I’m on my third transcontinental adventure and I’ve been on the road for about 2 years during this last trip. I get asked how to work and travel frequently. It is a question that I too have struggled with countless times. Finally, I have a few answers.

Option 1. Don’t.

I would recommend this to most people, especially recent graduates. A mistake that I made and that I see so many recent uni grads make is to think that the travel lifestyle is the end-all be-all and only if there was a way to be making enough money while traveling, then life’s pieces would all click into place, happily ever after.

It’s not like that at all. There are very few types of work you can do while traveling. There are more that you can do virtually. But traveling is about catching that last minute bus to some weird village that doesn’t have WiFi. Travel is about being able to say “Yes,” when a local asks you if you can joing them on some unique experience at the last minute. Work is typically having your time scheduled in advance. Work is going to bed early so you’re not tired the next day. Work is planning and stressing and budgeting. The travel mind and the work mind are both valuable, but truly they don’t coexist well.

I would personally recommend that you commit fully to each of them and give them your full attention seperately. If you just graduated, you probably don’t feel like starting your career and you probably feel like traveling. But you may also be broke. Read about Option 3below if that’s your scenario. If you can bring yourself to work and save for a while, really, just do that. Give yourself a deadline, maybe 6 months, maybe a year. On the magic date, no matter what, you cut the cord and travel. But that’s the catch – you must cut the cord.

The benefits of working and saving before traveling are:

-You have savings so you don’t have to stress over every single expense when you’re traveling. You think travel is glamorous. But you are in a foreign country with a foreign language. You are going to feel vulnerable. Do you want to feel financially vulnerable on top of this?
-‎You can INVEST savings. You should invest savings! If it’s not already in your head, put it there now. When you get money to start working for you, you get so much freedom in return. Unfortunately you need the seed money to start with. But you’ve got to make that happen at some point, right?
-‎You feel like you’ve earned it. Because, in fact, you have.
-‎I’ve looked…A LOT. The chances of finding decent virtual work right after graduating is hella slim (unless you’re a programmer) and the pay is pathetic. But if you put yourself in a company that may eventually allow you to work virtually, your work conditions and your pay are likely to be a lot higher…if the work and travel thing is what you do ultimately want to do.
-‎When you’re sick of traveling (sounds crazy, but I assure you it will happen), you’ll have a normal to return to. I am chronically nomadic and the downside of that is that when I’m sick of traveling, I don’t have a home to go back to where I feel like I can just rest back into a routine. When I crave routine, I have to recreate it from scratch time and again. That does in fact get old.
-‎You may realize you want to live in one of your travel destinations. It’s really hard to set up a new life when you’ve got a full work schedule and you’re just scraping by. Better to either have savings to get you started in your new spot or have a job and network back home where you can accumulate the resources to sustainably make the move.

While I am sort of advocating working before you start traveling, I do want to stress – DO NOT FORGET TO PULL THE PLUG. Once you have a job and promotion opportunities and the option to renew the lease in that apartment you just made feel so cozy, it is really easy to forget why you started working in the first place. But don’t. Set reminders in your phone. Write letters to future you. Whatever you have to do.

Oh, one more thing. Don’t expect your dream job after graduating. Most of us do. Most of us end up very disappointed. Don’t worry if the first job seems like a terrible fit. It probably will be. But time has a way of aligning things.

Option 2: Work and Travel

Well I guess I had to write this section after titling this article the way I did. Yes, you can work and travel. I hope Option 1 didn’t put you off too much. It’s just that it’s really hard.

Ways to Work and Travel. You can:

-Try to secure a virtual position from a company you already have a local position in. This is probably the best option, but many of us don’t have that starting company.
-‎Work for VIPKID (sorry, this is just for North Americans) although Talk51 is available for anyone. I am doing this now and really love it – you teach English to Chinese kids virtually. The pay is pretty good, it’s fun, and you can choose your schedule. The thing is you need really good WiFi (uncommon when traveling) and a sort of stable place. I’m at a point where I like to stay somewhere for a few months at a time now so this works great for me. If you want to be on the move all the time, this would not be a good option.
-‎Start a travel blog. I’m joking. Don’t expect to make a living off a blog. Everyone thinks of this. Virtually (haha, see what I did there?) no one makes enough to live off. And it requires soooo much work. And now that the Dipshit’s administration has killed the US’s net neutrality, this really isn’t an option. A blog is a great idea. A blog to survive from is not.
-Try to get virtual work from a source like Upwork.com. Spoiler alert: You’ll be competing for Bangladeshi minimum wage and you might get one (very sad) hook after an absurd amount of looking. I’ve gone to Upwork several times throughout the years and I always walk away without a job feeling like I’ve wasted my time.
-‎Try to start your own business. I’ve done this too. Starting a business makes you worried about every cent you spend. It is an utter pain in the ass to do while you are in transit. The level of risk, if this is your sole means of life support, makes life anxious and ultimately miserable. It will zap any pleasure out of traveling.
-‎Get a job abroad. The most available positions are teaching English but your options are limited to Asia if you want livable wages. Getting a work visa to Europe is nearly impossible and Latin America’s pay is laughable (or cryable rather).
-‎Do side work. I studied Thai massage when I was in Thailand so I give massages when I’m in a place for at least a couple of week. This pays really well but I definitely couldn’t live off it. Some people cut hair. Other people play music on the street. Don’t plan to survive off this. Side work is for the side.

Listen to me here. Do not leave without money and without a job. You will be miserable and you will end up exploited. A job and money are ideal, but you definitely need one of the two. Once again, do not start traveling with neither a job in line nor money.

Option 3: Work Trade

HelpX, WWOOFing, and Workaway.info are your options. I have used Workaway on nearly every continent and have had good luck again and again. There are over 20,000 work trade opportunities around the world on Workaway.

The premise of these platforms is that you work around 20 hours a week in exchange for accomodation (and food if you’re in a rural location).

Workaway is fun. You learn new skills. You meet interesting people from around the world. If you do the math, you would usually be making just a few dollars an hour for your work so if you want to be strategic, work beforehand or if you can manage to secure digital work, do that instead. But if you can’t be bothered or you’re already on the road, Workaway is great and the work is usually more fun than a more professional job anyway.

And there it is folks. I hope this helps you determine IF you should try to work and travel. If you do try, I hope this gives you some ideas on how to make it work. Comment anything I missed 🙂