Jennifer Leo: Travels Down the Written Road

Travel Interviews: Jim Benning asks the editor of a new story collection about blogging, women's misadventures and the challenges of a career in travel writing

11.04.05 | 1:00 PM ET

imageAt her weblog,, Travelers’ Tales editor Jennifer Leo chronicles her life as a travel writer and editor and offers tips to others charting their own course in travel publishing. It’s a combination that has earned her a loyal and enthusiastic following. Lately, Leo, 34, has been blogging about her 20-stop tour to promote The Thong Also Rises, the Travelers’ Tales story collection she edited. It’s the third title in a series mining the women’s humor travel vein—previous books are Sand in My Bra & Other Misadventures and Whose Panties Are These? The new book features contributions from dozens of writers, including Susan Orlean, Ayun Halliday and Christine Michaud-Martinez. I recently chatted with Leo by phone as she took a break from her book tour at a Seattle coffee shop.
World Hum: I’m concerned, Jen. After “Sand in My Bra,” “Whose Panties Are These?” and now “The Thong Also Rises,” you seem to be running out of women’s undergarments to use in book titles. Are you worried about this?
(Laughs.) No, I’m not worried about it. We’re going to wrap up the underwear series with another in April, a co-ed book called “What Color is Your Jock Strap?”
Great. You’ve moved on to men’s underwear. Will this be the final installment in the series?
For now. We’re ready to move on to other topics.
Well congratulations on the new book. These women’s travel humor books do well, don’t they? What do you think makes them so popular?image
They do. “Sand in My Bra” continues to be Travelers’ Tales fastest-selling book. It has a lot to do with reaching a general audience, rather than an audience interested in only a specific region or country. Every woman can relate to travel adventures gone wrong. The book can relate to a woman traveling with her family or a solo woman traveler. It reaches everyone.
When I read these stories, I feel almost as though I’m a fly on the wall of a hostel full of traveling women.

(Laughs.) The books include a lot of stories that women might tell one another when traveling through hostels. Sure there are some stories of traveling with husbands or lovers—or looking for love on the road. But I’d say when we hang out together we talk much more about men and sex than is shown in the series. These books are light, easy reading. Maybe in today’s world when women are doing so much, having a career or being a mom or both, they need some escape. With about 30 stories in each book, it’s easy to sample them on a quick break.

How did you get into travel writing and editing?
I was inspired by Tim Cahill and his books and articles in Outside magazine. It was my first winter out of college and I was working in Lake Tahoe at Northstar ski resort. I used to visit a mountaineering store in Truckee, and they had a box of old magazines. I would sit there on the store’s floor, reading Tim Cahill stories. The first story of his that got to me was called “The Howling,” and it was about camping in Alaska under the northern lights. It blew me away.
What was it about that particular story?
I’d never even heard of the northern lights before. I was like, there are places like this? I didn’t even know.  The story transported me to Alaska and made me want to go there.

How old were you then?
I was 23. I didn’t have much self-confidence and I was hanging on to this thread of a notion that I wanted to be a traveler. I wanted to be adventurous. I saw this ad in Outside for Adidas adventure sandals and the picture showed a guy doing all these things like mountain biking and paragliding. I saved up 75 bucks and got a pair of those shoes and wrote a bad poem about how this was going to make me adventurous.
That’s great. What happened after your winter in Lake Tahoe?
I moved to San Francisco and got a job as a nanny. I told the family I was working for that I wanted to be a travel writer. The dad said his college buddies had just started a publishing company. That was how I met Larry Habbeger and James O’Reilly at Travelers’ Tales. I met Larry at Book Passage after their second book. I signed on to be an intern when they were working on book three—India. Now we have more than 90 books, and 10 years later, I’m editing their fastest-selling books.
Yeah, I’ve come a long way. (Laughs.) Now I’m pals with Tim Cahill, I have a collection of books I’m proud of, and I’m ready for the next chapter - to start writing my own books.


