Matador Creators Spotlight: Robert Isenberg on How to Make a Living as a Travel Writer

Matador: Tell us a little about your background and what you feel sets you apart from other travel writers and content creators?

Robert Isenberg: I’m a writer and filmmaker based in New England, and I’ve done a wide range of work — mostly magazine-style journalism, but I’ve also written stage plays, published poetry, directed narrative films, photographed weddings, performed sketch comedy, and produced a mess of short documentaries. I love trying a little of everything. I feel the skills for each pursuit cross-pollinate with all the others. First-person essays are my favorite, especially when mixed with travel.

A selfie in front of the Forbidden City, Beijing. I was recently sent here to help research a guidebook to China. Photo: Robert Isenberg

How did you initially hear about Matador Creators and land a press trip?

I’ve followed Matador for years, and I even published a piece about cycling in Taiwan back in 2020. I also applied for several press trips, taking each rejection in stride. I know how rich and diverse the Matador Creators talent pool is, and I’m accustomed to pitching dozens of ideas monthly. Landing the Newport trip was a real honor, not least because I got to celebrate my adoptive state.

How long have you been working with travel brands and media, and how did you get started?

Depending on how you measure it, I’ve published stories about travel, off and on, for about 24 years. Some were small but mighty, like a 400-word sidebar about cycling the Great Allegheny Passage in a Moon Handbook. Others have been outstanding privileges, like long-form features for BBC Travel. Most of my professional work is hyper-local, published in the weeklies and glossies or wherever I was living at the time. But these behave a lot like travel pieces, helping locals discover the nooks and crannies of their hometowns.

What three tools do you rely on most when creating your travel content?

The readership is most important. Who are they, and what are they looking for? How familiar are they with a place, and what do they know and not know already? Second, I try to keep an eye out for surprises — to upend stereotypes, to humanize experiences, and often to find gentle humor. Third, I love local lore. What do the people who live in a place think about? Perseverate over? Treasure? Regret? I’m amazed at the things people will tell a complete stranger, and I try to respect that trust.

How has working with Matador helped your work in travel?

I routinely refer prospective editors to that Taiwan piece. This is exactly the kind of trip I love, and I tried to write it in a breezy, instructive way. This press trip to Newport also broke the ice with a lot of hospitality folks I wouldn’t have easily found otherwise, despite their living and working just 45 minutes from my front door.

What advice would you give someone interested in becoming a travel writer or content creator?

The bad news is that it’s certainly hard to make a living. I’ve coupled my travel work with myriad other projects for years. Rejection is part of the process, and it’s never fun. The good news is you don’t actually have to travel far. Most travel editors want experts in a given place, which translates to “people who live there.” I’ve written gobs about Rhode Island for travel publications, and when I lived in Costa Rica or Pittsburgh or Phoenix, I wrote about them as well because I learned their ekistics inside and out. It’s more romantic to take a jet to some distant island you’ve barely heard of, but to get started, pitch what you know, earn an editor’s esteem, and get more visionary with each new idea.

A passerby was kind enough to take this picture in Mutianyu. I love history and architecture, and my first visit to the Great Wall was a spirit-moving experience in cherry blossom season, no less. Photo: Robert Isenberg

What are some of the biggest misconceptions or challenges about being a travel writer or content creator?

Most of the authors we remember are sprawling memoirists of the Cheryl Strayed and Ernest Hemingway set. I love this kind of personal work, and the Pico Iyers and Kira Salaks of the literary world have inspired much of my own work. But those kinds of epic volumes are hard to complete and even harder to get published. Most travel writing is functional; people want to know what a place is like, what they’ll find when they get there, where to book a hotel, and what to watch out for. It’s short and invitational and has little to do with the author. I love almost all quality travel writing, from listicles to passionate memoirs. But for every On the Road, there are about a million 500-word blurbs about the best restaurants in such-and-such city. Keep at it long enough, and one can eventually lead to the other.

What are a few recent stories you’re particularly proud of?

Photo: Robert Isenbeg

I was lucky to find a niche a few years ago, writing about cycling. Travel is a big part of this niche, but the bicycle lends itself to a lot of other types of writing as well. Travel writers are often wise to find a similar love, something they love and can write about in a fresh, authoritative way. It could be freediving. It could be baking gourmet cupcakes. It could be a certain diaspora, religious or ethnic, that no one has adequately documented in a given language. A community and geography emerge out of that subject, along with a readership. This has led to my latest book, Mile Markers: Essays on Cycling, which was just released. The bicycle has gotten me all kinds of places, and writing about it has taken me infinitely farther. A niche is a wonderful way to proclaim your knowledge and abilities, especially in the era of blogs and podcasts, where not a single gatekeeper stands in your way.

Here are some of my favorite published articles.

”Taiwan’s Cycling Route #1 Has Everything You Want in a Bike Ride” for Matador Network

”The 19th-Century Hipster Who Pioneered Modern Sportswriting” for Longreads

”A guide to biking in Reykjavik” for Momentum MAG