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A friendly reminder that you're not as stuck as you thought you were. Stories, essays, and conversations about finding clarity and feeling less alone.

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PricingOnly free issuesPublishesWeekly
Issues147Founded2 years agoLast Issue6 days ago
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Latest Issues

June's Monthly Dispatch From Unobstructed

You find what you look for.

That’s something that’s stuck with me over the years. And since gratitude is a muscle that needs regular exercise like any other, finding an excuse to celebrate something is decidedly good for your health.

So i...

6 days ago
1

Another Level To Explore

Why did the gamer take a ladder to school?

They wanted to get to the next level.

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.

    • *...
11 days ago
2
2

Please Make Time For Keith And Charlie

Photo of Derek MacDonald and the 2026 HOBY junior staff team by Andres Tejeda.

When I was a kid, we lived in the suburbs of Boston and I dreamed of one day living a life of adventure far, far away from where I grew up. Gigantic mountain-sc...

21 days ago
5

Ok, This Is Getting Out Of Hand

Photo by Derek MacDonald

Trying to stay in-the-loop perpetually leaves me feeling exhausted and worse off.

In this age of instant information, we can’t possibly need to keep up with this many Joneses… I mean, how plugged-in are we really...

a month ago
5
2

May's Monthly Dispatch From Unobstructed

If you’ve ever asked yourself “why—WHY—did I say that??” after an especially awkward interaction, congrats—you’re in good company.

Thinking about my thinking is something I’ve done since I was little. Plenty of us do, to some extent, and i...

a month ago
1

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Authors

The writers behind this newsletter.

  • Derek MacDonald

    Storyteller and software simplifier. Former wilderness guide. Writing about systems thinking, emotional clarity, and feeling less stuck.

  • Caleb Walker

    Dad jokes, deep cuts and diatribes.

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