A Brief Interview About My Traveling Lifestyle

José, a friend of mine (or perhaps more accurately a “guy I know”) in the US recently asked me a bunch of random questions about my current travels, simply out of curiosity.

He wasn’t interviewing me but I’m going to share the back-and-forth with you here as if it were an interview, since I think some of you who are reading this might have the same or similar questions for me.

I’ve edited the actual texts slightly and embellished the end of the “interview,” since we never actually discussed how I can afford to travel the way I do.


Are you back in Japan?

No, I left Japan at the end of February. I’m traveling. I’ve been to Vietnam, Sri Lanka, and the Maldives, and now I’m in the UAE.

(You left Japan) for good?? LOL That’s awesome. I saw some of your pictures on Facebook.

Life is short! I just want to see the world, meet people, and have different experiences, good and bad 😂 (since traveling sometimes leads to delays, crappy places to stay, terrible weather, etc).

Very true, life is short. I feel like I’m wasting my days sometimes. Best of luck to you on your journey! Don’t you have a travel partner?

Yes, I do. My girlfriend, Masami. 😍

I didn’t want to assume but that’s awesome! Have fun.

I’m lucky that we have very similar traveling styles. She’s low maintenance like me. 😂

Nice. Did you plan all of your stops before going or are you playing it by ear?

Totally unplanned.

For instance, we were going to fly from Japan to Sri Lanka via Vietnam on two different airlines to get there as cheaply as possible, but after we bought the Japan to Vietnam leg and were about to pay for the Vietnam to SL leg, the price went way up.

Because of that, we decided we might as well stay in Vietnam for two weeks and then fly to SL, since flights were cheaper in March. So the stay in Vietnam was pretty random but we had a great time there and wanted to stay longer!

And when you fly to SL you can either request a 30- or a 180-day visa. We thought we’d only be there for about a month, so we asked for (and received) the 30-day visa, even though the price for both visas was the same ($50).

Oh, man… And when we got to the airport in Saigon on our way to SL we were asked for our visas, but we had done so little planning that we didn’t realize that we even needed visas (plus “proof” of an onward journey = a ticket that shows you are leaving the country on a specific date) in order to board the flight. Luckily, we arrived at the airport very early and had enough time to apply for the visa and purchase a “fake” onward flight. 🙂

And after only 2 weeks in SL, we could tell that we wanted to stay longer. That meant that we had to extend our visas, but to do so we either had to leave the country and come back (on a new visa) or stay in the country and pay to extend them. 🙁

We chose to pay. Unfortunately, the 60-day extension cost as much as the original 30-day visa, so we really screwed up by not getting the 180-day visa from the beginning. But whatever. Live and learn! So that gave us another 60 days (after which you can extend again for 90 days!) and we ended up staying almost the entire 90 days (the original 30 plus the additional 60).

Then we went to the Maldives and had no clue how long we would stay. The crazy thing is, immigration there also wants you to show them an onward ticket (plus booked accommodation for your entire stay!). We were ready for that, however, since I had actually researched the entry requirements for the Maldives.

Nevertheless, the customs officer in the Maldives didn’t ask for our onward tickets and only asked where we were staying (but didn’t request proof!), so our plan to play things by ear (via cancellable bookings and a “fake” onward ticket) worked like a charm!

As you can see, we are generally super spontaneous.

In SL, for example, we found a nice place to stay that was cheap, had a kitchen, had a great caretaker, and had decent wifi, so we booked one night.

Then we booked a second night and then a third night, and then we just told them, “we’re staying indefinitely!” LOL

That’s awesome. lol Did you find the place on Airbnb? I’ve never been to that part of the world but I’d love to go.

Yeah, Airbnb for the place in Sri Lanka, which was the second place we stayed at there. SL is so different from the US. Good things, better things, worse things. 😂

I can imagine. lol. I bet it’s a good overall experience for vacation but some days probably a little more rough than others. What’s your goal in these travels? Find the best beach?

😂 No, man, although we did find some nice beaches in SL as well as two amazing restaurants right on the sand at water’s edge in the Maldives.

There’s no real goal, per se, besides seeing the world.

We went to Vietnam and met a couple of nice guys. I reconnected with friends in Sri Lanka and we hung out a ton with them and other locals. We met a pretty nice local guy in the Maldives plus some of his friends.

