
In this episode, I answer the question: What’s the most dramatic way to ruin your own life for 24 hours?
Welcome to The Between Stories—a series where I take you into moments from my life that shaped the themes we explore in the main episodes.
For anyone who’s ever:
Hit "reply all" on something you shouldn’t have.
Been that person in a group text.
Woken up in cold sweat remembering something dumb you did in 2012
In this episode, I tell the story of my top-five most shameful life moments. It starts with a new smartwatch, a few misplaced button clicks in my backpack during an ice climb, and an SOS signal I didn't know I had sent. It ends with a full-scale search and rescue operation—while I was, completely obliviously, having the time of my life.
For a long time, I carried this story as proof that I was a burden—irresponsible, dramatic, the world’s most expensive inconvenience. But when I finally dared to tell it out loud, the shame I expected was met with something else entirely: laughter. The kind of laughter that cracks a story open and turns it into absurdity, connection, and relief.
This is the companion to our last episode with Brad Jenkins about using humor as a strategy—not just for persuasion, but for survival—and how the Obama White House used it to save the Affordable Care Act.
It’s a look at how humor isn’t just for coping—it’s one of the most powerful tools we have for connection, forgiveness, and even large-scale change.
Sometimes the only way out of our own shame is to find the punchline.
There’s more ahead. There always is.
— Molly
I used to carry this story as proof that I was a burden—until I told it out loud and people cried laughing.
This is the story about becoming the world's most expensive inconvenience.
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“That’s when I realized: humor doesn’t erase shame, but it can crack it open just enough to let something better in.”
— Molly, Ep. 9