[Start Here] Welcome to Unobstructed with Derek MacDonald

A weekly newsletter to uncover clarity, alignment, and growth—without the overwhelm.

Hi, I’m Derek, a leadership alignment & growth strategist and the writer of Unobstructed.

Creating weeks that don’t suck get you to good months and great years.

Searching for clarity in the chaos of work and life?

Feeling pulled in too many directions?

Stuck in endless overwhelm?

You’re in the right place.

That was me.

Unobstructed is where I share weekly essays that uncover clarity for work and life.

Untangle the clutter with Unobstructed.

I’m on a mission to uncover clarity, alignment, and growth—without the overwhelm.

• Weekly essays to help untangle clutter and realign focus.

• Honest ideas that challenge assumptions and spark new ways of thinking.

• Growth-focused perspectives from my journey toward clarity and fulfillment.

I’m figuring out this life thing, too.

This isn’t a place for promoting hustle culture or quick-fix productivity hacks—it’s for sharing ideas, trying new things, and finding small steps that make a real difference.

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What reading Unobstructed is like:

37. The Destructive Facade of "Male Loneliness"

28. How to Avoid Being Misunderstood

30. What Senior Leaders and Junior Team Members Get Wrong About Contribution

32. Why Jon Brosio is Using Lessons From Food Service to Build Digital Trust

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Get started with Unobstructed.

Once you subscribe, here’s what to expect:

• Welcome email: You’ll get a quick note from me confirming your subscription.

• Weekly essays: Stories and reflections that land in your inbox every week.

• Your access: Reply with your questions or thoughts to any post.

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More about me.

Wilderness emergency medicine taught me more about pressurized decision-making than any other aspect of my career. My journey with sobriety taught me more about ownership and prioritization than any job I’ve had.

My story includes victory, loss, gratitude, and winding roads through mental health.

My ability to be effective comes from experiences you won’t see on my resume.

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.

It became an obsession.

I've extensively studied high performing athletes, business founders, and psychologists.

My ability to rapidly scale a startup showed me that what I was learning really worked. In my 20’s I 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 rode the waves of depression.

• I navigated financial insecurity.

• I recovered from a traumatic brain injury.

I also 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.

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16. After the Collision, I Knew I Couldn’t Stay

Read more about my recovery from a traumatic brain injury here.

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Life outside of the office has shaped my skill set as much as my professional experiences have.

At work, I build better systems for activating strategies and teams. But, like you, l'm more than my job.

Admittedly, I spend a lot of my time nerding out on sustainable systems and approaches to development. When not training for a marathon or enjoying a sunrise with my snowboard, you can likely find me frequenting local coffee shops and live music venues.

A Massachusetts native, I grew up sliding on snow in Vermont’s Mad River Valley before moving to Jackson, WY in search of big mountains and unconventional approaches to a life well lived. In 2021, I answered the Green Mountain's call and returned to Vermont, where I currently reside.

Outside of work, I have volunteered with Massachusetts HOBY since 2010, developing staffing teams and implementing curricula that inspire young people to become catalysts for positive change in their home, school, workplace, and community.

I've also spent time volunteering for local advocacy programs and coaching freeride snowboard athletes. As a member of the board of directors for Carving The Future, I advised on marketing strategies that empowered underserved youth in Wyoming by providing gear, programs, lessons, and athletic scholarships.

My contributions to Jackson Hole Snowboarder Magazine and NOLS' The Leader seek to elevate communities and voices who've got this life thing figured out.

Get started with Unobstructed.

Once you subscribe, here’s what to expect:

• Welcome email: You’ll get a quick note from me confirming your subscription.

• Weekly essays: Stories and reflections that land in your inbox every week.

• Your access: Reply with your questions or thoughts to any post.