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

Are you toying with the idea of long-term travel? Then this is the article for you.

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

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

You can.

Learn what types of long-term travel exist, 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 the idea of long-term travel.

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

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

This discussion with myself went on for eight years, until finally, in late 2014, I sold my gym and hit the road.

It was all I had imagined — and it wasn’t. Some positives blew my mind, like the people you meet. Some negatives I had not anticipated, e.g., how hard it is to keep up your habits while traveling.

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

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. You simply make a decision, “This is what I’m going to do with my life.” Then you take the necessary steps.

The real problem is risk aversion. Specifically, it’s about money. Most people want to know exactly how they are going to earn while traveling. They also want to have a comfortable financial cushion before they leave.

And while it’s certainly a good idea to have a plan and some savings, ultimately, you just have to do it. Because that is how it works — you start traveling. Then you figure out the details.

You must embrace the uncertainty. Because that is what the first few years will be like. You will work long hours as a freelancer, barely scraping by.

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 even be able to save money.

Those who take the plunge 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 it exists.

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

In comparison, digital nomads are usually 30+. They held jobs before, then got fed up with the 9-to-5 life, and decided to try something new.

Backpackers usually stay in hostels. They want to 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 important. They still like to socialize, but rather at a rooftop bar than on Khao San Road.

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

Digital nomads are 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 akin to the office job that they used to have.

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

There is no right or wrong here. Try both.

When I started traveling, I still had some money left from selling my MMA gym. So, I went into full backpacking mode. I did a lot of sightseeing, went to bars, made new friends, hooked up, etc.

But when my money started to run out, I switched over to digital nomad mode. I would start working first thing in the morning, take video calls, make sure to put in 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 at the time, digital marketing. There was professional growth. Also, after a while, there was cash flow.

This is a common progression. You do the adventure thing first to get it out of your system. Once you have had all the wild hostel nights you can take, you switch over to a more sustainable way of traveling. But, if at any point, you feel like reverting to backpacking, you can.

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 for four weeks or so, these friendships never solidify. It is an endless string of goodbyes.

One option is to build a network of long-term travelers. Then, several times a year, you meet up in different cities all over the globe. There are communities like the “Dynamite Circle” (terrible name) that facilitate such networks. You get to meet other nomads through their forum and at in-person events. Those you like, you stay in touch with. 

Another option is to live a semi-nomadic life. For six months each year (usually during the winter), you travel. During that time, you do all the adventure stuff — exploring a new culture, meeting new people, etc. But once you have had your fill, you return home where you can hang out with your old friends. This way, you get the best of both worlds.

A third option is to revisit the same couple of places. Maybe each year, you spend the spring in Rome, the Summer in Berlin, the fall in Cape Town, and the winter in Phuket. Over time, you will build circles of friends in each of these places.

4. Adjust Your Relationship Expectations

How do you maintain romantic relationships while you are traveling? That’s a tough one.

Naturally, this lifestyle lends itself to a lot of short-lived affairs. You meet someone on the road, and there is a spark. But soon after, either you leave or they leave.

Within the digital nomad community, there have been attempts to resolve this. There are now groups and even apps for long-term travelers trying to find love with each other. The idea is to travel together.

However, these apps have a fundamental flaw — there are far fewer female than male long-term travelers. There will be hundreds of male suitors competing for the one-in-between female traveler.

Alternatively, you can try an ENM (=ethical non-monogamy) relationship. By not demanding sexual exclusivity from your partner, they are free to explore other options while you are off traveling the world. This model has worked reasonably well for me.

There are also gender-specific challenges. At some point, most women will want to have kids. For a female traveler, that probably means giving up on traveling and settling with a non-traveler. Theoretically, you could pick up traveling again once your children are a bit older; there are a few families who make it work. But it is rare.

Many male travelers I meet opt not to have kids. They are more excited about the adventure than about the prospect of family life. I myself fall into this camp. Of course, there is always the possibility that you come to regret this decision later. Time will tell.

5. Embrace Slow Travel

When you start 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 as possible.

I certainly fell into that trap. When I started traveling, I would sometimes spend as little as 2 weeks in one place before moving on to the next place. But by giving so little time to each destination, I never went deep. I never truly connected with the host culture.

That’s a mistake I would like you to avoid. The magic of long-term travel is not in working through a Lonely Planet guide. It’s in the aimless exploration.

It happens when you stroll through a neighborhood in Da Nang, Vietnam, and next thing you know, you are sitting down with a Vietnamese family, singing Karaoke, and getting fed homemade dishes until you are about to burst.

