How to Support a Life of Travel

Sitting in  Santorini  in our first month of travel after quitting our jobs.

Sitting in Santorini in our first month of travel after quitting our jobs.

Say Good-bye to Your Cubicle Forever

How to get started

After years working 9 to 5 in a stuffy cubicle, we had both had enough. Don’t get me wrong, we both have had some great experiences at our past jobs, but we just weren’t doing what we loved. To be able to really live the lives we wanted to, we knew there were changes that needed to be made. That’s why we packed up, quit our jobs, and headed out.

We took the knowledge that we had and the bags on our backs picking up travel tips along the way. We were lucky enough to run into a fellow traveler in Bali, an Englishman named Matt, who quickly became a great friend of ours. We swapped travel info and inspo and became even further acquainted with life on the road.

One of the issues with living a life of travel is trying to break the stigma of not having a “traditional” career. It’s not a concept that people totally understand yet and has definitely taken some getting used to. Matt told us that his grandma wouldn’t have the easiest time grasping the concept so he just tells her he’s a traveling computer salesman (he actually builds websites for clients while traveling… close enough).

What’s the Catch…

When thinking about beginning a life of travel, you might envision it as this giant, earth-shattering moment where it hits you that traveling should be your life. For Matt, and us as well, it was much more casual. After meeting fellow travelers, we have noticed that this tends to be a trend. Our advice? Try it out! What do you have to lose? If it doesn’t work out for you, all it takes is a plane ticket back. You’ll never know unless you try.

Traveling can become an incredible way to network and market ‘on the go’ career. You’re surrounded by so many new people who you are able to inform about your work and even others in your same situation. Many places now even have co-working facilities where people who work remotely are able to go to have reliable internet access and also network.

An office away from the office. Sitting in the city or suburbs of the US, this may seem like such a crazy concept because you don’t see people working this way. But once out traveling, you realize just how many people are able to work remotely and support their life of travel.

Working remotely

There are inevitably some challenges that you’ll run into working remotely while traveling. Time differences, physical distance, and the fact that you’ll want to be adventuring rather than working are all issues that come when you mix work with travel. And what about access to workspaces? It’s hard to believe, but Wifi isn’t just found everywhere.

There have definitely been times on our journey where we’ve had to set up shop in rickety cafes and pay to use internet access. Gets the job done, though! The biggest hurdle is realizing that your new “office” isn’t going to come with easy access to supplies and resources.

You’ll have to be able to figure out what you really need to work remotely and learn from experience with what works and what doesn’t. The trick to a remote office is finding ways to do it minimally. Take with you what you’ll need and leave behind what you won’t. Once on the road, you’ll realize how little you actually need to work efficiently.

time zone trouble

Time zones are a trickier obstacle to face. It’s important to always be aware of which time zone your clients or company is in and know when will be an appropriate time for you to work based on that. You may find that you’ll have to answer a few conference calls in the middle of a Friday night or work a day ahead of schedule to keep up on deadlines. You’ll fall into a routine that works with both you and your work. If you’re able to find a job that’s flexible enough, you may not ever run into this issue! Lucky you.

The Price You Pay To Travel

Saving up for a continuous life of travel may sound daunting, but it’s important to remember that the amount you have saved can be stretched depending on where you’re traveling. When talking with Matt, we both noticed that our time spent in Bali allowed us to stretch our savings the extra mile. What might have taken us 4 months to save for can be stretched for maybe 8 months if you travel somewhere where the cost of living is lower. Take that into consideration when both budgeting and planning out details.

Not everybody is able to get this done in one shot, either! Many people travel and work remotely, head back home where they are able to make steady income again and reevaluate their plans, then head right back on out to try it again. If you have the drive to do it, you’ll be able to make it happen whether it’s a change in career path, change in employers, or even just asking your current employer if working remotely is a possibility.

Time to Make the Move

The biggest task at hand is ripping the band-aid off and going for it. Finding that first client. Making that first order. The first steps are always the hardest but always the most crucial.  It is more than possible to support a life of travel! Continue to invest in yourself, your business, and your goals to make it all happen.

How to Make Money and Travel - Matt’s Story

Watch the full interview here: