EducationSelf-ImprovementSociety & CulturePlaces & Travel

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?

Play

Open in

32 episodes
weekly
Avg 29 min
English

Episodes 32

Newest Oldest Longest

All20 Unplayed20 In progress0 Played0

Counted on this page — what you have heard stays on this device, so it is not something the list can be paged by.

Today · 32 min
Ep 177 Why Being a Beginner Feels So Awkward in Midlife
You can run a household, lead a team, and still wobble on a paddleboard. Why does being a beginner feel so awkward when you're used to being capable? Listen and explore trying new things in midlife, the fear of looking foolish, and five ways to make room for adventure. From first-time paddleboarding to playing music on the streets of Rome, discover what becomes possible when you let yourself learn in public. Onward and awkward. ⭐⭐⭐⭐⭐ 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
November 5 · 32 min
Ep 176 This Is Mexico? Sailing the Sea of Cortez
A pod of 50 dolphins. Desert islands rising from emerald water. Snorkeling so good you go back three times in one day. Erik and Emily Orton share highlights from their latest sailing adventure out of La Paz, Mexico, into the Sea of Cortez. From secluded beaches and paddleboarding to quiet anchorages beneath the Milky Way, discover why this overlooked destination keeps becoming a crew favorite—and why an extraordinary adventure might be closer than you think. ⭐⭐⭐⭐⭐ 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
November 2 · 38 min
Ep 174 Sailing Norway's Lofoten Islands: What Surprised Us Most
What happens when you trade warm-water sailing for the rugged fjords of northern Norway? We recently sailed Norway's Lofoten Islands, and it was an adventure full of dramatic mountain scenery, remote fishing villages, steep hikes, cold water, and a few surprises along the way. In this episode of What Could Go Right?, we share what it was like to sail a monohull in a very different environment from our usual catamaran trips. We talk about exploring Norway from the water, learning about its fishing heritage, adapting when plans changed, and discovering the unexpected joys of stepping into unfamiliar roles. Emily also shares how taking on new sailing challenges helped build her confidence. And yes, there were freshly caught fish, beach fires, cinnamon rolls, and surprisingly cozy bunks. Come along for a northern Norway sailing adventure—and consider what might happen when you try something new, too. ⭐⭐⭐⭐⭐ 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
November 2 · 42 min
Ep 175 We Spent a Summer in Finland. Here's What Surprised Us.
Correction: Iceland is Nordic, but it is not usually included in the narrower definition of Scandinavia alongside Denmark, Norway, and Sweden. ⭐⭐⭐⭐⭐ 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
October 20 · 16 min
Ep 173 What Your Vacation Says About You (and Why Rest Matters)
What does your vacation say about you? More than you might think. In this episode of What Could Go Right?, Erik and Emily Orton explore Arthur Brooks's observation that where you choose to vacation can reveal what you truly value—and why Americans can be so much better at working than resting. From a demanding job that crowds out a long-awaited sailing trip to the surprising value of silence, solitude, and play, this conversation explores how to make time for the life you're working so hard to build. You'll discover why rest doesn't have to wait until your to-do list is empty, how to protect time off, and why having fun can be worthwhile even when it doesn't accomplish anything. Maybe you need a nap. Maybe you need a week away. What could go right if you made room for both? ⭐⭐⭐⭐⭐ 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
October 8 · 43 min
Ep 172 Beginner Sailing & the Surprising Benefits of Being New at Something
What if being a beginner again could make you more confident—not less? Trying something unfamiliar can be uncomfortable. You don't know the rules, you don't know what you're doing, and suddenly even simple things require your full attention. But that's exactly what makes new experiences so valuable. In this episode, explore what travel, adventure, and beginner sailing can teach you about adaptability, confidence, curiosity, and connection. You don't have to be a kid to be a beginner. And you don't have to feel ready before you start. What could go right if you tried something new? ⭐⭐⭐⭐⭐ 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
October 1 · 16 min
Ep 171 The Cold Water Principle: The Hardest Part is Getting In
What if the thing you’re avoiding isn’t actually as hard as you think? Sometimes the hardest part of trying something new is the few seconds before you begin. In Finland, Emily discovered this while swimming in a cold lake—something she was convinced she would hate. But once she got past the initial discomfort, she found something surprisingly joyful. That experience became a reminder that the same thing can happen with bigger thresholds: learning to sail, getting in deep water, trying something you’ve never done before, or simply becoming someone who does things you once thought weren’t for you. In this episode, we explore the cold water principle: how anticipation can make an obstacle feel bigger than it really is, and how a simple routine can help you cross the threshold and get to the good part. You don't have to love the leap. You just have to take the next step. ⭐⭐⭐⭐⭐ 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
September 24 · 21 min
Ep 170 What if you already have enough?
Where are you chasing more when you might already have enough? This episode explores how to rethink ambition, success, money, freedom, and purpose through the surprising story of George Washington choosing to walk away from power. You’ll consider what you’re really working toward, whether the sacrifices are worth it, and how defining the life you actually want can help you stop chasing arbitrary milestones and start living with more freedom, contentment, and purpose. ⭐⭐⭐⭐⭐ 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
September 17 · 22 min
Ep 169 What If You Decided It Was Possible?
What if the thing you’re dreaming about feels unlikely—even impossible—but you decided to go for it anyway? We celebrate American independence on the day it was declared, long before anyone knew whether that declaration would actually succeed. In this episode, you’ll hear how that idea played out in our own lives, including the unlikely beginning of our family’s year living aboard a sailboat. If you’re thinking about trying something new, starting an adventure, changing direction, or becoming someone you haven’t quite been yet, this is your reminder: you don’t have to know how it’s going to work before you begin. Sometimes the most important step is simply deciding—and putting that decision into words. ⭐⭐⭐⭐⭐ 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
September 9 · 30 min
Ep 168 The Odyssey - It's not about the destination
What The Odyssey, the Striver’s Curse, and sailing can teach us about being present in the journey without losing sight of where we're going. Christopher Nolan’s The Odyssey has us thinking about an ancient story with a very modern problem: “I’ll be happy when I get there.” We explore the pull toward “what’s next” and what sailing can teach us about moving forward without missing where we are right now. ⭐⭐⭐⭐⭐ 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
September 2 · 22 min
Ep 167 Can You Really Learn to Sail on Vacation? We Tried It in Croatia.
Can you really learn to sail on vacation? Our beginner sailing trip in Croatia put it to the test—with first-time sailors learning to sail, explore, and work as a crew. On our latest Awesome Factory sailing trip, our crew explored Croatia’s Dalmatian Coast while learning to sail along the way. They weren't just sightseeing. They were catching mooring balls, tacking, and putting their new skills to work—including during an unexpected man-overboard maneuver involving a six-foot cushion. We also share what we learned returning to Croatia for a second sailing experience, from new anchorages and better provisioning to finding a rhythm that made the trip even better. If you've ever wondered whether a first sailing trip could really teach you to sail—and whether you could do it—come along. ⭐⭐⭐⭐⭐ 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 26 · 21 min
Ep 166 Beginner Sailing Trips in Greece: Highlights from 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

Showing 1–20 of 32 episodes