Writer.
Storyteller.
Software simplifier.
Former outdoor educator working in
sales, marketing, and enablement tech.
Cover photo by Derek MacDonald
Contact.
By email.
By physical mail.
Derek MacDonald
PO Box 4292
Burlington, VT 05406
And, as always, the best way to stay connected to what I’m up to is by subscribe to my newsletter.
onward.
Me & my work.
I use stories and systems to help people create clarity, trust, and competence.
Find out more.
Stay connected.
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Explore my writing.
-> Daily Column.
- I think time travel might be real.
- I was just happy I made it back before dark.
- This is unequivocally the wrong venue.
Read more from the daily column.
-> Essays.
- No one else will do it for you.
- Especially when it's hard to hear.
- Look, we all make bad decisions when we're scared… ok?
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-> Podcast.
Browse more episodes.
-> Monthly Dispatch.
- 365 days of writing, resetting, and feeding two birds with one scone.
- Itching for an overhaul.
- There's more than one reason to celebrate!
Read more from the monthly dispatch.
-> 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.
Read more from the blog.
Features & favorites.
An Overview Of Everything I Publish
Check out my daily column, essays, and podcast episodes.
Read more.
The Most Popular Essay I Wrote In 2025
“What Lonely Men Won’t Say Online (Or In Person)”
Read more.
Praise For The Unobstructed Podcast
A top 10% most-shared show on Spotify in its first year.
Read more.
Subscribe to my newsletter.
Sign up to get my monthly newsletter on rethinking how you move through the world.