Meet OWAA member Matt Crossman

Matt Crossman is passionate about the intersection between fitness, adventure, mental health and loneliness, especially among middle aged men.

“I write about those themes constantly, and I daydream about starting an adventure company devoted to strengthening male relationships. For now, I’m content to organize trips for me and my friends and write about them with an eye toward fighting loneliness,” said Crossman.

“A friend and frequent adventure companion was recently diagnosed with cancer. The end of his radiation treatment corresponded with the start of a yearly trip I organize called 50-50-50, in which we hike 50 miles, bike 50 miles and canoe 50 miles. He went on the trip in spite of, or maybe because of, his treatment”.

“He told me that for much of his life, he lacked strong male friendships. But he joined a men’s fitness group five years ago, and he has more deep friendships now than in the rest of his life combined. And that has made a huge, huge difference as he has endured the strain of the diagnosis and treatment. There’s evidence that a person’s mental well-being, forged by strong relationships, helps them face hardship better. We talked about that during our long miles on the bike.”

“As we rode, he said something that floored me. I get choked up just talking about it.”

“He said: ‘Even if it doesn’t help – even if I die a few years from now – how do I want to spend the last few years of my life?’

“As he pedaled, he reviewed the options. He could sit around alone, feeling sorry for himself, sullen and withdrawn, angry at the world, angry at God, jealous of all those people who don’t have cancer. Or he could get outside and bust his rear end with his friends. ‘To do hard things with a bunch of great men is what I like to do more than anything else,’ he said. Even with all that, maybe the cancer will take him anyway. ‘At least I’ll be happy,’ he said. ‘Either way, it’s a win.'”

What are your areas of outdoor communication?

I like to find the edge of my comfort zone and take another step or two. I’m a try anything once guy—I’ve written about rock climbing, ice climbing, tree climbing, surfing, dog mushing, hunting, fishing, long distance biking riding, canoeing/kayaking, adventure racing, etc. Sometimes I write experiential stories, sometimes I embed with a group, sometimes I profile someone in the sport. If it involves getting outside and sweaty, count me in. I look for angles – either technology, or trends, or the people I encounter, or ‘what I learned’ – that make the story suitable for a wider audience. 

What drew you to the field?

At first it was necessity. I was a new freelance writer desperate to find work after nearly 20 years in staff jobs. My experience was in sports, but that’s a very crowded market for a freelancer. I needed to write about other stuff, too. By coincidence, I happened to be a newly passionate hiker. I hiked to keep myself sane as I tried to figure out this new way of life. I discovered, almost by accident, that there was a market for hiking stories for non-outdoors publications. I wrote about specific trails, or stories about people hiking, for many publications—regional, sports, business, military. I used that as a steppingstone into the outdoor world as a whole. Hiking became biking became endurance sports became adventure in general.

What enticed you to join the Outdoor Writers Association of America?

Networking and mentoring (both sides).

The other day, my daughter came into my office and asked why I was working in the pitch dark. I had been completely concentrating on turning the amorphous blob of words on my screen into a story I was proud of and didn’t even notice it had gotten dark. Working alone/for yourself, as I do (and I suspect many OWAA members do) can be like that. We are so isolated we don’t even realize we are sitting alone in the dark.

What is your favorite outdoor activity and how did you get into it?

Gravel bike riding.

One day four years ago, I was hiking with a new friend, with whom I have now gone on many adventures. I asked him, “what’s on your bucket list? Maybe we can do it together and I can write a story about it.” He answered without hesitation: “Ride the Katy trail.”

The Katy trail is a gravel trail that runs the width of Missouri, where we both live. It sounded like fun and had story potential, for sure. The only problems: I didn’t own a bike, I didn’t have any clients who published bike stories, and I had never gone on any rides longer than maybe 10 miles, while the Katy would require three straight days of 75 miles, 85 and 105. 

I said, “let’s do it!”

My freelance life in a nutshell: I say yes and figure out how I’ll do it later.

I borrowed a bike at first to start training and wrestled for months with whether to buy a bike first or sell a story first. Freelance writing budget being what it is, I waited to sell a story, which I eventually did.

Then I bought a bike, started riding it, and was absolutely positively gobsmacked at how much fun I was having. I was a 47 year old man, why was I giggling like a 7-year-old on this bike? I wish I had started riding at 17, 27, 37.  Anyway, five friends and I rode the Katy trail, and it was incredible. We immersed ourselves in Missouri’s silent, rolling hills. We pushed ourselves to exhaustion. Most important, we laughed.

One story on that trip turned into two. I rode the Katy again a few years later for a different publication. I rallied my friends to join me on another cross-state trip on a different trail (that one was all road, which I don’t enjoy nearly as much.) I’ve now had many assignments with longish bike rides, and I still enjoy it as much as I did on that first Katy trip.

Our minivan – Kia Sedona, don’t be jealous — is the best purchase of my adult life. I mean this sincerely, if you haven’t driven seven teen and pre-teen girls as they belt out Taylor Swift, you need to do so. The gravel bike is a very close second.

Portfolio and links to Matt Crossman’s work

Matt Crossman Portfolio

Did a legendary trout really ride the rails from California to Missouri? – By Matt Crossman

5 Lessons Death-Defying Adventure Taught Me About Facing My Fears as a Solopreneur – By Matt Crossman

A canoe, a GPS, and my quest for the ultimate social distancing – By Matt Crossman

Matt Crossman Substack