Every few weeks, I get an e-mail or a Facebook message from someone who has a few questions about writing: how to get their foot in the door, what it’s like to do it for a living, how to be self-sufficient. I thought I’d share some of my story, and hope it helps a few people, or at least provides some entertainment.
I’ve been writing full-time for almost four years, and full-time about adventure and the outdoors for almost three years. As much as I would like people to believe I spend most of my time writing longhand at a table in the Alps, as my former Facebook profile photo showed me doing, in reality, that type of thing has made up less than one-tenth of one percent of my time as a writer—about 20 minutes, one day during the summer of 2013. The rest of my work looks a lot like most people’s: I stare at a glowing screen, type things, click a trackpad, eat lunch at my desk, and get a little sad when I realize my coffee cup is empty.
Here are some things I sometimes tell people when talking about writing:
- “Well, like I tell my dad, it beats the shit out of working.”
- “When I tell people I’m a writer and they ask me what I write, I usually tell them ‘mostly e-mails.’”
- “I ran a very successful five-figure business out of a van for a couple years.”
- “Yes, Dad, I do have enough work coming in, thanks.”
There are many ways to get started as a writer. Going to a prestigious college and getting an MFA is a good one. So is landing an internship at the New York Times. Escaping from a penal colony in French Guiana after 14 years of wrongful imprisonment and then writing a manuscript about it has been successful for at least one person.
I had a bit of a different path, but in the interest of painting a realistic picture, here’s a brief timeline of my career as a writer:
- Age 21: During final year of pursuing a marketing degree, respond to ad in student newspaper seeking columnists. Write weekly column. Decide that I somehow want to be a writer, even though I will graduate with a marketing degree. Also realize I have no idea how to go about doing that.
- Age 23: Get accepted to graduate school. Before matriculating, complete five-week outpatient substance abuse treatment, or “rehab,” and a weeklong jail sentence.
- Age 25: Receive M.A. in Journalism. Just before graduation, publish first-ever magazine article, in IDAHO Magazine. Paid $40.
- Age 25: Get first post-graduation job, working sales floor at REI.
- Age 25: Get second post-graduation job, working for a bi-weekly suburban newspaper. Go down to part-time at REI.
- Age 26: Publish second magazine article, in Oklahoma Today. Paid $75.
- Age 26-29: Continue to pitch articles to magazines while working full-time at a newspaper. Published in Mountain Gazette. Catch attention of editor at Backpacker with application for job I don’t get. Pitch story ideas, none of which work out.
- Age 29: Leave newspaper job, take huge pay cut to work at nonprofit that takes inner-city kids on backpacking trips. Love it, starve, pitch and write outdoor stories in spare time.
- Age 32: Leave nonprofit job for remote copywriting job for huge software company. Work on outdoor writing in spare time. Start blog, Semi-Rad.com, resolve to write one blog post every week. After almost two years of pitching, publish first national magazine story, in Climbing. Six months later, publish first story in Backpacker. After a breakup, move into car and take “mobile office” seriously, working from coffee shops while driving around 10 different states.
- Age 33: Leave safe, well-paying remote copywriting job for full-time outdoor writing, a move made possible by first blog sponsor, Outdoor Research, and becoming a contributing editor at Adventure Journal. Move out of car and into a van.
- Age 34: Self-publish first book, The New American Road Trip Mixtape, with no real idea how to do that sort of thing. It sells 4,000+ copies in its first year. My dad finds a typo in it.
- Age 35: Hope it keeps going.
I should point out that I don’t write for many big famous magazines or literary journals, which may or may not be your definition of success. I succeed in writing for a living and working for myself. In a typical year, I write mostly for Adventure Journal, a couple features for Climbing (as well as a monthly column), a couple features for Backpacker, and this web site, which, thanks to a couple supporting companies, is something that I get paid for. I’ve written for National Geographic Adventure, Adventure Cyclist, Sierra, High Country News, Outside, Men’s Journal, Elevation Outdoors, RedBull.com, a couple German outdoor magazines, and several other publications. I juggle all these things all year, and at the end of each month, I can pay rent on a very small apartment, travel like a dirtbag about half the year, and every once in a while, pay someone else to make me espresso.
Here are some things people have told me about writing that have stuck with me through more than a few years:
Jeff Hull spoke to my Magazine Writing class at the University of Montana in 2004 and told us, “To be a successful freelance writer, you need one of two things: A trust fund, or an understanding spouse.” Meaning it’s pretty hard to get started at first, so it’s nice to have someone helping pay a few of your bills.
My friend Jed, when we were both first getting started writing 10 years ago: “I meet people at parties and I tell them I’m a freelance writer, and I can tell they think that means Rolling Stone and Sports Illustrated, and I want to tell them, ‘Well, if you read, say, Modern Drummer, or South Jersey Monthly, you might have seen my work.’”
Also Jed, when I said, “You wrote a skiing story for an airline magazine? You don’t even ski.”:
“Yeah, it doesn’t matter. I wrote a couple other things for them, and they said they like me because I turn in clean copy, and it’s on time.”
Anna Brones: “I feel like most of what I do is hustle.”
Jeff Weidman, former owner, Rutabaga Paddlesports, not talking about writing, but talking about working for yourself: “You’ll be the hardest boss you’ve ever had.”
