Why'd You Think You Could Do That?

This week on the Bravery Digest, Sam Penny explores the real difference between people who move boldly and those who stay stuck: the speed of their decisions. Discover why acting before your fear takes hold is the single most powerful habit you can build, and get Sam’s practical “Two-Minute Rule” for making braver choices—starting now.
Key Takeaways:
  • Bravery isn’t about being fearless—it’s about acting before fear talks you out of it.
  • Most people get stuck not because they don’t know what to do, but because they wait for perfect conditions or permission from someone else.
  • Fear thrives on hesitation. The longer you wait, the louder your doubts get.
  • Sam’s Two-Minute Rule:
    When you’re faced with a decision, set a two-minute timer and make the call before the buzzer. Don’t overthink it—move before fear gets a grip.
  • Momentum and confidence don’t come from waiting; they come from action—even if you don’t feel ready.
  • Your challenge for the week: Identify one decision you’ve been sitting on, use the two-minute rule, and notice what changes.
Listen for:
  • Sam’s honest take on why most people let fear call the shots
  • The science behind why fast decisions kill hesitation
  • Practical tips for breaking the waiting habit in business and life
  • A challenge to the audience: Move now, reflect later
Special Guest Announcement:
Don’t miss this Thursday’s interview with Lisa Blair—record-breaking sailor, climate advocate, and world-class action-taker. Lisa’s story is all about staring down huge fears, taking fast action, and redefining what’s possible even when the odds are stacked and the seas are rough. If you need proof that courage is about moving before you’re ready, this is the episode to hear.

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 the Bravery Digest, your weekly shot of courage, clarity and action on the Why Do Think You Could Do That? podcast. I'm Sam Penny. Today I want to talk about something simple but incredibly powerful. It's the speed of your decisions. We love to believe that brave people don't feel fear or that they have some special confidence, Gene. But here's the reality. Bravery is rarely about feeling fearless. It's about acting before your fear gets a grip.

You see, most of us don't get stuck because we don't know what to do. We get stuck because we let fear talk us into waiting. We wait for the perfect moment. We wait for confidence. We wait for someone else to say, you're ready. But here's what I've learned in business and in life. Fear loves delay. It thrives on hesitation and second guessing. The longer you wait, the louder it gets. So this week's idea is pretty simple.

decide faster than your fear can talk you out of it. here's how I recommend you put it into practice. Next time you're facing a decision, set a two minute timer. Give yourself a hard deadline, 120 seconds, and make the call before the buzzer. Don't overthink it. Don't wait for the perfect conditions. Move before fear has time to build a case against you. So why does this work? Well,

It's because speed chokes off fear before it has oxygen to grow. You get momentum. You train yourself to move forward even when you're uncertain. And honestly, most of the progress I've seen in myself and in my clients comes from not having all the answers, but from moving while the fear is still talking. Of course, I'm not saying be reckless, but most people could afford to act much sooner and much bolder than they currently do. So ask yourself this.

What's one decision you've been sitting on this week? What if you stopped waiting for confidence and just made the call? That's your challenge for the week. Try it. Use the two minute rule. Then let me know how goes. Message me, leave a comment, or just take a quiet moment to notice the difference it makes. Now, if you want a real world masterclass in courageous decision making, don't miss this Thursday's interview.

I'm going to be sitting down with Lisa Blair. She's a record-breaking sailor, climate advocate, and one of the boldest action takers I know. You see, Lisa's story is all about facing huge fear, taking fast action and redefining what's possible,

odds are stacked against her and the seas are rough. So if you need proof that moving before you feel ready is how extraordinary things happen, tune in Thursday.

This has been your Bravery Digest. I'm Sam Penny reminding you that playing it safe never built anything worth building. See you Thursday.