I spent 6 months traveling & working: Ask me anything.

Last year my wife (slash business partner) and I spent 4 months traveling Europe and the west coast of the U.S. We also didn’t miss a day of work the entire time, and every venture we were involved in experienced some really great growth.

A year later, we took a 2-month trip through Spain, Portugal, and Israel, and again never missed a day of work (except for the 1-week vacation I took at the beginning – which, of course, was the only time I got sick.)

You’ll also like: How to freelance while traveling the world: my 6 pieces of advice

Because of the many questions that have come in from Millo readers, I’ve answered some of your most common questions below.

I’m also open to answering many more.

If you have questions that aren’t answered below, leave a comment on this post. Ask me anything.

Meanwhile…let’s dive in.

Do you ever get tired of just endlessly traveling?

Yes, absolutely. Something about travel is innately tiring. Things you do at home without even thinking about them, like going for a run, etc., are suddenly a lot harder to do.

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You find yourself just with less energy.

Also, the little things wear away at you. Here in the States, if I need something, say a lightbulb, I know exactly where to go.

Outside of the country, you don’t have things like Target you can get anything from, so it’s really hard to find basic living stuff sometimes.

And also, even if people speak English in other countries (which, these days, they do, unless you’re in a very small, remote town or something), they communicate differently. You still have to re-learn how to navigate another culture.

While that is exciting and exhilirating at times, at other times, I found myself just longing for a good old American interaction. 🙂

Not sure if working on “vacation” is right for you? Check out this post: A solopreneur’s guide to working (or not) while on vacation.

How do you get physical mail? Or do you?

We had our mail forwarded to my mom. 🙂 When something important came in, she took a picture of it with her iPhone and emailed it over.

That was a huge help (thanks, Mom).

Any good friend or relative could do this for you. If you get a LOT of mail (we don’t) you might want to offer them some kind of gift.

How much should I have saved up before starting to travel while I work?

Just enough for at least a ticket home I guess, in case you have to go back in a hurry for some reason. If you plan on working the same amount that you do, you’ll earn the same amount, and so your expenses should stay very similar.

In a lot of countries, you’ll actually end up saving money.

For example, Lisbon and Prague were very inexpensive compared to what we were used to. You can eat very well at local places for $10 – $12.

And alcohol is VERY cheap outside the U.S. If you like to have a beer at the end of the day, you’ll end up spending $1 – $2 compared to $5 – $7 here in the States.

Do you work mostly with clients from your home country, the country you’re visiting, or anywhere?


Our businesses have never been rooted in one place. In fact, we rarely, if ever, have local clients, and even when we do, face-to-face meetings pretty much never happen unless we all just want to meet as friends and grab a coffee. 🙂

We always knew we wanted to be able to travel, so we set things up like this from the start, so we wouldn’t “pull the carpet out” from under any clients who would adjust to in-person meetings, etc.

What are options for storing your stuff while you’re traveling?

The first time we traveled, it was at the same time that we decided to move away from NYC. So we got rid of most of our things. What was left, the sentimental “been with us since birth” stuff, we just put in a simple storage locker that you pay monthly for.

What are the best (and worst) parts of traveling while working?

Best: Different cultures bring out different sides of you, as every culture has its morals and taboos.

  • In some places I found it a lot easier to be outgoing.
  • In other places, more sincere.
  • And in others, more sarcastic.

It’s cool to adapt to new ways of communicating / being.

Worst: Not having your own space.

I’m a home body, so that really gets to me sometimes. Lots of plane travel gives me tense, sore muscles. Living out of a suitcase gets old (but at the same time, you kinda form a special bond with your little storage friend).

Where do you pay taxes?

Whatever country you technically live in. We live in the States, so we pay taxes in the States.

How did you convince yourself (and your significant other) that you should give this a try?

No convincing was necessary. 🙂

NYC’s coldness and harshness convinced us we needed to GTFO and go anywhere but there for our first round of travel. We thought we were going to move to California.

Then, we realized we could work from anywhere with internet, so that was enough convincing to get us to do just that.

Read more here on how we “took the plunge:” How to freelance while traveling the world: my 6 pieces of advice.

How do you deal with the language barrier while traveling?

In a good chunk of the world, English is taught to people in school alongside math and the other courses. Almost everywhere in the world at this point.

This has gotten even more pronounced over the years. 4 years ago when we traveled through Europe, people barely spoke English outside of the UK. It was fun trying to pick up their languages.

Now, especially throughout Europe, English is almost a given.

For a while I felt kind of guilty about this. Who are we to force other cultures to learn our language?