Here are a few things I’ve learned:
It is hard to get started. You may write dozens of detailed pitch e-mails and get rejected, or more likely, just ignored. It’s not a personal thing. You do not suck. Your idea might suck. Your idea might also be amazing, but isn’t right for the magazine’s readership. It might be amazing for someone else. It might be amazing, and perfect for the magazine you e-mailed it to, but the editor doesn’t feel like he or she can take a chance on a new writer right now. Maybe the editor just doesn’t like some part of your story idea, because it’s in Texas, or it’s about artisan coffee, or winter, and they hate Texas or coffee or winter for no real reason, they just do. Maybe the editor doesn’t respond to anyone’s e-mails. You just have to keep pitching, and move on to the next publication, or the next idea.
Most of us have to start small. Yes, you want to write for National Geographic. No, National Geographic is most likely not going to take a chance on assigning you a huge feature story on baobab trees in Madagascar when they’ve never heard of you, and your only published writing so far has been in a college newspaper. Most of us have to start very small: pitching short story ideas to small magazines, sometimes for free. We get some 300-word stories published in a small magazine, then a longer story, then included clips of our bigger stories when we queried a slightly bigger magazine with a 500-word story idea. Then the slightly bigger magazine took a chance on our 500-word story, and we did OK, so then we pitched a feature story, and they went for it. And so on.
It gets easier the longer you work at it (assuming you work hard at it). As my friend Jed said, editors like to work with people who are reliable and turn in quality writing. Of course they like to work with creative geniuses who write beautiful sentence after beautiful sentence, but if that person causes the editor to lose hair and sleep every time a deadline comes up, you can imagine that they become less and less into working with them. I quoted my friend Jed to an editor of a national magazine once, and asked, “Isn’t that ridiculous, that they like him because he actually meets deadlines and spells correctly? Shouldn’t that be the bare minimum?” The editor shook his head and said, “You wouldn’t believe.”
You can start a blog, but that doesn’t automatically mean anyone will read it besides your mother. Compared to 20, or even 10 years ago, our world is a sea of media. When you write, you should strive to make something that matters to other people—especially people who don’t know you. What you write has to rise above a bajillion tweets, status updates, and fitness selfies, and if all it’s saying is “look at me,” it probably won’t get very far. If it’s funny, or insightful, or controversial, or it makes a reader think, then it has a much better chance of reaching people.
You can write about yourself. Theoretically, it should be the subject you know best. The people who are best at writing personal stories, though, don’t just write about themselves—they tell stories that are somehow relevant to everyone. They write about “we,” not “me.”
It isn’t easy to make money off a blog, but it can create a brand for you that people recognize, and other work can come to you through that. One of the best-case scenarios is Eben Weiss of BikeSnobNYC, who has parlayed his brilliant, formerly anonymous blog into a column for Bicycling Magazine and three books.
Spell people’s names correctly. As a writer, you should try to spell everything correctly, but people will forgive a few errors here and there, unless one of them is their name when you’re addressing them.
You will have what’s called “lumpy income,” or as my friend Justin calls it, “jagged income”: you will go weeks without getting paid, then get tons of checks in the mail all at once.
Don’t expect to get paid right away. Sometimes you will do work and people will not pay you for it for months. There are a multitude of reasons, almost none of which seem valid when you are trying to write a check to your landlord so you don’t get evicted. This, in my experience, is just reality. You have to remind yourself that the editors (who like you and your writing) are 95% of the time not the people who write the checks to faceless “accounts payable” such as yourself, so there is often an emotional disconnect. This is, as they say, just the way it is. Except in Germany. Those people have it dialed. They wire money into your checking account in a timely manner (often before the story you wrote has hit the newsstands) and the resulting warm fuzzy feeling from that has been at times nearly enough for me to purchase Rosetta Stone software and spend a year learning German.
You can spend $2000 on a trip to Italy for a story that will only pay you $2000. This is not a good business practice, but I like to think of it as a semi-paid, semi-vacation. You can also spend $500 in New Mexico for a story that will pay you $800, but the coffee isn’t as good there.
You can go rock climbing and call it “work.” Because it actually is. Some people dig through documents and do several rounds of interviews for a story, and some people hang off the side of a 1,200-foot sandstone wall for a story. Neither of us make too much money doing it.
By the end of several days of researching and writing a story, depending on the amount of time you spend in the field and the expenses you incurred, you can actually lose money on a story. Per hour, working at Subway can be more lucrative than writing. There is also the possibility I’m doing something very wrong.
It’s awesome. People sometimes say, “Do what you love and you’ll never work a day in your life.” I prefer the more realistic idea that if you love 30 percent of what you do and can tolerate the other 70 percent, you’re winning. If it didn’t feel like work sometimes, it would be called “fun,” and probably no one would pay you for it. Work can be fun, but it’s not fun as watching a sunset in the mountains or rolling around with a bunch of golden retriever puppies. Everyone’s job is stressful in some way, or sucks from time to time, and writing is no different. It’s hard work, but nothing like working on an assembly line or putting a roof on someone’s house. As a freelancer, I get to wake up every day and decide what I want to do, which is usually a decision of what I want to make. Sometimes being your own marketing, sales, and collections department isn’t that fun, but if you’re lucky, sometimes people read something you write, and it makes a difference to them, and sometimes, they even send you an e-mail or write a comment that says so. And that’s pretty great.
[top photo courtesy PatitucciPhoto]