“I had no idea what I was doing, at first.”
“I had no idea what I was doing, at first.” (Photo: Brendan Leonard)

My Path to Become Semi-Rad

An ode to doing what you love

“I had no idea what I was doing, at first.”

Outside's long reads email newsletter features our strongest writing, most ambitious reporting, and award-winning storytelling about the outdoors. Sign up today.

I’ve always been curious about how writers, artists, and other creatives “found their voice.”  I have listened to and watched dozens of interviews with writers, actors, musicians, and artists over the years, and I never get tired of hearing the stories about their journeys.

But occasionally, someone will ask me about finding my voice and I never quite know what to say.

Because I don’t know if I feel like I’ve “found” it with any real certainty …

As much as I just keep kind of wandering around looking for it, with some small successes along the way.

(I’m sure it’s a lot different, for, say, Drake)

Ten years ago this week, I put a website on the internet so I could publish my own writing.

That (eventually) was the start of a lot of great things for me, but I think the real beginning was a bit further back.

This is a photo of my 7th grade geography teacher, Mr. (Jeff) Button.

Mr. Button was the first person to encourage me to write—for the school newspaper he published on sheets of pastel copier paper and distributed around the hallways of Red Oak Community Middle School.  Writing articles about field trips and track meets, plus a monthly humor column, gave me two things:  (1)An outlet for the class clown energy I showed in Mr. Button’s geography class
(2) A creative extracurricular[1] activity, something that would resurface as a creative “side gig” in college and be a constant in my adult life.  [1] when campaigning for ‘president’ in Mr. Button’s class (just a class exercise, not ‘class president’), I subjected the class to five minutes of campaign promises that I rapped over the instrumental of ‘O.P.P.,’ an awkward stunt that was probably an example of the type of thing that made Mr. Button think that I had enough time on my hands for some writing

(My mom still has copies of all my columns from Mr. Button’s newspapers, and I hope they stay in a box forever)

My high school had only a small, one-page newspaper (all news, no columnists) so I expressed myself by seeing how much I could get away with in writing assignments in my regular classes.

My senior year, I got kicked out of my creative writing class (I forget the exact reason but I’m sure I deserved it). My mom met with the teacher, who agreed to let me finish the semester. (I believe my mom said something like “so you’re kicking him out for being creative?”)

In college, I struggled to find direction, going through five different majors before finally just giving up and settling on marketing. My saving grace arrived my senior year: the campus newspaper was hiring columnists.

It didn’t pay much, but it allowed me to write for an audience. Every once in a while, someone would come up to me at a party, or stop me on campus, or send me an email to say what they thought about my column. It was my first real experience of putting my writing out into the “real world” for adults to read, and I loved it.

The column didn’t get me a job or a fellowship or anything, but it did convince me to try to get a graduate degree in journalism. I only got accepted to two programs, and chose the University of Montana, despite never having visited and knowing next to nothing about mountains.

I learned a ton about writing, but maybe just as importantly, I started climbing mountains. I had no idea what I was doing, at first—I just loved finding places that made me feel small.

After I graduated, I worked at a couple small weekly newspapers from 9 to 5 to pay my rent—but I really wanted to be an adventure writer. So after work and on weekends, I tried to figure out how to make that happen. I came up with ideas for articles and pitched them to magazines—Climbing, Backpacker, Outside. Sometimes I wrote them in emails, but back then, a lot of times you actually wrote letters, which were these documents that you printed out and mailed through the postal service.

And then, a few weeks or months later, you’d get a letter back, indicating either acceptance or rejection of your proposal.

I collected a lot of rejection letters.

My first three years of freelance writing income went like this: Year 1: $40 Year 2: $150 Year 3: $1900  In 2006, I finally got a story into one of the publications I really respected: the funky, gritty, soulful, and legendary Mountain Gazette. It wasn’t a big paycheck, but it was a big validation.

I kept trying, writing regularly for the Mountain Gazette and a few small websites and publications, but no bites at the glossy outdoor magazines. By the start of 2010, I’d been trying for six years. That February, a friend invited me to bicycle across the U.S. with him, something I was sure would be amazing but probably wouldn’t get me a byline in a rock climbing magazine.

