All Episodes
Episodes
Ep 172 Beginner Sailing & the Surprising Benefits of Being New at Something
What if being a beginner again could make you more confident—not less?
Trying something unfamiliar can be uncomfortable. You don't know the rules, you don't know what you're doing, and suddenly even simple things...
View Episode
Ep 171 The Cold Water Principle: The Hardest Part is Getting In
What if the thing you’re avoiding isn’t actually as hard as you think? Sometimes the hardest part of trying something new is the few seconds before you begin. In Finland, Emily discovered this while swimming in a cold...
View Episode
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...
View Episode
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...
View Episode
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...
View Episode
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...
View Episode
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...
View Episode
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...
View Episode
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,...
View Episode
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...
View Episode
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...
View Episode
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...
View Episode
