How to Make It as a Travel Writer, According to Four Veteran Freelancers

If you asked freelancers what their ultimate gig would be, the most popular answer would almost certainly be travel writing. Getting paid to travel around the world, explore different cultures, eat amazing food, and write for your favorite publications? It’s the ultimate pipe dream of writers everywhere.

For those reasons, it’s also one of the hardest gigs to get. But for a select few, it’s more than just a pipe dream—it’s their reality. We talked to four successful travel writers to learn how they got to where they are, how travel writing has changed in the digital era, and what advice they’d give to anyone hoping to break into the field.

Four paths to the travel pinnacle

If there’s one thing that’s obvious from these four writers’ stories, it’s that there is no one method for success in travel writing. Each writer took their own idiosyncratic path to the top, though a combination of luck, drive, and personal brand-building connects them all.

Chuck Thompson, published author

Portland-based writer Chuck Thompson started his travel writing career with American Way, American Airlines’ in-flight magazine. Eventually, he moved to Dallas to work as the senior editor and followed up that gig with a series of editorial jobs at Travelocity, Maxim, Southwest Spirit, and Escape. Along the way, he developed a roguish, occasionally raunchy storytelling style which took flight in his memoir, Smile When You’re Lying, a comical expose of the travel media world.

Thompson is an interesting study in the dynamic between personal writing styles and the way publishers adhere to certain standards. His book is based on acerbic observations that reveal uncomfortable truths about the travel media business, something he found hard to do for magazines and other travel publications.

“There’s a difference between what you can write in travel books as opposed to sites or publications, [because they] have to answer to advertisers and other influential players,” he said. “You really can’t blame publications or websites for being sensitive to copy when they’re dependent on revenue from advertisers for survival.”

Robin Esrock, the “bucket list writer”

Known in Canadian media circles as the “bucket list writer,” Robin Esrock did the traveling first, thanks in part to proceeds from a personal injury insurance claim. The fame came later. After Esrock applied his experience as a web designer for BBC to build a website for recording his journeys, he started pitching newspaper editors on a whim.

“There’s always been a strong desire to see certain things and go to certain places before we die, but it didn’t have a catchphrase until The Bucket List was released in 2007, after which the term quickly took hold and became far more popular than the actual movie,” Esrock said. “Today, just about everyone knows what a bucket list is, and I’m thrilled to be able specialize in it.”

Thrilled but measured nonetheless. “I’ve come to believe that building a brand is half luck, half work. But mostly luck,” he said. Esrock has spent over a decade researching and writing material for his next book, The Great Global Bucket List, which is due out in 2016.

Tim Neville, New York Times contributor

Tim Neville is based out of Bend, Oregon, and freelances full-time for A-list publications like The New York Times, Outside, and Men’s Journal. His oeuvre strays well off the beaten path; he’s written about hiking in Albania, skiing in North Korea, and e-biking across the Swiss Alps. Many of Neville’s travels happen within the strict regulations of the Times‘s anti-freebie policy—which bars anyone from writing if they accept gifts, free rooms, and so on—but he’s managed to adapt.

“$1,500 isn’t very much when you need to fly to Europe or Asia. I’ve been able to make it work by piggybacking assignments and expense accounts from other publications and doing stories for the Times as well.

Great stories, it turns out, can even take place in your backyard.

“I wrote a coming-of-age essay for a collection called ‘A Leaky Tent Is a Piece of Paradise,'” Neville said. “It’s called ‘Once Upon a Time in a Tent. It’s about how I lived in a tent for five months after my high school girlfriend dumped me. I felt like a total failure in life and so I “gave up” on society and moved out of the house, but I didn’t go far—just into the backyard.”

Everett Potter, veteran magazine writer and blogger

Everett Potter was in the right place at the right time—the golden age of print magazines from the mid ’70s to late ’90s—selling story and photo packages from destinations like Tibet, at a time when the world seemed a whole lot bigger.

From the start, Potter knew the value of a steady gig. “The key to success was not settling for any old assignment but angling for a regular column. Or several columns, simultaneously, which became my modus operandi for decades.”

Outlets included The New York Times Syndicate, Diversion magazine, Ski magazine, and Smart Money. Potter parlayed that business experience into a weekly news blog, Everett Potter’s Travel Report, in 2006, which has since grown. “The stable now has more than forty writers,” Potter said, “most of whom I’ve worked with over the years. I guess I’ve become a ‘brand,’ but I’ve always thought it was most important to establish yourself as an expert in whatever niche you chose.”

How travel writing is changing the digital age

All four writers are ambivalent about the future. Thompson, Esrock, Neville, and Potter all agree that there’s tremendous potential in making the transition from print to digital, but also that compensation—which was never great to begin with—has been eroded by competition and lousy digital rates.

“Almost no one online is paying a living wage for writing,” Thompson said. “If you want to pay the bills by writing, it’s a tough go these days and will probably stay that way. But when I started doing this, all I heard from people was how impossible it was to get writing work and break into the racket. People manage to do it all the time.”

Both Esrock and Neville are helping raise young families, which can makes things all the more difficult.

“If you want to make a solid living, raise a family on your income and drive a reliable car, well, you better be a great hustler or be extremely talented,” Neville said. “The ways in which storytelling is delivered are changing, but humans will always find a way to make money off of other humans.”

Esrock believes that the pitfalls of freelancing—unpaid work, sketchy editors, and lowball fees—are becoming more common, but he added: “People will always need inspiration, and they’ll listen to engaging voices who can give it to them.”

At 63, Potter is the éminence grise of the group, and recognizes that times have changed. “The days when you could make a bundle selling five stories from one trip are pretty much gone,” he explained. “Today, with the lines blurred, partnerships and sponsorships seem to be the way that many writers work, out of economic necessity. The future belongs to those who can create marketing opportunities for themselves as well as write something worth reading.”

Thompson’s ultimate advice is to avoid limiting yourself according to genre.

“Focus on ‘writing’ as opposed to ‘travel writing,'” he said. “You can write about all sorts of things—politics, sports, the environment, games, movies, gardening, architecture, food, art history—and still travel. I feel an obligation to get better at it and try to elevate the standards of the game. Travelers deserve better travel writing.”