We’re back with a new installment of our Traveler Interview series! It’s been a while since we posted one, so it’s really about time we get back to business.

Today’s chat is with someone who’s been at this travel writing and world travel game since most travel bloggers were just young pups. He’s written for countless magazines, runs his own blogs, and writes his own books. Also, he’s a really great guy who we’re honored to be able to call a friend.

This guy is Tim Leffel. He originally started out as a part-time travel writer a couple of decades ago, backpacking around the world a few times with film and cameras and a sense of adventure. He eventually became a full-time writer, and has authored five travel books, including The World’s Cheapest Destinations and A Better Life for Half the Price: How to Prosper on Less Money in the Cheapest Places to Live.

Tim Leffel in Nicaragua

Tim has his own media company these days as well, which publishes a whole series of online magazines and blogs, including Cheapest Destinations and Perceptive Travel.

A Better Life for Half the Price by Tim Leffel

We originally met him when we were all living in Guanajuato, Mexico, where he spends quite a bit of his time with his family. We were also blessed to appear in one of his videos, as well as in one of his articles for Lonely Planet. We still keep in touch, and he’s always full of great info and a no-bullshit way of writing and living.

Tim Leffel and Jets Like Taxis in Guanajuato, Mexico

All right then, let’s get to it!

1. How long ago did you begin traveling, and what made you start?

My wife, who was then my girlfriend, said, “I’m going traveling around the world and I’d like you to come with me. But if you don’t come, I’m going anyway.” This was the early 1990s. I was hesitant because I had all the trappings of what you’re supposed to have when you grow up: a car, a condo, a real job in an office. But then I got fired by my idiot boss and her company went out of business, so we took it as a sign that travel was meant to be. We saved some money, and then took our first of three trips around the world.

2. Do you consider yourself a traveler, an expat, an explorer, or something else, and why?

Sometimes, I’m an expat and a traveler, sometimes an explorer. What has kept this career interesting is it keeps evolving if you let it. As life should.

3. Where are you from, where are you now, and where are you going next?

I grew up in rural Virginia, lived in Nashville, and then New York City as a music biz exec, then returned to Nashville after living in Istanbul and Seoul along the way. We now go back and forth between Tampa in the USA, and Guanajuato in Mexico.

4. How do you find living expenses to be, compared to your home country?

When we’re in Guanajuato, my family easily lives on less than half of what we spend in Florida, despite spending far more on fun: eating out, drinking out, traveling on long weekends, and going to cultural performances. There are cheaper places to live in Mexico, but it’s a terrific value in the colonial interior.

Tim and Donna Leffel in Guanajuato, Mexico

5. Where was your first big travel stop? How and why did you choose that to be the first one? How long did you stay?

We started our first round-the-world trip with two weeks in Japan, because my now sister-in-law was teaching English in Kyushu and had a house where we could stay. But after that, we spent months in Southeast Asia. We went there for the same reason most backpackers do: it’s exotic, cheap, and has great food.

6. What’s the average amount of time you spend in one place?

These days, that’s often dictated by school schedules for my daughter, so not nearly as long as I’d like, usually. That’s why we live abroad for years at a time. But, we spent two weeks in Oaxaca in the summer and only hit two places: the beach and the city. We try to make it slow travel even if time is limited.

7. Are you a planner, or do you tend to fly by the seat of your pants?

My wife’s a planner, I’m a seat-of-the-pants guy. So, that works pretty well on vacations. When I’m on a writing trip, I try to plan out the general timeline; but if it’s too tightly planned, it’s hard to get a good article out of it. Flexibility and serendipity — and getting lost — usually make for more interesting experiences.

8. What do you do for a living, and is travel an integral part of it?

I’m a full-time travel writer, which includes owning and editing websites, writing freelance articles, and earning royalties from book sales.

Tim Leffel in Nicaragua

9. Do you think you made the right choice overall by leaving behind the typical life in your homeland?

Absolutely! Through planning and determination, I have gotten into the position where my job is wherever I am. So, whether I’m in the USA, Mexico, Peru, or Bulgaria, I just need my laptop. I can’t imagine commuting to work in traffic and going into an office each day now. That seems so foreign, so wasteful in terms of time and effort. Most people have created a prison for themselves that’s of their own making, and now they’re trapped.

10. How do you think your life has changed for better or worse since you left for your adventure?

I learned far more in a year of travel than I did in four years of college, and it opened my eyes up to a lot of things. As I spent two more years traveling and teaching English, it became apparent that “the way it’s done” in America is a warped view of reality worldwide. It set in motion my plan to eventually get to a point where I could run my own life in a more sane manner. Once the internet came along and blogs took off, I saw my opportunity to leave the corporate world behind forever.

11. Do you still feel a connection to your old home, or did you really leave it all behind?

I’m not sure where “home” is anymore since I’ve lived in so many places for extended periods. I don’t miss the USA at all when I’m not there, but I can adapt when I return, and start enjoying hoppy beer and fast internet. I’m not ashamed to be an American, and that background is part of what has given me the drive to be successful. There are a lot of elements I hate though, especially the broken political system and the powerful influence of the gun lobby making it so unsafe there.

12. Do you go back often, and do people come visit you while you’re on the road?

When I live in Mexico, I go back to see relatives, and occasionally go to a business conference. More often, people come to visit us. We purposely bought a house with some room for extra beds.

Tim Leffel in Bolivia

13. Is there anything you miss from your home country that you can’t find when you’re traveling? If so, what is it, and how do you manage to get your hands on it while you’re on the road?

There are a lot of things I stuff in my suitcase when returning from the USA that are either cheaper there or hard to find elsewhere. Some are minor, like certain snack foods or natural peanut butter. Others are more substantial, like electronics. In the old days, I would get tired of my music or what movies I had access to. In that regard, it’s ten times easier now.

