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. 3D AGO

    Ep 140 – Why Celebrating Small Wins Builds Confidence & Lasting Habits

    What if you’re succeeding more than you think? Discover how celebrating small wins builds confidence and turns simple actions into habits that stick. ⭐⭐⭐⭐⭐ Rate. Review. Subscribe.   Resources: Try Living on a Sailboat for a Week:  Perfect for rookies who want to test drive the live-aboard dream. Yes, we let you drive the boat. Relax, explore, and get as much/little sailing experience as you want with stunning 360-views. 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

    34 min

  2. FEB 5

    Ep 139 – The Amalfi Coast by Sea: Italy's Most Iconic Islands

    What if Italy didn’t feel rushed? In this episode, we talk about seeing the Amalfi Coast from the sea — sailing to Procida, Ischia, and Capri, and discovering a slower, more human way to travel. It’s a conversation about choosing a different pace of adventure — one that leaves you feeling connected, nourished, and more alive. ⭐⭐⭐⭐⭐ Rate. Review. Subscribe.   Try Living on a Sailboat for a Week:  Perfect for rookies who want to test drive the live-aboard dream. Yes, we let you drive the boat. Relax, explore, and get as much/little sailing experience as you want with stunning 360-views. 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

    31 min

  3. JAN 29

    Ep 138 – Real Connection is Real Luxury

    The very things meant to make your life easier may be quietly making it lonelier. When everything is done for you, connection often disappears. What if shared work—cooking, cleaning, contributing—has become one of the most overlooked luxuries of our time? ⭐⭐⭐⭐⭐ Rate. Review. Subscribe.   Resources: Ep.129 If You're Not Having Fun Ep. 54 Your Guide to Letting Go with Y.E. Young Ep. 11 Marriage and Life Pivots with Y.E. and Jayne Young pt 2 Ep. 10 Marriage and Life Pivots with Y.E. and Jayne Young pt. 1 Try Living on a Sailboat for a Week:  Perfect for rookies who want to test drive the live-aboard dream. Yes, we let you drive the boat. Relax, explore, and get as much/little sailing experience as you want with stunning 360-views. 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

    43 min

  4. JAN 22

    Ep - 137 Bora Bora – Beyond the Postcard

    Imagine sailing Bora Bora’s calm lagoons, snorkeling with rays and small sharks, exploring vanilla farms, biking around the island, and dining where the floor is sand. In this episode, you’ll get a first-hand look at French Polynesia beyond the photos — from flat-water sailing and paddleboarding in protected lagoons to immersing yourself in the island’s local culture. Whether you’re planning a travel adventure or dreaming of a sailing trip in Bora Bora, this episode shows you why being there in person is worth every effort. On What Could Go Right?, we share personal growth and sailing adventures that transform lives. From sailing a year with five kids to chasing bold dreams, we show you how to go from fear to freedom — one adventure at a time. ⭐⭐⭐⭐⭐ Rate. Review. Subscribe.   Resources: Try Living on a Sailboat for a Week:  Perfect for rookies who want to test drive the live-aboard dream. Yes, we let you drive the boat. Relax, explore, and get as much/little sailing experience as you want with stunning 360-views. 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

    25 min

  5. JAN 15

    Ep 136 – How to Pack Light: Your Suitcase and Your Life

    Ever feel like you’re carrying more than you need—just in case? In this episode, Explore how real growth often comes from packing lighter, not adding more. Through stories from life at sea, hear how intentional choices, a growth mindset, and a little boldness can help you move from fear to freedom and step more fully into the journey you’re on right now. Welcome to the What Could Go Right? Podcast. We’re your hosts: Erik Orton and Emily Orton. We talk about personal growth and sailing. In 2014, with little experience and less money, we bootstrapped a year on a sailboat with our five kids and it changed our lives forever. We tell the whole story in our book Seven at Sea. On this podcast, we want to help you go from fear to freedom one adventure at a time. ⭐⭐⭐⭐⭐ Rate. Review. Subscribe.   Resources: Try Living on a Sailboat for a Week:  Perfect for rookies who want to test drive the live-aboard dream. Yes, we let you drive the boat. Relax, explore, and get as much/little sailing experience as you want with stunning 360-views. 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

