Why'd You Think You Could Do That?

In this Bravery Digest, Sam Penny reminds us of a truth that stops far too many people from doing something extraordinary: you don’t need permission.
Most of us wait — for the right time, the right feeling, or someone else’s approval. But bravery isn’t about waiting. It’s about acting before you’re ready.
In this 2-minute burst of courage, you’ll discover:
  • Why waiting for permission keeps you stuck.
  • How action creates momentum, clarity, and confidence.
  • A simple reflection to push you into your next bold step.
And stick around until the end — Sam reveals this Thursday’s guest on Why’d You Think You Could Do That?: Jim Penman, the man behind Jim’s Mowing. You’ve seen the vans, you’ve seen the beard, but there’s far more to Jim’s story than you might think.
Take the step. Don’t wait for permission.

And don't forget: If you want to work 1:1 with Sam, he has a small number of coaching spots available. Head to sampenny.com/action

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 you think you could do that and another edition of the bravery digest your weekly injection of courage, clarity and action. I'm Sam Penny and today's quick bold idea is simple. But I tell you what really powerful. It's this you don't need permission to chase something extraordinary. Most of us don't stay stuck because we lack talent.

We stay stuck because we're waiting, waiting for the right moment, waiting for confidence, waiting for someone to tell us, now you're ready. But here's the truth. The bold ones, they don't wait. They move before it makes sense. They act before the path is clear and they start scared. When you take that first step, even without permission, three things happen. Firstly, momentum beats motivation. You move forward because you've already started. Second,

Clarity comes from action. The path reveals itself as you walk it. And finally, confidence is earned in the doing. your way into confidence. You build it by acting before you're ready. Bravery isn't about waiting for certainty. It's about choosing action in the face of discomfort. So here's your reminder this week. Stop waiting, stop asking, and take the step.

The only approval you ever truly need is your own. Let me leave you with this. What have you been waiting to feel ready for? Now flip it. What's one bold step you can take this week, even if it feels too early, too messy or too scary. That's your move. Take it. Now that's your bravery digest. It's fresh courage, served actionable. And before I go, make sure you don't miss this Thursday's full episode.

I'm sitting down with Jim Penman, the man behind one of the greatest brands in the southern hemisphere. You've seen Jim's mowing trailers, you've seen the beard, but there's far more to Jim than you might think his story, I tell you what, it's really going to surprise you. So hit follow and I'll see you Thursday.