Travel & Destination

The best ways to Travel While Working: Hacks For Software Application Engineers and Freelancers

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The following is based on my personal experience as a traveling engineer and founder. Feel free to contact me any time at [email protected]

I’ve lived and worked remotely overseas in approximately 30 countries since I finished school three years ago. I’ve been running Toptal, a venture funded company growing hundreds of percent year over year—all from my laptop, phone, and tablet.

Croatia · Hungary · Bosnia · Italy · France · Switzerland · Germany · Austria · Georgia · Romania · Serbia · Slovenia · Spain · Ukraine · Morocco · Brazil · Canada · Paraguay · Argentina · Uruguay · New Zealand · Australia · Hong Kong · USA · England · Turkey · Chile · Slovakia · Czech Republic · Lebanon

I don’t have an apartment. I don’t have a house. I don’t have an office.

I hate the cold, so I summer hop.

Everywhere I go, I meet great traveling or local overseas engineers who end up becoming invaluable parts of Toptal.

I encourage everyone in Toptal from freelancers to developers to employees, to travel, and a lot of us do. Some of us travel for week long “breaks” throughout the year, and some of us live out of a suitcase like me. Few of us ever stop working for a full day.

I’m writing this because…

I was repeatedly asked if I had some sort of guide or checklist for traveling and working abroad the way I do. Especially for first-timers, the idea of adventuring overseas while working can be daunting. There are a lot of details to consider, and I’ve learned a lot from my own trial-and-error.

The more I thought about it, the more I realized a guide like this was actually missing for traveling engineers and freelancers.

The Four Hour Work Week was great, and I like Tim Ferriss a lot. But what if you want to work more than 4 hours a week? I like working crazy hours. I don’t want a lifestyle company. I want to solve hard problems. I want to build something big and give it my all.

So are there other guides?

Well, Remote by the guys at 37 Signals was the the biggest disappointment of 2013 (I loved Rework and therefore had high hopes). The book was for old people who need help convincing their bosses that they can try working remotely. A fair premise, but I didn’t learn anything. I wasn’t even inspired.

I want a book on how to create a billion dollar company while becoming a fighter pilot. (I’m trying to build a world-changing company while becoming a professional polo player.) That would be inspiring. But until it comes, maybe this post will be helpful to a few traveling freelancers out there.

Why travel as an engineer or freelancer?

  • The secret benefit: avoiding burnout.
    I don’t take vacations. I don’t want to work hard to build a company that makes lots of money so I can piss off and go on holiday. I’m at a start-up. I’m a part of it, and it’s a part of me. This is a marathon, and there will be a winner. Traveling and working allows you to go non-stop. There is no burnout. There’s no staring at a clock or calendar waiting for the EOD/weekend/break. You’re refreshed weekly, and you can hone your focus and structure your time so you are a cross functional superstar who never stops learning.

Playing polo (often with Toptal developers) in Argentina. Total cost for sponsorship: 400 pesos (~$40) for t-shirts.

Length of travel

I usually stay in places for ~3 months. Why?

  • It gives you time to relax and focus in between the stressful travel sessions.
    Power trips of 9 countries in 3 weeks are for students on holiday. You need to be able to stop traveling and focus on work.

  • It helps with costs.
    Trips of this duration help you negotiate special medium-term deals on apartments, cars, vespas, etc.

Who to go with

  • A close friend/colleague
    You can split costs for a lot of things like cars, hotels, etc. You can also split the research and push each other to do things you might not do yourself (like go out to new places, go on adventures, rent a boat, etc.).

  • Alone
    Not for the faint of heart but not everyone has the flexibility you do as a traveling software engineer. If you don’t have anyone to go with, don’t let it stop you. With Internations and a network like Toptal, you can almost certainly go anywhere and immediately find people with lots in common.

  • A girlfriend/boyfriend
    Can be by far the most expensive option, but it’s probably the most rewarding and fun. Nothing brings compatible people together like adventure. However, nothing drives incompatible people apart like stress, so be careful. The other thing to consider is whether your significant other will also be working during your travels. If so, that’s tremendous, and you are very lucky. If not, that can be very hard. The added costs of having a dependent aside, you don’t want to be in a position where someone resents you for constantly working during what they’ve misunderstood to be a vacation. Luckily there are many interesting traveling freelance careers in addition to software engineering that are now doable remotely (e.g., executive assistant, translator, designer, tutor, entrepreneur, etc.).

What to take on your freelance travel adventure


Always a carry on. Pretty much always with me.

  • Passport
    Take photos of this on your phone and also email them to yourself.

