Two big questions asked by aspiring digital nomads is how to take the plunge & how to choose the next destination. You can plan everything ahead, even though it might eliminate the element of spontaneity, or to just go with the flow and deal with any unexpected inconveniences as they come. Sort of like a challenge.

When Eli and Dan were recording this episode, they each had a different stance on this important question. They were both in Europe at the time. Eli was in Spain, trying to escape the cold of the Old Continent, and Dan had just arrived in Berlin, where he planned on settling for longer than he ever had since adopting this nomadic lifestyle.

A very interesting conversation developed as they shared their experiences and plans for the future, which quickly evolved into reflecting on the meaning of each person’s experience.

Listen to the full pod here: Choosing Adventures: Plan Ahead or Carpe Diem?

Different Perspectives on Choosing Nomadic Destinations

Although being a digital nomad implies, by definition, a lack of a fixed structure, some people are great at planning ahead even in the most chaotic situations. But others thrive in uncertainty and like living day by day.

Eli introduced this topic of discussion when he mentioned off-handedly that, whenever he left his home base in his native Israel, he did so having no idea where he would go next. He was never good at planning too far ahead, but he also found that the few times he did, he didn’t enjoy it as much. He always found himself kind of discouraged whenever he saw his calendar full of future plans, preferring to be free to hop on any spontaneous plan that might lead to a great new experience.

While Dan understood the sentiment, at the time they recorded the episode, he was really looking forward to some sense of routine. He had spent the past two years bouncing around different cities in the United States, and Berlin brought both a change of scenery and the comfort of a city he could find himself setting a semi-permanent base in.

“Even just walking to the grocery store (here) gives me a thrill,” he joked. In all seriousness, though, Dan made a big commitment moving to Berlin. The apparent reason was to get his Master’s at a university there, but he freely admits that that was partially an excuse. He wanted to be able to live in a new and exciting place, but still have something that tied him there. He defined it as a way to become “semi-nomadic”, and Berlin was the perfect place for that.

Finding A Place That Matches Your Energy

As the conversation expanded on Dan’s bold move to Germany, the topic of picking the right city came up.

Whether you’re rolling the dice on how and where you want to spend the next month or so of your life, or you have a specific goal in mind about the next step you want to take, it’s always important to be in tune with the energy of the place you’re staying at.

Research can be useful for that. It doesn’t have to be extensive, maybe just ask a few friends or read some comments online about certain cities. Those experiences don’t always match with yours, but they’re good references to have when choosing nomadic destinations.

For instance, Eli shared that, while he liked Valencia well enough, all his friends who visited came back telling him that he would feel right at home there, and that wasn’t what happened.

Dan had the opposite experience with Berlin, which was lucky, because he would spend a long time there. Most people describe the city as a nomad and global hub, the perfect place for both expats and tourists. The city is energetic and vibrant, and Dan found he had great chemistry with it. Which is, honestly, the most important thing.

Most of the time, as Eli eloquently put it, it’s not about the place, it’s about what you’re looking for, and therefore how you will connect with it. And that can change in just a few years, because human beings change constantly, so don’t dismiss any destinations until you’ve tried them at least twice.

How To Choose The Next Nomadic Destination

Cautious or impulsive… There always might be a reason to choose one place over another.

There are practical reasons, of course. If you are a remote worker who depends on having a good internet connection for your livelihood, then you probably won’t stay at a rural, disconnected place for weeks on end. Or, if you are sponsored to go somewhere, that might take the decision off your hands.

But still, there are always personal preferences, even for choices that might seem random. Planners mostly have it easier when it comes to choosing their next destination. They sit down and analyze the pros and cons, and have an idea of what their next steps will be after arriving wherever it is they decide. But it might be harder for the people who don’t have that ability, or that find that the meticulous planning sucks all the fun out of the process.

Luckily, Eli has them covered. He explained his process for choosing nomadic destinations, which basically consists of establishing a few broad guidelines that don’t feel restrictive but still orient the search so it becomes less overwhelming. When he first became a digital nomad, Eli wasn’t picky. He had two rules: 1) find the cheapest ticket to the cheapest destination, and 2) it had to be a place he had never been. Easy, right?

Of course, with time, he became conscious of other things, such as the time of the year he was traveling, and what that would mean for the chosen destination. Also, and more experienced nomads will be able to relate to this, the social aspect becomes relevant. When you’ve been traveling for a long time you’ve most likely formed relationships in different places. Will you be able to connect with them where you go? Can you coordinate your travels with them? Nomadism is often solitary; don’t underestimate the importance of meaningful connections.

Another thing, and this is also part of what we discussed about the chemistry with the city you’re visiting, is taking into account how receptive you think the place you’ll be traveling to will be.

Can you speak the language? Is it somewhere nomads tend to visit? Are the locals used to expats? Again, not a lot of planning is needed to know this, just a few quick Google searches.

Also, ironically, hashing out these details might allow you to be more spontaneous later. If you know you’ll have someone you like in the next destination, you’ll probably be able to go on adventures together. If you speak the language, you’ll probably make friends quicker or enjoy more of what the city has to offer. If you visit a cold place in the Summer, you won’t risk having to miss out on attractions because they’re closed due to the weather. Something to think about.

Finding A Balance When Choosing Locations

At the of the day, there is no right way to be a nomad. And just because something worked for you a few times, it doesn’t mean you have to hold on to it when it doesn’t anymore. You won’t be any less spontaneous if you feel uncertain about something and want to have a game plan when choosing nomadic locations.

Sometimes having a safety net can make things more enjoyable. You won’t drown if you let yourself go with the flow. You might end up finding new adventures you wouldn’t have experienced if you’d adhered to a rigid schedule.

Sometimes it’s great to know what the future holds. It builds expectation and you enjoy it even before it happens. But there is also something beautiful in the feeling that everything is possible, and you shouldn’t feel guilty about either option.

Every traveler will find meaning in each trip in their own way, and whatever it is, as long as you feel fulfilled with it, will be worthwhile. Don’t let anything — neither other people’s opinions nor your own beliefs — keep you from enjoying your very best nomadic life, no matter what that looks like.