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.
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?
Because it’s unbelievably awesome.
Now is the time: it’s feasible like never before. You can put in a full work day no matter where you are. If you’re standing in line for airport security, you can listen to The Changelog. If you’re in the Hungarian countryside, you can work perfectly via 4G. If you’re flying across the world, you can work from the moment you buckle in to the moment you stand up to get off the plane. The airport will have WiFi to push a commit if your plane didn’t. You can travel while producing some of the best work of your career, and you will grow with every new stamp in your passport.
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.
Length of travel
I usually stay in places for ~3 months. Why?
It fits under the constraints of the typical tourist visa.
More on that in a second.
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 gives you time to really explore and get to know a place and people.
There are almost certainly local tech meetups, and there are likely to be other Toptal engineers wherever you go now as well.
You can really try local culture.
Learn to play polo in Argentina. Practice capoeira in Brazil. Go to trance festivals in Europe. If you don’t know where to start, join Internations and go to expat meetups.
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.).
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.
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.
I use a MacBook Pro 15” Retina.
Get a local SIM card (usually a prepaid or pay-as-you-go for between $20-$50 at T-Mobile, Vodafone, etc., with a few GBs of data that you can top up as-needed) everywhere you go so you can always be online and never stress about what you’re missing. Don’t leave the store until you have the phone in your hands with working Internet. If you’re on an iPhone 5, you can almost always cut a micro SIM to fit the nano SIM and it will work just fine.
You’re an engineer. Use Airdisplay to enable your tablet as a second monitor. It also makes it much easier to work on planes: I used an iPad Mini to write this post on a flight from LAX to Auckland, New Zealand.
I rent cars and explore places a lot, so this is key. I have a Garmin Nuvi. I try to download the maps before I leave to go to anywhere new.
iPhone batteries are terrible, and this saves the day.
For work, I use the ones that come with everything Apple. They never fail, and I live on Skype. I see lots of people with more expensive systems and they constantly have problems. It’s pointless.
WiFi doesn’t always work.
You’ll use this everywhere. If you ever find yourself without one, ask the hotel if they have an extra.
New whiteboard marker
It saves the day at least a couple times a year, whether it’s because you’re collaborating in a coworking space and all the markers are dead or you need to work out something John Nash-style.
Take photos of this on your phone and also email them to yourself.
Take photos of this on your phone and also email them to yourself.
SIM card collection
Olympic gymnasts use these for resistance training. With 6” of rubber, you can do a full body workout anywhere. When you spend long hours on your computer, you need to get up and exercise every hour.
For headaches and general aches and pains.
For motion sickness.
For digestion. Traveling can be stressful, and new foods do unexpected things.
Don’t let yourself expire.
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.