Real Travelers Share Their Secrets
Imagine having a job where you can come and go as you please. Where you could work in the Caribbean one week and then in Europe the next. Your wanderlust wish is easier to achieve than you might think.
While certain professions like cruise ship workers and flight attendants lend themselves to paying people to see the world, an increasing number of people are finding non-traditional ways to make money on-the-go.
More and more people are making an income while traveling whether by freelancing, starting their own businesses, working remotely for major companies and startups or joining a group of like-minded folks who travel and work remotely together for up to a year via companies like We Roam, Remote Year and Hacker Paradise.
Get inspired by these travelers who are making money on the road.
Be Your Own Boss
“It is fun to wake up in a different city, have coffee, eat local food and still be able to earn an income,” said Dr. Cali Estes, the CEO of The Addictions Coach and The Addictions Academy. Estes teaches webinars from around the world, conducts mobile rehab and travels with her addiction clients to help them stay sober.
“Imagine traveling to the beach with a client and sitting there on the sand having a great discussion about their life and goals…and getting paid to do it,” said Estes, who travels across the U.S., Canada and Mexico.
Become a freelancer
Two years ago, Kate Gilbert left her 20-year career as a marketing executive in the healthcare sector, sold her home and everything in it, and hit the road to travel full time at age 45. She is a freelance strategic marketing consultant and splits her time between traveling around the U.S. in an Airstream trailer and renting apartments and homes around the world.
“I quit my full-time job mostly because I wanted more flexibility in my schedule,” said Gilbert, who, along with her husband, drastically reduced their expenses to travel full-time. “Switching to a freelance role that was location independent has allowed us to pursue a life that prioritized our goals rather than being trapped in a corporate job that dictated our schedule.”
Gilbert has spent the last five months in Southeast Asia and is headed to Chiang Mai, Thailand for her final month in the continent before heading back to the Airstream for the summer.
“As long as I can get online, which is now almost anywhere, I can work with my clients,” said Gilbert.
Fuel your creativity with travel
UX designer Esther Kuperman, CEO of consulting company Pure UX, designs and develops mobile apps for large tech companies and startups.
“I think part of being a great designer is drawing inspiration from everywhere. Travel is one of my main sources of inspiration,” said Kuperman, who has worked and traveled through Central and South America. “When I’m traveling, I get some of my best ideas. It allows me to be free to think without the daily grind.”
Kuperman generally works remotely for one or two months and then returns to San Francisco before heading out again.
“I usually get up super early and finish all my work by 2 p.m. Then, I can go out and surf, learn Spanish, whatever floats my fancy.”
Open an online store
Husband-and-wife Karolina and Patryk Kleśta are full-time travelers thanks to their online store, which they started three years ago. The couple sells products made in China to retail customers in Europe using a drop-shipping model. Managing their online store via a fast laptop and Wi-Fi has enabled the couple to travel to more than 30 countries so far.
Start your own company
Growing up, Joshua Schall’s family didn’t travel very often, so after graduation, Schall decided he would like to explore the world as much as possible while also working. After balancing travel and a traditional office job for several years, Schall started his own company, J. Schall Consulting.
Schall is a fitness business strategy consultant, traveling 70 percent of the time and remotely manages sub-contractors. During the past three-and-a-half years, Schall has traveled to Belize, Canada, Germany, Netherlands, and 40 states in the U.S. He typically travels for two to three weeks and then comes back home to Austin, Texas for a few days to repack.
Work as a team
Working remotely isn’t just for solo travelers. Couples can pool their skills and income to fund perpetual travel. Rob and Tracey Tullis decided to work remotely and travel because they wanted to have more time to be together as a family. Both left their careers in 2012; Tracey was a retail manager and Rob was a financial planner. Since 2014, the couple has worked and traveled with their 7-year-old son, Makai (they sold their home and belongings to make the journey possible).
“We left to prepare for perpetual travel, pursuing our home business on a full-time basis to fill the gap,” said Rob Tullis. “Our home business involved selling my art and goods we imported while traveling at markets throughout our home province in Canada. Working our home business was a lot less demanding so we had more time to learn skills we needed to find work online and be able to work remotely.”
The couple works full time from their laptops and the road from places like Canada, Colombia, Ecuador, Panama, Romania, Spain, Turkey, and the United Kingdom. Tracey is a freelance writer and does public relations work while Rob helps online business owners and offers WordPress maintenance and SEO optimization services.
Become an e-commerce entrepreneur
Max Robinson always wanted to see the world and “did everything I could to have the lifestyle,” said Robinson, who hardly traveled in his youth. “I purposely avoided relationships and studied languages at university in the hope of working as a freelance translator. But the final push that forced me to consider a life of traveling was simply a lack of income!”
After spending several months traveling across Morocco. Robinson started researching ways to make money online and came across the Amazon Affiliate Program, Amazon.com’s e-commerce program that allows bloggers to make money via affiliate links.
