What Could Go Right?

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Ever feel stuck facing obstacles and unsure whether to keep going or pivot? This episode helps you overcome challenges, make better decisions, and grow personally by showing how to trust your instincts and navigate life’s toughest moments. You’ll discover practical ways to turn obstacles into opportunities, evaluate fear versus new information, and move forward with clarity, confidence, and intention. ⭐⭐⭐⭐⭐ 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

 Do you actually know what you want in life right now? Not what you should want—what you truly want. In this episode, explore why getting clear about your desires is a powerful form of self-discovery. When you ignore what you want, life can start to feel reactive—and resentment is often the first signal. Tune in for practical tips that can help retrain your brain to notice new possibilities and move toward a more fulfilling life. ⭐⭐⭐⭐⭐ 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    

Feeling stuck, lost, or in a season of stillness? In this episode of What Could Go Right?, Emily and Erik Orton talk with Ganel-Lyn Condie about navigating life transitions, including identity shifts, empty nesting, and unexpected pauses. They explore trust, vulnerability, and personal growth, uncovering how quiet seasons — even unwanted ones — can lead to insight, resilience, and meaningful change. Connect with Ganel-Lyn on Instagram or get your copy of Sourdough and the Savior ⭐⭐⭐⭐⭐ 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

You don’t have to move to Rwanda to change your life — but you might have to do something that scares you. In this episode of What Could Go Right?, Mark shares how travel took him from rural Indiana to teaching coding in Rwanda, fully immersed in local community life. We explore how stepping outside your comfort zone through cultural immersion and long-term travel can spark deep personal growth. If you’ve been wondering what could happen if you finally said yes to the adventure, this conversation will expand what feels possible. ⭐⭐⭐⭐⭐ 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

What happens when retirement finally arrives… and a perfect lawn isn’t enough? In this episode, Paul Fowler, soft-spoken, thoughtful, and nearing 70—reveals how he became an unlikely world adventurer. From a life-threatening evacuation on Mount Everest to walking the Camino for healing and connection, he shares how travel, courage, and conversations with strangers helped him rebuild confidence after trauma. If you’ve ever wondered whether big adventures still belong to you, this story will change what you believe is possible. ⭐⭐⭐⭐⭐ 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

Matt and Julie LeCroix started their sailing adventure with us in Greece—and it sparked a journey that took them to the Bahamas and the U.S. Virgin Islands once Matt became a certified skipper. They share the thrill of exploring new waters, building lasting friendships, and stepping boldly into experiences that change your perspective. If you’ve ever wondered what could go right when you say yes to adventure, their story will inspire your next trip. ⭐⭐⭐⭐⭐ 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

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

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

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

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

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

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

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

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

POV: What it’s like to sail the Exumas, part of the Bahamas’ stunning island chain. If you’re curious whether this style of travel fits you—and want a real sense of what a week sailing out of Nassau is like—this episode is your guide. Discover the rhythm of life onboard and the joy of exploring uninhabited islands you can only reach by boat. Experience shallow, calm waters, excellent snorkeling, quiet beaches and trails, and the simple pleasure of days spent between turquoise seas and brilliant constellations. 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

Progress isn’t always loud. Sometimes it shows up as tiny improvements you barely register: handling stress better, recovering faster, or responding with more patience than the old you. This episode explores how to track those gains and trust that forward motion is happening even when it doesn’t feel like it.   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

If you’ve spent years giving to everyone else—your kids, your partner, your parents, your job—and now feel emptied out, this episode is for you. You want to give from a place of love, but the burnout is real. In this conversation, we unpack how to recenter, rediscover what brings you joy, and rebuild a life of meaning that fuels rather than drains. 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

Think success has to be hard? What if having more fun could actually be the key to living a more intentional, fulfilled life? Too many of us chase purpose while forgetting joy. In this episode, we guide you—our hero—toward a life where fun fuels productivity, health, and connection. Through stories from sailing, play, and everyday adventures, you’ll discover how to make work, relationships, and goals more enjoyable without losing meaning. 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

We’ve spoken with over 1,000 people about our sailing trips, and we’ve gathered the questions you ask most. In this episode, we’re answering the updated FAQ based on what we’ve learned from more trips, more locations, and refining our best practices. From packing tips to life aboard the boat, we’ll help you feel prepared, confident, and excited for adventure. Got a question we haven’t covered yet? Send it our way—every great journey starts with curiosity. 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

