Why'd You Think You Could Do That?

Welcome back to Why’d You Think You Could Do That? and another Bravery Digest — your weekly shot of courage with Sam Penny.
In this episode, Sam unpacks a powerful idea: Discomfort Debt. It’s the hidden cost you pay every time you avoid a bold move, delay a hard decision, or put off the conversation you know you need to have.
Avoidance feels easier in the moment — like buying peace on a credit card. But the interest compounds. That weight shows up later as stress, second-guessing, and fatigue that doesn’t make sense.
You’ll learn:
  • Why discomfort never disappears just because you ignore it.
  • How avoidance drains your energy, focus, and confidence.
  • The simple way to start “paying down” discomfort debt today.
And stick around for the end — Sam reveals this Thursday’s guest: Erden Eruç, the first person in history to circumnavigate the globe entirely by human power. He’s rowed oceans, cycled continents, and climbed mountains - all without an engine. If you’ve ever thought your dream was too big, too far, or too impossible, this conversation will change that.
Take the step. Stop paying interest on avoidance.

Want to work 1:1 with Sam?
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Creators and Guests

Host
Sam Penny
Sam Penny is an adventurer, entrepreneur, and keynote speaker who lives by the mantra “Say YES! to the Impossible.” From swimming the English Channel in winter to building and selling multi-million-dollar companies, Sam thrives on pushing boundaries in both business and life. As host of Why’d You Think You Could Do That?, he sits down with ordinary people who have done extraordinary things, uncovering the mindset, resilience, and bold decisions that made it possible — and showing listeners why their own impossible is closer than they think.

What is 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.

Sam Penny (00:00)
Welcome back to Why Do Think You Could Do That and another Bravery Digest, your weekly shot of courage. I'm Sam Penny and today I want to talk about something I call the discomfort debt. It's the hidden costs we all pay when we avoid the brave move we know we need to make. Think about it. Every time you hold back from a conversation you need to have, every time you avoid making that decision you know is overdue, every time you tell yourself you'll deal with it later,

You're not dodging discomfort. You're just putting it on a credit card and that interest compounds. At first, it feels easier. You breathe out, you convince yourself you've bought some peace, but underneath the weight is building. That email you didn't send, that call you didn't make, that step you were too scared to take.

They start circling in your mind, they drain your energy, your focus and your confidence. That's what discomfort debt feels like. It's not the sharp sting of bravery. It's the slow leak of avoidance. And the longer you carry it, the heavier it gets. And here's the truth. Discomfort doesn't disappear just because you ignore it. It grows, it gets louder, it comes back with interest. And that interest shows up as stress, as second guessing.

as fatigue that you can't quite explain. So how do you start paying it down? Well, you stop running. You turn around and you face the thing you've been avoiding. Not all of it at once, just one step. You make the call, you set the boundary, you take the action you've been kicking down the road. It doesn't have to be perfect. It just has to be brave enough to sting. And when you do that, something

powerful happens. The weight begins to lift. The energy you are losing starts to return. And suddenly the next brave step doesn't feel so impossible anymore. So let me leave you with this. What's the thing you've been putting off? The thing that's quietly eating at you because you haven't dealt with it. Today is the day to stop paying interest. Today is the day to take

the step. This is your bravery digest. It's short, sharp and actionable. And before I go, make sure you don't miss this Thursday's full episode. I'm sitting down with Erden Eruch, the first person in history to circumnavigate the globe entirely by human power. He's rowed across oceans, cycled continents and climbed mountains, all without an engine, all powered by his own body.

If you've ever thought your goal was too big, too far, too impossible, this conversation will change that. Don't miss it.