Former wilderness guide.
Software simplifier.
Storyteller.
Helping people navigate complexity.
Cover photo by Derek MacDonald
Contact.
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Derek MacDonald
PO Box 4292
Burlington, VT 05406
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onward.
Me & my work.
I use stories and systems to help people create clarity, trust, and competence.
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-> Daily column.
- I thought it might be sore but I didn't expect it to hurt.
- I don't know why I never thought of it like that.
- Trying to stay in-the-loop perpetually leaves me feeling exhausted and worse off.
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-> Newsletter.
- The amount of things we take on is just… totally unrealistic, right?
- What I finally discovered about being understood.
- The choice between holding on and letting go.
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-> Podcast.
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-> Blog.
- Discerning what to share and where to share it.
- Discerning what to share and where to share it.
- Discerning what to share and where to share it.
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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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