Trying something new always sounds simple… until it’s your turn. Those first steps—whether it’s pressing “send,” showing up, or saying yes—can feel monumental. Because they are. In this episode, we talk about the courage it takes to start when you don’t feel ready, the doubts that show up right on time, and why even a small step can be a big deal. Forward doesn’t have to be flawless—it just has to be forward. 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

Our most requested sailing destination is the British Virgin Islands. Today, we’ll share what makes it so special — from secluded snorkeling spots where the fish are the only crowds to playful granite caves — and why we keep coming back for more. Correction: The underwater coral archway mentioned in this episode is at The Indians not The Dog Islands 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

Life is short—no matter how long you live—and facing that reality can actually help you live with more clarity, love, and purpose. This month, we’ve been confronted with death more than usual—funerals for friends, the passing of public figures, and a book that reminded us none of us can take our stuff with us. It’s left us wondering: what does it really mean to live fully and without regrets? These moments have reminded us that we can curate our lives each day around what matters most. From decluttering your stuff to clarifying your actions and values, this episode explores how facing mortality can be a practical and poignant guide to living fully—so that even if your work is incomplete, you don’t leave behind unfinished business. 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

You know that feeling when you’re trying to follow a map, but it keeps changing and you’re not sure if you’re going the right way? That’s where values come in—they’re your compass, steady and always guiding you, while goals are just helpful maps along the journey. In this episode, we share stories from our sailing adventures and show how trusting your compass helps you make choices that feel intentional, even when the path ahead isn’t perfectly clear. 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

Are your anchors keeping you grounded… or holding you back? In this episode, we explore the difference between being anchored in stability or stuck in fear. You'll get life lessons from our own sailing adventures so you know when to hold fast—and when to let go.  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

You don’t have to cross an ocean to live with more adventure. In this episode, we share simple, creative ways to break out of your daily routine and spark wonder right where you live. From flipping a coin at every corner of your neighborhood walk to finding the global destination spots near you (hint: National Parks) there are endless ways to discover the unfamiliar and wake up your sense of curiosity and courage.  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 help you go from fear to freedom one adventure at a time. ⭐⭐⭐⭐⭐ Rate. Review. Subscribe.   Resources: Miracle on 34th Street movie Vagabonding by Rolf Potts Rich Dad, Poor Dad by Robert Kiosaki 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

esign your dream sailing trip: your people, your destination, your adventure. What if you could choose the destination, curate the guest list, and create a week of laughter and connection at sea? In this episode, we reveal how private sailing trips work—and why you don’t need to be a celebrity to design an unforgettable escape with your favorite people. 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

What if 2026 could be the year you stop saying “someday” and finally give yourself the gift of adventure? In this episode, we unveil our new sailing season—spanning the British Virgin Islands, the Abacos and Exumas in the Bahamas, La Paz Mexico, Raiatea to Bora Bora in French Polynesia, Norway, Athens, Naples, and Croatia—and share what makes each destination unforgettable. You’ll hear why putting adventure on the calendar matters, how anticipation itself can be transformative, and how you can claim a special flight credit toward your trip. 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

Sometimes travel shows us the world is bigger, richer, and more layered than our daily lives let us remember. Croatia did that for us—through pebble beaches, ancient ruins, local cuisine, and connection. This episode is an invitation to discover a new country and rediscover wonder. 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

What does adventure really mean — and how do you make it possible for every member of your family? Paul and Valerie Osborne share how sailing 37,000+ nautical miles with their kids, including their son with Down syndrome, taught them lessons in emotional intelligence, perspective, and balancing big goals with family life. Their story proves adventure isn’t just for the elite — it’s for anyone willing to try. Takeaways: Make adventure achievable at your own pace Grow emotional intelligence on the journey Balance big goals without losing what matters Include kids of all abilities in your adventures. Find the Osbournes at https://www.osborneadventure.com/ 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

Ever wonder if you could turn your love of travel into something bigger? In this episode of What Could Go Right?, travelpreneur Christina McEvoy shares how adventure, recovery, and clarity can transform not just your trips, but your whole life. 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

If you’ve been waiting to feel ‘ready’ before chasing a dream or making a change, this episode will show you why readiness is built through action—and how to start right where you are. 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 Sailing 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