Andy Isaacson is a freelance writer and photographer whose stories have appeared in The New York Times, Smithsonian, AFAR and National Geographic Traveler. He’s the recipient of four Lowell Thomas Awards for travel writing and photography. He lives in his hometown of Brooklyn.

How did you get started traveling?

The summer before college — after a year “off” spent teaching skiing at a Colorado resort and traveling the Southwest — I took my first solo international backpacking trip, to Northern Italy. I was 19. I began in Rome, learned Italian at a language school in Florence, hiked hut-to-hut through the Dolomites, did the prosciutto-cheese-bread and museum/church thing across cities and hill towns. I slept in hostels and rifugios and occasionally town parks. I’d say this was the trip where I found my groove as a traveler — where I first gained my chops. It was also a kind of “coming of age” journey.

How did you get started writing?

Fast forward to age 26. I was living in San Francisco, and working at a giant corporate PR agency. The job wasn’t personally the right fit, but “media relations” had exposed me to journalism and professional writing. Eventually, I needed a course correction, and quit, and then booked a ticket to Asia. It was meant to be a six-month trip, but I just kept going: Japan, Thailand, Laos, Cambodia, Vietnam, China, Kyrgyzstan, and India — 11 months in all, mostly overland without a plan. Along the way, I wrote periodic emails to family and friends. They read like dispatches — travelogues with some reportage — and people really enjoyed them! Meanwhile, I felt in my element: off-the-beaten path, immersed. Their feedback, as well as the experience of “reporting” and writing, told me that I’d hit on something. I returned to the States and pursued this new career. I had no interest in being sequestered in graduate school, so I fashioned my own kind of curriculum, with internships at KQED, CNN’s SF Bureau, and the Center for Investigative Reporting. That year of dabbling spit me out onto the writing and photo path.

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

I began my journalism career with an unpaid internship at KQED Radio’s “Forum” show in San Francisco. While putting together an hour-long program on immigration, I came across the Minuteman Project, an association of right-wing Americans — you could call them vigilantes — who were congregating on the Arizona-Mexico border to stop migrants from crossing. Months later, once I set out to freelance write, and got an assignment with an Internet publication to report the story. All the major outlets were down there — CNN, Los Angeles Times, AP. I had zero travel budget, which forced me to summon my scrappy backpacking skills: I camped out with the vigilantes, and diverted from the herd of reporters, coming away with a 7,000-word story on illegal immigration told from both sides of the border. That published piece led to another one in the San Francisco Chronicle — and I’ve been freelancing ever since. And still hoping for another break.

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

I’ll answer that with an anecdote. Five years ago, on a travel magazine assignment, I spent one month on the island of Tristan da Cunha. Tristan (U.K.) is regarded as the world’s most remote inhabited island: it sits all alone in the middle of the South Atlantic, and is home to 260 British citizens. Many of them have never left the island. Only eight ships a year — mainly fishing vessels — make passage there. One consequence of Tristan’s isolation is that memories there are long, and over the years the islanders have been slighted in the press from time to time — cast as backwards, etc. They’ve never forgotten this. In fact, introducing myself as a “travel writer” was even worse than a “journalist” or “reporter,” as the only media type ever to have been banned from the island was Simon Winchester. I was extremely sensitive to this legacy and their wariness. I tried not to be seen taking notes or interviewing people, at least not for the first half of my stay, and was very polite and respectful. Still, building trust in such a close-knit and skeptical community, in which you’re effectively trapped, was a great and intimidating challenge. Some people assumed I carried around a powered-on recorder tucked in my pocket. Others were just reluctant to talk, concerned that their words would be twisted, and so politely avoided me. I hadn’t expected this at all. But I had a job to do there, and the job requires you to chisel at those barriers, earn trust, and warm people to you.

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

Telling a good story. The Tristan experience offers an example: during my month there, nothing really happened. I mean, I had a fascinating and memorable experience on the island, and it’s an interesting place historically and anthropologically, but it lacked many elements of a good travel story — like, an obvious narrative. Did I go through some personal change during my stay? Not really. Were there events on the island that I witnessed which could provide intriguing fodder? Not really. I cobbled things together, but ultimately my story got by on the uniqueness of the place. Narratively, it never really goes anywhere, and suffers because of that. (In retrospect, I don’t think a travel story was the best way I could’ve written about the place.) So even if you seem to have many elements of a subject stacked in your favor, you still need to find a way to tell a compelling story. Then, there’s the further challenge of authorship: working (and often compromising) with magazines/editors who may have a different voice or vision for your story than your own.

What is your biggest challenge from a business standpoint?

Selling stories. Rather, ideas for stories (I usually write only after I’ve secured an assignment). One business strategy is that you write fewer, higher-paying stories. Another is that you churn out volume for lower fees. I’m just not a fast or prolific writer, so I opt for the former strategy, which is more of a patience game, and also a gamble. Fortunately, I also photograph, which earns me supplemental fees.

Have you ever done other work to make ends meet?

For a time I participated in focus groups — the kind where companies seek feedback from Joe Consumer on a forthcoming product — and these netted me some extra dough. And I should mention that these days I mainly write non-travel stories for non-travel media.

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

Video Night in Kathmandu, by Pico Iyer. My mom gifted it to me — I must’ve been in high school at the time. The book was about the globalization of culture, a subject that really interested me, and Pico’s observations — his way of seeing — resonated with me. My eye also turns toward, and is amused by, incongruities and contrasts (the monk in the Mickey Mouse shirt). I tend to look for those.


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

The fact is that the bread-and-butter of today’s travel media is in providing “service” — useful information that is of value to readers. My first advice to anyone considering going into travel writing would be to put aside initially those ideas of getting your 4,000-word travel story published by a magazine, and ease your way in. Think of yourself as a travel correspondent: What places do you know really well? Or, when you travel somewhere, what can you find out? At first, pitch these service pieces — dish the inside scoop. Make some money this way. Meanwhile, write your travel narratives. Just remember that few people want to read about what you did on vacation.

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

Seeing the world and its humans, of course, but doing so with a purpose — a reason — and also being the eyes for thousands of people who may not have the ability or good fortune to travel these places themselves.