    39 min

  6. JAN 8

    Ep 135 – Magical Mexico: Sea of Cortez

    Feeling like life has piled on responsibilities and left little room for joy or adventure? In this episode, we take you to the stunning Sea of Cortez, Mexico, where guests discovered play, wonder, and connection. From walking with stingrays in Balandra Bay to snorkeling with thousands of fish, spotting a gray humpback whale, and even learning to backflip off the boat—after 50—they proved that magic and growth have no age limit. If you’re ready to reclaim curiosity, laughter, and adventure, let us guide you to your next unforgettable experience. Welcome to the What Could Go Right? Podcast. We’re your hosts: Erik Orton and Emily Orton. We talk about personal growth and sailing. In 2014, with little experience and less money, we bootstrapped a year on a sailboat with our five kids and it changed our lives forever. We tell the whole story in our book Seven at Sea. On this podcast, we want to help you go from fear to freedom one adventure at a time. ⭐⭐⭐⭐⭐ Rate. Review. Subscribe.   UPDATE: Greece 2026 is SOLD OUT Resources: Try Living on a Sailboat for a Week:  Perfect for rookies who want to test drive the live-aboard dream. Yes, we let you drive the boat. Relax, explore, and get as much/little sailing experience as you want with stunning 360-views. 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

    25 min

  7. JAN 1

    Ep 134 – From Stuck to Soaring with Curtis and Irene Hill

    Curtis had six kids, just lost his job, and wondered if he’d ever get ahead—or live his lifelong dream of flying. Alongside his wife Irene, he navigated big fears, bold risks, and life-changing decisions, from investing in a groundbreaking ed-tech startup to finally buying the small airplane he’d always dreamed of. In this episode, Curtis and Irene share their story of courage, partnership, and adventure, offering insights for anyone ready to take a leap, invest in a dream, and turn fear into freedom—one adventure at a time. Welcome to the What Could Go Right? Podcast. We’re your hosts: Erik Orton and Emily Orton. We talk about personal growth and sailing. In 2014, with little experience and less money, we bootstrapped a year on a sailboat with our five kids and it changed our lives forever. We tell the whole story in our book Seven at Sea. On this podcast, we want to help you go from fear to freedom one adventure at a time. ⭐⭐⭐⭐⭐ Rate. Review. Subscribe.   Resources: Try Living on a Sailboat for a Week:  Perfect for rookies who want to test drive the live-aboard dream. Yes, we let you drive the boat. Relax, explore, and get as much/little sailing experience as you want with stunning 360-views. 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

    56 min

  8. 12/18/2025

    Ep 133 – Behind the Scenes: Progress in Real Life

    Real growth isn’t a glow-up—it’s a beautiful mess. In this episode, we open up about the transitions, challenges, and quiet wins happening inside our family and business this year. If you’ve been feeling behind, this conversation will remind you you’re not alone—progress is progress, even when it’s slow. And asking What has gone right? might just shift everything. Welcome to the What Could Go Right? Podcast. We’re your hosts: Erik Orton and Emily Orton. We talk about personal growth and sailing. In 2014, with little experience and less money, we bootstrapped a year on a sailboat with our five kids and it changed our lives forever. We tell the whole story in our book Seven at Sea. On this podcast, we want to help you go from fear to freedom one adventure at a time. ⭐⭐⭐⭐⭐ Rate. Review. Subscribe.   Resources: Try Living on a Sailboat for a Week:  Perfect for rookies who want to test drive the live-aboard dream. Yes, we let you drive the boat. Relax, explore, and get as much/little sailing experience as you want with stunning 360-views. 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

    41 min
See All (140)

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
    140
  • Rating
    Clean
  • Copyright
    © 2023-2026 The Awesome Factory
  • Show Website
    What Could Go Right?