I am a Dirt Bag. It has been a life goal. Or a mantra. Not sure at this point. You probably wouldn't think I was a Dirt Bag if you met me. You would think I look pretty "normal" Rugged good looking perhaps but not a Dirt Bag. Kidding about the good looking part obviously. I shudder when I see photos of myself. But I digress. Why do I consider myself a Dirt Bag? My parents were reluctant hippies. My dad was about as WASPY as they come. Grew up in Chestnut Hill. My Grandfather was an Army surgeon. Harvard educated. I went to the Chestnut Hill Country Club in a little man suit every Sunday. So how in the hell could I turn into a Dirt Bag and not a Lawyer or some other suitable gentlemanly pursuit?
The 60s happened. My parents like I said were wannabe hippies. They could never be true hippies as like I said dad was deeply trust funded and that would never go down. My mom was from a broken Irish home and worked her ass off to get through Nursing school to make a better life for herself and her family. But the ideals of hippies mattered to them. The music which I hated. The views which I took on by osmosis. We did lots of hippie type stuff. I grew up fairly non-traditional in a traditional setting which has it upsides and downsides. Around high school things sort of headed off track and fully to the Dirt Bag lifestyle. I quit hockey for karate. I went deep into the rabbit hole of eastern thought. I went to Art School. I windsurfed and dreamed of actually surfing.
I took my High School graduation money and booked a trip to Maui from the back of a windsurf magazine. It was like I woke up from a bad dream when I landed in Maui and found my true self. But I hadn't accepted the Dirt Bag lifestyle yet. I didn't get it. I didn't get that you could just drop the fuck out and surf. My ties to my family and obligations to them would never allow that anyway but a boy can dream. The ocean and dojo became my salvation. When I returned from Hawaii things would never be the same. I probably should have dropped out of Art School and figured shit out. But as a true Dirt Bag I went all in and while registered as an "Illustration Major" I basically was a painter. I studied painting and figure drawing non-stop. But I was a crappy art student. My heart and soul was on the ocean. Every chance I could get I would take off and go windsurfing. Its not a cheap sport. I drove a beatdown Subaru that was barely worth what one sail would cost. I don't really remember eating or partying. Those things really weren't important. When I wasn't windsurfing I was hightailing it up to Boston to study Kung Fu now in South Station. I am not sure what my parents were thinking. But the roots of my life as a Dirt Bag were forming.
I somehow graduated. No idea how. I waited for my girlfriend to graduate UMASS while working in a Hospital. I would go to work with two black eyes, cracked ribs, split lips. No one asked too many questions about it. It was Boston after all. Once Pam graduated we packed my jeep with our possessions and headed West to SF. We had debated between Laguna Beach and SF for a while. Pam has two brothers. One lived in Laguna and one in SF. It was sort of like how Charlie Sheen's character was pulled in two directions in Apocalypse Now. We settled on SF because Laguna just felt too nice. And too focused on money. SF had soul. But Laguna is damn pretty. We made the right choice. Thank god we moved to SF.
The reality of moving to SF with a Jeep, 2k in cash and a microwave and zero prospects for work was some lifestyle shifts had to occur. The windsurfer was sold. Kind of crushing but rent had to be paid. Martial Arts was too expensive so that went out the window. I worked three or four jobs. Bartender at night, brunch place in the am, intern at a magazine in the design department when I could get the hours. Luckily, I had some actual design experience from when I was in High School. Art School gave me zero skills for the actual work force. What a shocker. The magazine I worked for was called California Bicyclist. It was a free regional rag that's strength was events. This was pre-internet. Finding races and events wasn't easy. We had a pretty huge circulation for a regional magazine.
My Dirt Bag lifestyle was about to go on steroids. The sport of mountain biking was created by Dirt Bags. Literally. They lived like surf bums or ski bums but on bikes. They lived hard. Meeting and riding with the founders of mountain biking was an eye opener. I was hooked. It was the closest thing to surfing I had a ever done. My first bike was a Bridgestone Mb-3. I coveted the Mb-0 but didn't have the funds to pull that off.
So what is all the point of this? The point is the outdoors sports media seems to be romanticising and monetizing the Dirt Bag lifestyle. I went on a bit of an internet tirade about a certain video that was posted that literally made my head want to explode. I am not trying to be one of those old dudes who are like you have no idea how it was in the day! My point is the Dirt Bag lifestyle exists right now. But it does not require one to be an Instagram celebrity. The Dirt Bag lifestyle can be freeing. Being shackled to a super phone and curating an instagram feed is not freedom. Nor is it aspirational or inspirational. It is a mockery of why Dirt Bags "invented" mountain biking. A legion of surf bums, ski bums, climbers, fly fisherman have led this lifestyle for decades. It is not without its dark side. But if you choose the Dirt Bag lifestyle the rewards are endless. The greatest one to me is just freedom. End of rant