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 going to share daily reflections in a short-form email series I'm calling BUDS, or Becoming Unobstructed Daily Snippets.
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 this dream. Sure, I've tried many different paths of trying to get there, but it's always been in service of reaching the same goal. I've held it close since I was a kid, and it's something I've only recently let myself say out loud.
Here's what's happening.
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.
Ok, so to understand how The Artist's Way fits into a year-long plan of chasing my dream, you'll need to know a few things.
First, 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 childhood dream. 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 would be a writer, too. I even had a big idea for how it would work.
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... I'd be creating the thing I wished existed, myself, when I was a kid.
Secretly, I began wondering, "what if I started my own media company where I could orchestrate these publications and projects?"
Was I good enough?
In the 2010s, an outdoor leadership program foundationally changed me; reshaping the skills I used to manage myself and others. While I'd studied marketing and communication, 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 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 what I still do as the strategist in pursuit of writing.
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 guiding and toward full-time tech life (instead of splitting my time 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 coaching people through actually solving their 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. The idea scared the shit out of me, so I knew I was on the right track. This was it. 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 went for it.
But it wasn’t the business I’d dreamed of... it was a safer version of taking the leap. One that used my skills, sure, but it also meant ignoring my gut. That took me 7 months to admit. Which is how I found myself trying to position myself to be profitable, but not fulfilled.
I tried shaping my business into doing what, historically, had taken full-teams to achieve: repositioning and resetting business operations to run more smoothly. And it was working for me as a solo consultant. At least, until I could start hiring a team.
But it didn't feel like my dream. It was like my dream with a bad haircut. At a party where he didn't belong. And wearing a neon sign that said, "I'm here because I should be." So, then the realization sank in. And it changed things for the better.
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.
My partner asked me that when talking about this. It's the same question that led me to dream of starting a media company all those years ago. Because what she'd really asked was, "how do you want to spend your time every day?"
And then I asked myself 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 it doesn't mean you should do it all. I got good at building businesses so I understood the operations "under the hood" exceptionally well.
Money was the motivator for a long time. And that's how I found myself drifting from the path to the destination I really wanted.
But my dream never left. It's the same reason why I've tried to create different media publications over the years. It's even why I finally started a newsletter in 2024. And a podcast in 2025. Even though I've been publishing weekly, I've never talked about what it's been like to build the scaffolding I'm using to chase my dream.
Nobody's seen the work going in, just the newsletters and podcast episodes that go out.
So, here's where that changes.
Here's what I've learned:
So that means 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 and podcasts that help people.
The MAP acronym (Milestone Accountability Plan) comes from a dashboard system I once built. I used to use with my teams and clients, but I'm reclaiming and repurposing it to help keep me accountable to my own goals this year.
While my dream isn't exclusively snowboard media anymore, it's still very much alive in a different form. I'm still chasing my dream of building a media company. Only, now it's focusing on what I've been learning throughout the ups and downs of this journey.
The MAP Year is all about leaning into this, but calling it what it actually is: the journey to becoming a full-time, professional writer. And documenting the the digital infrastructure I'm creating to support it.
It's why I'm completing The Artist's Way over the next 365 days. It feels like a goal that moves me closer to the dream I’ve had all along. So I'm giving myself the creative constraints of my old snowboard movie heroes, and the permission to let my artistry run wild.
One day, I still plan for The Unobstructed to include a version of those annual storybooks I'd dreamt of. Except, now, they'll look like a collection of essays and stories about people who haven't given up on chasing their dreams.
I hope this project keeps me pointed in that direction.
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 with it. 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.
I’ll keep sharing weekly essays and podcasts, same as always, right here. If you want additional, daily reflections from the MAP Year journey sent to your inbox, you can opt in below.
Here are a few examples to start with:
No pressure, this is for the folks who want to follow along a bit more closely.
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 frickin stoked about this and I hope you are too!
onward.
-dmac