[Start Here] Welcome to Unobstructed with Derek MacDonald
Design a clear path to a more capable self. Systems for making your work feel easier and your life feel calmer—from a wilderness guide turned tech simplifier. 2x a week, right in your inbox.
Feeling stuck between keeping up and getting ahead sucks.
At least, it did for me.
Unobstructed helps you make work feel easier and life more simple.
Hey I’m Derek, the guy behind the Unobstructed newsletter & podcast. This place is about designing a clear path to a more capable self.
What is Unobstructed?
As a former wilderness guide turned tech simplifier, I believe in building a life that does more than just work. That’s what I’m doing with Unobstructed.
This isn’t about the hustle culture rah rah or shiny-object-chaser stuff.
It’s a way to figure out the tools and systems keeping you stuck.
It’s for people looking to simplify work and life.
It’s a weekly newsletter and podcast.
There are no magic pills for doing it all here… but we do build systems you can use to make your work feel easier and your life feel calmer. As a subscriber, you’ll start to see how the following core themes are the interconnected roots of the Unobstructed ecosystem.
Theme 1
→ Leadership GPS ←
Stories and systems for navigating work and life with more Grace, Pace, and Space.
Theme 2
Protecting your time and energy so you can prioritize what to say “hell yes!” to and what to say “no” to.
Theme 3
Untangling the tools and tech that clog your workdays and cloud your focus.
Why Unobstructed?
I didn’t understand what people meant by, “if you don’t schedule a break, your body will do it for you.”
And then I crashed. Hard. So I admitted defeat and tried following the "less is more philosophy." Because doing less is actually the answer, when it's the right kind of less.
It creates the space for:
Days that don’t involve red-lining your nervous system.
Sleeping at normal hours, for appropriate lengths of time.
Life outside of work to enjoy with friends & family.
I first learned about the power of "less is more" as a wilderness guide. And then re-learned it in the 9-5 world climbing corporate instead of mountains (lol).
That’s what led me to start simplifying the tech I used. Which became a full reevaluation of my systems, forming the foundation of Unobstructed. Because flipping between trying to get ahead and just trying to survive really, really sucks. And red tape is harder to see when it’s your own system settings.
So now I help people navigate it.
“Wait... a former mountain guide… who now maps tech systems?” Yep, pretty much.
And yeah, I get it. But it really is the same job… It’s about making sense of tough challenges. And helping folks escape the metaphorical riptide and get back to enjoying the beach.
That’s what the Unobstructed ecosystem is about.
Challenging your mindset.
Sharpening your skills.
Leading with clarity.
So work can feel easier, instead of like you're barely keeping up.
How Unobstructed works
When you’ll get new posts.
Subscribers get two posts each week:
New resources every Sunday.
New podcast episodes every Wednesday.
What to know about subscriptions.
Free posts are to help you see things differently, paid ones are to help you do things differently. That’s where we go from designing a clear path to walking one.
Paid subscribers get:
Monthly longer-form essays.
Behind-the-scenes systems access.
First dibs & discounts on new resources.
Curious about what a subscription’s like?
Here are a few good places to start:
So, what led me to start Unobstructed?
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.
Unobstructed blends strategy, storytelling, and systems.
I built a career focused on helping people overcome challenging situations—first as a wilderness guide, then as a sales & marketing leader. From mountains to boardrooms, my work has always focused on helping people find clarity under pressure.
The goal is uncovering the best way to spark progress, not burnout.
I’m building this space to help people challenge their thinking, sharpen their skills, and act with clarity.
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.
So, is this you?
Ready to design a clearer path forward?
To challenge your mindset?
To sharpen your skills?
To lead with clarity?
Or pick a topic to explore:
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 🤗