Saying YES to the Impossible, Doing Batshit Crazy Things, and Also Knowing When Enough is Enough

06/01/2026 22 min Episodio 50

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Episode Synopsis

I didn’t expect this episode to go where it did. On paper, Sam Penny looks fearless. TEDx speaker. Business exits. Ice miles.But halfway through our conversation, he said something that made me think.Cold water. Dark morning. No one had ever done this before. Swimming the English Channel IN WINTER!A few hours in he decided he needed to stop and go back to shore. Not because he was weak. But because he listened to his team and his body(hypothermia).He talked about the weight of that decision. Going back to his room. And feeling that decision.The crazy cool thing is that support poured in. From strangers. From people who had never met him. From people who understood that trying matters more than finishing and that failure doesn't exist when you learn a lesson from it. This isn’t a story about conquering fear.It is about naming it. Living with it. And realizing that failure doesn’t isolate or demote you the way your mind tells you it will.Sam shared what it’s really like to:• Feel imposter syndrome before a TEDx talk• Train for things that genuinely risk your life• Step away before the finish line and still stand proud• Learn that people don’t judge effort. They actually rally around itAt the end of the episode, I asked him the question I ask every guest.What’s the opposite of fear? His answer came without hesitation.Start.If you’ve been holding back because you’re afraid of failing, being judged, or not finishing strong…This episode might shift something for you.

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