Derek MacDonald got sober, got broken up with, and moved across the country—all in the same week. Most people would call that rock bottom. Derek called it a foundation.
Four and a half years later, he’s the creator of Becoming Unobstructed, a newsletter and podcast reaching readers in 32+ countries. He’s published 450,000 words in 18 months—the equivalent of eight copies of The Great Gatsby. And he’s living proof that the choice between creativity and stability is a false one.
This conversation goes deep into what happens when you stop performing, start being honest with yourself, and discover that the things you thought made you “less than” were actually pointing you toward your truest creative expression. Derek’s journey from working three jobs in a Wyoming mountain town to building a thriving creative practice isn’t about hustle culture or overnight success—it’s about what becomes possible when you remove the obstruction of substances and get square with who you actually are.
Show Notes
[05:30] The Week Everything Converged
Derek planned his sobriety date after multiple failed attempts, giving himself the illusion that “on this day I will get sober and my life will be beautiful”
Reality hit hard: got sober, started a new job the next day, got broken up with, had to move out, and relocated across the country—all in one week
His entire life in Wyoming was wrapped up in drinking culture: working as a snowboard guide, in the service industry, and doing freelance marketing/writing projects from sunrise to bar close
The outdoor industry bonding mechanism was “let’s grab beers after we do some fun activity”—his social world and work world were inseparable from alcohol
[09:20] Running in Quicksand: The Tipping Point
Derek describes feeling like he was “running in quicksand”—putting in massive effort but going nowhere
He got “sick and tired of being sick and tired” and realized stopping drinking might let him actually see progress
The breakup and move forced him to confront his relationship with alcohol without the safety net of his established social world
Moving across the country became an unexpected gift: “I literally could not get a drink if I tried”—he had to start over completely
[15:45] The Spreadsheet That Changed Everything
About six months into sobriety, Derek started tracking his habits in a simple spreadsheet to gauge happiness
The act of tracking itself became a form of presence and mindfulness—he realized he’d been living on autopilot
That spreadsheet evolved into a system, which became a business plan
Three years ago: meditated every single day for a year. Two years ago: designed his business, website, newsletter, and podcast. One year ago: launched it all
[23:12] Discovering ADHD and Unmasking in Sobriety
Derek learned he had ADHD as an adult—the “H” (hyperactivity) hid behind masking behaviors developed since middle school
Alcohol became part of his masking toolkit: a way to fit in, cope with sensory overload, and navigate social situations
Getting sober meant confronting the fact that he’d been performing for most of his life rather than showing up authentically
Understanding his neurodivergence helped him recognize he wasn’t “broken”—he just needed different strategies
[28:40] Relearning Connection Without Alcohol
Derek had to learn how to exist in a room full of people and connect without the social lubricant of alcohol
His solution: focusing on things that genuinely excited him and letting people who enjoy similar things find him organically
He stopped chasing career ladders and titles that he thought would compensate for what he “lacked”
Sobriety revealed he’d been using professional achievements as justification for the parts of himself he didn’t like
[35:18] The MAP Year: Building Systems for Sustainable Creativity
The MAP Year Project is Derek’s framework for helping people make room for both creativity and stability
It’s built on his personal system of tracking, presence, and intentional design
The philosophy: you don’t have to ditch your creative dreams to survive, and you don’t have to burn out to build something meaningful
Core components include meditation, exercise, nutrition, sleep—foundational practices that increase confidence and life enjoyment
[38:12] Creativity and Sobriety: Permission to Just Do the Thing
Derek used to think creativity was the opposite of stability—that he had to choose one or the other
Getting sober and being honest with himself helped him realize he didn’t need to perform or chase validation anymore
Writing had always been how he expressed himself, but he was embarrassed about it for years
In 18 months, he’s published 450,000 words—eight Great Gatsbys—and had to confront the story that he “wasn’t a writer”
[42:56] From Proving You’re Creative to Opening the Door Wider
Derek’s mindset has shifted from “trying to prove I’m allowed to be creative” to asking “what else am I limiting myself on?”
