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Why'd You Think You Could Do That?
Sam Penny
39 episodes
1 day ago
They’ve swum oceans, scaled mountains, launched empires, and shattered expectations. But before they did any of it, someone, maybe even themselves, thought: “You can’t do that.” Hosted by Sam Penny, Why’d You Think You Could Do That? dives into the minds of people who said “screw it” and went for it anyway. From adventurers and elite athletes to wildcard entrepreneurs and creative renegades, each episode unpacks the one question they all have in common: “Why'd you think you could do that?” If you’re wired for more, haunted by big ideas, or just sick of playing it safe, this is your show.
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Self-Improvement
Personal Journals,
Education,
Society & Culture
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They’ve swum oceans, scaled mountains, launched empires, and shattered expectations. But before they did any of it, someone, maybe even themselves, thought: “You can’t do that.” Hosted by Sam Penny, Why’d You Think You Could Do That? dives into the minds of people who said “screw it” and went for it anyway. From adventurers and elite athletes to wildcard entrepreneurs and creative renegades, each episode unpacks the one question they all have in common: “Why'd you think you could do that?” If you’re wired for more, haunted by big ideas, or just sick of playing it safe, this is your show.
Show more...
Self-Improvement
Personal Journals,
Education,
Society & Culture
https://is1-ssl.mzstatic.com/image/thumb/Podcasts221/v4/10/2b/eb/102beb6b-b39d-d303-4488-987c9bbe68d6/mza_10102112814905434969.jpg/600x600bb.jpg
Speak the Truth Anyway: Kathy Lette and the Courage to Laugh Through Fear
Why'd You Think You Could Do That?
5 minutes
1 month ago
Speak the Truth Anyway: Kathy Lette and the Courage to Laugh Through Fear

In this week’s Action episode of Why’d You Think You Could Do That?, host Sam Penny takes inspiration from one of the sharpest minds in modern feminism — Kathy Lette — the woman who turned outrage into comedy, sexism into satire, and shame into storytelling.


At just 17, Kathy co-wrote Puberty Blues, a book so raw and real it was banned from schools — but instead of backing down, she doubled down, using wit as her weapon and laughter as her form of protest. Across her career, she’s proved that humour can dismantle hypocrisy faster than fury ever could.

This episode is your invitation to take that same fearless approach and apply it in your own life. Because bravery doesn’t just happen in the extremes — it happens in everyday conversations, in workplaces, boardrooms, and dinner tables where the easy thing would be to stay silent.

Sam challenges you to complete one sentence:

“One thing I will do to make a difference…”

Maybe it’s calling out a double standard. Maybe it’s sharing your true opinion in a meeting. Or maybe it’s finally admitting what you really want. Whatever it is, say it — with honesty, with kindness, and, if you can, with humour.


Because as Kathy reminds us, laughter doesn’t diminish truth; it makes it digestible. It opens hearts that anger closes. And when you use it with courage, it turns confrontation into connection.


This is your week to speak up anyway — to say the thing that scares you most, to turn your own fear into fuel, and to be part of a ripple effect that starts with one brave conversation.

“The most powerful thing you can do this week isn’t to be perfect — it’s to be real.”

Tune in, take the challenge, and discover why sometimes, bravery doesn’t roar — it giggles, it winks, and it writes a banned book.

Why'd You Think You Could Do That?
They’ve swum oceans, scaled mountains, launched empires, and shattered expectations. But before they did any of it, someone, maybe even themselves, thought: “You can’t do that.” Hosted by Sam Penny, Why’d You Think You Could Do That? dives into the minds of people who said “screw it” and went for it anyway. From adventurers and elite athletes to wildcard entrepreneurs and creative renegades, each episode unpacks the one question they all have in common: “Why'd you think you could do that?” If you’re wired for more, haunted by big ideas, or just sick of playing it safe, this is your show.