdam that it hits you. You can pay for followers.

    Like, not forever, but just for an initial batch. People have social media managers all the time. Just a few followers from the right crowd, and your content will go viral, you figure.

    So, you hire a few people—just temporarily—to build up your digital presence. A real business, you realize. I’m supporting myself.

    Just one problem. Your Insta isn’t making any money.

    The thing is, you don’t really believe in monetizing content. The words you craft, the art you make, the music—that should be free for anyone. But you need to be profitable: you’re getting tired of only having two USB-C ports.

    It’s late-night TV that saves you. You’ve been learning some Netherlandish—the subtitles help—and you catch just enough for a brilliant idea.

    See, there’s all these celebrities selling hand lotions and body soaps and frozen dinners. Why couldn’t you get a sponsorship like that?

    You make a few more hires. Strategic, minimal. Trying to stay as true to the digital nomad lifestyle as possible. You land a deal. Well, your agent lands you a deal based on your last name, but it feels very earned.

    You’ll be the public face of Birkenstocks. All you have to do is keep traveling, keep posting to Instagram, and take pictures of your feet.

    Finally. Real work.

    In Paris you decide dreads will help you be more woke. You’ve taken to reading critical race theory in between work and sipping pumpkin spice lattes.

    Let’s be honest: you’re terrified of being cancelled.

    When a someone sporting a different skin tone than you sits near you, you smile. You ask him to watch your things when you go to the bathroom, and you feel good about the trust you’ve built in society, bridging racial differences. You return and smile again at him. He doesn’t smile back. He moves to another table.

    Progress is slow, you think, but definitely happening. As if in answer, a sunbeam comes through the Starbucks window.

    The job is harder than you thought it would be.

    You decide it’s time to really get lost somewhere different. You wander over to Egypt, to rest from the hubbub of technology and go into the wilderness of the soul. Of the desert.

    Plus, the Birkenstocks and pyramids picture gets you enough buzz to take a little break.

    You lay off your social media managers. You look everywhere for a camel, but it turns out everyone drives here, just like everywhere else.

    Your Uber driver shows you a picture of yourself on his iPhone. Some headline about firing employees without severance.

    Back in your hotel room, you break your digital fast to look up the word severance. You tweet a statement saying it was an honest mistake, that you didn’t know, that it’s been remedied now. This does not make the situation better.

    When you go live on Insta to talk the people down, they point out your terrible sunburn, which mostly derails the conversation into mockery.

    As much as the Internet hates you, the Egyptian shopkeepers seem to love you. People wave at you on the street, smiling. Everyone speaks to you in English.

    You didn’t know it was such a civilized place.

    The only problem, really, is that you have to keep buying water bottles, because the hotel manager said the tap water is temporarily not good for drinking.

    You could stay here for a while, you realize, adjusting the A/C by the window. You look down on the city and think, really, how small everyone’s problems are—even yours.

    Before you check out of your hotel, you make sure to stack all the empty water bottles neatly against the wall. You laugh. There’s enough there to float someone across the Mediterranean.

    The next few countries pass by in a bit of a haze. In memory, you struggle to differentiate between South Africa and Nigeria, Greece and Turkey. There was a girl you dated in one of them, but not for very long. Everywhere is starting to look like not-home.

    You try Canada, but it just kinda feels like Minneapolis.

    It’s at this point that you have another realization. There’s nothing wrong with being a digital nomad in the States.

    You don’t tell your parents, but they figure it out from your Birkenstock reels. Your dad calls, tells you, now that you’re back it’s time to get a real job. To work for the family. He knows a guy who can scrub your feet right off the Internet.

    You weigh your options. Being a nomad, however digital, has been harder work than you thought. You’ve developed some nasty callouses from walking around in sandals all the time. Was this how Jesus felt?

    You’re back in LA anyway, and your dad’s company is just a few blocks from the hotel.

    The Uber Lux is a Tesla, and you realize you’ve always wanted to drive an iPad. On a whim, you ask the driver to buy his car. The guy laughs and names a price. You make the bank transfer in front of him.

    You pull up to your dad’s office building in style. You’ve put on a suit, loose-collared. Some real shoes. You’ve come full-circle, but with real-world experience now. Who hasn’t taken a gap year to figure some things out?

    Plus, the job’s not as hard as you thought it’d be.