All Episodes
Episodes
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...
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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....
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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...
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Ep 157 Field-Tested Gear for Sailing Trips
If you’re dreaming of sailing trips or planning your next adventure, discover the field-tested essentials that help you stay comfortable, protected, and ready for anything—plus where to find their curated favorites at...
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Ep 156 Milestones and New Beginnings
What if your biggest milestones are still ahead of you? In this episode of What Could Go Right?, we explore what happens after graduation, after the big life moments, and into midlife transitions—when life opens up in...
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Ep 155 Sailing the Abacos for the First Time (And Why It Surprised Us)
What if your next vacation felt easier… calmer… and more beautiful than you expected? In this episode, you’ll get an inside look at what it’s really like to sail the Abacos in the Bahamas—especially if you’ve never...
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Ep 154 Hidden Perks on our Sailing Trips (+ Travel Insurance, Learning to Sail, and Gear Favorites)
What if planning your adventure felt easier—and a lot more fun—than you expected? In this episode, we’re sharing a few “hidden perks” of our sailing trips to help you feel more confident, flexible, and ready for the...
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Ep 153 Burnout, Productivity, and Why Rest Is the Missing Skill
What if you’re not stuck because you need to push harder—but because you don’t know how to rest? Explore how growth works more like sailing than constant effort—progress depends on rhythm, not nonstop pushing. Rest...
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Ep 152 The Real Reason Travel Changes You (It’s Not the Destination)
You can plan the perfect trip—but the moments that change you rarely go according to plan. You’ll hear how unexpected detours, uncomfortable moments, and off-script experiences became the stories that mattered most....
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Ep 151 Exhaustion vs. Motivation: How to Know When to Push and When to Rest
Explore the tension every thoughtful adult faces: How do you keep stepping up… without burning out? How do you honor your drive… while protecting your most important asset—your physical and mental well-being? This...
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Ep 150 New Growth Over Glory Days: Why Your Best Adventures Are Still Ahead
If you've been wondering whether your best days are behind you, this conversation might shift everything. Explore why clinging to past achievements can drain your vitality and what real thriving looks like. With a...
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Ep 149 New Favorite Boat? Tour the Leopard 4600
Step aboard one of the newest models we’ve been exploring—the Leopard 4600. We share some of our favorite features from past boats (including Lagoon and Bali models), and what we’ve learned after years of living,...
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