All Episodes
Episodes
Ep 170 What if you already have enough?
Where are you chasing more when you might already have enough? This episode explores how to rethink ambition, success, money, freedom, and purpose through the surprising story of George Washington choosing to walk...
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Ep 169 What If You Decided It Was Possible?
What if the thing you’re dreaming about feels unlikely—even impossible—but you decided to go for it anyway?
We celebrate American independence on the day it was declared, long before anyone knew whether that...
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Ep 168 The Odyssey - It's not about the destination
What The Odyssey, the Striver’s Curse, and sailing can teach us about being present in the journey without losing sight of where we're going.
Christopher Nolan’s The Odyssey has us thinking about an ancient story...
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Ep 167 Can You Really Learn to Sail on Vacation? We Tried It in Croatia.
Can you really learn to sail on vacation? Our beginner sailing trip in Croatia put it to the test—with first-time sailors learning to sail, explore, and work as a crew.
On our latest Awesome Factory sailing trip, our...
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Ep 166 Beginner Sailing Trips in Greece: Highlights from Athens and Corfu
Learn to sail on vacation? Yes. In Greece. We're reporting from our most recent back-to-back sailing trips in Greece. Our first group of beginner sailors sailed out of Athens and explored the archipelago known as the...
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Ep 165 Sailing Adventures Build Belonging
Discover why sailing together is such a powerful setting for you to feel that you matter. We'll start with Jennifer Breheny Wallace's new book, Mattering: The Secret to a Life of Deep Connection and Purpose. We'll end...
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Ep 164 Travel Like a Beginner: The Curiosity Advantage - Lessons from Finland
What if being a beginner is actually an advantage? This summer in Finland, we've discovered how approaching travel with curiosity—rather than trying to know exactly what we're doing—can lead to better adventures,...
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Ep 163 The Hidden Cost of Playing it Safe
What if you've mistaken fear for wisdom? At what point did being "responsible" start meaning you stopped choosing joy? In this episode, we explore the surprising "hassle factor" that stands between you and the life...
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Ep 162 How to Stop Overthinking Your Next Sailing Trip
Have you ever felt like one forgotten detail could ruin the vacation you've been dreaming about for months? When time off is precious and travel is a big investment, it's easy to let the pressure of getting everything...
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Ep 161 Why Greece Is Perfect for Your First Sailing Trip
The Saronic Islands are of the best regions for a first sailing trip. Discover what makes Greek sailing unique—from calm waters and hidden coves to incredible food, rich history, and beginner-friendly routes. If...
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Ep 160 From Tourist to Contributor: A New Way to Experience Travel with Christopher Hill
This episode explores how meaningful travel—from sailing trips to impact-driven experiences—can transform not just the places you visit, but who you become.
Meet Christopher Hill, founder of Hands Up Holidays, who...
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Ep 159 Why Sailing Trips Are the Ultimate Reset (Backed by Science)
What if the reset you’ve been craving isn’t a life overhaul—but time on the water? In this episode, we explore the science behind why sailing trips reduce stress, improve sleep, and help you feel like yourself again....
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