“I knew countless people who used Amazon on a daily basis, and figured that if I created a website which targeted certain products that I could make a decent income,” said Robinson, who started Fish Tank Bank Ornaments, a website devoted to fish tank ornaments. His original goal was to make $20 per day; he claims the website makes roughly $2,500 per month.
“I’ve tried to replicate the success that I’ve had with Fish Tank Bank Ornaments with other websites, but it has never really worked. I think I got really lucky with FTBO and found a niche that people were passionate about,” said Robinson, who spends eight months annually traveling and has worked remotely from Australia, France, Germany and Morocco. “Now I can travel freely, and I’m not limited to a budget of $20 per day!”
Write about your travels
Freelance writer, journalist and editor Andrea Anastasiou always wanted to travel. With no mortgage, debt, or anything tying her to a particular place, she decided in 2014 to leave Dubai, where she had been working as a journalist, and just go for it. She’s been a working nomad ever since.
“While I still had a full-time job, I started freelancing on the side in order to build up contacts. I wrote articles for various newspapers and magazines,” said Anastasiou, who blogs about her solo travels on her blog Scribble, Snap, Travel and earns an income from writing articles for magazines and newspapers and copywriting for websites and brochures. “After a while, I had a good working relationship with a number of editors, which gave me the confidence to quit my office job and go solo.”
Run a virtual company
Andy Abramson is so adept at working remotely that he was named Business Traveler of the Year by Business Traveler magazine in 2015 “Not for miles or nights away, but for how I traveled, worked and lived on the road,” said Abramson, the CEO of Comunicano, a global value creation communications agency that focuses on audience engagement.
Abramson has traveled 200+ days a year for the past 12 years while running a completely virtual company. Abramson works remotely and so does his team. He likens his travel-work arrangement to a “WorkCation” where “One visits a part of the world where work can continue and yet, part of the time, while you’re away is like a vacation or where you can easily travel on weekends to place one would like to visit, or meet up with friends and colleagues you don’t normally connect with as often,” said Abramson.
Design websites
Jeremy Belcher is a freelance UX designer who works remotely for American design agencies that are also remotely staffed. He lives in New York with his wife and son, but his job has allowed him to work remotely and travel for long stretches of time like six-month stints in Buenos Aires, Argentina in 2011 and Tokyo, Japan in 2014 while working remotely for American design agencies.
Be a motivational speaker
Barry Maher travels all over the world as a motivational speaker.
“I love to travel and I love to talk. When organizations started asking me to speak at their meetings, it was a perfect fit,” said Maher, who has traveled extensively from Ohio to Oahu, Hawaii to the Sultanate of Oman.
Through his company Barry Maher & Associates, Maher has been making money by doing keynote speeches and workshops at conferences and corporate meetings for the past 20 years. His clients include ABC, Budget Rent a Car, Canon, Hewlett-Packard, Lufthansa Airlines and Verizon Wireless.
Be a copywriter
Jackie Tucker wanted the lifestyle and freedom that comes with working remotely and loves to travel, so she made that her business. Tucker is a freelance copywriter who started Shoofly Copywriting two years ago and is currently living in London. She does the majority of her work online via web conferences and email.
“Before leaving the States, I consulted with my clients to let them know I would be traveling abroad and provided them with various ways to reach me: Skype, Web conference software, email, etc.,” said Tucker. “I also mapped out my plan and timeline for completing upcoming projects to reassure them that the work would still be finished.”
Be a digital nomad
Jonathan Weber is the founder of Marathon Studios, Inc. and runs the tech and media company that builds websites and apps from his laptop while backpacking around the world.
“One of the best things about my job, and any job that involves working on a computer, is that while I’m working, I can be physically located anywhere, so long as I have my laptop and Wi-Fi,” said Weber, who spends up to six months a year traveling around the world.
He visited 64 countries so far, bunking at hostels and guesthouses in far-flung places like Croatia, Kyrgyzstan, Thailand and Turkey.
“There’s a whole community of people from around the world who work while traveling, most of whom are self-employed or work remotely over the Internet, and many countries have started to develop infrastructure like co-working offices on the beach to cater to them,” said Weber, who allows his employees to work remotely too.
“Why would I sit in an office and work on the computer when, instead, I can sit on the beach in Thailand and work on my laptop?” said Weber.
Sell art
Artist Michelle Eshelman has spent the last two years backpacking through South America and Asia while running her online art business Paintspiration Art. She quit her job as a mental health counselor in Washington, D.C. to follow her location independent passion. She was first introduced to the idea of a long-term travel and work arrangement during the first date with her now-fiancé.
