12 Things I Wish I Had Known About Long-Term Travel

Are you considering long-term travel? Then this is the article for you.

I have been on the road almost nonstop since early 2015. It has been an extremely rewarding but also sometimes challenging experience.

Most of these challenges I did not even foresee. Had I, I could have saved myself a lot of headaches.

You can.

Learn what types of long-term travel there are, why it’s so hard to get started, and how to deal with loneliness on the road.

After reading “The 4-Hour Workweek” in 2007, I fell in love with long-term travel. Or rather, I fell in love with the idea of it.

Fresh out of college, I had just started my first business, an MMA gym — about the least portable business model you can imagine. There was no way I could go off and travel the world with a backpack.

Yet, the idea wouldn’t leave me. I was both in love with it and mortally afraid of it. How would I pay for it? Wouldn’t I get lonely? Could I even manage in a strange country without speaking the language?

This internal monologue went on for eight years, until finally, in late 2014, I sold my gym and got on the road.

It was all I had imagined — and it wasn’t some. Some aspects of it blew my mind, like the people you meet. Other aspects I had not even foreseen, e.g., how hard it is to keep up your habits while traveling or how difficult it becomes to be in a relationship.

If you are on the verge of starting long-term travel, I hope I can spare you some of these trials. This is the article that I wish I had read when I started long-term travel.

1. Just Do It

When I tell people that I am a long-term traveler, I often get reactions like, “Oh, you are so lucky. I wish I could do what you do.”

The truth is, you can.

People don’t just stumble into traveling. At some point, they make a commitment that this is what they are going to do with their lives. Then they take the necessary steps.

The real problem is risk aversion.

People are hesitant to make this kind of fundamental lifestyle change. Before they do, they want to have a financial cushion. They want to know how exactly they are going to earn while they are traveling.

And while it’s certainly a good idea to have some savings and a plan, ultimately, you just have to do it.

Because that is how it works — you start traveling. Then you figure out the details.

Understand — there will never be a perfect time to start long-term travel. You need to get your feet wet, aka get on the road.

And yes, in the first few years, there will be a lot of uncertainty. You will work long hours as a freelancer, barely getting paid, while having to take on terrible projects.

Just to give you an idea — for a while, when I was still working as a freelance copywriter, I would write about bolt guns to kill cattle with. That bad. Even I started to wonder if this travel thing was a crackpot idea after all.

But if you keep at it, better projects will come your way. Your financial situation will improve. You will have more options while also being able to save some money.

Those who take the plunge will get rewarded. Just do it.

2. Backpacking vs. Digital Nomadism

Long-term travel comes in two flavors — backpacking and digital nomadism. The line is sometimes blurry, but there is a line.

Backpackers tend to be younger (even though I have met some hippie backpackers who could have been my parents). Think early twenties, right out of college.

In comparison, digital nomads are usually 30+. They usually held jobs before, then got fed up with the 9 to 5 and decided to hit the road.

Backpackers usually stay in hostels. They want to constantly meet new people, make new friends, and hook up. Also, they want to save money.

In contrast, digital nomads usually stay in Airbnbs. To them, a certain level of privacy is preferable. They still like to socialize, though, just not on Khao San Road.

In essence, backpackers are more concerned with fun and adventure. Income is more of an afterthought. They are okay with working as a ranch hand or as an English teacher for a month here and there before they travel on.

Digital nomads are relatively more concerned with their jobs (even though there is still plenty of hedonism to go around). They put in a certain number of hours each day, more similar to the office job that they used to have before.

So, as an aspiring long-term traveler, what should you choose?

There is no right or wrong here. Try both.

I’ve tried both myself and enjoyed them both.

When I started out, I still had some money left over from selling my previous business. So, I went into full adventure mode. I did a lot of exploring and sightseeing, went to bars, made friends, hooked up, etc.

But when my money started to run out I switched over to digital nomad mode. I started working first thing in the morning, got on video calls, and made sure to work a certain number of hours per week, etc.

