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The Keys To Being A [Successful] Working Traveler

Updated on June 10, 2016

When I was planning on being a journalist in school, the one thing we always through was even a wilder dream than being an employed writer in New York City was the travel blogger. For most of the people in my classes, they’re still trying to get their way to the Big Apple. But for me, I’m traveling, and writing, and really living a wonderful (self-made!) life. And the best part: it’s sustainable as long as you’ve got a little bit of know-how.

I like to say that the real secret to being a working traveller is flexibility; ultimate flexibility trumps about every other possible recommendation I could give in all honesty. But when it comes down to actual things that make my day to day as a person who takes her life on the road and still manages to pay the bills (almost, but we’ll get to that), there are just a few things that really make a difference: finding a place to work, looking for great deals, being financially smart(ish), making sure you have working technology, and being creative.

Find Your Happy (Work)place.

In my case, writing is how I make sure the piggy bank remains full enough to keep the adventure steam engine running, but there are plenty of freelance opportunities (design! photography! social media! consulting!) that make traveling a more cohesive, and regular, part of your lifestyle. The one thing that doesn’t change between the different directions is that location is really key, but not in the way you think.

One of the golden rules of writing, and a way many people learn how to turn a hobby like traveling into a career is to create a semblance of routine.

When you’re traveling it’s hard, but I like to work in the same place (i.e. a coffee shop or something similar) and at the same time (I’m always writing by 11am no matter what) on my work days. While it may be difficult to work a schedule that includes flight changes, hostel wifi outages, and the unexpected, it’s certainly easier to change my plan a little than to not have one at all.

Learn To Spot The Great Opportunities.

When I was at home and wondering how to finance my Great Adventure, I stumbled upon a lot of bad deals before I found good ones. Now I know there’s a few go-to’s that make my life easier every time and I stick with them.

First, GoEco is what took me on my first adventure, and I keep following them to many adventures because it was such a great platform for me to dip my toes into international travel and working. While some of the programs are high priced (definitely out of my league), they have hostel internships in Europe and the Middle East, and then a couple of incredible opportunities (take photos on the Serengeti with a Nat Geo photog? Yes please!) that you can save up for. Also, they have an ambassador program where loyal customers can get discounts on their next adventure--which sounds pretty good to me.

Second, I’m a big, huge fan of Booking.com, Kayak, and Airbnb. Booking.com is self-explanatory; not only a place for me to get the best deal on a hostel, but also home stays and guesthouses as well. As for Skyscanner and Kayak, they always provide options for me when I’m traveling, whether it’s a better deal on a flight just a day later or helping me plan a whole excursion while being mindful of the cheapest rates (I’m all about pinching pennies where I can, and completely unashamed about it), I feel good about booking flights because I know there aren’t any better deals out there. And while it’s not really financially awesome for me to use Airbnb in my home country, in Europe, Africa, and almost everywhere else, Airbnb is significantly lower than hotel prices for when I’m needing a little R&R between hostel stays.

Two additional saving opportunities: Groupon, and travelers Facebook groups. I went skydiving in Florida once for $30 because I found an incredible deal and was able to use it; there are more of these incredible deals out there, you’ve just got to spend the time sifting through the things that are parading as good deals (but are really just expensive mistakes). As for the traveller groups, you might find a friend, a mentor, or someone who gives you the idea for your next adventure. Even if you like to travel alone, there’s nothing wrong with keeping an arsenal of people who have been there and done that in your back pocket.

Get A Credit Card & Pay (A Little More Than) Your Minimum.

Ok, I have a confession to make: I book flights not knowing when I’ll be able to pay them off. Is this risky? Sure it is. Does it stop me? Not usually. And this is where the credit cards come in.

While I’m not into endorsing anything in particular, I will say that bonus flight miles is usually the deal I go with because I’m always in the air. If you’re more of a train, bus, or hitchhiking traveller, this doesn’t apply. The next things I look into are interest rates, transaction fees, and accessibility of cash. Interest rates are going to hurt you either way, but I never pay for a credit card and I always look for the lowest interest rate, that way I’m not killing myself trying to pay back my ticket. Second, I always see how much it’s going to cost me to pay for things in a different currency, and how much they will charge me to get cash out of the ATM. I won’t name any names, but there are companies out there hoping you won’t know that they charge more interest on cash withdrawals than card ones—so be careful.

