While sucking wind during my first-ever alpine trail run recently, I thought about something Brendan Leonard said on the phone two days prior when I’d mentioned that I was about to drag my carcass around the Sierra and felt nervous about whether I could actually manage running at high elevation.

Last year, he told me, he’d mentioned to two separate ultrarunner buddies that he was going to sign up for a hundred-miler near Scottsdale, Arizona, thinking that flat, desert terrain offered easier running (we all know there is no “easy” in ultrarunning, but roll with me here). In both instances, his friends responded, “Why would you do that? That’s so much running.” Their winning strategy? Choose steeper races so you can spend more time walking. Obviously.

He laughed and I laughed, but I also felt a touch more motivated for my own slog. I wasn’t going to run a hundred miles, but I figured I could probably bang out, oh, thirteen, as long as I hiked the steep stuff, which now two pro ultrarunners, plus Leonard, who is maybe not a pro, but still knows his way around hefty mileage, said was cool. Validation!

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Inspiring everyday folks who dream big, but maybe can’t always go big is kind of Leonard’s thing. It’s why the multi-hyphenate (writer, illustrator, filmmaker, editor, slow runner, one-man humor factory) launched his website Semi-Rad in 2011—to offer copious chuckles, relatable adventure inspo, and a little bit of solidarity to the outdoorsy everyperson who just can’t resist screwing around with their campfire.

“I think the whole thing from the beginning has been to just sort of shine a light on what most of us are experiencing out there as opposed to the really high achievers,” says Leonard. “It’s so much more fun to be able to say, Hey, did you ever notice we all do this and it’s really dumb, but we do it anyway?”

That initial year of weekly musings and goofy line drawings morphed into what’s become a meaningful—and at least from an outsider’s perspective, wildly productive—career. Aside from his weekly blog posts and illustrations, Leonard compiles a thoughtfully curated newsletter, is developing a podcast with Blister Review’s Jonathan Ellsworth, and creates joy-filled, often heartstring-tugging short films (Chocolate Spokes, How to Run 100 Miles, Ace and the Desert Dog) that cast non-famous folks as the heroes we all could use.

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He’s also authored ten books (and counting), including a pair of memoirs (The New American Road Trip Mixtape, Sixty Meters to Anywhere), a climbing guidebook, an adventure cookbook, and a collection of hilarious line drawing charts. Leonard’s most recent release is Bears Don’t Care About Your Problems: More Funny Shit in the Woods ($18.95, Mountaineers Books), which serves as a sort of gut-busting greatest hits from the annals of Semi-Rad, complete with fresh illustrations and a forward written by AJ’s own Steve Casimiro, who helped launch Semi-Rad to a wider audience when he began posting Leonard’s musings eight years ago.

Leonard is characteristically self-deprecating when discussing Bears Don’t Care (which, by the way, was drummed up after a bookstore-owning friend of his said of a previous bound collection of Semi-Rad posts, “The formatting in this is so terrible, it hurts my fucking eyes,” to which he agreed). “I don’t know anybody who reads my blog every week besides my mom,” Leonard says when describing why it seemed like a good idea to package up an analog highlights reel. “Like, my friend Ben used to; I think he’s really busy with kids and work now, though.”

Still life with slice, San Rafael Swell, 2018. Photo: Steve Casimiro

That sort of jokey humility is part of Leonard’s charm, but I get the sense that underneath it all, he feels pretty damn lucky to create things that help bring joy to others. As someone who has found inspiration, more than a few warm fuzzies, and plenty of laughter in his writing and artwork over the years, I’m grateful for it, too—and thus was happy for the chance to talk with Leonard about his own gratitude, impressive work ethic, and secret musical ambitions.

From an outsider’s perspective, you seem to have an impressive work ethic. Do you have any sort of daily routine or writing ritual?
Oh, hell no. I taught a writing course on a raft trip a couple of weeks ago and I handed out a sheet with quotes from three different writers about their writing routine. It was Hemingway, Haruki Murakami, and Cheryl Strayed. The first two were like, Get up at 4:00 AM or get up at 5:00 AM and write for six hours and blah, blah, blah, every day. And then Cheryl Strayed is like, You know, I have kids. I get a hotel for two days and I binge write for 48 hours and that’s what I do.

