Questions for a Full Time Traveler

    How do you afford to travel to all these places?

My original plan has always been to work online and be location independent. I started coaching Beachbody weight loss groups online 2 years before I quit my day job. That helped me to pay off a lot of debt and I intend to keep growing that business to support my travels. I also paint travel themed watercolor artworks and sell the prints online, though the artwork income is very sporadic. When I first started traveling I had a small amount of cash saved up, plus I sold most of my belongings. I also had a couple house sitting gigs (for friends) and they both paid me a little cash.

Some of my travel artwork.

Some of my travel artwork.

I use free travel websites: couchsurfing.com, airbnb.com, workaway.info, meetup.com, as well as new apps. I network with travelers as I go and save their contact information. The past few months I have flown an airplane, sailed the Atlantic on a catamaran, biked across Marathon island, gone to many beaches, kayaked rivers and ocean, swam in a natural spring, all for free. Traveling and “taking a vacation” are very different. I have only stayed in a hotel one night in the last 2 years. I never spend money at restaurants. Instead I pack my own food in a cooler and cook meals in bulk before I leave each destination. Once I began this journey it snowballed. I now get invitations from friends that want me to visit, dogsit, or join them on adventures such as diving or sailing. I plan to substitute teach or work an odd job the next few months to replenish, do some car maintenance etc.

Flying over the Keys with a friend from the beach.

Flying over the Keys with a friend from the beach.

    What inspired you to go on this adventure and why did you choose this route?

During my 2nd year of teaching (I taught for 5 years) I realized I wasn’t happy. I had no intentions of marriage or kids, and my career was killing me. I started searching online for people that loved their jobs. That led me to many authors and blogs, but two in particular changed my life: Tim Ferriss and Chris Guillebeau. Tim Ferriss wrote The 4 Hour Work Week and his blog is subtitled “Experiments in Lifestyle Design.” Chris Guillebeau’s blog was subtitled “The Art of Nonconformity.” At the time that I discovered Guillebeau, he was on a quest to visit every country in the world, which he has now completed. I read everything these guys wrote, and followed and read every resource they recommended. I immersed myself in the world of online bloggers, entrepreneurs, and full time travelers.

Then I wrote down the things that made me happy (art, fitness, travel, learning, writing) and travel was always at the top of the list. I thought maybe I could combine all my interests and monetize them somehow to make full time travel possible. My career was so depressing and stressful that I spent every day planning my escape.
I should also mention that from a young age, my dad taught me to love travel, read maps, visit natural parks, and trust strangers. My healthy habits come from him too. When he packed up the family in a boat or RV and took us across the country to Key West, the Redwood Forest, Yellowstone, and the Grand Canyon, I gained an appreciation for this amazing earth. Nothing in life compared to those experiences.

My first sailing experience - free through workaway

My first sailing experience – free through workaway


    What advice would you give someone who decides to journey around the nation/world for an extended period of time?

It doesn’t cost money. And it is addictive. Pack your bags and drive off in your car. Sell your abundance of crap. Learn to cook and avoid restaurants. Stop eating meat at every meal because it’s unhealthy, expensive, and it spoils too quick. And most importantly….learn how to network. I visit every friend I have in every region, and the list of friends to visit never runs out because I am always meeting new people.

Food for a day trip.

Food for a day trip.

    Did you plan everything out down to the last detail or did you have a general outline and wing the rest of the journey?

For full time travel, I have a general outline month to month. On my Europe backpacking trip in 2012, I planned every detail. In the United States I am more flexible. I also typically go places where I know at least one person nearby that could host me in case of emergency. For example, before packing my car to drive to my first workaway assignment in Florida, I knew I had 3 friends and a relative also in Florida that would help if anything crazy happened. Now that I have experience with full time travel, I am not afraid to go somewhere without that safety net.

    What did you do to prepare yourself in the early stages of your journey? Was it a gradual move or did you jump right into your travel adventure?

I did it in phases. I traveled in college to visit my dad around the U.S. and traveled with college groups. I went on my first solo trip at age 25 to San Diego. That first solo trip is like when you go to a movie theater alone for the first time, an interesting mix of emotions occur. When I was a teacher I planned all kinds of trips for summers and holiday breaks, including my month in Europe with a friend and a 7 day Colorado road trip (in Colorado I planned a KILLER itinerary that I have yet to convince anyone else to follow). Then I planned a solo 30 day West Coast road trip as my reward for quitting teaching. I networked on that trip, stayed with friends, couch surfed, and attended World Domination Summit (look it up if you’re curious).

Making friends at an AirBnb workaway gig.

Making friends at an AirBnb workaway gig.

These experiences prepared me for full time travel. They made me very comfortable alone, in airports, in public transportation. When you travel solo there is this wonderful peace that takes over your mind and body. It’s the greatest feeling I have ever had. It’s the exact opposite of vacation stress or anxiety that people get when they work all year for a two week vacation that feels like more work than relaxation. Solo travel is the dreamy escape that comes with seasoned experience and appreciation for the ultimate freedom. It’s just you, your bag, and endless possibility.

Driving down the East coast.

Driving down the East coast.

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