But then, at a train station in Italy, a couple of German girls couldn’t communicate with the Italian clerk in either Italian or German, so they switched to English. Instantly, everyone understood each other.

At that moment, I realized English was no longer “my” language – it had become the world’s language. People from countries that don’t even natively speak English use it as a way to connect. Pretty cool.

How do you ensure you have wi-fi to do your work wherever you’re going?

We use AirBnB to find our pads, and when we write people, we ask them to do a speed test of their connection and send us the results.

How often do you change locations?

Hmm…this can vary. We’ve spent as long as 1 month in a place and as short as 5 days.

How do you decide where you’re going to go next?

Somehow, kind of magically, whenever we’re in a place, the next place just sort of reveals itself to us.

We’ll overhear a conversation, stumble across an article out of nowhere (when not even looking), or some other happening of life nudges us a certain way. It becomes very clear very fast where we’re going next 😉

PS – check out Jake’s Millo post on how to select a starting point: How I built a freelance career while traveling the world.

Does traveling change the way you do business? If so, how?

Not at all.

At least, for us. In some cases, it helps us build rapport, because we’ll get an inquiry from someone in country X and we just so happen to be there. 🙂 In other places, it was actually kind of easier.

For example, if you’re in Europe, business in the states doesn’t start until like 2:00-3:00 in the afternoon.

As a night owl, this was nice. It meant I could sleep in, still have time to go out and explore in the morning and early afternoon, then settle into working for the afternoon / early evening, then go out for dinner and explore more at night.

On the weekends, it was all exploring and eating though. 🙂

I think if you’re really motivated and passionate about your work, that alone is enough to ensure you find a good work / explore balance overseas and get done what you need to get done. In fact, we started our newest company, Reliable PSD, while traveling. Its first 4.5 months of existing occurred while we were in about 10 different countries.

If you love your work, you’ll want to do it. It’s that simple.

What would you say to someone who’s on the fence about all of this?

I think the biggest concern people have is probably money.

Most of us are lucky enough to have at least some kind of safety net – even if it’s just a relative who could wire you just enough money to get a ticket home.

The first time we traveled, 4 or 5 years ago, we were almost broke. We were supposed to give talks / workshops in the UK to earn more but it completely fell apart.

We had just enough money saved for 2 weeks of travel (without working), but because of the talks / workshops, we had extended it to 5 weeks. 

However, because those didn’t work out, it meant we had 2 weeks of money that had to somehow pay for 5 weeks of living. And at that time, the British Pound was worth TWO DOLLARS (crazy…) and the Euro was worth a dollar fifty. So really, we barely had enough for even 2 weeks.

To this day, whenever I have any doubt or fear whatsoever about things not working out or falling apart, I remember that trip. It truly was amazing how everything came together and saved our behinds. From finding money on the ground right after our debit card got eaten by the ATM to even more insane “coincidences,” everything turned out OK.

I’ve found ever since then, and even before, when you take risks following your heart, things tend to come together. (That way of life actually is what inspired the name and tagline of our creative agency, “Unexpected Ways, Things Come Together.”)

So just go for it. Why not? 😉

Do you have other questions about traveling while you work?

Leave a comment. Maybe we can do a round 2 of Q&A 😉

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About David Tendrich

David Tendrich is the co-head of creative agency Unexpected Ways, as well as the co-founder of Reliable PSD: the first-ever PSD to HTML & PSD to Wordpress service run by designers, for designers. He co-runs his companies from Portland, Oregon with his lovely wife and biz partner, Lou Levit.


More about David’s business: David is co-founder of Reliable PSD – what happened when a group of designers got fed up with PSD to Code companies… and created their own. Check them out, and see why freelancers & agencies are head over heels for this amazing new service.


  1. Hi! I was wondering if you needed to obtain work permits before traveling to new countries? I’d love to do be able to work while traveling.

    • Hey Jeca,

      For U.S. citizens like ourselves, and for the kind of work we do, we didn’t need any special permits or anything.

      If you’re from the U.S. as well and will just be running your usual freelance biz while you travel, I’m sure it would be the same for you.

      If you’re not from the U.S., unfortunately I can’t be of much help 🙁

      Does that answer your question?

      Thanks for stopping by 🙂

  2. Sharon Pettis McElwee says

    What about traveling with children? Any good resources on that if you don’t have any?

    • Hey Sharon,

      That I don’t yet know about lol 🙂 I think when we’re at that stage we’ll bring a nanny or relative along who can help us out so we can still enjoy some “us time” too while abroad.

