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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
The most recent episodes — sign up to get AI-powered summaries of each one.
- 2 days ago32 min
Ep 176 This Is Mexico? Sailing the Sea of Cortez
A pod of 50 dolphins. Desert islands rising from emerald water. Snorkeling so good you go back three times in one day. Erik and Emily Orton share highlights from their latest sailing adventure out of La Paz, Mexico, into the Sea of Cortez. From secluded beaches and paddleboarding to quiet anchorages beneath the Milky Way, discover why this overlooked destination keeps becoming a crew favorite—and why an extraordinary adventure might be closer than you think. ⭐⭐⭐⭐⭐ 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
- 5 days ago42 min
Ep 175 We Spent a Summer in Finland. Here's What Surprised Us.
Correction: Iceland is Nordic, but it is not usually included in the narrower definition of Scandinavia alongside Denmark, Norway, and Sweden. ⭐⭐⭐⭐⭐ 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
- 5 days ago38 min
Ep 174 Sailing Norway's Lofoten Islands: What Surprised Us Most
What happens when you trade warm-water sailing for the rugged fjords of northern Norway? We recently sailed Norway's Lofoten Islands, and it was an adventure full of dramatic mountain scenery, remote fishing villages, steep hikes, cold water, and a few surprises along the way. In this episode of What Could Go Right?, we share what it was like to sail a monohull in a very different environment from our usual catamaran trips. We talk about exploring Norway from the water, learning about its fishing heritage, adapting when plans changed, and discovering the unexpected joys of stepping into unfamiliar roles. Emily also shares how taking on new sailing challenges helped build her confidence. And yes, there were freshly caught fish, beach fires, cinnamon rolls, and surprisingly cozy bunks. Come along for a northern Norway sailing adventure—and consider what might happen when you try something new, too. ⭐⭐⭐⭐⭐ 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 <span style="colo
- 2 weeks ago16 min
Ep 173 What Your Vacation Says About You (and Why Rest Matters)
What 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 choose to vacation can reveal what you truly value—and why Americans can be so much better at working than resting. From a demanding job that crowds out a long-awaited sailing trip to the surprising value of silence, solitude, and play, this conversation explores how to make time for the life you're working so hard to build. You'll discover why rest doesn't have to wait until your to-do list is empty, how to protect time off, and why having fun can be worthwhile even when it doesn't accomplish anything. Maybe you need a nap. Maybe you need a week away. What could go right if you made room for both? ⭐⭐⭐⭐⭐ 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
- 4 weeks ago43 min
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 require your full attention. But that's exactly what makes new experiences so valuable. In this episode, explore what travel, adventure, and beginner sailing can teach you about adaptability, confidence, curiosity, and connection. You don't have to be a kid to be a beginner. And you don't have to feel ready before you start. What could go right if you tried something new?
- Oct 1, 202616 min
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 lake—something she was convinced she would hate. But once she got past the initial discomfort, she found something surprisingly joyful. That experience became a reminder that the same thing can happen with bigger thresholds: learning to sail, getting in deep water, trying something you’ve never done before, or simply becoming someone who does things you once thought weren’t for you. In this episode, we explore the cold water principle: how anticipation can make an obstacle feel bigger than it really is, and how a simple routine can help you cross the threshold and get to the good part. You don't have to love the leap. You just have to take the next step. ⭐⭐⭐⭐⭐ 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
- Sep 24, 202621 min
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 away from power. You’ll consider what you’re really working toward, whether the sacrifices are worth it, and how defining the life you actually want can help you stop chasing arbitrary milestones and start living with more freedom, contentment, and purpose. ⭐⭐⭐⭐⭐ 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
- Sep 17, 202622 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
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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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