Social media initially “fucked with his head” and brought him back to that early sobriety lesson: do it for you, not for what others think
Falling in love with the process—not the metrics—has helped him find authentic connection with other creators
Doing things that inspire us leads us to things that keep inspiring us
Key Quotes
“I just kind of reached a point where I got sick and tired of being sick and tired. I was putting in so much effort to try to change my situation and move myself forward, but I wasn’t going anywhere. I felt like I was running in quicksand.” - Derek MacDonald
“My entire life was wrapped up in drinking and drinking culture. The problem was, to make that change [to sobriety], I had to uproot everything.” - Derek MacDonald
“I used to think that to choose things that would provide a stable life—stable income, stable relationships—meant I had to not choose creativity. It was one or the other. And I don’t think that’s true anymore.” - Derek MacDonald
“I always told myself I wasn’t a writer, and then here I am. I just wanted to start doing the thing. I was like, okay, I think I might be a writer. And so now the question is, what else am I limiting myself on?” - Derek MacDonald
“Getting sober and being honest with myself allowed me to understand why I had been chasing these other things—these career goals or ways that I thought would bring me fulfillment. I could let some of that go and embrace: hey man, you love writing and storytelling. You don’t need anybody else to give you permission. You can just go do that.” - Derek MacDonald
Resources Mentioned
Becoming Unobstructed - Derek’s newsletter and podcast (theunobstructed.com)
The MAP Year Project - Derek’s framework for navigating agency, grief, and creativity
The Great Gatsby by F. Scott Fitzgerald - Referenced when Derek calculated he’d written the equivalent of eight copies in 18 months
Where to Find Derek MacDonald
Website: theunobstructed.com
Podcast: Becoming Unobstructed
Your Next Step in Creative Clarity
If Derek’s story resonates with you—if you’ve been running in quicksand, putting in massive effort but not seeing the progress you know you’re capable of—you don’t have to keep running alone.
Maybe you’ve told yourself the same story Derek did: that choosing creativity means sacrificing stability, or that building something meaningful requires burning out. Maybe you’re using alcohol to mask, to fit in, or to quiet the voice that says you’re not enough. Maybe you’ve been so busy performing that you’ve forgotten what it feels like to show up authentically.
Derek proved something essential: the choice between creativity and stability is false. But getting to that realization required removing the obstruction—the substance that kept him performing instead of creating, proving instead of being.
The Sober Creative Method™ is a 90-day journey designed specifically for creative professionals who are ready to remove alcohol as the barrier to their greatest work. It’s not about willpower or deprivation—it’s about building a life so compelling that drinking becomes irrelevant. It’s about discovering what becomes possible when you stop trying to justify who you are and start embracing what you actually love.
Derek wrote 450,000 words in 18 months once he stopped proving he was allowed to be creative and just started doing the thing. What’s waiting on the other side of your obstruction?
If you’re curious about what your life and work could look like with complete clarity, let’s talk. Let’s explore what’s possible when you stop performing and start creating.
Thank You
A heartfelt thank you to Noelle Richards, Karen K and everyone else who joined us live for this conversation, and to Derek MacDonald for his extraordinary honesty and wisdom. Your presence and engagement make these conversations possible.
What’s Next
The Sober Creative is more than a newsletter—it’s a movement of professionals reclaiming their creativity by choosing clarity over coping.
🎯 Take the Clarity Quiz: This assessment reveals certain areas where alcohol may be the exact thing that is quietly sabotaging your creative potential. It’s free and only takes a few minutes.
✍️ Read the Essays: Stories and strategies for building a clear, creative, and intentional life.
🎙️ Join Clear Conversations: Honest talks with creative professionals navigating the intersection of sobriety, self-discovery, and breakthrough work.
💬 Curious about your next step? If you’re sensing that something’s holding you back, but you’re not sure what—reach out. Coaching, community, or clarity—it all starts with a conversation.
✨ The Sober Creative Method™ is a 90-day journey to remove alcohol as the barrier to your greatest work.
Each step forward is an act of becoming who you’re meant to be.
Thanks for walking this path with me.
Josh
P.S. Missed previous episodes? Browse the Clear Conversations archive to explore more conversations with creative minds in sobriety.