It was less thrilling than before, but also more rewarding. I was building a new skill set — digital marketing — which I would then apply to my side hustle, aka my personal brand. There was the promise of growth.

I think that is a typical progression. You do the adventure thing first, get it out of your system. Once you have had all the wild nights with other hostel guests that you can take, you switch over to a more sustainable way of traveling.

And, if at any point, you feel like going backpacking again, you just do.

3. Deal With Loneliness

One of the biggest issues with long-term travel is loneliness.

Sure, you will meet lots of new people and will make plenty of new friends.

But if you are only around each other for 4 weeks or so, these friendships never solidify. It is goodbye over and over again.

One solution is to build your personal network of long-term travelers. Then, several times a year, you meet up in different cities all over the globe, and spend a few weeks together. This works well.

There are also paid communities like the DC that facilitate such arrangements. You get to meet other people who share your lifestyle both online and at in-person events. Then you pick and choose whom to sync your travel plans with. 

Another option is to live a semi-nomadic life. For six months or so each year (usually during the winter) you travel. During that time, you do all the usual things — exploring, meeting new people, etc.

But once you have had your fill, you return home where you get to hang out with your regular friends, the people you have known for years. This way, you get the best of both worlds.

Finally, you can visit the same couple of places again and again. Maybe you spend the spring in Rome, the Summer in Berlin, the fall in Cape Town, and the winter in Phuket. If you do that every year, you will slowly take root in all of these places.

4. Adjust Your Relationship Expectations

How do you maintain romantic relationships while you are traveling?

That’s a good question that I am still struggling with myself.

Obviously, this lifestyle lends itself to a lot of short-lived affairs. You meet someone on the road, either a local or a fellow traveler, and you get close. But soon after, you part company. Either you leave or they leave.

I know that within the digital nomad community, there have been attempts to resolve this issue. There are now specialized groups and apps for long-term travelers trying to find love with other long-term travelers. The idea is that you can potentially travel together.

I hate apps. But if you are not opposed to them, that is one way to go.

However, these apps have a fundamental flaw — there are way fewer female long-term travelers than their male counterparts. A screwed gender ratio is already a hurdle with regular dating apps, but these digital nomad apps take it to the extreme. There will be hundreds of male suitors competing for the one-in-between female traveler.

One way around this — that will not be a solution for everybody — is to engage in ENM relationships. By not requiring sexual exclusivity of your partner, they are free to explore other people while you are away. They can get what they are not getting from you from somebody else. This has worked reasonably well for me; some of my mobile ENM relationships held up for years.

However, at some point, most women will want to settle down and have kids. There are of course some exceptions, but those are, well, the exceptions.

As a female traveler, that either means giving up on traveling and settling with a non-traveler, at least for a while. You could theoretically pick up traveling again once your children are a bit older. There are families who make the long-term travel lifestyle work for them.

For male travelers, opting for not having kids is a common solution. I regularly meet 35–45-year-old male travelers who tell me that’s the choice they made. I myself fall into this camp. Of course, there is always the possibility that you might one day come to regret this decision. Time will tell.

5. Embrace Slow Travel

When you start out with long-term traveling, you will go into a frenzy.

You will hop from country to country and from city to city, cramming in as many sights and experiences as possible.

I certainly fell into that trap. When I started out I would sometimes spend as little as 2 weeks in one country before moving on to the next country. It burned me out.

By giving so little time to each destination, you will never go deep. You will be too busy checking off sights and things to do.

But the magic doesn’t happen from working your way through a Lonely Planet guide. It happens when you aimlessly wander.

It happens when you walk through a neighborhood in Da Nang and next thing you know, you are sitting down with a Vietnamese extended family, singing Karaoke together and getting fed with local specialties until you are about to burst.

It happens when you drop your laundry off and you meet this friendly American older gentleman who then continues to tell you about his heydays as a large-scale drug dealer in communist Laos.

