What Could Go Right?
by Erik Orton + Emily Orton
Latest episode
Ep 173 What Your Vacation Says About You (and Why Rest Matters)
Ep 173 What Your Vacation Says About You (and Why Rest Matters)
About this podcast
Living Boldly On and Off the Water
What if the life you want is waiting on the other side of one brave decision? On What Could Go Right? you’ll discover how to face fear, take meaningful risks, and step into deeper connection, adventure, and a more intentional life.
Hosted by lifelong explorers and the founders of The Awesome Factory, we don’t just talk about adventure — we practice it, inviting you into playful, guided sailing experiences around the world, where growth happens through laughter, learning, and shared moments of awe.
Each week, we’ll help you trade 'what could go wrong?' for a far more energizing question: What could go right?
Episodes
The newest 20 of 173 episodes
- Ep 173 What Your Vacation Says About You (and Why Rest Matters) · 17 minWhat does your vacation say about you? More than you might think. In this episode of What Could Go Right?, Erik and Emily Orton explore Arthur Brooks's observation that where you…
- Ep 172 Beginner Sailing & the Surprising Benefits of Being New at Something · 43 minWhat 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…
- Ep 171 The Cold Water Principle: The Hardest Part is Getting In · 17 minWhat 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…
- Ep 170 What if you already have enough? · 21 minWhere 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…
- Ep 169 What If You Decided It Was Possible? · 22 minWhat 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…
- Ep 168 The Odyssey - It's not about the destination · 31 minWhat 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…
- Ep 167 Can You Really Learn to Sail on Vacation? We Tried It in Croatia. · 23 minCan 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…
- Ep 166 Beginner Sailing Trips in Greece: Highlights from Athens and Corfu · 21 minLearn 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…
- Ep 165 Sailing Adventures Build Belonging · 24 minDiscover 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…
- Ep 164 Travel Like a Beginner: The Curiosity Advantage - Lessons from Finland · 33 minWhat 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…
- Ep 163 The Hidden Cost of Playing it Safe · 41 minWhat 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"…
- Ep 162 How to Stop Overthinking Your Next Sailing Trip · 31 minHave 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…
- Ep 161 Why Greece Is Perfect for Your First Sailing Trip · 32 minThe 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…
- Ep 160 From Tourist to Contributor: A New Way to Experience Travel with Christopher Hill · 43 minThis 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…
- Ep 159 Why Sailing Trips Are the Ultimate Reset (Backed by Science) · 30 minWhat 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…
- Ep 158 He Let a Beginner Sail a 47-Foot Boat – What Great Captains Know with Matt Holt · 52 minThe first time Erik took the helm of a 47-foot sailboat, he was heading straight for another boat. No panic. No yelling. Just a calm voice beside him: “Maybe turn a few degrees…
- Ep 157 Field-Tested Gear for Sailing Trips · 24 minIf you’re dreaming of sailing trips or planning your next adventure, discover the field-tested essentials that help you stay comfortable, protected, and ready for anything—plus…
- Ep 156 Milestones and New Beginnings · 23 minWhat if your biggest milestones are still ahead of you? In this episode of What Could Go Right?, we explore what happens after graduation, after the big life moments, and into…
- Ep 155 Sailing the Abacos for the First Time (And Why It Surprised Us) · 29 minWhat if your next vacation felt easier… calmer… and more beautiful than you expected? In this episode, you’ll get an inside look at what it’s really like to sail the Abacos in…
- Ep 154 Hidden Perks on our Sailing Trips (+ Travel Insurance, Learning to Sail, and Gear Favorites) · 18 minWhat if planning your adventure felt easier—and a lot more fun—than you expected? In this episode, we’re sharing a few “hidden perks” of our sailing trips to help you feel more…