  • Insurance card
    Take photos of this on your phone and also email them to yourself.

  • Ibuprofen
    For headaches and general aches and pains.

  • Deodorant
    Don’t let yourself expire.

Suitcase 1

Checked on flights. Leave your Louis Vuitton luggage at home. It just makes you a target, and your stuff will get stolen. Some traveling engineers or freelancers swear by expensive luggage, but I’ve used a basic 5-piece luggage set since I graduated high school in 2004, and it’s worked fine.

  • Clothes. You can figure out the basics but I usually carry the following:
    • Dress shirt
    • Dress shoes
    • Gym shorts
    • Running shoes. Running is a great way to explore places.
    • Swim shorts
    • Flip flops. For gyms, pools, and beaches.
  • Toiletries.
    • Shaver
    • Toothbrush
    • Floss
    • Toothpaste
    • Sunscreen

Suitcase 2

Aka the toy bag; also checked on flights.

  • Snowboards, polo equipment, surf boards, or whatever you need for your specific trip.
    It sounds strange, but always make sure your stuff is clean. Some countries (like New Zealand) are very protective, and if there’s dirt, sand, grass, hair, etc. on your stuff, they may take everything and sanitize it for you (in God knows what) at the airport, or even confiscate it.

Where to stay

  • Always ask for a better room or free upgrade when you check into a hotel.
    You’ll get something about 50% of the time.

  • Similarly, always try to negotiate a special weekly or monthly rate on housing and cars.

  • Don’t stay in hostels.
    You’re not a kid. You’re a professional engineer, and you need dedicated time to focus on work.

How to pull it off

  • The longer you wait, the more expensive it is
    That said, I hate planning, and I find that last minute usually works out fine. Worst case scenario: you’re uncomfortable for a little while (red eye flight, stuck in traffic while it’s 900 degrees, etc.) but you end up with a funny story and an adventure.

  • Rental cars (above)
    If you’re American, learn how to drive a stick shift before you go overseas. They are much cheaper to rent, and it’s often impossible to find an automatic.

  • Money
    I always try to carry a few hundred USD. It’s easily exchanged whereas others currencies aren’t always. Before you travel, you’ll also need to call your banks and let them know in which countries you’ll be using your debit card. Otherwise they may block it after your first transaction, and you’ll have a mess to untangle. Also, be sure to download a currency converter app so you know how much things cost; and when you need more cash, pull it from an ATM instead of an exchange in order to reduce fees.

  • Skype number
    Get one and add credit to it so you can call clients, hotels, etc. any time. It’s also wise to have it forward to your current mobile number so your clients and colleagues can call you when they need to.

  • Lost a charger or adapter?
    Ask the hotel desk. They usually have a box of them that other guests have left behind.

When to go


As I mentioned earlier, most countries permit a three-month stay under their tourist visa. (Specifically, 90 out of every 180 days.) This is great for contract work overseas as a traveling engineer.

  • Most counties are very easy to go in and out of.
    The worst is always the US where I’m treated like a terrorist virtually every time I enter or leave. (I refuse to fly into Seattle–Tacoma International Airport ever again). For many countries (in my experience, as an American), all you need to do is show up at the border not looking like a criminal, and they will give you a tourist visa as you go through the airport. In some countries like Turkey, you’ll have to pay a small fee (~$20). In others, you need to fill out paperwork beforehand and pay a larger fee (e.g., Argentina and Brazil). I carry a printout of a recent bank statement and copies of my return tickets (if I have them) just in case a customs agent asks to see them (and some countries like New Zealand require them).


  • Communication with clients.
    If the technical ability is there, then now it comes down to communication and reliability. I always tell traveling engineers and their clients that if I were to take each into a separate room, they need to always be able to give identical answers to the following three questions:

    1. What are you working on now?
    2. What were you just working on?
    3. What will you be working on tomorrow?

    Maintaining that level of communication and transparency is not difficult in an office, but it’s also not difficult when you’re remote or overseas. Always be connected and proactive.

  • When flying, always check the rates for business class.
    If you’re checking multiple bags, sometimes business class can be cheaper because the bags are free.


Shit will happen. Try to let it go immediately.
You don’t need to (nor can you) plan every last detail when you travel, and you don’t need to follow every rule. Sometimes you need to wing it. Be impulsive. Seize an opportunity to jump on a train to Oktoberfest with a group of brand new friends. Invite the girl you can’t stop thinking about to a wild weekend in Turkey. Go to Georgia and party like Russia might come back tomorrow.

That’s when awesome happens. Welcome to Toptal.


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