How to Succeed as an Adventure Storyteller

Have you ever dreamed of making a living by telling your own stories? Brendan Leonard has been successful at doing just that. He has carved out his own unique niche as an adventure storyteller with a comedic flare which has allowed him to reach millions of people and have fun doing it.

Brendan is a writer and filmmaker whose work centers around adventure, travel, and “human experiences with both of those”. He the founder of Semi-Rad.com, author of four books, and a contributing editor at Climbing Magazine, Adventure Journal, and The Dirtbag Diaries. His stories have also appeared in publications like Backpacker Magazine, National Geographic Adventure, Outside Magazine, Men’s Journal, and Adventure Cyclist.

Adventure Storyteller

Brendan’s career as an adventure writer began by happenstance. One of the requirements for his graduate school magazine writing class was to get published in a magazine. “At the time, the thing I was most passionate about was music. But I thought, ‘holy shit how am I going to get published in Rolling Stone?’,” he laughs.

A girl in his class told him to write a story for Idaho Magazine because they publish anybody. Recently becoming interested in the outdoors, Brendan submitted a story about a weekend trip in Idaho. He was paid $40. Brendan then realized he could write about his normal weekend activities and theoretically get paid for it.

“The outdoor industry is a really cool place to learn storytelling,” Brendan said. “Climbing Magazine is not the New Yorker. I don’t want to say it’s a lower bar of entry, but it’s easier. Even in film-making. The films you see at The Banff Film Festival are not made with enormous camera crews and huge productions. In adventure film a lot of times you can’t even take that stuff with you.”

Brendan made his most recent film with a DSLR camera, a tri-pod, and a few thousand dollars. “I was entering it into a film festival and one of the categories was low-budget, under $100,000. I was like are you fucking kidding me, I made this film for three-grand.”

You’ve Got Mail

Late in his senior year of college, he responded to an ad for a columnist position at the college newspaper. “That was a really fun experience that really changed my life. People would come up to me on campus or email me. And this was 1999 when email was a big deal so getting an email from strangers was kind of crazy,” he laughs. “That made me think, ‘how can I actually do this for a living?’.”

He decided to go to graduate school for journalism to “learn how to actually write instead of just making dick jokes or the immature kind of humor you do as a collegiate newspaper columnist”. After bouncing around for a few years in entry level newspaper jobs at small papers, he became discouraged and decided to quit. All the while, he pitched story ideas to adventure magazines like Climbing, Backpacker, and Outside. “I had zero experience writing and not that much experience doing outdoor stuff so it wasn’t that shocking they were turning down all my story ideas.”

IBM & Semi-Rad

Brendan found himself at IBM as a marketing copywriter. “I didn’t want to lose touch with outdoor writing and just write about computers and business consulting, so I started a blog”. This was the beginning of Semi-Rad.com; a website, as Brendan puts it, “for those of us crushing it, kind of”.

“I don’t think any professional writer would recommend starting a blog and giving away your best stories for free. But at the time, I was struggling to get into magazines and wanted to write features. But you’re not going to pitch a magazine article about ‘how much beer you buy somebody according to what favor they do in the outdoors’. No magazine is going to publish that, so I put it on my blog.”

He wrote one post per week for two years before making any money blogging. As Brendan often says, quoting Jocko Willink, “don’t count on motivation, count on discipline”. He soon realized that his blog essentially became an online resume. “For lack of a more soulful term, it was building a brand for me”. Other websites began approaching him to write articles and he simultaneously was getting more magazine articles published.

Eventually he had enough writing work and sponsors to quit his job and go full-time adventure writing. “I wasn’t confident I was actually going to make enough money to not starve. I had a full time job for 8 years before I could do full time adventure writing which I always did on the side. After doing it for 4.5 years full-time, it’s just a collection of those same side gigs.”

In his first month of posting, Semi-Rad had 400 page views; currently it draws 1.2 million per year.

Filmmaker

Back in 2008, Backpacker Magazine sent Brendan to interview Fitz Cahall, founder of the Dirtbag Diaries Podcast and film production company, Duct Tape Then Beer. Fitz, who Brendan now considers a friend and inspiration, has evolved as a creative across many mediums. “He and I were out climbing and I told him I had an essay in mind about things that inspire me”. The essay became the script for “35”, a dedication to the joys of the climbing life.

A year and half later, Brendan came up with the idea for a film about a climbing guide named Frank at Devil’s Tower National Monument in Wyoming. With very limited experience in shooting a film, Brendan and his friend, Forest Woodward, went to Wyoming and improvised. “Neither of us really knew what we were doing, but I knew this character Frank would come through”. He sent Fitz a clip of Frank playing the piano and Fitz told him to send all the footage which he turned into “Frank and the Tower”.

