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Why'd You Think You Could Do That?
Sam Penny
39 episodes
2 weeks 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
Finding Meaning in Failure
Why'd You Think You Could Do That?
6 minutes
1 month ago
Finding Meaning in Failure

Twice he set out to row the Atlantic. Twice he failed. One attempt ended in humiliation, splashed across newspapers as “Captain Calamity.” The other haunted him for years as he questioned whether he was really an adventurer — or just a pretender.

But failure didn’t end Mark Agnew’s story. It gave it meaning.

In this Spark → Struggle → Breakthrough episode, we break down the pivotal moments in Mark’s journey: the spark that pushed him into adventure, the struggles that almost crushed him, and the breakthrough that redefined what resilience really means.

👉 Explore more about Mark at sampenny.com/mark-agnew

🔑 Key Takeaways

  • Spark: Adventure begins with a small invitation, a spark of curiosity.
  • Struggle: Failure doesn’t just stop you — it questions who you are.
  • Breakthrough: True resilience isn’t about being tough. It’s about reframing failure into meaning.

✍️ Try It Yourself

Follow the same arc Mark lived through with these prompts:

  • Spark: I want to… I am going to…
    Example: I want to write a book that inspires others. I am going to draft the first chapter this weekend.
  • Struggle: I am afraid that…
    Example: I am afraid that if I share my writing, people will think it’s terrible and I’ll be embarrassed.
  • Breakthrough: Even though I am afraid of… I will… anyway.
    Example: Even though I am afraid of being judged, I will finish my draft and send it to a friend anyway.

Closing

Mark’s story shows us that failure doesn’t define us — it refines us.

👉 Hear his full interview on Thursday at sampenny.com/mark-agnew
.
👉 And if you’re ready to tackle your own Spark → Struggle → Breakthrough with me directly, learn more about my 1:1 coaching at sampenny.com/action

If this episode resonated, hit subscribe so you never miss the next story of someone saying yes to the impossible.

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.