So, I do write a little bit every day, but not in the way that you would think. A weekly deadline has been the best thing for me. I could produce one thing that I thought was quality, and slowly grow, as opposed to trying to come up with something every single day. I just don’t have that much shit to say; I don’t think anybody does!

I always think about writers as icebergs, sort of—people see our articles and other “content,” but don’t always see the sometimes random things we do to keep the lights on. Does that resonate with you?
Oh, totally. I would take any work for a long, long time. I wrote for several websites that don’t exist anymore. I wrote for a car insurance company at one point because the money was great. I wrote catalog copy for Outdoor Research. I just did a set of drawings for Tuft and Needle, the mattress company. A friend who used to work for an agency that represented Gore-Tex moved on to Tuft and Needle and he said, Hey, you should do some stuff for us. And I was like, Cool, man. I like sleep.

Otherwise you’ve got to get a real job and that really takes time away from being able to write the stuff you want. I just think it’s always going to be a chart of stuff you’re really psyched on versus stuff you’re not that psyched on. It all pays the bills. You do an increasing amount of stuff you’re psyched on, hopefully, and a decreasing amount of stuff you’re not psyched on, eventually.

I think a lot of folks look at freelancers and think we’re living a dream life—and of course, we both know there are a lot of wonderful aspects to freelancing. But are there challenges to juggling so many different hats?
I look at people my age now, and I see them pull into a parking lot somewhere and I go, Why don’t I have a nice car? Then I think, You spent, like, three months in Switzerland cumulative at this point, you know—that’s why you don’t have a nice car, you fucking idiot. You made that choice. Like, would you rather have a nice car? And I think, nah, I wouldn’t, I’m good.

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When I sit and think about what I do on a daily basis, I’m like, man, I worked with these ladies on this assembly line at this factory and that’s work. Those people go into work and they’re not sitting around going, My job sucks! They just sit down and do the work. They’re done after eight hours, they clock out, and that’s life, you know? So I’m not really pissed about what I have to do for a living. I just tell my dad: This beats the shit out of working, for sure. I’m going to get up, I’m going to drink some coffee, I’m going to play around on this iPad and hopefully make something that makes people laugh and if not, I’ll try again tomorrow. That’s a pretty good life, you know.

You’ve written in so many forms and genres, from guidebooks to cookbooks to memoir, but I think most people know your humor writing. What is it that draws you to writing in that style?
I prefer it vastly to what I think the alternative is, which is arguing with people or pissing people off in order to get their attention. That’s not a way I want to make a living; I’m too emotionally sensitive for that. There’s so much negativity in the world right now, and it seems like so much of what’s on the internet is just people arguing with each other and making each other mad. It’s like, to make somebody potentially laugh—if they don’t think you’re funny, they’re usually not going to be angry about it; they’re just going to ignore you.

I think to try and make somebody’s day a little bit better through a sort of shared humor is a good thing for me. I’m thankful that I’ve just kind of backed my way into that being a good way to make a living. I mean, I’ve written about things like my grandmother dying and other serious things. But by and large, my life has been very happy for the last, I don’t know, I’ll say seven years since I met Hilary [Oliver, his wife]. So I’m not going to that dark place very often. Sometimes I listen to The National a lot and I can get there, but it’s kind of hard to, so humor is much more natural.

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Photo: Hilary Oliver

Something I’m really impressed with is how you’ve managed to do really cool stuff in so many different mediums. Is there a medium you haven’t really pursued that you’d like to give a shot?
I would actually really like to do something with music and I haven’t quite figured out how to make that work. I mean, I’m an adventure writer and maybe I can branch out a little bit and get into other things, but nobody’s ever gonna pay me to write about hip-hop because I don’t really have any sort of insider knowledge or anything; I just have this emotion that comes with it. That would be the biggest thing I’m curious about—if I could produce something that would be meaningful to a completely different audience.

You’ve been going at all of this for eight years; what do you want the next eight to look like?
Boy, I would like to be alive. That’d be great. I am really not that good at long-term. I mean, I’d like to still be doing this. I’m really having a great time, so if it just continues for eight years, I’m not pissed about that.

When you were young—or when I was young, anyway—I had these delusions of grandeur that you could be huge and famous and really successful. But to be honest, just to be able to make a living and reach a few people in a good way—I mean, that’s more than I could’ve expected of any job I had in an office.


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