The impossible question I'm asked most often about being a digital nomad—and my best attempt to give some useful answers to it

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FOR THE TWO and a half years I’ve been travelling, no question has confounded me more than the question of where to go. Overwhelming choice, fear of missing out, and unpredictable urges have often made choosing a destination feel confusing at best.

Two friends who are getting ready to travel asked me this question and it gave me the chance to reflect. As I see it, there are four ways that I’ve tried to approach it myself, with varying degrees of success, including (1) knowing my escapes, (2) prioritising the right priority, (3) creating a purposeful mission, and (4) relinquishing control.

Method 1: Understand what I’m running from, and to, and why

At the start I didn’t realise that what I was mostly looking for was anything that was different from here. “Here” was London. I’d lived there for ten years, studying, startup-ing, and squeezing onto crowded buses. By the time travel finally came a knockin’ I thought to myself, “All I want is sun, sea, sand, and sangrias. It’s as simple as that!”

But it was only simple in hindsight. Back then I definitely felt stupefied by all the possibilities. There was no precedent for any of it. And the whole enterprise felt like nothing but a giant leap into the unknown. Thus it blinded me from one of the most obvious ways to determine where to go: how much it contrasts with where I currently am.

Now I know one simple approach is to ask myself what three things I am trying to get away from, and what three things I am trying to get towards in a new location. Climate, tempo, cuisine, language, art, infrastructure, people, budget—the question is: what do I want next?

When I’m overstimulated, I crave the beach. When I’m too much in my own head as a writer, I crave the buzz of co-live houses. When I haven’t cleaned myself properly in a month because I’ve been practically living in my flip flops and having cold showers, I crave the robust and heated bathing facilities of a hotel in the city.

My friend (the one who asked me the question that sparked this piece) said that because his small town offers only what is “necessary,” he craves big cities where he can find activities that are interesting because they’re not strictly necessary. He’s onto something. So, think about it, what do you not have now that you’d like?

Method 2: Prioritise my needs, not travel

Initially it was tempting to think that my new-found freedom was the most important thing in the world. Almost like my new identity. It was as if my work, relationships, and health, whilst obviously still important, were no longer my main focus. This is how the professionals do it, right?

Actually, that's not true. Once I’d been travelling for long enough to outtravel the honeymoon period, I realised the things that have always been most important to me were still the most important. “Travel isn't the project,” I said with a slap of my wrist, “travel’s just the backdrop against which other projects thrive.”

I needed to identify my non-negotiables for being a functioning human: air conditioning, reliable Wi-Fi, proximity to restaurants, regular fresh fruit and veg. I don’t like working from home so I need nearby cafes and co-works. Those spaces must have comfy seats and quiet zones. And I need space outside to run in the mornings. And safety’s important too.

Once I figured this out, some locations became obvious whilst others were ruled out. Goa was a case in point. I went there thinking I was some vagabond who could follow the wind. But unreliable Wi-Fi and inescapable humidity made work too difficult. I left India early and imagined returning when I could give that big, ancient country the attention it deserves.

To be honest, there aren’t that many places I can go that are off the typical nomad trail (the trail being essentially towns with thriving cafe cultures). Whilst Oaxaca, Lisbon, and Chiang Mai are certainly very different, my digital nomad needs demand a lifestyle in each place that isn’t so distinct. On the one hand that’s kinda shit. But from a decision-making standpoint it’s good as constraints make it easier to choose.

But are those constraints enough?

Method 3: Create a purpose-driven reason to visit

Creating a mission or project, what I call “mission-based nomadism,” is hands-down the most meaningful way that I’ve travelled. Nothing has been more effective at breaking down the cultural or linguistic barriers that would otherwise exist, and deepening my connection with local people and their customs.

It gives you, as a stranger, a unique story and position in the communities you visit. It's easier for people to trust you when you tell them about you project. Eating soup in every town in Moldova. Walking across the U.S. Tracing Africa’s longest underground internet cable. Photographing disappearing villages in rural Asia. These are all missions that travellers have invented to decide where to go and enrich their expereince. So my question for you is: what ideas do you have?

Me and my wife invented a mission early in our journey because we began to feel lonely. We needed to connect with locals. We needed to give ourselves some more discipline and purpose. So we interviewed local business owners and wrote city guides based on their perspectives.

We went from “enjoying lockdown with better scenery,” as my wife neatly called it, to living with a Oaxacan mezcal producer, dining with a New York gelato mogul, and being hosted (free of charge!) in a 5-star resort by a Dominican hotelier—all because we made local people the heroes of our story instead of us.

It doesn’t really matter what your mission is. Just consider your skills and interests and come up with something specific. Then use it as your entry point into destinations and conversations—and watch how doors open for you.

A word to the wise though: try not to make your missions too ambitious, otherwise they’ll add more overwhelm. Which now makes me wonder: where else am I over-engineering my travels? 🤔

Method 4: Ignore methods 1, 2, and 3

A common battle me and Corina fight is over navigation. We’re trying to get from A to B, we both assume control, and invariably we end up bickering over the best route. It’s a fight we’ve fought on many terrains. But it reached its fiery climax in ‘23 during a routine commute through Osaka. We were screaming at each other in the middle of a busy metro station, standing in the way of hundreds of annoyed Osakans.

I said, “FINE! YOU can navigate EVERYWHERE from now on!”—a decision made in the heat of a tantrum, for sure. But we tried it for a week, and something amazing happened. I learned that I didn’t need to be in charge to feel like a man. And Corina overcame an old story about not being good with directions. I also discovered that being led allowed me to think about other things, like my writing, in a way that being in control didn’t.

Travel's greatest appeal, in my opinion, is the promise of adventure and discovery. Not just discovery of new places, but of who you are by encountering new versions of yourself, like the less controlling, more flexible me I discovered in Osaka.

Choosing to be less controlling over your travel destination and instead “going with your gut” is a perfectly principled way to do it. Forget what you’re running from. We’ve chosen the beach in Mexico, the financial district in Bangkok, and a remote island in Okinawa, simply because our instinct told us to.

Following what's interesting leads to unexpected rewards. In life, what we’re proudest of now is probably not what we planned when we left school, and travel can be approached in just the same way. Many legendary travellers, like Rolf Potts and Rita Golden Gelman, would insist on it even. They’d say that the most remarkable travel experiences should not be planned too much.

You can apply this principle at every level too. We’ve picked countries and towns based on a generalised impulse. And once we got there, we’ve spent afternoons walking around without a plan, following the colour pink, experiencing a destination like an interesting conversation instead of a rehearsed script.

Now that I think about it, this final method might be the most important.

So there you have it. But the question of where to go is still very slippery, even after two and a half years. Tellingly, I’ve noticed that when I start to feel like I need to know where I’m going and why, it usually coincides with me feeling stressed in other areas of my life. I become more controlling the more stressed I am.

I wish I could finish this piece with a neat bow on top and a clear signpost for guiding other nomads towards decision-making nirvana. But my honest view is that the difficulty deciding where to go stems from a broader social problem. Many of us who can travel are facing what the writer Michael Easter calls a “crisis of comfort.”

The fact is I am so privileged relative to most, with so much freedom, I’ve begun to accept that the struggle of choosing where to go is the price I must pay for it. To think that I can solve this problem too? And have every single part of the travel experience just the way I like it? Nah. I don’t think so. That’s taking one too many liberties.

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just me and Corina last Saturday sippin’ vino tinto in Mexico’s leading wine-producing area, as you do. If you’re still struggling to choose where to go, you could always start here

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Thanks to Brandon at

Brandon’s Substack

for reading drafts of this.

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