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
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👉 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.

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)
it's the word we spend our whole lives trying to avoid. At school, failure is circled in a red pen. At work, failure costs us promotions, reputations, even livelihoods. In life, failure can feel like proof

that we're not enough. But here's the truth. Failure is not the end of the story. Failure is what gives the story meaning. Mark Agnew knows this better than most. He tried to row across the Atlantic twice. The first time, his crew had to be rescued within 48 hours. The press mocked them as Captain Calamity's crew. The second time, he made the decision to step off the boat. Rational, yes. But to him, it felt like quitting.

For years that failure haunted him and yet it was failure that taught him the real meaning of resilience. And it was failure that set the stage for his greatest achievement, Becoming the first person to kayak the Northwest passage. I'm Sam Penny and this is why do you think you could do Every adventure begins with a spark.

And sparks often look so small, so ordinary that we don't recognize them until later. For Mark, it was a message from a university friend, a video of people rowing the Atlantic. Three simple words, let's do this. That was it. No master plan, no step-by-step roadmap, just curiosity, excitement, and the willingness to say yes. History is full of sparks like this.

The Wright brothers sketching their first flying machine. Edmund Hillary looking up at Everest. Rosa Parks refusing to give up her seat. The spark is never the guarantee of success. It's the invitation to possibility. And now it's your turn. Complete this sentence. I want to, and then I'm going to. And here's an example. I'm going to write a book that inspires others. I'm going to draft the first chapter this weekend.

because sparks mean nothing until you act on them. But sparks collide with reality and reality can be brutal. Mark's first Atlantic attempt, it was a disaster. 10 people crammed on a flimsy catamaran, water pouring through hatches sealed with pool noodles. Within 48 hours, the boat was gone and the dream was over. The tabloids laughed, the headlines mocked. Imagine it,

You set out to achieve something extraordinary and instead you become a national joke. but the second attempt cut even deeper. This time it was just two people. No chaos, no circus, just raw endurance until fatigue and storms and broken equipment forced Mark to make a call. He stepped off the boat, rational, sensible, logical. But in his heart, it felt like

quitting and that decision ate at him for years. Every time he saw a headline about another Atlantic crossing, the wound reopened. Every story whispered, you failed. You're not enough. You don't belong. This is what failure does. It doesn't just stop you. It defines you if you let it. And now I want you to try complete this sentence. I'm afraid that

Here's an example. I'm afraid that if I share my writing, people will think it's terrible and I'll be embarrassed. You see how it builds? You wanted to write the book, but now the fear shows up, the fear of failure, of judgment, of being exposed. That's the struggle. Mark's breakthrough didn't come from success. It came from failure, through reflection. And with the help of psychologists, he began to see that he had been chasing the wrong things.

titles, records, validation, and he realized something profound. Resilience isn't about being the toughest. If you're too tough to adapt, too tough to laugh at yourself, too tough to lean on others, you're not resilient at all. True resilience is about carrying your fear with you, about finding joy in uncertainty, about redefining failure as part of the story, not the end of it. History shows the same truth.

Shackleton's men didn't survive the ice because they were the toughest. they survived because they adapted, because they kept laughing, because they held each other up. Nelson Mandela didn't endure 27 years in prison by proving he was unbreakable. He endured because he found meaning in struggle. Mark rediscovered adventure in Hong Kong's stormy seas, kayaking into uncertainty.

and learning to delight in it. So when the chance came, last minute, to attempt the Northwest Passage, he was ready. Over 103 days he and his team battled storms, hunger, ice, and polar bears. They became the first to kayak the passage, two world records, but the real breakthrough wasn't the record. It was the realization that fear had always been his greatest teacher.

And now it's your turn, complete this sentence. Even though I'm afraid of, and then this one, I will anyway. And here's an example. Even though I'm afraid of being judged, I will finish my draft and send it to a friend anyway. Do you see how this connects? First the spark, I want to write a book, then the struggle. I'm afraid that people will hate it. And now the breakthrough.

Even though I'm afraid I will finish it and share it anyway. That's what it means to find meaning in failure. It doesn't erase fear. It transforms it into fuel. And that was Mark Agnew's spark, his struggle and breakthrough, a story of failure, resilience and redemption. On Thursday, you'll hear the full interview, the storms, the polar bears and the mindset shift that turned his biggest failures into his greatest meaning.

And on Friday, I'll break down the lessons you can take into your own life. If this episode struck a chord, don't just walk away, hit subscribe or follow right now, because the next story might be the spark you need. I'm Sam Penny, and this is Why Do Think You Could Do That? And remember, failure isn't the end. It's where meaning begins.