Derek MacDonald

About me.

My bio.

I create stories and build software systems that people trust.

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

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

Derek MacDonald is the founder and head of editorial for Unobstructed, a literary publication exploring the small, but meaningful, moments that prompt people to rethink how they move through the world. He writes stories about pivots, patterns, and new perspectives in his daily column, Kickturn, and chats about navigating daily life with more agency and clarity as the host of The Unobstructed Podcast.

As a speaker, Derek’s been featured on GBH’s Stories From The Stage and regularly competes in The Moth’s StorySLAM competitions. He also talks to students and organizations about the crossover between outdoor education, emotional literacy, and proactive mental health. In 2026, he was recognized as HOBY’s Volunteer of The Year, for his help facilitating workshops on leadership development, which he’s done for over 15 years.

Throughout his career, Derek also worked as a wilderness guide, operations manager, and enablement director. He lives in Burlington, Vermont, where he like to go trail running, build websites, and get lost in a Fredrik Backman novel with a strong cup of coffee.

Learn more at derekmacdonald.com

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My work.

I make sure messaging and values match, and that they stay consistent across teams and platforms.

Doing that well comes from developing repeatable frameworks to protect strategy, decision-making, and publishing 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.

Doing that, I’ve found, 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.

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My background.

Writing is how I make sense of the world and my place in it.

When I created Unobstructed as a built-in-public multimedia platform, it was to show what it’s like to design and evolve an editorial system that prioritizes clarity, voice, and trust. Formative years spent as a wilderness guide and snowboard instructor showed me that stories—not explanations—are what help people navigate fear and uncertainty. That shaped my 15+ year journey through editorial strategy, content operations, and organizational alignment in a pretty major way.

Now, I’m proud to do work that supports billion-dollar organizations, lean teams, and global audiences across 37+ countries. I believe that has a lot to do with chasing a dream through the Rocky Mountain West as a kid from New England, and then finding a home, and myself, in Vermont years later.

Thanks for being here. The best way to stay connected is to subscribe to my newsletter.

Or, to get in touch, you can contact me here.

onward.