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

It happens when you meet this attractive stranger on Oxford Street in London, who then turns out to be a TV celebrity.

But for any of these things to happen, you need to slow down. You need to create the space for these interactions to play out. What I recommend is that you plan for at least four weeks per city, up to 6 months. Your mindset will switch from, “I’m a tourist,” to, “I live here now.” It will make 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 explore as you please, without having to worry about video calls or project deadlines.

The downside is that 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 the 9-to-5 life.

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. You get to run free a little, so you can be a good corporate slave again afterward.

Find a way to pay for your travels while traveling. This way, you can escape the rat race for good.

7. Don’t Overplan

Many people start planning their around-the-world trips a year ahead (or longer). They will try to think of absolutely everything:

  • What is the weather going to be in each destination?
  • What clothes should I pack?
  • Which accommodation should I stay in?
  • Which sights should I see?
  • Which excursions should I book?
  • What’s the security situation?
  • Where is the next hospital?

The list goes on.

I think that defeats the purpose. The 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 lot of money. Also, take care of the visa situation well in advance; some embassies are pretty slow to process these requests. But after the basics are taken care of, go with the flow.

8. Uphold Your Routine

While I am not a fan of planning your travels in too much detail, I am a big advocate of planning for your habits.

That’s because habits like working out or cold-calling a prospective client each day are crucial. They will make or break you. You cannot afford to let these behaviors slide. And it is easy to let them slide while traveling.

For one, there will be a lot of friction on the road. All the things that we take for granted at home, we suddenly need to figure out anew:

  • Where is the supermarket?
  • How much does it cost to withdraw cash?
  • Where can I buy a local SIM card?
  • Where is the next gym?
  • How do I separate waste?
  • What’s the social etiquette?

And a million other things.

When you are busy figuring out these essentials, you are more likely to put your habits on the back burner.

Also, you will be distracted by your new surroundings. “There is so much to explore!” You indulge your curiosity while your habits fall by the wayside.

To counteract this, you need to have strong mental models. My favorite one 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 determine who you become in the future. If you work out every day, five years from now, you will have a great body. If you cold-call three new clients every 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. 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.

9. Eat Healthy

One of the biggest challenges while traveling is eating healthy.

There are three factors at play here:

  1. Willpower
  2. Price
  3. Convenience

Eating healthy while traveling requires a lot of willpower. That’s for two reasons. First, you are in vacation mode and want to treat yourself. Second, you will want to try all of the local cuisine, which is typically not that healthy.

Then there is price. Especially if you are a budget traveler, you will have to eat as cheaply as possible; otherwise, you won’t be on the road for long. That means unhealthy food choices.

Finally, convenience. If you are traveling, cooking becomes a real hassle. First, you must go grocery shopping. 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.

Then you might not have all the cooking utensils you need in your Airbnb. But is it worth buying a bunch of kitchen gear if you know you will be moving on soon?

Bottom line — eating healthy and long-term travel are somewhat at odds with each other. Realistically, you can have two out of three:

  1. You can have healthy and cheap, but then you will spend a lot of time grocery shopping and preparing your meals.
  2. You can have cheap and convenient — think street food —, but then you will eat unhealthy.
  3. You can have convenient and healthy, but then you will spend a lot of money at high-end, healthy restaurants.

Personally, what I do is to 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 willpower, price, and convenience. It is far from perfect, but it’s doable.

10. Pack Light

I recommend traveling as lightly 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 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, every relocation will be a pain in the butt. You will dread every part of the process — packing, getting to the airport, checking in, driving to your new accommodation, and unpacking.

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 matches with everything else. I just buy everything in black. It also makes doing laundry 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 ebook reader.
  • Get a decent backpack. These things have to take a lot of abuse. They also contain all your valuable electronics. I always come back to Osprey. They are not especially pretty or nifty, but reliable.

11. Get Travel Insurance

This should be a no-brainer, but you’d be surprised how many people go on trips around the world without having travel insurance.

Call me overly German, but it’s a terrible idea. If you get into an accident abroad and have to get surgery, this could ruin you financially.

Don’t be stupid, get travel insurance.

12. Don’t Harbor Illusions

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.

It’s important to acknowledge that, as many long-term travelers are under the illusion that they can somehow leave it all behind. “I will move to a tree house in Bali, and everything will be different!”

No, it won’t. You will still be you.

Traveling can kick-start change. By exposing yourself to new stimuli, you will be challenged in new ways. Your current values will come under scrutiny and you might come to revise some of them. But it’s not a magic bullet. This process will still take time and hard work.

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