Why continue to travel as a nomad

once you’ve decided to settle down?

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Hey folks,

This is a post about the hardest thing I’ve faced as a digital nomad.

It's been a while since I’ve written about, or really even thought about, travelling and my nomadic lifestyle.

The last time I was on the road was back in March this year. I got a sudden call that my dad had been taken ill in hospital. Between then and now, I've pretty much been back on home soil the whole time. My dad passed away. And then I had to get ready for my wedding, which took place this weekend at my wife’s family’s place in Denmark, so it's been months since me and my wife have felt like the full-time working travellers that we were for all of 2023.

We're getting back on it, going to Tokyo for five weeks in November, and at that time of year, even the vaulting crystalline skyscrapers will be no match for the explosive superabundance of burnt gold, yellow, red, and orange autumn leaves. We’ll get lost in the 7-Elevens, slurp ramen and tsukemen, and wander around the neon-lit labyrinths and warrens. We'll ride the air-conditioned subway trains under roads and over viaducts, listening to that familiar yet alien announcement wrapped in my favourite Japanese sound that I still can’t decipher—something like "massimass."

Thinking of Tokyo, I'm struck by how much more it excites me than any other place on earth, visited or not. We can't wait to go. And we've already started reading books, watching videos, and listening to podcasts all about it.

But we have an issue. And the issue can be summed up in one simple question:

What are we doing in Tokyo?

We've got to decide where we will stay, what we will do, and why we will do it. And it turns out that as digital nomads, this is actually one of the most perplexing decisions you have to make.

I've thought about why this is.

Firstly, there’s too much freedom. When there are literally hundreds of countries you can go to, and when you come from a country with a relatively powerful passport like Denmark or the UK, it's pretty much limitless—not to mention your economy gives you huge arbitrage all over the world. You really are spoiled for choice, and that freedom can be overwhelming.

Related to this is the privilege that comes with it, which we both feel keenly. Whereas some people are forced into nomadism by war, such as the Ukrainian guy Maxim who we met in the Chiang Mai coworking space, we've chosen to do this of our own volition because we have the freedom and resources. And so there's an element of wanting to atone for the guilt we feel for being in such a privileged position.

On top of all this, we learned very quickly on the road that without some sort of mission or project, nomadism can start to feel aimless and meaningless.

All in all, it's turning out to be very tricky deciding where to go and what to do in Tokyo. This post is an attempt to unpick that problem.

If you live a settled life in one place, and you go to Tokyo for a holiday, then it's pretty clear where you'll stay and what you'll do. You'll stay within easy access of holidaymaking amenities—restaurants, parks, museums, shops, transport hubs, etc—and you'll split your time between planned touristy things and unplanned touristy things: eating, drinking, cavorting, visiting shrines and waterfalls, buying merch, taking pictures, and generally making all the people back home red with envy.

Your whole MO as a holidaymaker in Tokyo will be to unwind or, put another way, to avoid having to think too long about reality, which includes work, general life admin and relationships with folks back home.

When you're on holiday, you also tend to avoid deeper questions about your purpose and your dreams. But as we all know, the counterintuitive thing about holidays is that it's precisely because you unplug and disenthrall yourself from reality that you end up, by the end of your trip, having those very existential crises, questioning your life back home, your job, your friends, and your decisions.

Probably you'll return home from a holiday inspired in some way to change something, however small, and the holiday will have served its purpose, so to speak. The momentary rest from reality gave you the distance you needed to renew it, to catch issues before they got worse, and to seize opportunities before they evaporated.

Generally speaking, this is what happens on holidays, and that's why, on the whole, it's not so tricky to decide the wheres and what-fors of a Tokyo vacation. Holidays have a blueprint. They are departures from the norm. And you actually have to work pretty hard to fuck a holiday up.

But when you're a digital nomad, when you're going to Tokyo, as we are, as part of an unpunctuated and as-yet endless train of nomadic trips, then there is no blueprint. There is no departure from the norm since travel is your norm. And it's very easy to end up feeling like you're fucking everything up.

The fastest way to fuck up your nomad trip is to try to make it a holiday, or to adopt the holidaymaker’s mindset. This is because you're not trying to escape or take a break from anything; you're actually trying to get on with your real life. And therefore, the activities that typify holidays—eating, drinking, sightseeing, lounging around—don't fulfil you, at least not for very long. They eventually start to chip away at your self esteem.

For life as a nomad to be meaningful, you need more substance, and the substance has to come from the reality-related things I already mentioned: work, relationships, and purpose.

Once you've done enough nomadic trips to work this out, this important insight scurries upstream like a giddy salmon and starts to form part of your whole planning and decision-making process when you're deciding where to go. And so the question of "What are we doing in Tokyo?" starts to take on a whole new shape.

