What Could Go Right?

Erik Orton + Emily Orton
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  • Self-Improvement
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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. 1 day ago

    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

  2. 29 Jul

    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

  3. 22 Jul

    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 you’re curious about Greek Isles travel and sailing for beginners, this is a great place to start. ⭐⭐⭐⭐⭐ 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. 15 Jul

    Ep 160 From Tourist to Contributor: A New Way to Experience Travel with Christopher Hill

    This 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 Hill, founder of Hands Up Holidays, who introduces a different kind of travel—one that blends adventure, connection, and meaningful contribution.  From building homes in South Africa to creating life-changing experiences for families around the world, Christopher shares how travel can go beyond sightseeing and become something transformative. If you’ve ever considered sailing trips, beginner sailing trips, or simply want a more meaningful way to explore the world, this conversation will expand what’s possible. Because the best trips don’t just show you new places—they change how you show up in the world. Hands Up Holidays: https://handsupholidays.com/destinations/ ⭐⭐⭐⭐⭐ 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. 14 Jul

    Ep 159 Why Sailing Trips Are the Ultimate Reset (Backed by Science)

    What 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, and help you feel like yourself again. Discover how just a few days near the ocean can shift your perspective, calm your mind, and create lasting connection.  ⭐⭐⭐⭐⭐ 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. 1 Jul

    Ep 158 He Let a Beginner Sail a 47-Foot Boat – What Great Captains Know with Matt Holt

    The 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 to starboard…” That voice belonged to Matt Holt—our sailing instructor, and one of our greatest mentors. In this episode, you'll hear what makes a truly great captain—not just on the water, but in life. From teaching teenagers at sea to building a life in the British Virgin Islands, Matt shares the philosophy that’s shaped thousands of sailors (including us). You’ll walk away thinking differently about leadership, confidence, and what it really means to guide others. Because sometimes, the most powerful thing you can do… is stay calm. Stay at Matt Holt's villa on Tortola, British Virgin Islands https://www.seachangebvi.com/ ⭐⭐⭐⭐⭐ 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. 1 Jul

    Ep 157 Field-Tested Gear for Sailing Trips

    If 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 where to find their curated favorites at the Awesome Factory shop. ⭐⭐⭐⭐⭐ 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. 11 Jun

    Ep 156 Milestones and New Beginnings

    What 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 midlife transitions—when life opens up in new and unexpected ways. Through real stories from our sailing trips, we talk about personal growth, trying something new, and finding purpose in your next chapter. From learning to sail to building confidence and reimagining what’s possible, these are the milestones that don’t come with a ceremony—but change everything. If you’ve been feeling curious, restless, or ready for more, this episode will help you see that you’re not behind—you might just be getting started. ⭐⭐⭐⭐⭐ 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

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
    163
  • Rating
    Clean
  • Copyright
    © 2023-2026 The Awesome Factory
  • Show Website
    What Could Go Right?