They eventually got the film sponsored, but everyone went into the project working for free. “I think it’s smarter to go to a company and say ‘I’m making this film, do you want to sponsor it’? I tend to be really stupid about it and try to do things first and sell it after which doesn’t always work,” he laughs. “Film festivals aren’t getting you rich. Most of the money is from sponsorships.”

Since then, Brendan and Forest have made many more films together including their most recent (in collaboration with gnarly bay) called “The Time Travelers”; an inspiring story about the U.S Men’s Rafting team attempting to break a speed record down the Colorado River.

Moving Your Needle

As an adventurer and self-proclaimed weak climber (relatively speaking), Brendan has often found himself in many uncomfortable and dangerous situations. “I’m less comfortable with sketchy stuff now than I was 6 or 7 years ago, but there were times I got into a lot of situations. I’ve always looked at those things as building mental toughness. There’s this Navy Seal saying called the 40% Rule. What you think you can actually do is about 40% of what you’re actually capable of; as long as you don’t accept that as your limit. I think the mountains are a great place to discover that. I’m always asking myself the same question, ‘am I tough enough?’. You’re Mom isn’t going to swoop in and be like ‘okay let’s go home, I’m sorry you had a bad day in the mountains’. You just gotta do it.”

Brendan believes that your “needle” moves as you expose yourself to things that make you uncomfortable. “Challenging yourself physically is a great way to put yourself in those mental states and conditioning yourself for other things you want to do in life that are terrifying.”

Although he has made a living writing about activities that terrify most people, public speaking terrifies him. “I’m shaky, nervous, and can’t sleep the night before. Now, this year I’ve done 50 public speaking dates (for his book Sixty Meters To Anywhere) and it’s way less scary. It’s just like climbing. People tell me, ‘I’m scared of heights, I can’t climb’. I say of course you’re scared of heights, I am too, that’s a good thing. But the more you exposure yourself to it, the less scared you get of it.”

The Grass Is Always Greener

Instead of focusing on the distant future, Brendan stays focused on his next five or six projects. “I’m not very good at thinking strategically so I just kind of do the next thing. I feel like I’m just throwing shit at the wall and hoping it sticks, ya know”. Currently he is pitching and signing contracts for more books, brainstorming a potential fiction book, and shooting a film about ultra-running — his latest personal-mental-mental-toughness challenge.

“I don’t know man, I feel like I’d do better if I was working on a brand or sticking to one medium, but I don’t know that you have to. I look at friends who just write books or just write magazine articles and are amazing at it, and I think about how cool that would be. Then we get together for lunch and they say ‘tell me about how you make films’. I think… ‘really? You just wrote a best-selling book, why would you want to do that?’,” he laughs. “But it’s funny, we are all looking at what each-other is doing and thinking ‘wow that would be really cool to be doing what they do’.

Right now, Brendan is happy to be having fun doing what he loves and creating on a daily basis. “[I’m happy that I can] reach people and be a part of someone’s day, whether it makes them happy or inspired.”

Drive & Permission

According to Brendan, the difference between people who create and people who want to create is drive and giving yourself permission to pursue your goals.

“In a job interview, 9 out of 10 people say they are extremely self-motivated. But when you run your own business, you have to be self-motivated so that’s the true test. I’m not going to bullshit anybody, I’m totally self-motivated because I have to be.

“A lot of people say ‘I want to do this or that someday’ and they just go sit at the bar, go rock climbing, or binge watch Game of Thrones. Most people just lack that kick in the ass, like ‘fuck it I’m going to do it’. I was kind of late to the game of giving myself permission. It took seeing a lot of people around me doing their own thing creatively to realize there is nothing different about them versus me, except that they’re doing it.”

It’s easy to look at creative people from the outside and think they are unfocused free-spirits. But this idea seriously discredits the tenacity it takes to make a living as a creative. “There are people out there that may say ‘oh there’s this free-spirit artist who just goes up into the mountains to paint landscapes, I don’t know how they make a living’. That’s bullshit. Yea that’s what they put on social media, but they’re at home shipping out their stuff, trying to market, and doing a bunch of less romantic things on the side that you’re not seeing. Everyone’s working pretty damn hard. I work more than I climb or do anything else because I do things that don’t make very much money,” he laughs “, but I’m having a blast.”

To find out more about Brendan and his latest book “The Great Outdoors; A User’s Guide”, visit his website at semi-rad.com. Or follow him on Instagram at @semi_rad. Do you have a passion that you wish to pursue? I hope you found inspiration in this story and if you did, please share. Comment below or email me at editor@theunconventionalist.com to let me know what you think!