An untethered educator teaching about shit that actually matters. Writing for people ready to stop escaping their life and start building one that's actually theirs. Still figuring my shit out and learning out loud as I go.
| Platform |  | Pricing | Only free issues | Publishes | Weekly |
|---|---|---|---|---|---|
| Issues | 36 | Founded | 2 years ago | Last Issue | 3 days ago |
| Active | |||||
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iamryanhennessey.substack.comLatest Issues
Make That Shit GOLDEN
The older I get, the more I crave a certain kind of exhaustion.
Not the soul-sucking kind.
The kind that leaves my hands aching, my body worn down,
and my soul fucking alive.
When I was a teacher, I exhausted my colleagues because I...
Getting High on Becoming
We all have moments that define us. Moments seared into our memories as inflection points beyond which our lives were never the same.
There is a particular flavor of grief that accompanies these moments—the death of a dream, the loss of id...
Thank You. Fuck You. (A Year Later)
A year ago, I wrote the most-read thing I’ve ever put on the internet. This week, I needed it again.
A few days ago, I listened on the phone while a close friend told me he and his wife are ending a nearly 30-year relationship. It stirred...
Microdosing Friction
Came across this photo the other day. Taken twenty years ago in Alaska, when we used to hike to the creek for water, heat it on the stove, and hang the can from the ceiling to shower. Twenty years later, I’m back to hauling water.
We try...
Stubborn with the Dream, Flexible with the Plan
So a funny thing happened. I wrote this post a week ago, feeling awesome about actually working ahead for once… and then the next right thing changed. Quite drastically. So here I am, up late the night before my self-imposed deadline, rewri...
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Authors
The writers behind this newsletter.
We need more well-intentioned rule breakers. I write for people ready to ditch autopilot—leaving jobs, relationships, lives that don’t fit. Former teacher, father, recovering people-pleaser.
I turn stories into strategy and vulnerability into a leadership superpower. Helping SMB Owners speak with power, presence, and purpose. Keynote Speaker | TEDx Coach | Linkedin 75K | Twitter 465k | Instagram: 43k Followers
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