Eshelman started out by selling her canvas paintings on Etsy and, once she hit the road, she expanded by selling her artwork printed on various mediums like paper prints, throw pillows, and phone cases on her own website and on Amazon. Eshelman creates the artwork, lists the items and manages customer service and a blog. She teamed up with a manufacturer who makes and ships her products as orders come in.
Engage in portable public relations
Jackie Jones wanted to accompany her husband, a veteran journalist, on his travels on assignment around the world, so she turned to entrepreneurship to make it happen. She combined her passions for networking, marketing, business and travel to create TruthPR, an online news distribution company that distributes media releases via radio, TV, print and social media.
Seven years ago Raminta Lilaite started Lilas Communications.
“After having worked in PR industry in New York, I felt I was ready to look for my own clients and to start working from wherever I wanted – and that did not include an office cubicle,” said Lilaite, whose clients range from luxury hotels to brand new startups. Lilaite also partnered with a group of entrepreneurs to launch Riviera Maya Property Consultants, a real estate company in Tulum, Mexico that provides real estate and architectural services.
Use your experience
“Making money wasn’t my original goal, but I started using my experience in advertising to help charities and hotels with their marketing,” said Blakely Downs, who used her advertising experience to create a website, Round The World Lovers, to chronicle her travels with her husband, who worked in commercial real estate. Writing for herself has led to writing opportunities at websites like The Huffington Post, Glamping.com, and Honeymoons.com.
“The key is to use your experience and strengths while you travel, not try to create a whole new career; just refocus the old one,” said Downs.
Be versatile
Frank (Skip) and Gabrielle (Gabi) Yetter quit their media executive jobs, sold their home, sold or gave away most of their possessions, and moved to Cambodia in 2010 to work, write, volunteer and travel. Both had public relations, marketing and journalism experience that has served them well during their worldly travels.
“Initially, we volunteered through a U.S. organization, but over the course of the next three years, we developed a network of outlets and sources that led to a series of writing assignments and consulting jobs that, combined, created a steady stream of income,” said Skip Yetter.
The couple left Cambodia in 2013 and have been traveling the world, which is funded by house sitting and writing (the couple co-wrote Just Go! Leave the Treadmill for a World of Adventure, a book about their experiences). Skip wrote and published K.I.S.S. Kooking: Simple Cooking, Simple Meals, for Simple Kitches (and Simple Minds), a cookbook, and Gabi just released a children’s book, Ogden, the Fish Who Couldn’t Swim Straight.
“Travel feeds learning and developing different perspectives on the world is perfect to nourish a writer’s mind,” said Skip Yetter. “We get creative ideas wherever we go, and since we’re both writers and editors, we are constantly bouncing ideas off of one another and helping develop concepts.”
Things to know before you go
Ready to hit the road and work remotely? Follow these tips:
- Conduct a self-evaluation. “Find your strengths, skills and abilities; then find a way to make a living doing that remotely,” said Tucker. “If you’re a writer like me, look for freelance/contract work or a company that is fine with you working abroad.”
- Develop skills. “Develop online working skills and have a consistent income coming in before you leave to travel,” said Tullis. “Traveling long term has many challenges as it is, but trying to do it and learn a new work skill set at the same time can be both incredibly stressful and hard.”
- Plan ahead. “Always, always, always have a plan,” said freelance journalist Anastasiou, who has worked and traveled to Cambodia, India, Indonesia, Thailand and Vietnam and has been in Europe for the last 12 months. “It’s easy to look at the photos ‘digital nomads’ post on Instagram, Facebook, etc. and think ‘wow, that’s so glamorous and fun!’ and that it’s the easy alternative to a stable office job. It really isn’t.”
- Save money and be patient. “It took me about a year just to build up the contacts that I needed in order to go solo; save enough money in order to sustain myself in emergencies/when the work doesn’t come in – trust me, this happens more often than people like to admit,” said Anastasiou. “First, build up your freelance work while you’re still in a stable office job, save as much as you humanly can, and come up with a plan on how you actually intend to make money. Also, be prepared to put in a lot of hours, especially at the beginning – it really isn’t an easy job, but when done the right way, it can be so rewarding.”
- Set expectations. “It’s not always a bed of roses,” said Tucker. “Consider the effects your travel has on family and friends. You will most likely not be around for some important events that may occur in your friends and family’s lives, such as graduations, births, deaths and the like.”
- Do your homework. “Location of where you work is key. Fortunately, I’ve been a regular visitor and traveler across Europe for over 30 years, so I’m quite familiar with the transportation systems, how to best travel and get around, using the approach of behave like a local, not a tourist,” said Abramson who found great apartments in Portugal via airbnb and rented an “office” in Lisbon from Regus that served as a place to receive packages and included staff to coordinate local activities.
- Learn about technology. “Learn as much as you can about the resources and infrastructure that’s developed to cater to digital nomads,” said Weber. “There are dozens of organizations that can hook you up with everything you need to work remotely in a foreign country – including office space, an apartment, and a whole community of other people doing the same thing – for pennies on the dollar compared to what you’d pay to stay at home!”
