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Reader supported stories, essays, and conversations about rethinking how you move through the world. Helping people navigate daily life with more agency by revealing things, not prescribing them.

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Substack
PricingOnly free issuesPublishesWeekly
Issues159Founded2 years agoLast Issue18 days ago
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Latest Issues

September's Monthly Dispatch From Unobstructed

I think connection might be overrated.

Maybe.

I’m not saying it’s always a bad thing, but I am saying that it’s not always a good thing. Know what I mean? I guess it sort of depends on what it costs you.

First off, connecting with someo...

18 days ago
3

Loneliness Isn’t ‘Male,’ So What’s The Problem?

Why does the conversation about the male loneliness epidemic completely skip over the part where experiencing loneliness has nothing to do with, well… being male?

In fact, I don’t think loneliness is even the actual problem.

A byproduct,...

20 days ago
1

Maybe Time Travel Really Is The Answer To Being Human

Photo of Ava by Derek MacDonald

Long before there was social media, smartphones, or AI, it seems like people more or less had this “being human” thing figured out.

Simultaneously, I’m seeing a rise in notebooks, typewriters, websites, blo...

a month ago
4
2

August's Monthly Dispatch From Unobstructed

Resources and results from The MAP Year Project

Make it real first, make it make sense later.

While this adage doesn’t apply to everything in life, it applies to much of what I’ve uncovered throughout the past year.

Going from August to...

2 months ago
2

You’re Right To Push Back On That

I heard they have a new pill for treating skepticism.

I’m not buying it…

Hey, I’m Caleb. Welcome—or welcome back—to my monthly column, Breaking Trail, where we kick things off with a dad joke. Just like this, just because.


a month...

2 months ago
3

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Authors

The writers behind this newsletter.

  • Derek MacDonald

    Former outdoor educator working in tech. Exploring identity, creativity, relationships, work, and adventure through narrative nonfiction.

  • Michaela Kellogg

    Redesigning grief. Because death deserves a little more life.

  • Caleb Walker

    Dad jokes, deep cuts and diatribes.

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