14. How is the language barrier for you when you go somewhere new, and do you make an effort to learn the local tongue?

I usually just bring a phrase book and learn enough to get by. The only one I’ve gotten functional in is Spanish, and even that is hard because I’m working all day in English. I find the longer I travel, the more prevalent English becomes everywhere. It’s the language of tourism and commerce, which is good for me because I’m definitely not a natural and have trouble finding the motivation for spending eight hours on studying, instead of eight hours creating content for a book or for my business.

15. What has been the biggest challenge for you? Bureaucracy? Finding new friends? Something else?

Bureaucracy is a pain, yes, and there are always things about your adopted country that get on your nerves. Honestly, the biggest challenge has been the far-from-fast internet in Mexico. There’s a telecom monopoly here, and it shows.

16. How hard is it to make friends and have a social life? Do you ever feel alone?

I find it easier to make friends in a foreign country than at home. People aren’t so over-scheduled, and many have moved in order to take back control of their time. The city I live in is not so large, and the hub of activity is the historic center. That, combined with the fact that there are probably only 200-300 expats here [in Guanajuato], means you tend to run into other foreigners a lot and the social life is good. My wife has more Mexican friends than I do; she’s out and about more, and meets up with other moms from our daughter’s school.

Tim Leffel and Family in Guanajuato, Mexico

17. If you could change something about how and when you became a traveler, what would it be?

I wish I had started sooner. The only places I had been before going backpacking around the world were Canada, a Mexican border town, and Jamaica.

18. Do you think it’s easier or harder to become a hardcore world traveler today, versus when you started?

Good god, it’s so much easier now. It’s like night and day. Too easy, really: many backpackers now book all their accommodation and plane tickets in advance, and then spend the whole time at night talking to their friends back home on Facebook. There’s very little sense of adventure in that scenario. On the plus side, it’s far easier to earn money in a location-independent capacity now, so you don’t have to live off savings for years, or go the traditional route of teaching English or bartending somewhere to replenish funds.

19. What crazy story can you tell us about a terrible travel experience, and what, if anything, did you learn from it?

Nearly every bad travel story I have falls into two categories: 1) I was on a bus and thought I would die; or 2) It was India.

I guess the lesson from that is: Don’t take a bus in India. Although, we took what was supposed to be a 24-hour train ride there once that turned into 36 hours; so sometimes, the mode of transportation doesn’t matter. Here’s a bad trip story that won a writing award though, and it doesn’t fall into either category.

20. What about a good experience you had that makes it all worthwhile?

Oh, there have been hundreds of those. And sometimes, they’re right after the bad one. That story I linked to above was about a hellish ferry ride that led us to one of the most gorgeous little tropical islands I’ve ever visited, where we paid $4 a night including all three meals. We took another hellish ferry ride, then a hellish jeepney ride in Palawan, Philippines, one time and arrived at…one of the most beautiful spots I’ve ever seen. Sometimes, even the worst journey results in a great payoff at the end. It’s always worth it if you don’t die or get maimed.

Tim Leffel in Bolivia

21. Do you have any favorite places that will always bring you back, or that hold special memories for you?

My fondest memories are from visiting places that seemed otherworldly and so utterly foreign to where I grew up. Spots like Sukothai, Borobodour, Fez and the Sahara in Morocco, the villages with no roads in the mountains of Nepal, Inca ruins in the Andes mountains, the game reserves of Botswana, Cappadoccia in Turkey, Bryce Canyon in Utah, the Uyuni Salt Flat of Bolivia…

22. What about places that are nothing but a turn-off, regardless of whether you have visited them before or not?

I can’t imagine a worse place to spend a day than a cruise ship port on a Caribbean island. You might as well visit your local shopping mall where you live now.

23. What dos and don’ts can you offer a burgeoning traveler?

Take your time — it’s not a contest. Savor the moments, and not just by snapping photos to share. Leave some things to chance. Wander without a map sometimes. Trust your gut when things feel wrong, but don’t be paranoid about meeting strangers.

24. Would you recommend people follow your path?

Not the whole path maybe, but I firmly believe long-term travel makes you a better person. It’s hard to be dogmatic, rigid, and closed-minded when you’ve spent six months or a year traveling around the world, seeing how people from developing countries live their life. You become a much more well-rounded, knowledgeable person, and have a more finely-tuned bullshit meter after that. You also become more adaptable and creative — prized traits in the modern work world.

Tim Leffel in Real de Catorce, Mexico

25. Do you think you’ll ever stop traveling and settle down somewhere?

Nah. When I’m old, I’ll probably just do three months here, six months there, but keep moving until I can’t anymore. I don’t really see a point in retiring, since what I do is not all that physically taxing. I enjoy what I’m doing; I’ll just maybe dial back the hours.

26. In a parallel universe, what would be your ideal lifestyle, and why?

Not many people can say this, but if I designed my perfect lifestyle, it would be pretty close to what I’m doing now. I’d just magically make more money from it so I could work fewer hours.

27. If you could be a beverage, what would you be, and why?

A pale ale. It looks surprisingly simple on the outside, but there’s a lot of complexity once you get to know it.

28. Any last words of wisdom or warning?

If you have read this far, you have far more patience and curiosity than the average Joe, so you are obviously meant to be a long-term traveler or an expat!

Tim Leffel on the Inca Trail

And that’s a wrap! Thanks so much to Tim for giving us the time and answering our questions. Hopefully, he’s been a source of information and inspiration for you as you follow your own path. You can visit and follow him at the following locations:

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What’d you think of the interview or the answers? Let us know your thoughts in the comments!