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What Could Go Right?: Daily Summaries Delivered
by Erik Orton + Emily Orton
Living Boldly On and Off the WaterWhat 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?
Latest Episodes
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- 4 days ago22 min
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 declaration would actually succeed. In this episode, you’ll hear how that idea played out in our own lives, including the unlikely beginning of our family’s year living aboard a sailboat. If you’re thinking about trying something new, starting an adventure, changing direction, or becoming someone you haven’t quite been yet, this is your reminder: you don’t have to know how it’s going to work before you begin. Sometimes the most important step is simply deciding—and putting that decision into words. ⭐⭐⭐⭐⭐ Rate. Review. Subscribe. Try Living on a Sailboat for a Week: No experience required—and yes, you’ll take the helm. Not a party charter. Not a certification course. A small-group, hands-on sailing experience that’s been called the “unicorn of sailing trips.” See if it’s your kind of adventure: Sail with us. Erik + Emily Memoirs: Seven at Sea: Why a New York City Family Cast Off Convention For A Life-Changing Year On A Sailboat Knock: The Spiritual Journey of a Door-to-Door Salesman Connect with Erik + Emily: Email Subscribe to Encouragement Youtube Like, Comment, Subscribe Instagram Facebook
- 1 weeks ago30 min
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 with a very modern problem: “I’ll be happy when I get there.” We explore the pull toward “what’s next” and what sailing can teach us about moving forward without missing where we are right now. ⭐⭐⭐⭐⭐ Rate. Review. Subscribe. Try Living on a Sailboat for a Week: No experience required—and yes, you’ll take the helm. Not a party charter. Not a certification course. A small-group, hands-on sailing experience that’s been called the “unicorn of sailing trips.” See if it’s your kind of adventure: Sail with us. Erik + Emily Memoirs: Seven at Sea: Why a New York City Family Cast Off Convention For A Life-Changing Year On A Sailboat Knock: The Spiritual Journey of a Door-to-Door Salesman Connect with Erik + Emily: Email Subscribe to Encouragement Youtube Like, Comment, Subscribe Instagram Facebook
- 2 weeks ago22 min
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 crew explored Croatia’s Dalmatian Coast while learning to sail along the way. They weren't just sightseeing. They were catching mooring balls, tacking, and putting their new skills to work—including during an unexpected man-overboard maneuver involving a six-foot cushion. We also share what we learned returning to Croatia for a second sailing experience, from new anchorages and better provisioning to finding a rhythm that made the trip even better. If you've ever wondered whether a first sailing trip could really teach you to sail—and whether you could do it—come along. ⭐⭐⭐⭐⭐ Rate. Review. Subscribe. Try Living on a Sailboat for a Week: No experience required—and yes, you’ll take the helm. Not a party charter. Not a certification course. A small-group, hands-on sailing experience that’s been called the “unicorn of sailing trips.” See if it’s your kind of adventure: Sail with us. Erik + Emily Memoirs: Seven at Sea: Why a New York City Family Cast Off Convention For A Life-Changing Year On A Sailboat Knock: The Spiritual Journey of a Door-to-Door Salesman Connect with Erik + Emily: Email Subscribe to Encouragement Youtube Like, Comment, Subscribe Instagram Facebook
- 3 weeks ago21 min
Ep 166 Beginner Sailing Trips in Greece: Report on 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 Saronic Islands. Our second group chose to get up close and personal with Corfu, part of the Ionian Islands, a chain of islands off the west coast of Greece in the Ionian Sea. All the history. All the culture. All the gelato. And... learned how to sail. ⭐⭐⭐⭐⭐ Rate. Review. Subscribe. Try Living on a Sailboat for a Week: No experience required—and yes, you’ll take the helm. Not a party charter. Not a certification course. A small-group, hands-on sailing experience that’s been called the “unicorn of sailing trips.” See if it’s your kind of adventure: Sail with us. Erik + Emily Memoirs: Seven at Sea: Why a New York City Family Cast Off Convention For A Life-Changing Year On A Sailboat Knock: The Spiritual Journey of a Door-to-Door Salesman Connect with Erik + Emily: Email Subscribe to Encouragement Youtube Like, Comment, Subscribe Instagram Facebook