Meeting locals is great. So we hope to do that.

We want to try different foods. We want to listen to different languages. We want to see how people live in different countries.

Maybe we’ll figure out where we want to live.

We’ll also be visiting other friends later, primarily in Europe.

Are you essentially traveling indefinitely until you land somewhere you like?

Basically. We don’t have a plan. 😂 I teach online so if I don’t get fired or if the company doesn’t go under I can continue to earn some money while we’re traveling, which helps.

Is your girlfriend interested in moving to a different country as well?

She definitely wants to try living outside of Japan. Japan is cool but it’s so old-fashioned and monotonous.

And Japanese don’t know how to enjoy life.

I guess maybe we’ll move back to Japan at some point, but I think I’ll get tired of that again quickly.

I’m from California, so I kind of want to live there, maybe, but California is too expensive. 😂 Sucks.

What if you try a different location in Japan if you do decide to try that again? And, yes, California is DUMB expensive to live in. It makes no sense to me.

Yeah, we’ll see. We loved how peaceful, beautiful, and close to the sea our place in Japan was but the city itself was pretty boring. For entertainment we either went to Starbucks or McDonald’s. 😂

That’s pathetic and says it all.

Japan isn’t for me long term. I’ve already spent nearly 10 years there in total.

Wow, so it’s safe to say you’ve experienced everything Japan has to offer. Very interesting. Have you visited Mexico?

Yes, I’ve been there 3 times. The first time was just a day-trip to Tijuana. The second time was an even shorter stay in TJ when I finished a cycling trip from Vancouver to TJ and simply had to end the ride by entering Mexico, so that time we just crossed into Mexico and got in line to get back out. And the third time I spent about 3 or 4 days in Mexico City on my way back from Cuba to China. 🙂

There are many young people that don’t know what they want to do in life and want to see the world. How does one get started in teaching online, to make a living and be able to travel?

Back in 2019, I got a job teaching English at a private school in Japan. After two years they decided not to give me a new contact. So I went back to the USA for a month before returning to Japan. I started looking for work, but got nothing. After 6 months, the company I’m working for now found me. I started off working full-time for them, but now I’m just working part-time because I want a chance to explore wherever I am or just relax. My girlfriend and I are low-maintenance so we don’t really need that much money to travel. And I saved up over the years so I have some reserves. We simply try to cover our costs as well as possible so we don’t have to dip into my savings.

Speaking of money, how are you able to afford all the travel?

You’d be surprised.

We generally avoid expensive destinations. Vietnam was pretty cheap. Sri Lanka was very cheap. The Maldives was surprisingly affordable, primarily because we were there in the off-season. Even the prices in the UAE are quite reasonable, as long as you shop around.

Also, we usually find cheap flights. We’re very flexible with our travel dates and destinations, so we often simply look for a good price and destination and go. 🙂

And we don’t mind paying less for a more uncomfortable flight, within reason. So if we can save money by flying at 2am instead of 2pm, for example, we’ll do it. And if we have to transfer planes 2 or 3 times to save a couple hundred bucks, we’re usually in. That also means we occasionally have to sleep in airports but so be it. 🙂

Furthermore, we don’t always have to pay for accommodation, since I’m lucky to have a lot of friends around the world who can host us for a day or two or even a week or two sometimes. And we just started house- and pet-sitting when we arrived in the UAE, so we haven’t had to pay for accommodation since our last night in the Maldives, back on June 15!

A lot of people think you have to be rich to travel as much as we do, but you really don’t need to have a ton of money to do it.

When you travel, your three greatest expenses are transportation, accommodation, and food, so if you can cut out one or more of those or at least limit how much you spend on them you can really stretch your dollar!

That’s really cool! I gotta go out and explore more!

I agree!

Thanks, man!

You’re welcome!

The three biggest takeaways for me from this conversation I had with José were:

  1. Life is short, so do as much as you can before it’s too late!
  2. You don’t need to plan your entire life; just let things happen naturally.
  3. You don’t need as much money to travel as you think. As long as you are adaptable, flexible, and resourceful, you should be able to get by just fine on modest amounts of cash.

I know my (current) lifestyle isn’t for everyone, but I definitely encourage you to go out to learn about all sorts of cultures, taste different foods, speak a bunch of languages, make a lot of friends, and be kind to others. The world will thank you!

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