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 154 Hidden Perks on our Sailing Trips (+ Travel Insurance, Learning to Sail, and Gear Favorites)

    What if planning your adventure felt easier—and a lot more fun—than you expected? In this episode, we’re sharing a few “hidden perks” of our sailing trips to help you feel more confident, flexible, and ready for the experience. You’ll learn how to: Protect your trip with simple travel insurance (including cancel-for-any-reason options) Start learning to sail with beginner-friendly online and on-the-water resources Show up feeling confident—even if you have zero experience Upgrade your trip with our favorite travel and sailing gear We’ll also show you why our approach is different—no pressure, no tests—just real adventure, hands-on learning, and a chance for you to actually enjoy the experience. If you’ve been curious what it’s like to live on a sailboat—or you’re ready to try something new—this episode will help you take that first step. So… what could go right? ⭐⭐⭐⭐⭐ 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

    18 min

  2. May 21

    Ep 153 Burnout, Productivity, and Why Rest Is the Missing Skill

    What if you’re not stuck because you need to push harder—but because you don’t know how to rest? Explore how growth works more like sailing than constant effort—progress depends on rhythm, not nonstop pushing. Rest isn’t always stopping, but sometimes switching gears. Discover how sailors naturally adjust instead of forcing their way forward. You’ll also learn how to tell the difference between fake rest and the kind of recovery that actually restores clarity and energy.  If you’ve been feeling tired, stuck, or like your effort isn’t paying off, this episode will help you find a more sustainable rhythm for moving forward. ⭐⭐⭐⭐⭐ 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

    28 min

  3. May 14

    Ep 152 The Real Reason Travel Changes You (It’s Not the Destination)

    You can plan the perfect trip—but the moments that change you rarely go according to plan. You’ll hear how unexpected detours, uncomfortable moments, and off-script experiences became the stories that mattered most. If you’ve ever wondered why some trips stay with you long after you return… this will change how you see travel. What could go right? ⭐⭐⭐⭐⭐ 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

    28 min

  4. May 7

    Ep 151 Exhaustion vs. Motivation: How to Know When to Push and When to Rest

    Explore the tension every thoughtful adult faces: How do you keep stepping up… without burning out? How do you honor your drive… while protecting your most important asset—your physical and mental well-being? This isn’t about doing less. It’s about learning when to push… and when to protect what you’ve built. Because the goal isn’t to squeeze more out of life—it’s to have the capacity to actually experience it. ⭐⭐⭐⭐⭐ 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

    24 min

  5. Apr 23

    Ep 150 New Growth Over Glory Days: Why Your Best Adventures Are Still Ahead

    If you've been wondering whether your best days are behind you, this conversation might shift everything. Explore why clinging to past achievements can drain your vitality and what real thriving looks like. With a controversial take on Bruce Springsteen's "Glory Days," we dig into the dangerous myth that humans peak early. You still have adventures ahead—and the courage to chase them. The best is yet to come. Resources: Erik playing techno accordion on Instagram @erikorton  Essentialism by Greg McKeown (affiliate link) ⭐⭐⭐⭐⭐ 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

    39 min

  6. Apr 16

    Ep 149 New Favorite Boat? Tour the Leopard 4600

    Step aboard one of the newest models we’ve been exploring—the Leopard 4600. We share some of our favorite features from past boats (including Lagoon and Bali models), and what we’ve learned after years of living, sailing, and hosting guests at sea. Then we dive into what makes this boat different… Captain might have found a new favorite. WATCH on YouTube ⭐⭐⭐⭐⭐ 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

    23 min

  7. Apr 9

    Ep 148 The Knock That Changed Everything: Overcoming Fear, Burnout, and Starting Over Midlife

    Considering a midlife career change or searching for more purpose, money, and freedom? This episode reveals what it really takes to reinvent your life—and push through fear to do it. After a life-changing sailing sabbatical, one man (who also hosts this podcast) returns to his cubicle… and knows he can’t stay. What follows is a raw journey into door-to-door sales, where rejection, doubt, and discomfort forge something deeper: confidence, clarity, and purpose. We unpack the breaking points, the unexpected rewards, and a wild final chapter that somehow blends a summer theatre and a sales office into one life. A conversation about courage, reinvention—and what’s waiting on the other side of the knock. ⭐⭐⭐⭐⭐ 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

    43 min

  8. Apr 2

    Ep 147 How to Rewire Your Brain for Self-Trust, Resilience, and Joy

    Feeling stuck in negative thought loops or like your mindset keeps pulling you down? This episode explores how savoring positive moments can literally rewire your brain for resilience, emotional well-being, and self-trust—without ignoring life’s hard realities. Learn the science-backed practices behind gratitude, mindfulness, and visualization inspired by experts to shift your mental patterns and create more uplifting, empowering states in everyday life. (As an Amazon affiliate, The Awesome Factory earns from qualifying purchases) Rick Hansen – Hardwiring Happiness: The New Brain Science of Calm, Contentment, and Confidence ⭐⭐⭐⭐⭐ 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

    27 min
See All (154)

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
    154
  • Rating
    Clean
  • Copyright
    © 2023-2026 The Awesome Factory
  • Show Website
    What Could Go Right?

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