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.
- Update frequency
- every 2 days
- Average duration
- 27 minutes
- Episodes
- 21
- Years Active
- 2025
Spark: Chipping Away at the Impossible with Aaron Linsdau
Most people will never step foot in Antarctica. Even fewer will ski across it. Almost no one will spend longer alone on that continent than Aaron Linsdau. For 82 days, it was just one man, two sleds,…
The Power of One Step: How Small Actions Spark Big Change
Making a difference doesn’t always mean changing the whole world overnight - it begins with one undeniable step.
In this short, powerful episode of Why’d You Think You Could Do That?, Sam Penny takes …
The Human Swan: Sacha Dench’s Impossible 7,000km Flight
What does it take to face your deepest fear, strap a propeller to your back, and follow swans 7,000 kilometres from the Russian Arctic all the way to the wetlands of Britain?
In this inspiring episode…
Turn Fear Into Your Superpower
What if the very thing holding you back could become the force that carries you forward?
For Sacha Dench, fear of flying nearly stopped her in her tracks. A storm in a small plane left her terrified o…
Facing Fear: The Key to Making a Difference
In this episode of "Why'd You Think You Could Do That?", host Sam Penny explores the power of confronting fears to unlock potential. Discover how Sacha Dench transformed her fear of flying into a bol…
One Spark Can Shift the World
Most people see a bird fly overhead and think nothing of it. But Sacha Dench saw swans migrating thousands of kilometres and asked herself: What if I could fly with them?
That one wild idea led to an …
Rowing Into the Impossible: Erden Eruc’s 5-Year Journey Around the World
What makes someone believe they can row across oceans, cycle across continents, and spend more than five years completing the first solo human-powered circumnavigation of the planet?
In this episode o…
Why Avoiding Hard Choices Makes Life Tougher!
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 hidd…
More than a Man with a Mower: How Jim Penman is Trying to Change The World
When you hear the name Jim’s Mowing, you probably think of the trailers, the uniforms, and the empire of small business owners mowing lawns across Australia. But behind the mower is a man whose true …
Stop Waiting for Permission!
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 fe…
What Broke Him, Built Him: Paul Watkins on being an Ordinary Guy with Unordinary Grit
What if the bravest thing you ever did wasn’t crossing a finish line, but starting again after falling short the first time?
In this gripping episode, Sam Penny sits down with Paul Watkins, pharmacist…
Fear to Fuel: How to Move Anyway (Even When It’s Hard)
🧠 What You’ll Hear in This Episode
In this short solo drop, host Sam Penny flips the script on fear.
We all feel it—whether you're leading a business, standing on the edge of a bold new move, or simply…
"I was in Agony!": Brianna Thompson’s Double Channel Crossing at just 17
What were you doing at 17?
Brianna Thompson was swimming the English Channel; not once, but twice, in one go. In this epic episode of Why’d You Think You Could Do That?, Sam Penny sits down with the s…
Courage or Comfort: Which One’s Leading You?
In today’s Bravery Digest, Sam Penny throws down the gauntlet: Are you leading your life from courage, or coasting in your comfort zone?
This isn’t just another motivational pep talk. Sam introduces t…
“I Was Going to Die”: Lisa Blair on Facing Fear, Fighting for Survival, and Breaking Records
What do you do when your mast snaps in the middle of the Southern Ocean, 1,000 miles from land, no engine, no sails, no rescue on the way? You fight. You survive. And then you go back and finish what…
Fast Decisions Beat Fear
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 tak…
“Life Isn’t a Dress Rehearsal”: Gerrard Gosens on Living Like He Means It
Episode Summary
Gerrard Gosens has never seen the path ahead — literally. Born completely blind, Gerrard has defied every limitation the world tried to place on him. In this episode, Sam Penny dives …
You Don’t Need More Motivation - You Need a Braver Environment
Most people wait to “feel” brave. But what if that’s the wrong game entirely?
In this Bravery Digest, Sam Penny breaks down why you don’t rise to the level of your motivation — you fall to the level o…
The Man Who Destroys People For Fun: Inside the Mind of Lazarus Lake
This Man Destroys People for Fun | Lazarus Lake on Endurance, Suffering & Why Most People Quit
📝 Episode Description / Show Notes:
In this episode, Sam Penny sits down with the legendary Lazarus Lake—…
Build Your Brave: The 90-Second Habit That Changes Everything
Welcome to the Bravery Digest — your weekly 3-minute mindset reset from Why’d You Think You Could Do That?
In this first mini-episode, host Sam Penny reveals one of the most powerful habits for steppi…