- Keep it simple and flexible. “We have aggressively downsized our lives,” said Skip Yetter. “We have gone from being top consumers to rarely buying anything, other than airline tickets and hotels when we’re not house sitting, and we love the simple, uncluttered lifestyle.”
- Keep an eye on the clock. “Be cognizant of time zones when deciding where to travel,” said Belcher. “Southeast Asia is a lot of fun, but if you are working for companies in the U.S., the time change can be brutal. You’ll have to keep some pretty weird hours in order to make that work, as in 3 a.m. Skype calls.”
- Plan for the unexpected. “I had to problem solve lots of issues, from poor or no Internet connections to getting my computer stolen!” said Eshelman. “It’s good to be flexible and plan ahead when possible. For instance, if I know that I likely won’t have Internet for three days while visiting Machu Picchu, I can enable an auto-responder so that my customers know they won’t hear from me for three days, or, since I knew the potential for theft exists, I had everything backed up online and carried insurance that covered my losses.”
- Make time for self-care. “Plan it as a working vacation. Work for a few hours and then enjoy yourself,” said Estes of The Addictions Academy.
- Stay connected. Make sure you have good Wi-Fi that you can take with you everywhere. Don’t rely on your hotel/hostel to provide it, said app developer Kuperman.
- Stick to a schedule. Kuperman likes to work from 6 a.m. to 2 p.m. It’s important to find a steady place to work. When Kuperman stayed in Nicaragua last summer for two months, she worked from the beach and a coffee shop.
- Get the job done. “Remember to treat your job as a job,” said motivational speaker Maher. “You need to enjoy the trip, that’s the whole point. But if you let the trip interfere with getting your work done, the job and, of course, the trips will soon come to an end.”
- Be flexible. “Make sure you have an extreme grasp of time management and you also can go with the flow,” said Schall. “Anyone that has traveled a lot knows that delays, cancellations, or other things come up often, so you need to know how to keep your emotions centered so you can continue to work effectively daily.”
- Be creative and be open. “There are plenty of ways to meet needs with your skills and create a life of travel and choice in the process,” said Skip Yetter, who says workaways, volunteering opportunities, couch surfing and websites like Warm Showers are valuable resources for flexible people who want to travel on a budget.
- Carefully consider your job. “Some roles are more suited to remote work than others. We meet many web developers and graphic designers during our travels,” said Gilbert, who is traveling the world with her husband. “You need to be self-motivated and willing to work on your own a lot. Not everyone wants or is able to do that.”
- Don’t wait. “Work out a way to live the life you want. If you have a yearning to travel, do it, as soon as you possibly can,” said Gilbert, author of The Happy Camper: How I Quit My Corporate Job and Sold Everything to Travel Full Time. “Don’t wait for the “perfect time” and don’t delay your happiness. What is the worst that can happen? You can always come back to your old life. You’ll regret not doing it more than you could ever regret travel.”
- Consider your personal relationship goals. “The brutal truth is that if you’re in a relationship and looking to start a family or rely on support from friends and family, then it is probably very unlikely that you’ll ever actually be able to work remotely while traveling,” said Robinson.
- Have a Plan B. “Part of the risk, and, for me, excitement, of working remotely is the unpredictability involved. Only certain types of people feel comfortable with such an unpredictable way of life, so before embarking on your journey, have a backup plan and be sure that this is definitely the lifestyle that you want,” said Robinson. “I won’t pretend that I’m always 100-percent happy with my lifestyle and will admit that there are days when I consider giving it all up and getting a stable job – ‘growing up’ as some might call it – but I can’t see that happening anytime soon!”
- Network. “Reach out to like-minded people and ask questions – lots of them, and use online networking tools to build a community,” said Skip Yetter, who landed his consulting jobs by word of mouth. “We give a lot – counsel, advice, support – and it comes back in a steady stream.”
- Create a community. “We use Facebook, our blog and email to keep in touch with people we have met around the world, and to keep our friendships and networks alive and intact,” said Skip Yetter, who notes it’s also how he and his wife keep in touch with family and friends, which includes his two daughters and a grandson in the U.S. and his wife Gabi’s family in England. The couple plans their travel around visits to their family and uses Skype, WhatsApp, email and Facebook to keep in touch while traveling.
- Don’t give up. “It’s always difficult to start, no matter what you are doing. The Internet is still new, and it’s relatively simple to make money online,” said Karolina Kleśta.
- Don’t worry. “We have met tons of people who set out to travel and found ways to make a living while on the road. Some tend bar, wait tables, trade work for room and board,” said Skip Yetter. “My only regret about pursuing the nomadic lifestyle is that I didn’t get at it a few years earlier than I did.”
Featured image: istock.com/jasmina007