At the end of the day, I’m young, not responsible for a mortgage, a family, or anything else, and I’m trying to see the world. Is it worth buying a $400 flight and maybe end up paying $800 for it by the time the credit card bill is paid off? To me, absolutely. You can’t put a price on experience, and since I don’t have any other loans (no school, no nothing), I consider this an investment in my education.

Be A Tech Guru.

When it comes to staying on track and staying budget, I’m not just looking for free, I’m looking for a good deal. For staying in touch with contractors and staying on top my schedule, I keep up with three specific things: 1. Good organization, 2. Good records, and 3. Good communication.

Good organization comes at a cost; you’ve got to declutter. I’m a big fan of essential packing with only two or three trinkets that are unnecessary, and when it comes to my work, I have to completely get rid of the unnecessary. I have my laptop, my charger, and my headphones with me at all times (always in the carry-on, never in the checked bag) and that’s it. The things on my computer are more important than anything outside of it, so don’t get sentimental about extra gadgets. Inside, I’m all over Google Docs (perfect sharing capabilities, and essentially Microsoft Word for free), Trello (a task-based social media platform to chart to-do lists, set up alerts, and communicate with my partners), and Instagram (for travel bloggers, Instagram can bring in big followers).

Good records include everything from receipts to eyeglass prescriptions, flight changes to a blog. For receipts, flight changes and eyeglass prescriptions, this is my idea of being prepared without having to be dragging papers with me everywhere. How do I keep track of these many slips of paper? I don’t. There are many apps to help you keep organized, but I think taking a picture and storing it in your iCloud (or email) is the easiest way of having this info at your fingertips.

As for the blog, this is essential even if you aren’t a natural writer (which I would personally say everyone is). People want bloggers to try their product, their adventure, their websites, and some will give you great deals to do so, or even provide things for free. The other (even better) perks are meeting fellow travellers and also having a great diary of all the amazing things you’ve done. Down the road, you won’t care so much about whether you have a tendency for run on sentence, but you’ll really dig having a full record of great stories. Places like OffExploring, Trip Tripping, and Pink Pangea are great places to get started with a traveling writer community—and they’re free!

Good communication is all down to my phone. Without my phone, I’m lost figuratively and sometimes literally as well so my key to keeping the phone working wherever I am is not in an international plan, but in SIM cards (don’t tell the cell phone companies!). I’ve got a pretty intense collection over the span of two years, and I have no plan to stop grabbing them now.

The SIM card allows you to pay what the locals are paying, get the local connection, and only use as much as you need so you’re never wasting. I grab one in the airport at a cell phone kiosk, pop it into my phone, and reload via their website when I run out. Everything should start working and if not, you just need to unlock your phone. But the technicians are usually helpful and will more often than not do everything for you!

Get Creative.

There are clever ways to get to travel, like grants, being sponsored by a company, or finding work-stay programs in a hostel. And while these are hard to find, they aren’t impossible. Grants to study are common, and grants to travel are as well, as long as you can provide a service in exchange or prove that your trip is worthwhile. If it’s not disrupting your other work, I say go for it.

Being sponsored by a company, to either use their new gadget or promote their product on social media, may seem like a cop out, and a way to be that spokesperson who everyone unfollows, but depending on what the terms are, it might be a really great deal. Also, if you’re blogging and take one of these opportunities, it’s a great way to someday market yourself as a professional traveler where all of your expenses are taken care of. Does it mean curbing your independence to include their plan? Absolutely. But it’s also a great way to see the world.

As for work-stays in hostels, it’s my secret weapon #1. All over Europe I’ve found places that will trade a night in a bunk for a few hours working at their in-house bar, making beds in the morning, or taking pictures of their guests for their social media accounts. If you get one that will work with you, you can even access a whole string of them when they own, or know people in hostels all over the world. I’m totally for working to travel, and if you’re not too proud to get your hands a little dirty, it’s totally possible to finance an incredible journey. So grab your supplies, your one backpack and one carry-on, and get to exploring.

Bon voyage!

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    • Stephen C Barnes profile image

      Stephen Barnes 15 months ago from St. John's, Newfoundland and Labrador

      Thanks for the tips Claire, I am sure they will be helpful with my planned midlife career change. I look forward to reading more of your work.