      Otherwise, sorry, I don’t have firsthand experience yet 🙁

  3. Robert Whitcomb says

    This is something I hope to do with my wife some time. We just started our own full time freelance careers from home together, and this is one of the perks I hope to lean on when we get a steady enough revenue stream.

    • Hey Robert,

      That is awesome, man 🙂 I hope you guys can get there soon 🙂 Let me know if you have any questions while you’re on your way.


      • Robert Whitcomb says

        Just waiting til we have a steady enough revenue stream 🙂 Looking forward to giving it a try hopefully within the next 1-2 years

  4. Hi, Can you discuss your workflow process? Saving and accessing files,clouds, setting up meetings, apps you use for a seamless process for clients?

    • Hey ProfCrystal,

      Pretty much the same as it is States-side 😉

      For saving and accessing files, we’ve got Dropbox / our computers with us, for meetings we use phone and email, etc. Nothing really changes 🙂

      Or did you have a more specific question? What are you concerned about exactly as far as your own workflow? Maybe I can help if you tell me a bit about that.

      Thanks for your question 🙂

      • ProfCrystal says

        Thanks for your response! I have private clients, I teach online and work full time. I’m working on my own intuitive naming conventions, so I can organize my files across all of my projects. I was wondering if you’ve done something similar.

  5. The post I was waiting for 🙂 This is exactly what I plan to do for a month in the coming year. Way to live, thanks

  6. Bridget Johnson says

    Living the graphic designer’s dream 😉 very inspiring.
    How do you get around for exploring your current area? Rent a car or public transportation….both?

    • Hey Bridget,

      Yes, it’s really been something 🙂

      It depends. Mostly we walk (we’re big walkers), otherwise the bus or subway, and only if we really need it do we rent a car.

      I like to travel really light, and having a car feels kind of “heavy” to me energetically, so I try to avoid it.

      Thanks for your question and thoughts 🙂 Let me know if you have more.


  7. Luke Goetting says

    Awesome info. Regarding receiving mail, I recommend a service we use called https://www.scanmailboxes.com/ that basically receives your mail for you and scans it upon request so you just get all the info via email. So even if we work from home or change offices, our mailing address stays the same and we get our mail from anywhere!

  8. Good stuff, David! Actually everything you talked about my wife (and also biz partner) and I are doing right now. We’ve been trying to build our business to travel as well — been in the works for a few years. We put some things in storage, mail going to some family & all that you mentioned, lol!

    This morning we found this awesome Café around the corner from where we’re staying in Bogota Colombia, we had a fun time trying to figure out what they were asking about Credit Card payment. Apparently in Bogota — not sure if it’s the same elsewhere — you can break up for payments into months via CC payments. Pretty cool! Even though my wife speaks Spanish we didn’t know what they were asking and took everyone in the little Café to help explain ha!!

    We’ve also used Airbnb a lot in the past to travel, but only in the US. This is our first stay out of the US using Airbnb… same great experience. That was a nice tip with the internet speedtest.net, was very helpful!

    Keep this stuff coming! ????????

    • Hey Darren!

      Thanks, my man 🙂

      The hard part is having the business built up that lets you do everything. The rest, as it sounds like you guys figured out, is pretty simple 😉

      So glad to hear you guys are enjoying Columbia 🙂 That is definitely HIGH up on my list of where to maybe go next.

      Talk soon,

  9. I like this idea a lot. I just have a technical question – what type of visa are you getting while doing that, if you’re going outside of the states? Working visa or tourist?
    I am from Europe and I’d like to travel within the US for a couple of months while freelancing, but I am just wondering if I work online and pay my taxes back in my country, does it technically count as working on a tourist visa? Thanks for all the info you have:)

    • Hey Katerina,

      I’m sorry, I have no clue 🙁

      I think going from Europe to the U.S. is different than the other way around. We didn’t need a special visa or anything. Anyone coming from the U.S. “automatically” has a 90 day visa for the Schengen and even longer for the UK.

      So for us it was quite easy, but I would check with your local government to ask these questions so you can be safe.

      Thanks for your question 🙂

  10. Hi David, very helpful article! Thanks for sharing!

    “I am a big believer in “cold” letters,
    be they in printed or email form. Some of the best opportunities we’ve had came
    from sending the right letter with the right message to the right person.”

    I’ve recognized the same for us. It takes some effort to personally reach out, but it’s
    definitely worth it. I am mean you always face the risk of getting a bad feedback, which can be quite hard. But in most cases we could use the feedback to improve ourselves.

    Keep up the good work!


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