A Sense of Place: Great Travel Writers Talk About Their Craft, Lives, and Inspiration by Michael Shapiro. “The heart that Michael put into this book, and the lifetimes that these travelers have shared with us, have inspired me to dig deeper with my own writing.” The Sex Lives of Cannibals: Adrift in the Equatorial Pacific by J. Maarten Troost. “Troost is an absolute find. He’s living proof that you you can just decide to write a book, and come off with a killer. He’s hilarious and I’m dying for his next book!” Cuba Classics: A Celebration of Vintage American Automobiles by Christopher P. Baker. “The first time I cracked open this book I wanted to rip the pages out and frame them. I can’t stop telling people about this book.”

What do you have in mind?
I’m not ready to leak the whole thing but it will be a bridge between the women’s humor series and personal memoir.
You’ve mentioned to me in the past that your family’s view of your writing career has changed over the years. Can you talk about that? I know it hasn’t always been easy.
Socially, it’s been tough. Some people get it and some people don’t. My family did not get it at all until I was on tour with “Sand in My Bra” and my brother, who I’ve had a trying relationship with, was reading the blog I was writing. Until then, he thought I was wasting my education when I could be making more money doing something else. Seeing my name on the cover of a book and seeing a fan base following me around helped him to see that this wasn’t just about the money. Then he was able to go back and explain what I was doing to the rest of my family at their weekly dim sum gatherings. That helped. My father came around. He told me that our ancestors were nomadic Cantonese, and he said that’s why I am the way I am. My family is very loving and supportive. But it’s still hard for them that I’m not living a more conventional life.
You’ve been nomadic for some time now, haven’t you?
About three years. Sometimes it has worked well and sometimes it hasn’t. When it worked the best was when I went to live in London and Belgium. A lot of editors began giving me assignments. It boosted my freelance career.  And now I’m fortunate to have friends all over the world who open their doors to me.
Do you think it’s harder to be a woman travel writer? It seems that more travel writers are men.
It depends on the woman’s family. Some women have zero support and others have lots of support. Ayun Halliday has hopped jobs all over the world and hasn’t stopped writing because she’s married or has two kids. Holly Morris is doing it. Stephanie Elizondo Griest is doing it. And I know Written Road is inspiring others because they tell me it is. So I think it’s great.
How important has your blog been in developing your career?
It’s been one of the cornerstones of building my name and advancing my career. When I started it, I just wanted to share information as I was getting it. Part of it is about my journey of being a travel writer, and the other half offers market leads and travel writing tips. But what the blog turned into was a community, and I wasn’t expecting that. And I wasn’t expecting newspaper and magazine writers and book publishers to be reading it. Who knew I’d have a caliber of readership that included people from Time, USA Today, Frommers, The Seattle Times and more? It has definitely helped me, but the best part is when Written Roadies write in and tell me that they’ve gotten assignments from leads on the site.
You write other blogs, too, don’t you?
I’m writing VivaLasVegasBlog and JenLeoLive, which is a blog I recently started because my friends and my family don’t know where I am. It’s much more personal. It’s keeping the personal stuff off the other blogs. And I’m developing another one I can’t divulge yet. I love blogging.
Is VivaLasVegasBlog about poker? I know you love poker.
No, it’s a travel Web site for anyone coming to Vegas. But yes, I do love poker. I’ve been a craps player since I was 21. The gambling comes from the Chinese side of my bloodline. My great-grandfather ran an underground casino in Portland, Oregon.
Travel writing is a notoriously difficult way to make a living. How do you make ends meet?
I don’t. I make less than $2,000 a month. I’ve chosen to put my freedom above a stable financial life. You can only do that for so long, and I’ve passed the point where I can afford that luxury. Some people could view the years I’ve spent working for low pay as getting a master’s degree in travel publishing. I’ve certainly gained enough knowledge through all these years and I’m ready to start making more money. I’m ready to seek higher paying opportunities.
That sounds like a good plan. Being a starving writer who loves gambling sounds like a dangerous combination.
It’s very dangerous. (Laughs.)

So what’s next?
I’m editing the next humor book for Travelers’ Tales, which is due out in April. I’m working on a book and going to take my blogs to the next level. You could say my laptop and me are good friends.

Good luck with all of it.
Thanks, Jim.

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