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...

  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...

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 fro...

  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 silen...

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&nbs...

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 sam...

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 m...

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...

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 wher...

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 sk...

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...

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 Sailb...

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'r...

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....

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 excitemen...

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 W...

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...

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 Liv...

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. Fro...

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. No...

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...

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...

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-th...

What if you’re not stuck because you need to push harder—but because you don’t know how to rest? E xplore how growth works more like sailing than constant effort—progress depends on rhythm, not nonstop pushing. R est 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...

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.    ...