Derek MacDonald

Writer.
Storyteller.
Software simplifier.

Former outdoor educator working in
sales, marketing, and enablement tech.

find out more.

explore my work.

_{Cover photo by Derek MacDonald}

Hey, I’m Derek.

For over 15 years, I’ve been helping people and brands create systems for learning new things.

Sometimes that looks like closing the gap between what gets said and what gets heard. Other times, it’s about designing a more intuitive user experience for sales and marketing software. Done well, my work helps people know where to go, what to do, and how to find the things they need along the way.

While I’m a definitely a “systems person,” I’m also a storyteller.

I love writing my daily column, essays, and monthly newsletters. I also like building websites, running, and getting lost in a good book with a strong cup of coffee. Oh, and working on my podcast. I like that a lot, too.

Thanks for being here!

Have a look around; learn a bit about me and feel free to get in touch with any questions, comments, concerns, or fun facts.

onward.

Explore my writing.

I write narrative nonfiction stories on identity, creativity, relationships, work, and adventure. Writing real stories—in ways that bring people into an experience—does something that instructions and frameworks just simply can’t: help people metabolize what they consume.

I try to make it so folks can picture what it’s like to see and care about the dots before they get connected.

-> Daily Column.

365 Days In A Row
August 31, 2026
Now that it's here, it sort of just feels like any other day.
August's Monthly Dispatch From Unobstructed
August 31, 2026
Make it real first, make it make sense later.While this adage doesn’t apply to everything […]
Huh, That's New
August 30, 2026
"Just the coffee?"