It’s not “Where is the best spot for unwinding?” but “Where is the best spot for engaging?

It's not "How can we put work out of mind?" but "Where can we do our best work?"

And it's not "Which places will impress us and the people back home?" but "Which places will we find new friends and opportunities in?"

Another way to think about the difference between booking a holiday to Tokyo and booking a nomad trip to Tokyo is the difference between fashion and function. Holidays are like going to the shop to buy a designer coat, while nomading is like buying a mountaineering jacket.

One purchase is frivolous, pricey, intuitive, and short-lived. The other is considered, economical, rational, and long-lasting. One’s about looking good, the other’s about being good. One pampers today’s version of you, the other nurtures the future version of you.

The metaphor breaks down a bit, I admit, but there is still a lot of truth in it. And this is what makes choosing where to stay and what to do in Tokyo, for us, much higher stakes than it may sound.

There are two levels of abstraction where this high-stakes decision-making operates.

The first level is the city of Tokyo itself, zoomed in and bounded by the five-week duration and the particular time of year. All these questions of work, relationships, and purpose prime and shape every decision we will make about Tokyo, and will become the criteria by which we judge how successful it was as a destination.

The second level of abstraction is more zoomed out. It’s about the role and impact that Tokyo has on our reality as part of, and in relation to, the other places we visit within the year. These same questions of work, relationships, and purpose are every bit at play in the grander scheme of things and across longer time horizons.

It means that questions about what we're doing in Tokyo ultimately ladder up to questions about what Tokyo is doing in our life more broadly, since, to reiterate, as nomads, we're not escaping reality, but investing in it.

When you're planning a trip to Tokyo as a nomad, you're not postponing your goals and personal growth; you're actually paying them your full and undivided attention. So questions of where we'll be and what we'll do need to start from there.

We just got married. We're trying for kids soon. We're both in our 30s, and we no longer have a decade of freedom to travel around without considering where we'll raise kids. Naturally, we've started thinking about our proverbial “village.” Neither of us wants to return to our hometowns or even our home countries. And having discussed it, we think that Spain ticks a lot of boxes.

We love Spain’s climate, culture, food, and language. It's close enough that friends and family can visit or be visited. And it's got good direct flight options to Central and South America, where we can continue to enjoy travelling and practising our Spanish.

Our goal is to settle in Spain, perhaps around Barcelona or Valencia, learn the language, and find our community.

For this, we've earmarked up to six months in two stints for visiting Spanish towns in 2025. It could, and probably will, take much longer and throw up all sorts of dead ends and surprises. But that's our plan.

With all this in mind, where does that leave Tokyo?

Before we'd made our Spain plan, any place we visited, no matter how exotic or far away, had the potential to be a settlement site for us.

This was particularly true when we were in the earliest stages of digital nomadism, thrilled by the novelty of it, lured towards ever newer destinations, and blind to the fact that, in reality, there were always going to be factors determining roughly where we'd end up and constraining our options somewhat—proximity to family being one of the main ones.

Now that we know we definitely will not settle in Tokyo, it means we have to approach it differently once again. On the one hand, it's going to be nothing like a holiday for all the reasons I gave above. But neither is it a potential home base, and this changes things profoundly.

It feels to us now like we ought to somehow incorporate our Tokyo trip into our Spain plan.

Maybe you're thinking, "Why don't you both just relax and enjoy Japan? Treat it like a holiday before you settle down." And I know that sounds simple, easier, and enjoyable.

But honestly, we know that it won't be any of those things beyond the first week if we fail to attend to the real issues in our lives: work, relationships, and purpose.

Settling in Spain, there's a lot of work to do—a lot of research and writing and conversations to be had. And we feel it would be foolish not to use the opportunities we have now to move our Spain project forward. If we don't, we're just delaying it and kicking the can down the road.

Not only that. The prospect of combining our Tokyo experience with our Spain plan sounds more interesting than not doing so. It's always most interesting at the intersection of ideas.

And doing so would make our social life a lot more interesting too. Even just telling people we meet in Tokyo about our plan to move to Spain will end up colouring our experience in a specific set of ways, open certain doors, and set in motion events and situations very different from those of an aimless nomad.

As I've written about before, when you have a goal, a mission, a project, or an anchor for the mind, people open up to you more. It's because goals and projects show them more of who you are. By placing value on something, you're revealing your tastes, beliefs, decisions, and skills. And when you reveal, rather than conceal, people have an easier time trusting you and wanting to hang out.