- Aug 19, 202624 min
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 up chasing gray whales in Mexico and having peaches on French toast in Croatia. ⭐⭐⭐⭐⭐ Rate. Review. Subscribe. Try Living on a Sailboat for a Week: No experience required—and yes, you’ll take the helm. Not a party charter. Not a certification course. A small-group, hands-on sailing experience that’s been called the “unicorn of sailing trips.” See if it’s your kind of adventure: Sail with us. Erik + Emily Memoirs: Seven at Sea: Why a New York City Family Cast Off Convention For A Life-Changing Year On A Sailboat Knock: The Spiritual Journey of a Door-to-Door Salesman Connect with Erik + Emily: Email Subscribe to Encouragement Youtube Like, Comment, Subscribe Instagram Facebook
- Aug 12, 202632 min
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, unexpected surprises, and experiences we never would have planned. From cold lake swimming and Finnish sauna to learning the language and mistaking a plastic swan for the real thing, we're sharing what surprised us, what changed us, and what we're bringing home. We'll also talk about why this beginner mindset is at the heart of the sailing trips and adventure travel we love, from Naples, Athens, Split, and Corfu to the Lofoten Islands of Norway—and why being willing to try something new can make travel so much more rewarding. Come travel like a beginner with us: be curious, expect the unexpected, and let yourself be surprised. ⭐⭐⭐⭐⭐ Rate. Review. Subscribe. Try Living on a Sailboat for a Week: No experience required—and yes, you’ll take the helm. Not a party charter. Not a certification course. A small-group, hands-on sailing experience that’s been called the “unicorn of sailing trips.” See if it’s your kind of adventure: Sail with us. Erik + Emily Memoirs: Seven at Sea: Why a New York City Family Cast Off Convention For A Life-Changing Year On A Sailboat Knock: The Spiritual Journey of a Door-to-Door Salesman Connect with Erik + Emily: Email Subscribe to Encouragement Youtube Like, Comment, Subscribe Instagram Facebook
- Aug 5, 202640 min
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 you want—and why the very thing you've been avoiding might be the doorway to more delight, confidence, and connection than you expected. This isn't really about sailing or even Finland. It's about recognizing the stories that quietly keep your world small... and asking what might happen if you chose differently. ⭐⭐⭐⭐⭐ Rate. Review. Subscribe. Try Living on a Sailboat for a Week: No experience required—and yes, you’ll take the helm. Not a party charter. Not a certification course. A small-group, hands-on sailing experience that’s been called the “unicorn of sailing trips.” See if it’s your kind of adventure: Sail with us. Erik + Emily Memoirs: Seven at Sea: Why a New York City Family Cast Off Convention For A Life-Changing Year On A Sailboat Knock: The Spiritual Journey of a Door-to-Door Salesman Connect with Erik + Emily: Email Subscribe to Encouragement Youtube Like, Comment, Subscribe Instagram Facebook
- Jul 29, 202631 min
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 "just right" steal the joy before your adventure even begins. In this episode, we explore why preparation sometimes turns into perfectionism—and how to leave home with more excitement and less stress. Whether you're planning your first beginner sailing adventure, one of our sailing trips, or your own dream vacation, you'll discover simple ways to quiet the mental load, let go of the impossible standard of a "perfect" trip, and protect the gift of anticipation. Because the best adventures don't belong to the best planners. They belong to the people who are willing to live boldly, stay curious, and trust themselves to enjoy whatever unfolds. ⭐⭐⭐⭐⭐ Rate. Review. Subscribe. Try Living on a Sailboat for a Week: No experience required—and yes, you’ll take the helm. Not a party charter. Not a certification course. A small-group, hands-on sailing experience that’s been called the “unicorn of sailing trips.” See if it’s your kind of adventure: Sail with us. Erik + Emily Memoirs: Seven at Sea: Why a New York City Family Cast Off Convention For A Life-Changing Year On A Sailboat Knock: The Spiritual Journey of a Door-to-Door Salesman Connect with Erik + Emily: Email Subscribe to Encouragement Youtube Like, Comment, Subscribe Instagram Facebook
About What Could Go Right?
Living Boldly On and Off the WaterWhat 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?
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