What Could Go Right?

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.    ...

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...

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...

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.  ...

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 disco...

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...

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 intent...

 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 a...

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 chan...

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....

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 aft...

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 t...

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 e...

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 Sailbo...

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....

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...

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? Po...

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 magi...

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 ad...