Jason Robinson is a rambling man.

Pro snowboarding keeps him moving all winter, and come summer he’s still rolling, ready to go, always and anywhere. Jump a train to Minnesota, barge out to Mt. Hood for a minute, explore Europe on the Absinthe premiere tour? Sure. He’s there. Dude’s down to be out on a moment’s notice. See, he’s got that freedom. No rent. No mortgage. No significant other. Just a custom built micro-home on wheels. Right now, it’s parked in an alley in Kalispell, Montana. Someday, Jason’s going to haul it up to Alaska and park it in Haines. Let him tell you about his encounters with hobo culture and those rambling ways.

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You’re from Whitefish, just north of Kalispell. What was it like growing up in the Flathead Valley?
It’s a perfect place to grow up. The resort is super awesome and my parents both worked up there, so that was just a built-in babysitter. We’d just tag along with them in the morning, kill time for an hour or two before the chairs open and then ride until the end of the day.

[aesop_quote type=”pull” align=”right” quote=”My goal is to set my life up so I can live off a few hundred bucks a month. And not just live, but flourish.”]

The mountain itself is super awesome — such a good place to learn and progress. It’s super featured. There’s steep terrain, but it’s short and safe, so it was good to learn on. There’s some intermediate to advanced terrain to ride. There’s all sorts of freestyle hits, natural hits, so it’s also good for that.

There’s a lot of stuff to do too. There’s endless forests and lakes here. There’s Glacier National Park, if you’ve never been there it looks like you’re in the Swiss Alps or something.

You kind of take that for granted when you’re a kid. We just wanted to skateboard, you know? We just wanted a sick skatepark, which now they have.

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You really value your freedom, don’t you? Why not take up a more secure life, maybe have a fixed address?
Well, I think the idea of security is just an illusion; there is no security. I think people are lying to themselves. You never know what’s going to happen.

The Wisdom of Insecurity is this book by Alan Watts. It’s all about that idea. There really is no such thing as security. Everything’s impermanent you know? Everything is temporary.

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And I don’t know how much I believe in Astrology, but if I did, I’m a Sagittarius and adventure is one of our traits. But the big motivation is just keeping my expenses down — to have that freedom. If you’re somewhere and you want to go somewhere new, but you own a house or are renting a house, you’re kind of committed to that place. And while that may have been what you wanted at that point, it may change. You may want something different. You never know what’s going to happen in the world. And that’s part of the beauty of it — you don’t know — that’s exciting. I’d rather just be ready for whatever happens.

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Biggie said it: Mo money, mo problems.
Yeah, some of the happiest people I’ve ever met didn’t have a dollar in their pocket.

Like the hobos you ran with this summer? Tell me about that.
Yeah, I met this kid who had been riding freight trains for 10 or 11 years and we totally connected. I ended up taking him out to the Bode Merrill Mini Pipe contest at Mt. Hood and he was so stoked on snowboarders. He kept drawing the parallels between our lifestyle and these hobos who are traveling with little to no money, sleeping outside but still loving life. He found that same connection with snowboarders.

And he was telling me about this Hobo National Convention, about the Hobo Jungle, the Hobo King and Queen, all this crazy stuff. I was like, “Are you serious, that’s a thing?”

So after this trip to Oregon he offered to take me out to the Hobo National Convention. He was going to take me on my first freight ride. Hop on in Whitefish and hop off in Minnesota, then hitch a ride down to Britt, Iowa.

I had my bag packed and I had a friend drop me off in Whitefish, and I was looking for him and couldn’t find him anywhere. I remember thinking I’d have to be an idiot to do this by myself. All I knew was I had to get on a train that was two shipping containers tall, those are the ones that go all the way to Chicago. That’s literally all I knew about riding trains.
But yeah, I couldn’t find him anywhere that day. And I hear a train rolling through. And I got this feeling, this excitement, you know? It was the right kind of train, so I just ran out there and jumped on.

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“Current mood. Free as a bird, happy as a hobo. Excited, afraid, focused, nervous, inspired, yet fully present to feel and welcome the wide range of emotions I’m currently experiencing. #outsidetheboxtraveling #travelingisfree”

I definitely learned a lot spending some time at the Hobo National Convention, learning about what really is important and what really matters. You don’t need money to be happy. Those were some of the happiest people I’ve ever met. And they’re just hitchhiking and riding freight trains with no real destination, no timeline. It’s a beautiful thing, seeing that mentality. And if we could all incorporate a little more of that into our lives, we’d be better off.

Watch also: MTN Life Design: Marie-France Roy’s Vancouver Island Paradise

Editor’s note: After months of preparation, Jason drove his home-on-wheels to Alaska fueled by used vegetable oil, at that.

Follow Jason on Instagram

Originally featured in Snowboard Magazine 12.4: The Detour Issue