It happens when you see an attractive stranger on the streets of London, give her a compliment, and go on a date with her. As it turns out, she is a reality TV star, a world completely different from yours but all the more interesting.

For these things to happen, you need to slow down. You need to create the space for these interactions to play out.

What I typically recommend is that you plan for 4 weeks per city, up to 3 months. That gives you ample of time to meet people and build a deeper connection with them. Your mindset will switch from “I’m a tourist,” to “I live here now.” It makes all the difference.

6. To Save Ahead or Not

Should you save up for your trip, so you won’t have to work while traveling?

The upside is that your days will be wide open. You can freely explore without having to worry about any work commitments.

The downside is you must strictly adhere to a budget. You only have an amount X to spend. Once you run out of money, it’s back to your 9 to 5.

This is why I am not a fan of this model. It doesn’t solve anything.

On the contrary, your travel escapades support your 9 to 5 prison. It’s like being let out on parole. You get to run free a little, so you be an even better corporate slave afterward.

Find a way to pay for your travels while traveling. This way, you get out of the rat race for good.

7. Ditch Planning

I have known people who started planning their trips a year or longer ahead. They would try to think of everything:

  • What is the weather going to be like in each destination?
  • Which hotels/Airbnbs should we book?
  • Which sights do we need to plan for?
  • Which trips should we book ahead?
  • What national holidays are coming up?

I think that is a mistake. The whole point of traveling is to introduce an element of spontaneity in your life. By planning your travels out like it was your wedding, you kill that spontaneity.

What you should do is book your one-way flight and your first accommodation several months ahead, as this will save you a good chunk of money. After that, go with the flow.

8. Uphold Your Routine

While I am not a fan of planning your travels in too much detail, I am an advocate of upholding your habits while traveling.

That’s because habits like working out or meditating each day are what will make or break you. You cannot afford to let these crucial behaviors slide.

And it is especially easy to let them slide while traveling.

First, since you are constantly in a new environment, there will be a lot of unexpected friction.

All the things that we take for granted at home, we suddenly need to figure out anew:

  • Where is the supermarket?
  • How do I pay for subway tickets?
  • Where is the next gym?
  • How do I charge my local SIM?

And a million more things.

When you are so busy figuring out all the essentials, it is tempting to ignore those healthy habits. You just put them on the back burner.

Second, you will be distracted by your new surroundings. There is so much to explore, and so many interesting things to try. So, you indulge your curiosity while your habits fall by the wayside.

To counteract this, you need to have strong mental models. They will ensure that you stick with your habits, even when it is tempting to let them slide.

My favorite is a quote by strength coach Dan John:

“If it is important, do it every day. If it’s not important, don’t do it at all.”

The things you do every day, without fail, determine who you become in the future. If you work out every day, five years from now, you will be lean and strong. If you cold-call a dozen clients each day, five years from now, you will be wealthy.

But if you implement a new behavior, then stop, then continue, then stop, etc., it will be as if you had never started in the first place. There will be zero gains.

There is no point in doing things occasionally. You might as well stop doing them altogether.

Whenever I feel like letting my habits slide while traveling, I will revisit this truth. Then I will go do them anyway.

Also, define your habits in writing. As studies have repeatedly shown, you are much more likely to go through with resolutions if you pen them. It removes any vagueness and anchors the desired behavior in your unconscious mind.

Then put your list of habits up in a place where you must regularly look at it, e.g. in the kitchen or the bathroom. This will further reinforce compliance.

9. Eat Healthy

One of the biggest issues is eating healthy on the road.

There are three factors to consider here:

  1. How healthy vs. unhealthy do you want to go?
  2. How cheap vs. expensive do you want to go?
  3. How convenient vs. inconvenient do you want to go?

In general, it is tempting to eat unhealthy while on the road. That’s for several reasons.

The first reason is that you are in vacation mode and want to treat yourself.