Put yourself in their shoes. If you were in a Tokyo bar and someone was about to walk in who you knew you had to spend the whole night drinking with, would you rather it be:

a) a holiday maker who just happened across the bar?

b) a digital nomad who's travelling full-time but has no notable aims? or

c) a digital nomad who's on a mission—a mission to, say, eat a certain soup in every town across Japan… or hike across the country tracing the route of its longest subterranean internet cable… or take photos of tiny villages that are disappearing due to climate change… or investigate which towns in Spain they’d like to raise a family in?

Each of those is a real example of projects that travellers have had. And a traveller with a project is not only having a more fulfilling experience themselves, they're more interesting to you too, more approachable and more memorable.

The mission can be anything, except "not having a mission." That's what holidays are for, remember? Holidays are goalless. Nomad trips are goalfull.

So, to loop back around to my question: what does our Tokyo trip mean for our Spain settlement plan?

Does it mean that we'll end up spending most of our time being in Tokyo but thinking about Spain? I hope not. I would like to be present and mindful of Tokyo while I'm there.

But it could easily happen. We do have a tendency to dwell on the next place and to spend a fair amount of time planning for the onward journey.

And there's another sense in which you often dwell on someplace other than the one you’re in: you dwell on home. The place you're travelling in is always in conversation with home. Most obviously, it's a point of comparison:

“Beer is expensive here!” [compared to home]

“People here get three years of maternity!” [compared to home]

“Did you know they have two-hour lunch breaks here?!” [compared to home]

When you're comparing and contrasting as a holidaymaker, deep down you know that you're not really going to pack your bags and relocate there. So, all of your fantasies about living in Tokyo or Tijuana are a bit like flirting. They are a promise without a guarantee.

But when you're comparing and contrasting as a nomad, you have already relocated. You've skipped past the flirting stage AND the dating stage and instead moved straight in together. Nomadism is the lifestyle design version of Married at First Sight.

In fact, it's actually more serious than that even, since contestants on Married at First Sight know it's just a TV show—they're not expecting to keep marrying different people at first sight until they find a match. Whereas, as a digital nomad, that's exactly what you're doing. Before our Spain plan, we were marrying different destinations at first sight, hoping to find "the one."

And we took our marriages seriously as nomads, which meant that each time we entered into vows with a place, our goals and projects coalesced with them.

What does it mean to commit to Tokyo when we're already betrothed to Barcelona?

Should we view Tokyo as a stag do or bachelorette party? That does sound fun. But it doesn't feel quite right. It feels too holiday-ish.

Should we view Tokyo as an affair? Go all in for a month-long romance and pretend like Spain doesn’t exist? Again, it sounds fun, but it still doesn't feel right.

We think that Tokyo has to become some kind of preparatory step that enables and supports our happy marriage with Spain.

Summing up now.

I said earlier that a nomad mission can be practically anything. But in reality, we’re convinced that our most important and urgent life goal—finding our “village”—should be informed by our Tokyo trip.

I’m gonna be thinking about questions that can guide our planning of Tokyo (and beyond):

• What are the most prevalent and relevant Japanese rituals and beliefs that we can learn from on our mission? How, for example, do concepts such as wabi-sabi and ikigai inform community building?

• And what could we give to Tokyo in terms of our own energy and output that would create meaningful learning experiences for us and those we meet?

Quick thought experiment: if we were still settled in London, if we had never travelled and we weren't going to travel anywhere before moving to Spain, what would our Spain planning process look like? How would we go about answering our Spain-related questions and what resources would we leverage?

Probably we'd lean heavily on internet research as normal. We'd reach out to people in our networks who've moved to Spain and ask them for help. And we'd visit Spain armed with a plan—a plan that we would have put together from the singular vantage point of life in London.

But then if you said, "Hey, as part of your research, you can go visit Tokyo for five weeks," then how would we make the most of that? How would that impact our perspectives and our planning? And what could we learn in Tokyo that only Tokyo could teach us?

Lots to chew over!

I'll pick up this Tokyo-Spain thread again in a few weeks' time once me and Corina have done more research and had more conversations about it.

In the meantime, if any of you, my subscribers and followers, have left your hometowns and either found or created a community in another country, please will you get in touch with us? Let's start a conversation.

And if you're a digital nomad who struggles to choose where to go, for any of the reasons mentioned here or any of your own, I'd also love to connect and share insights and ultimately support each other.

It is a very privileged position that we're in, and the last thing I want to do is take any of it for granted.

So, please don't be shy. I definitely want to talk to you about this, and you can either email me, DM me in Substack, or leave a comment below. I’ll reply to every one.

Thanks for supporting The New Workday. I’ll see you next time.

Harrison x

⬥

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