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What Could Go Right?

Erik Orton + Emily Orton

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?

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21 episodes
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English

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Wednesday · 21 min
Ep 166 Beginner Sailing Trips in Greece: Report on 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
August 19 · 24 min
Ep 165 Sailing Adventures Build Belonging
Discover why sailing together is such a powerful setting for you to feel that you matter. We'll start with Jennifer Breheny Wallace's new book, Mattering: The Secret to a Life of Deep Connection and Purpose. We'll end up chasing gray whales in Mexico and having peaches on French toast in Croatia. ⭐⭐⭐⭐⭐ 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
August 12 · 32 min
Ep 164 Travel Like a Beginner: The Curiosity Advantage - Lessons from Finland
What if being a beginner is actually an advantage? This summer in Finland, we've discovered how approaching travel with curiosity—rather than trying to know exactly what we're doing—can lead to better adventures, unexpected surprises, and experiences we never would have planned. From cold lake swimming and Finnish sauna to learning the language and mistaking a plastic swan for the real thing, we're sharing what surprised us, what changed us, and what we're bringing home. We'll also talk about why this beginner mindset is at the heart of the sailing trips and adventure travel we love, from Naples, Athens, Split, and Corfu to the Lofoten Islands of Norway—and why being willing to try something new can make travel so much more rewarding. Come travel like a beginner with us: be curious, expect the unexpected, and let yourself be surprised. ⭐⭐⭐⭐⭐ 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
August 5 · 40 min
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
July 29 · 31 min
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
July 22 · 31 min
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
July 15 · 42 min
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
July 14 · 30 min
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
July 1 · 51 min
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
July 1 · 24 min
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
June 11 · 22 min
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
June 4 · 29 min
Ep 155 Sailing the Abacos for the First Time (And Why It Surprised Us)
What if your next vacation felt easier… calmer… and more beautiful than you expected? In this episode, you’ll get an inside look at what it’s really like to sail the Abacos in the Bahamas—especially if you’ve never done anything like this before. You’ll hear what makes the water look unreal, why this part of the Bahamas feels so quiet and uncrowded, and what your days could actually look like out there—from sailing and snorkeling to finding hidden beaches and simple island towns. If you’ve ever wondered, “Could I really do something like this?”—this episode will help you picture it. And you might be surprised by the answer. ⭐⭐⭐⭐⭐ 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
May 28 · 17 min
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
May 21 · 27 min
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
May 14 · 28 min
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
May 7 · 23 min
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
April 23 · 38 min
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
April 16 · 23 min
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
April 9 · 43 min
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
April 2 · 27 min
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

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