It was my dream to become a writer when I was growing up. Lately, I've been thinking about this a lot. Something I'm pretty proud of is that I've never given up on it. Sure, I've tried many different paths of getting there, but it's always been in service of reaching the same goal. It's one I've held close since I was a kid, and it's something I've only recently let myself say out loud.
You might have heard of a Gap Year… well, that sounds like putting something off to me. So I’m taking a MAP year to take something on instead: I’m redrawing the life I want to live. And I'm sharing the journey in a daily column.
The MAP acronym (Milestone Accountability Plan) comes from a dashboard system I built to use with past teams and clients. But, I'm reclaiming and repurposing it to help keep me accountable to my own goals this year.
The MAP Year is all about daring to ask the world for what you want—AND—following it up with measurable action.
I hope this project keeps me pointed in that direction.
First off, my career path looks pretty non-traditional. I used to work as an outdoor educator and guide. Now I'm a business strategist who pivoted to start a media company. More on that later.
Second, in the early 2000s, I was big-time into snowboarding. And writing. So that's when I'd hatched the idea to chase my dream of becoming a writer. The time I'd spent reading snowboard magazines and watching their sponsored video projects each year is where I quietly began scheming.
I loved the artistry of it; I still do. There's just something about the freedom of expression and the desire to create a new story each year that speaks to me. Not to mention, snowboard media revolves around working with whatever Mother Nature decides... the entire format has built-in constraints. So I started piecing together how I might one day earn a spot on a snowboarding brand's athlete roster. The thing that would set me apart, I'd reasoned, was that I'd become a writer, too.
My plan was was to pitch a "yearbook" style print edition to go with a brand's annual movie. I envisioned it like a storybook of the film project. Something like a who's who of the people behind the scenes. These would be the guides, photographers, logistics coordinators, and folks working the camera... it's something I'd wished existed, myself, as a kid.
Secretly, I began wondering, "what if I started my own media company where I could just create these publications and projects myself?"
Was I good enough?
In the 2010s, an outdoor leadership program foundationally changed me; reshaping the skills I use to manage myself and others. While I'd studied marketing and communication in college, I ended up pursuing a career as a mountain guide. At least by day. But by night, I was ruthlessly learning, trying, and failing my way forward in a marketing technology career.
Building a business in college was the best crash-course I could've ever hoped to find for understanding the inner workings of different job functions and what they require. Tinkering is how I learn best—I need to see how something works to understand its mechanics.
This is something I still do.
Although it looks different than it did (I'll get into how), that process of tinkering, trying, and failing is how I kept inching closer to my dream. With the outdoor education influence, it shape-shifted. So, instead of becoming a snowboarder who contributed his writing to sponsored projects, I figured I could learn the skills to extend that into a life-long career of guiding, too.
Dream big, right?
In the 2020s, I suffered a traumatic brain injury.
As I lay still for many months in a dark room, I was forced to completely reevaluate what "stability" meant to me. Inactivity and financial strain nudged me to a difficult and heartbreaking conclusion: I needed to walk away from life in the mountains and toward full-time tech life instead (rather than splitting my time between them, as I had been).
Before my TBI, I led people through technical mountain terrain. I was good at identifying sticky situations and teaching folks how to avoid them. But helping people learn to solve their own way out of those situations? That's where I really thrived. So I focused on using those skills—in combination with my tech skills—to build enablement teams.
Specifically, teams creating programs for learning new marketing & sales software.
Now that you have some context, remember: the goal's always been full-time writing.
After getting laid off in 2024 I saw an opportunity, one that scared the shit out of me. So, I knew I was on the right track. If I was serious about chasing my dream, why not go for it? Why not start my own business? I'd gained enough experience from building businesses before that I could give my dream a real shot.
So I did.
But it wasn’t the business I’d dreamed of... it was a safer version that used my skills, but that meant ignoring my gut. That took me 7 months to admit.
I'd set out to build a consulting company, but in my effort to attract new customers, I discovered that I loved building publishing systems but hated consulting...Whoops.
I'd been creating shiny stuff to present to the world... for a business I wasn't even sure I should be building anymore. Which is why I took a step back to let go of what wasn't working.
"What would you do if money wasn't the motivator?"
My partner asked me that when talking about all of this. It's the same question that made me want to start a media company all those years ago. What she'd really asked was, "how do you want to spend your time every day?"
And so then I thought about a few follow up questions:
The trouble with getting good at doing a lot of things is that the world starts rewarding you for it, but that doesn't mean you should do it all. I got good at building businesses so I understood the operations "under the hood" exceptionally well.
My corporate skillset was supposed to be a way to fund my dream, not prevent me from reaching it...
The way I can bring my best self to the benefit of others, is through a dedication to creating. In this case, building the digital space of my dream media company and then stocking its shelves with writing, podcasting, and print publications that help people.
I've actually tried to create different media publications over the years and I finally started a newsletter in 2024. Then a podcast, full publication, and daily column in 2025.
Even though I'd been publishing weekly, I've never talked about what it's been like to build the scaffolding beneath it all. Nobody's really seen the work going in, just the newsletters, essays, and podcast episodes that go out.
So, here's where that changes.
I’m doing a full year of The Artist's Way.
Julia Cameron's book on creative recovery has helped many reclaim their artistic dreams. Typically a 12 week process, I'm turning it into a 12 month journey instead. It's like a self-paced course, featuring a combination of narrative storytelling, exercises, and journalistic prompts. The Artist's Way is part of how I'm giving myself the creative constraints of my old snowboard movie heroes, and the permission to let my artistry run wild.
But here’s the catch... I need accountability.
No, seriously, my neurodivergent-self puts anything of moderate importance directly in front of my face so I’m forced to trip over it rather than forget to follow through. Clearly, I thrive on structure. Which is ironic, seeing as structure also makes me itch.
I need structure that has boundary lines but plenty of room to maneuver between them—like bumpers at a bowling alley. That's why I'm creating enough of it to guide me through this thing. Done right, it will still encourage lots of play and discovery.
And I'm writing about the journey daily for others to learn from, and so there's somewhere I can stack visible progress for myself.
While my dream isn't exclusively snowboard media anymore, it's still very much alive in a different form. I building a media company, only now it's focusing on what I've been learning throughout the ups and downs of this journey. I’ll keep sharing weekly essays and podcasts, same as always, right here.
If you want additional reflections from the MAP Year journey sent to your inbox, you can opt into receiving my daily column.
No pressure. Unsubscribe whenever you want, if you want.
When I was coaching competitive snowboarding I used to say, “if you’re not having fun you’re doing it wrong” and it’s about damn time I took my own advice. I’m stoked about this and I hope you are too!
onward.