How to Start Travelling #2: Find a Flexible or Digital Work Situation

“But I don’t have the money,” is the most common phrase (usually uttered with a sad sigh) I hear from people who want to travel, but don’t (or, as they would say, can’t). The second most common is, “if only I had the time off work!”

So how can you have the money to travel as well as the time? It’s a tricky balance, but you can do it with carefully arranging your days off at work, working overtime to save cash, picking up a “side hustle” like casual dog walking or bartending, or you can commit to long-term travel and figure out a way to find a flexible or digital work situation.

Especially if you want to travel long-term (meaning more than the days off you would have from a ‘normal’ job) then it’s necessary to find a balance between earning money and spending money on travel. Here are a few things to try:

1. Try to find a “remote” version of your current job if you like it. Are you a language teacher? Great, look at italki.com, pandatree.com, or some of the other online language schools. An engineer? Ok, that’s a little harder but see if there are any consulting companies that would suit you where you could work on projects from anywhere and discuss with your clients on Skype for the most part.
2. If you’re ‘testing the waters’ with the idea of remote work, ask to arrange some time with your employer where you can work from afar and see how it goes. Perhaps pitch a lighter workload, or a trial period where you simply work from home to build trust in your responsibility as a digital employee. I’ve seen this succeed first-hand for a friend who works at a large aerospace company, slowly slowly he spent more days working from home and eventually his supervisors agreed that he could be almost completely remote.
3. If your job can’t be translated into remote work, consider a sabbatical, or weigh up how important that particular career path is to you versus what you might gain from travelling.
4. You can also consider trying to find employment with a travel-related company such as an airline where your benefits will also decrease the cost of traveling.
5. If your job is merely a “j-o-b” then you can always look into ‘How to Start Travelling Tip #3’ soon and pick up seasonal work around the world when you run out of money while travelling.

I won’t say it’s been easy working remotely for the past 11 years. Finding clients can be a challenge, you are still tethered to the internet even though you’re not in an “office”, you’ll find yourself missing out on that full moon party in Bali because you have to try and upload a massive presentation PDF through WeTransfer at 1am because it’s your client’s 8am and they’re freaking out (yes, this has happened), and sometimes you feel as though you can never really disconnect.

All that being said, the freedom to move about the world and yet feel confident you’ll have the money to buy yourself that next plane ticket is, for some, worth more than gold.

If you were in the last category above and you don’t really give two sh*ts about your current work, or the idea of picking up jobs around the world interests you then check back soon for How to Start Travelling #3: Choose Seasonal Work…