[Start Here] Welcome to Unobstructed with Derek MacDonald
Make your work easier with systems from a wilderness guide turned tech simplifier—2x a week, right in your inbox.
Hey I’m Derek, the guy behind the Unobstructed newsletter & podcast.
Before working with business systems and software, I was as a wilderness guide.
Yeahhh, I know. Different setting, same job though—helping people assess risk and navigate challenging conditions.
Unobstructed is for people who are tired of feeling trapped by the systems that were supposed to help them get ahead. Folks like you and me. Who quietly question what’s working, why you’re stuck doing things that way, and whether it’s even worth it.
And if you’re reading this, you’re probably:
Torn between upkeep and keeping up.
Doing more but kind of not sure if it’s helping…
More than anything, you’re looking to stop saying, “if I can justtttt [wishful thought], THEN I can start living my life again…”
Been there.
That was me, too.
More than once, actually.
This newsletter is where I write about how I navigated out of that doomloop—and how I keep myself from backsliding in the moments I forget.
Your guide to this page:
What is Unobstructed?
How this newsletter works.
What to expect as a subscriber.
When you’ll get new posts.
Why I love doing this.
What is Unobstructed?
It’s a way to figure out the tools and systems keeping you stuck.
It’s for people making sense of how we live and work.
It’s a weekly newsletter and podcast.
How this newsletter works.
BUT it’s not about the hustle culture rah rah or shiny-object-chaser stuff.
Yeah, that’s not really my jam either.
Oh, totally cool if it’s yours, but this is more of a place to help you rethink things like, “how do I actually want to be living” and “what do I want my days to feel like?”.
That kind of stuff.
And then “how can I do that by subtracting instead of adding more?”.
I won’t promise a magic pill to having it all—Unobstructed is about sharing what’s working for me along the way, too. Real questions mixed in with some practical thinking.
And an invitation to simplify the pieces of your puzzle that’ve gotten too loud.
What to expect as a subscriber.
Posts weave between three main themes:
→ Leadership GPS ←
Stories and systems for navigating work and life with more Grace, Pace, and Space.
Protecting your time and energy so you can prioritize what to say “hell yes!” to and what to say “no” to.
Untangling the tools and tech that clog your workdays and cloud your focus.
Each post gets assigned one of these tags.
That way, you can also click on the tag if you want to read more like it.
When you’ll get new posts.
You’ll get two posts each week:
A newsletter (every Sunday).
A podcast episode (every Wednesday).
Paid subscribers also receive bi-weekly long-form essays that dive deeper into things like leadership skills and mental wealth—for big-picture clarity with next-step nuance.
Here are a few good places to start:
So, What's My Story?
At work, I help leaders and execs untangle their revenue systems to make room for living their lives.
But, like you, l'm more than my job.
I’m a former wilderness guide turned software simplifier. My own journey as a Mental Wealth Investor uncovered many, many ways of navigating an unobstructed life. Guiding other people with similar goals helps me learn even more.
It’s what I love to do.
Why do I love doing this?
If you’re reading this, there’s likely some part of your work that’s keeping you from fully living the rest of your life.
Well, that was me.
Burnt out from trying to get ahead by going faster than the clogged systems. Until I tried something different and figured out a way that gave me my life back.
I see so many people still caught in the washing-machine spin cycle. And I love helping them get out of the riptide and back to enjoying the beach.
My sweet spot is the overlap of high performing athletics, business strategy, and cognitive psychology.
Wilderness emergency medicine taught me more about pressurized decision-making than any other aspect of my career.
At 19 I studied risk management and effective decision-making in a 3 month, immersive leadership development program. I also started consuming as much information as I could from thought leaders like Simon Sinek, Adam Grant, Tim Ferriss, Brené Brown, Gabor Maté, Angela Duckworth, Rich Roll, Michael Gervais, Mel Robbins, the Gottmans, and so many more.
Since then, my curiosity has only intensified.
It led to a career including roles as a:
Director of Strategy & Operations
Revenue Growth Consultant
Leadership Staffing Director
Made possible by expertise with:
Sales
Copywriting
RevOps Strategy
Growth Marketing
Technology & Automation
What I've learned along the way.
My ability to rapidly scale a startup showed me that what I was learning really worked.
In my 20s I also guided backcountry expeditions in the Rocky Mountain West, coached big mountain snowboarders qualifying for the Freeride World Tour, and ran the Boston Marathon after recovering from a traumatic brain injury.
I worked on the crew of a sailboat in the Caribbean, toured New England as a keynote speaker, and weaved through the service industry in a way that I like to think would make Anthony Bourdain proud.
Or, at least, make him scoff a bit.
Now what?
If you’ve read this far, you’ll fit right in.
Still looking around?
Pick a topic to read next: Leadership GPS, Mental Wealth Investing, Software Simplified.
Or, check out the Unobstructed podcast.
P.S. For more ways to simplify your work, so you can actually go live your life, check out DMDC Systems. That’s where you can learn about the work I do with clients.
What a life and story Derek! I have so many questions...I think I need to interview you.
You're my hero role model Derek,and I love being on podcasts connecting, especially as the Unmuffled MindShift Mechanic and Plumber 🤗