Without thinking of it in terms of any sort of “professional development,” I decided to write a daily blog about our bike trip. It was nothing fancy, just a daily report for our parents and a few friends.

I kept it up every day of the trip that we had wifi, and it didn’t exactly set the world on fire, but by the end, a few dozen people were reading it and commenting on it.   A few months after our trip, I had coffee with my friend Josh, who worked in branding. I told him I was thinking about starting a blog called “Semi-Rad” where I could put all the writing that I couldn’t get published. Josh said the thing he liked about our bike trip blog was that it was so regular—every single morning.

So I decided it had to be regular. I couldn’t do something every day, but every week. I figured I’d write one post every week until something happened or I got sick of it. So I got to work.

I wrote about things that I thought were funny, having fun with (and poking fun at) the unique/strange ways that we, as climbers, skiers, hikers, and cyclists see the world. I wrote satirical “how-to” pieces, fake “gear reviews,” but also some real essays about my experiences. I was trying to figure out what worked.

Practically overnight, it was a massive success. . . . Just kidding. That did not happen at all. The first month, the site got 646 page views. The second month, 1,810 page views. Then 2,000. It went like that for a while. A few people started to notice, including Steve Casimiro, who asked me to write for his website, Adventure Journal. I said yes, and it started to get my writing in front of a much larger audience.

Completely coincidentally, within a few months of starting my website, a couple of the glossy magazines I’d been bugging for years gave me a shot at writing feature stories. I started to contribute semi-regularly, but kept up my weekly posts on my website, where I could do whatever I wanted. I never felt like I could deliver quite what magazine editors were looking for. At one point, I was on the phone with an editor, discussing a story, and he said, “write it like you’d write it for your blog,” which was the craziest shit I’d ever heard.

Eventually, I got enough regular writing work that I decided I could quit my day job, only 49.9% sure I was making a huge mistake. I was “free,” but I needed to make money, so I said yes to everything, and I tried everything.

One day in 2013, I sat in a coffee shop and drew a flow chart about pooping in the woods. When I put it on my website, it became the biggest thing I’d ever published.

I realized the appeal of simplifying a joke and drawing it in a chart, and started to incorporate drawings into my writing and my Instagram posts.

It was a way of trying something new (that I was arguably very unskilled at) to keep things fresh for myself, and for readers and followers.  Nowadays, far more than back when I was learning newspaper writing, it feels like media is changing so quickly. If you want to create, you have so many options, which can feel fortunate or dizzying.  I am aware of editorial and marketing concepts like “plans,” “strategies,” and “calendars,”

But every week for me just feels like another blindfolded swing at a piñata.   And the only real “plan” I have is to keep swinging.

I guess maybe if I had some sort of career strategy, it would be: try to make a small thing.

And try to do it often.

And eventually, it’ll become a big thing.

This is the exact same formula people use to climb a mountain, or run a marathon, or finish a really long bike ride: put your head down, go, look up, adjust as necessary, put your head down, keep going.

After six and a half years of writing every week, an editor at Outside had the idea to make my Semi-Rad blog a column on Outside’s website, which was pretty much a dream come true for 2004 me.

But it’s not like it was some award that came with a plaque and an oversized check made out to me for enough money to kick back and take it easy for 25 years.  It’s more like the saying: The reward for hard work is more hard work.

Which is just fine with me. After 10 years, I think I’ve written about 800 or so posts for Semi-Rad.com and drawn something like 1,500 charts and illustrations. It’s a dream job, which, like any job, is fun sometimes, and sucks sometimes. But it’s still a dream job, so I’ll keep swinging at the piñata every week.

And I’ll keep wandering around on the lifelong search for my creative voice.

I might go ahead and take next week off, though, if that’s alright with everyone.

Brendan Leonard’s new book, I Hate Running and You Can Too, is now available for preorder.

Lead Photo: Brendan Leonard

When you buy something using the retail links in our stories, we may earn a small commission. We do not accept money for editorial gear reviews. Read more about our policy.

promo logo