Eva Holland is a freelance writer and editor based in Canada’s Yukon Territory. She’s the co-editor of World Hum, a former associate editor at Up Here and Up Here Business magazines, and a founding contributor to Vela Magazine. She’s a regular contributor to SB Nation Longform and a former online columnist for Outside. Her stories were recently listed as notable selections in The Best American Essays 2013 and The Best American Sports Writing 2013.

How did you get started traveling?

I didn’t really travel much growing up. My dad and I drove the same stretch of highway to my grandparents’ house outside Toronto a couple times a year, and we made rare visits to family elsewhere in Canada, but by the time I left home to start university I’d only just dipped my toe into the world of travel. A couple of months before I graduated from high school, I spent an all-inclusive week in Acapulco on a group binge with 1000 other soon-to-be grads from several high schools in my hometown, Ottawa. (Not the most culturally significant starting point.)

All of that changed during my university years. My dad had started a second career in the foreign service when I was in high school, and after I graduated he took his first posting, three years in Malaysia. Every summer after classes ended I’d go to visit him in Kuala Lumpur and stay for a month or two. The two of us would make weekend visits to Vietnam, Thailand, Singapore, or elsewhere in Malaysia, and I’d go off on my own for two or three weeks, too. I traveled solo to Australia, New Zealand and India on those three summer visits, and I was hooked.

Later, I went to graduate school in northern England and used that as a base to explore the UK and continental Europe, and then my dad took a second posting, four years in Barbados, right as I was looking to become a freelance travel writer. That was pretty convenient.

How did you get started writing?

I’d wanted to be a writer for as long as I can remember. I still have a binder full of the half-baked (at best!) fantasy novels I attempted to draft when I was 10, 11, 12. One of them actually made it to about 100 pages, written out in cursive. I went to an arts-focused high school and “majored” in creative writing there, so I spent four years cranking out angsty poetry, scripts and short fiction. I also got into the idea of journalism in high school, and briefly aspired to become a newspaper sports writer.

But I wound up deciding, in my infinite teenage wisdom, that writing wasn’t a viable career, just something to do as a hobby. I kept writing poetry and essays through college (including some travel-focused stuff resulting from my Malaysian travels), and then when I moved to England for grad school I started a (short-lived) travel blog and wrote a couple of short dispatches for the travel section of my hometown paper. At some point partway through my Masters degree, it occurred to me that maybe writing for a living was worth a shot. I came home after I finished my degree and started trying to figure out how to become a freelance travel writer.

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

In August 2007, eight months after I started trying to get serious about freelancing, I attended the Book Passage Travel Writers and Photographers Conference in Corte Madera, California. To get there, I liquidated my frequent flier miles and asked for donations to my conference tuition for my 25th birthday. I’d been getting exactly nowhere freelancing – no one ever answered my emails, even to reject me. But at Book Passage I learned a ton about pitching and selling and writing, and I met people like Tom Swick, and Jim Benning from World Hum, and you! Within a month or so of Book Passage I was writing regularly for both World Hum and Vagablogging. That got things rolling.

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

My natural introversion. It takes effort for me to talk to strangers, although I’ve gotten a lot better at it over the years. My early travel stories were these mostly empty long descriptions, because they resulted from me sitting quietly and just watching the world go by. There might have been some pretty turns of phrase, but they lacked characters, conflict and action – the essential components of a story.

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

I think I’m still learning about story structure and organizing my material. I got past the urge to just write my way through a trip chronologically a long time ago, which is a problem in a lot of travel writing (if your story starts with you waking up early in the morning and heading to the airport to start your trip, something really interesting had better happen in the cab ride there), but I’d like to feel as though I have a stronger command of structure, of knowing what the reader needs to know when and spinning the story out in a compelling way. I think I’d like to be more adventurous with structure, but that takes a confidence that I’m still developing.

What is your biggest challenge from a business standpoint?

Paying the bills, I guess. Finding a balance between the “sell the story, get paid” imperative and the time required to dig into a story I care about and really do it justice. I’m a pretty pragmatic person, and I live alone without anyone else’s income to fall back on, so sometimes I’ve worried that I make too many practical, money-oriented decisions instead of just focusing on doing the best work I possibly can. That’s gotten easier, though, as I’ve gotten more established and it’s been possible to get paid more for the stories I love.

Have you ever done other work to make ends meet?

Yep. During the first year and a half after I came home from grad school and started trying to freelance, I worked briefly as a snow shoveler, at a deli counter making bagel sandwiches, and as a server before landing an office job in my field, working as an archival researcher-for-hire at a private consultancy in Ottawa. Law firms would hire us to dig up historical documents at the national archives, mainly for First Nations land claims cases. I quit that job to freelance full-time in April 2008. Three years later I ran out of writing work temporarily, and for four months in 2011 I worked as a manual laborer for a mining company here in Whitehorse. These days, I work very part-time for a local radio station, reading the news and sports.

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

There are so many great travel books, but I think reading shorter stuff can also be really helpful when you’re starting out. One of the first things I did when I started trying to get published was to read through all the Best American Travel Writing anthologies. Another anthology that I love and rarely see mentioned is Wild Stories, a collection of the best of Men’s Journal.

But I’ve also enjoyed a lot of the classic travel books: Paul Theroux, Pico Iyer. I adore Jonathan Raban’s Passage to Juneau. I really enjoyed Four Corners, by Kira Salak, and Undress Me in the Temple of Heaven, by Susan Jane Gilman. An essay in Backpacker magazine, “The Source of All Things” by Tracy Ross, really opened my eyes to the possibilities of travel writing fused with memoir or personal essay. It was later turned into a book. David Grann‘s excellent The Lost City of Z is the type of book I’d love to try to write myself someday, with its mixture of first-person travel, historical research, and reporting.

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

Make sure that you’re going into it for the right reasons. Sometimes I see people talking about getting paid to travel, but really you get paid to write. The travel can be wonderful, but the bulk of the work is reporting and writing (well, and selling). If you don’t enjoy the meat of the work, you won’t enjoy the job, no matter how great the perks can be. And there’s no point attempting to do a job as competitive, non-remunerative and all-consuming as this one if you’re not having fun.

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

For me, it’s the writing. I was spending my Friday nights writing just for myself long before I got my first passport, and while I love traveling, I love writing more. Being able to build a life that lets me make a living writing stories is really incredible – sometimes I still can’t believe I’m making it work.