Writer & systems consultant.

About.

My bio.

I use stories and systems to create clarity, trust, and competence.

That’s the short version. I help people make sense of stuff. Untangling, revealing, translating, recalibrating—those kinds of things.

My longer, more official-sounding bio below basically says the same thing, but with more detail:

Derek MacDonald is a writer and systems consultant who’s spent 15+ years building resilient communication strategies and enablement teams. He’s the founder of Unobstructed, a literary publication committed to elevating emotional clarity and personal agency. Derek credits his formative years as a wilderness guide and snowboard instructor with showing him that authentic storytelling is what best helps people navigate fear and uncertainty. This eventually led him to compete in The Moth’s StorySLAM competitions and to be featured on GBH’s Stories From The Stage.

Throughout his career, Derek’s been passionate about working with both students and organizations alike to help them better understand the crossover between systems thinking, outdoor education, and proactive mental health. In 2026, he was recognized as Massachusetts HOBY’s Volunteer of The Year, for his help facilitating annual workshops on leadership development, which he’s been doing with them since 2010.

Derek lives in Burlington, Vermont, where he likes building websites, running, and getting lost in a good book with a strong cup of coffee. You can learn more about Derek, his writing, and his podcast at derekmacdonald.com.


My work.

I design strategies and learning environments that people trust.

Doing that well comes from developing repeatable frameworks to protect strategy, decision-making, and processes as things change (because they always do). So I like to find and prioritize the most effective puzzle pieces in a given situation to create leverage.

I’ve found it also makes things more efficient along the way.

Some of that looks like shaping:

  • Content systems & publishing governance.
  • Editorial direction & voice alignment.
  • Long-form narrative strategy.
  • Audience trust & retention.

You can view my detailed background (also pronounced ré·su·mé) here.


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onward.

Me & my work.

As both a writer and systems consultant, I help people create clarity, trust, and competence.

Find out more about me and my work.


Stay connected.

Sometimes a different way of seeing things is all it takes to get unstuck.

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Explore more of my work.

-> Daily column.

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-> Podcast.

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-> Blog.

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Features & favorites.

An Overview Of Everything I Publish

Check out my daily columns, essays, and podcast episodes.

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The Most Popular Essay I Wrote In 2025

“What Lonely Men Won’t Say Online (Or In Person)”

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Praise For The Unobstructed Podcast

A top 10% most-shared show on Spotify in its first year.

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