All Episodes
Episodes
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,...
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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...
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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...
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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...
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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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