The second reason is that you want to try all of the local cuisine (which is rarely that healthy).

Then there is money. Especially if you are a backpacker/budget traveler, you will have to eat as cheaply as possible; otherwise, you won’t be on the road for long. And that almost always means unhealthy food choices.

Oh, and convenience. If you are moving around a lot, you simply won’t have time to cook. And even if you do have some time, it means you will have to go shopping first.

But often, there is no Western-style supermarket close by. You’ll have to buy your food at local markets, which often don’t carry everything. So, you’ll have to visit different markets and shops. That complicates things.

Not to mention that you might not have all the cooking utensils you need in your Airbnb. You’ll need to buy those as well. But is it worth it to buy a bunch of kitchen gear if you know you will be moving on soon?

Generally speaking, you can have two out of three:

  1. You can have healthy and cheap, but then you are going to spend a lot of time shopping and preparing your meals (inconvenient).
  2. You can have cheap and convenient — think street food —, but then you are going to eat pretty unhealthy.
  3. You can have convenient and healthy, but then you are going to be eating at rather expensive restaurants.

There are no easy answers here; it depends on what you value the most.

What I usually do is define a set of minimum health standards that I won’t compromise on. For example:

  • I will only drink water — no soft drinks, no fruit juices, no alcohol.
  • I won’t eat any sweets (except for fruits and dark chocolate).
  • In terms of carbs, I will eat rice and potatoes, but no bread or noodles.

For me, this is the sweet spot in terms of healthiness, price, and convenience. It is not perfect, but it’s doable. You can eat almost anywhere, it is still going to be cheap, and you are doing some damage control in terms of health.

10. Pack Light

I would really recommend traveling as light as possible.

For example, all the things I own (except for my video gear) fit into my carry-on backpack; the video gear is a recent addition, and I am already pondering ditching it in favor of an ultralight vlogging setup.

Carrying as few things with you as possible will make you ultra mobile. You will be able to switch locations at a moment’s notice. Just throw all of your stuff into your backpack and drive to the airport.

Vice versa, if you are schlepping around, several pieces of luggage — the dreaded frontpack-backpack setup or maybe even several suitcases — every relocation will be a pain in the butt. You will dread every part of the process — packing, getting to the airport/bus station, checking in, walking to your new accommodation, etc.

Stay mobile, pack light.

Here are a few tips:

  • Instead of trying to pack for every weather, just pack a few essentials. You can always buy whatever you need locally (and often much cheaper).
  • Make sure that every piece of your wardrobe can be worn with everything else. Personally, I just buy everything in black. It also makes washing stuff easier.
  • Prefer multifunctional items. My BJJ shorts also act as my everyday shorts and my swimming trunks. A tablet can also serve as an extra monitor and your ebook reader.
  • Get a decent backpack. These things really have to take a lot of abuse. They also contain all your valuable electronics. I have tried different brands but always come back to Osprey. They are not especially pretty or nifty, but they are reliable.

11. Get Travel Insurance

This should be a no-brainer, but there are plenty of people who go on trips around the world without getting travel insurance.

Call me overly German, but this is a terrible idea. If you get into a serious accident abroad and have to get surgery or maybe even be flown out back home, this could ruin you financially, especially since most backpackers don’t have that much money to start with.

Don’t be stupid, get travel insurance.

12. Your Problems Stay With You

No matter how far you travel, your problems will always stay with you.

Your lack of discipline will still keep you from achieving your goals.

Your social anxiety will still prevent you from meeting people.

Your victim mentality will still make you blame others.

That’s important to realize, as long-term travelers are often under the illusion that they can somehow all leave it behind. “I will go to the Philippines and everything will be different!”

No, it won’t. You will still be you.

What traveling can do for you is that it can kick-start change. By exposing yourself to new stimuli, you will be challenged in new ways. Your current set of values and behaviors will come under scrutiny and you might come to revise some of these.

That is incredibly valuable. But it’s not a magic bullet. It will take time.

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