Bob Payne is a freelance travel writer who has visited more than 140 countries and had his work appear in such publications as Outside, Men’s Journal, Islands, and Bon Appétit. He was a long-time contributing editor at Conde Nast Traveler, where he believes he remains the only one of their writers to put the cost of a Polynesian tattoo on an expense report. He is the author of the memoir Escape Clauses: Getting Away with a Travel Writing Life.

How did you get started traveling?

I ran away at 15 and spent a summer hitchhiking alone around the U.S. When school started, I returned home, and the following summer my parents, demonstrating a spectacular lack of good sense, allowed me to fly to Mexico City to visit the family of a school friend. I stayed for a day then, unannounced, climbed aboard the first of a long series of local buses that would take me the length of Central America to Panama.

How did you get started writing?

I wrote a (sadly, never-published) account of my hitchhiking journey, which I polished and re-worked and polished some more before finally losing the entire manuscript when I had to leave it in the care of a woman who did not tell me until inconveniently late that she was married, to a husband on his way home, from prison. I still think about that woman, and when I do I remind myself how important it is to make a copy of everything you write and keep it in a safe place.

What do you consider your first “break” as a writer?

I’d been traveling to little-known parts of the world, writing about them mostly for Sail magazine, when by chance I found myself in the Maldives, which at the time was visited by almost no Americans. Although I’d never written for a travel magazine, I pitched an idea about these hideaway islands to Conde Nast Traveler, which to my amazement they ran as a cover story. I can’t tell you how happy I was, when they wanted to know if I’d paid my own way to get there, that all the letters I’d written asking for free airfare had gone unanswered.

As a traveler and fact/story gatherer, what is your biggest challenge on the road?

Chronicling your last journey, gathering details from the current one, and planning for the next, you must often live in the past, present, and future all at the same time.

What is your biggest challenge in the research and writing process?

Knowing when to stop researching, when to stop writing, and when to just turn the damn thing in.

What is your biggest challenge from a business standpoint?

The same as for most writers of every genre. Making sure to marry well.

Have you ever done other work to make ends meet?

For short, haphazard stints, I’ve been a newspaper reporter, a magazine editor, and an advertising copywriter. At the latter, I made more money and was more miserable than at any other time in my life.

What travel authors or books might you recommend and/or have influenced you?

For their humor: Redmond O’Hanlon, Tim Cahill, and Mark Twain. For their ability to draw out the stories of the people they encounter: Paul Theroux and William Least Heat Moon. For her gloriously sharp eye: Freya Stark, who observed of a traveling companion, “…the country seemed to be thick with relatives of people he had killed, and this was a serious drawback to his usefulness as a guide…”

What advice and/or warnings would you give to someone who is considering going into travel writing?

When you fly, always ask for the middle seat. It doubles your chances of hearing a good story.

What is the biggest reward of life as a travel writer?

Being able to return home from far places with stories to tell.