The Worst Road Trip Ever, A Relentless Grandma, and A Baseball Star Who Couldn't Let Go | Ep. 86 | Wyatt Matters
Podcasts > Wyatt Matters
Sunday, June 21, 2026
"Never quit."
It's one of the most popular pieces of advice you'll ever hear.
This week, Wyatt Matters asks whether that's always true.
From a wildly impractical road trip across Africa to a woman who spent years chasing a driver's license she probably shouldn't have received, the crew explores stories of determination that crossed into something else entirely.
Then the focus turns to former MLB star Curt Schilling, whose legendary competitiveness fueled both incredible success and painful failure. His journey becomes a powerful example of what can happen when one goal consumes everything else.
Through humor, stories, and practical wisdom, Steve challenges one of our culture's favorite assumptions: sometimes quitting isn't weakness. Sometimes it's wisdom.
Because one of the fastest ways to nuke your own life is refusing to let go of something that should have ended a long time ago.
🎙️ This week’s co-hosts:
John Samples – https://www.jsam.com/ & https://www.youtube.com/jsamtv
Bruce Templeton – https://www.instagram.com/coltoncross
Kimberlee Herman – https://www.promisehillpodcast.com/ & https://www.redeemedhopeaz.com/
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