Cassandra Overby grew up hiking and camping in the beautiful Pacific Northwest of the United States. She started adventuring internationally in college, when study abroad programs in Austria and Germany got her firmly hooked on travel. Her adventures have taken her all over the world, from Central America to Southeast Asia, but she loves exploring Europe more than anywhere else. Both hiking and traveling continue to shape her life—and her career. As part of her travel company, Explore on Foot, Cassandra regularly gives talks and teaches classes on how to explore Europe on foot. She also offers travel consultations for people who’d like some help putting together their dream trip. .
Books by Cassandra include: Explore Europe on Foot: Your Complete Guide to Planning a Cultural Hiking Adventure; Explore France’s Alsace Wine Route on Foot; Explore Germany’s King Ludwig’s Way on Foot; Explore France’s GR 34 on Foot; and Home Base Hiking Europe: An Explore-on-Foot Guide to Unforgettable Destinations.
How did you get started traveling?
My parents weren’t travelers, so it wasn’t until I was in college and did study abroad programs in Austria and Germany that I first really traveled. Those experiences were life changing and set the course for my career and my adult life.
How did you get started writing?
I was always a writer, even as a kid. I just never thought to make money at it or do it for a job. When I was younger, I loved to write stories and short chapter books. It wasn’t until I was in Guatemala, on a trip around the world and writing a travel blog, that I received a lot of feedback on my writing and had a two-part epiphany. One, most people don’t like to write—and I do. And two, most people are pretty bad writers—and I seemed to have a knack for it.
What do you consider your first “break” as a writer?
After I had my epiphany, I used my business degree to hang my own shingle and write marketing content for companies. It paid—I was a real writer! The only problem was that the writing was SO boring! A couple of years later, I got my first break doing writing that I actually enjoyed: writing about hiking and the outdoors (I’m an avid hiker) for a Washington state-based nonprofit and their magazine.
As a traveler and fact/story gatherer, what is your biggest challenge on the road?
My challenge these days is that I am a mom of two young kids, currently 5 and 8, and I don’t want to be away from them a lot—tough when you’re a travel writer. So I chunk my research and go to Europe for 3 months every other year and bring the whole family along. My husband can work remotely. I used to do all of my hiking research with my kids on my back, but now they’re too big to carry—and too little to do most of the adult-level hikes I do as beta for my hiking-based travel books. So I have to find childcare for them while I’m hiking. The logistics of working in Europe for 3 months at a time, while guaranteeing that my husband can still work his job and my kids have care and are happy, are wild. I could write a book on that alone.
What is your biggest challenge in the research and writing process?
Since every day of that 3-month trip counts, I wait until I’m back home to write everything up. It can be daunting to recreate every hike, village and experience through my notes to the level that I need to. I’ve gotten very good at taking excellent notes and keeping great digital records (GPX tracks, pictures, etc.) of everything. Funny enough, my other big challenge in the research and writing process is that I don’t like to be inside—or sit down. (You can imagine why I never truly enjoyed business, my first career. I’m living my best life when I’m on trail, researching! ) When I’m writing, I have to write for 5–6 hours a day, which is a lot. Thank goodness I have a standing desk, a treadmill pad and a big window to look at when I’m working.
What is your biggest challenge from a business standpoint?
My biggest challenge is that authors make very little in the traditional publishing model. I love writing books, but more of my business income comes from giving talks and doing travel consultations.
Have you ever done other work to make ends meet?
Yes! I am also an editor. I copyedit for the hiking magazine I used to work full-time for, as well as other nonprofits and companies. I like that editing makes me a better writer and writing makes me a better editor—the combo works well. Also, editing pays a lot better than writing.
What travel authors or books might you recommend and/or have influenced you?
Rolf Potts, of course. Vagabonding was my go-to book when I was researching for my trip to Guatemala all those years ago. I have also taken a lot of inspiration from Rick Steves, who has mentored me and platformed me a great deal on his radio and TV shows. He’s a kind person, a wonderful writer and also a very smart businessman.
What advice and/or warnings would you give to someone considering travel writing?
The money isn’t in books. Books establish you as the expert and help you build your platform, but the money comes from other avenues around your writing: higher-paid magazine work, classes, lectures, etc.
What is the biggest reward of life as a travel writer?
The memories! I’ve had such a full life because of my travels and writing, as well as experiences that most people could only dream of. And it’s really cool that I have something tangible—books and magazine articles—to show for these experiences.