What Could Go Right?

Erik Orton + Emily Orton
  • 5.0 (14)
  • Self-Improvement
  • Updated Weekly

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?

  1. 5d ago

    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

  2. Oct 8

    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? ⭐⭐⭐⭐⭐ 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. Oct 1

    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

  4. Sep 24

    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

  5. Sep 17

    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

  6. Sep 9

    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

  7. Sep 2

    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

  8. Aug 26

    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 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

See All (173)

5
out of 5
14 Ratings

About

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?

Information

  • Creator
    Erik Orton + Emily Orton
  • Years Active
    2023 - 2026
  • Episodes
    173
  • Rating
    Clean
  • Copyright
    © 2023-2026 The Awesome Factory
  • Show Website
    What Could Go Right?

You Might Also Like