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What Could Go Right?

What Could Go Right?

Hosted by: Erik Orton + Emily Orton

With little experience and even less money, we moved aboard a sailboat in the Caribbean with our five kids. We spent the next year sailing it back to our home in Manhattan. That changed everything. We wrote all about...

All Episodes

Episodes

Ep 122 - Adventure Right Where You Are

You don’t have to cross an ocean to live with more adventure. In this episode, we share simple, creative ways to break out of your daily routine and spark wonder right where you live. From flipping a coin at every...
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Ep 121 - Planning Your Private Sailing Trip

esign your dream sailing trip: your people, your destination, your adventure. What if you could choose the destination, curate the guest list, and create a week of laughter and connection at sea? In this episode, we...
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Ep 120 - 2026 Sailing Schedule

What if 2026 could be the year you stop saying “someday” and finally give yourself the gift of adventure? In this episode, we unveil our new sailing season—spanning the British Virgin Islands, the Abacos and Exumas in...
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Ep 119 - First Trip To Croatia

Sometimes travel shows us the world is bigger, richer, and more layered than our daily lives let us remember. Croatia did that for us—through pebble beaches, ancient ruins, local cuisine, and connection. This episode...
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Ep 118 - Adventure for Everyone with Paul and Val Osborne

What does adventure really mean — and how do you make it possible for every member of your family? Paul and Valerie Osborne share how sailing 37,000+ nautical miles with their kids, including their son with Down...
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Ep 117 - Travelpreneur Christina McEvoy on Adventure and Growth

Ever wonder if you could turn your love of travel into something bigger? In this episode of What Could Go Right?, travelpreneur Christina McEvoy shares how adventure, recovery, and clarity can transform not just your...
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Ep 116 - The Readiness Myth

If you’ve been waiting to feel ‘ready’ before chasing a dream or making a change, this episode will show you why readiness is built through action—and how to start right where you are. Welcome to the What Could Go...
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Ep 115 - Navigating Disappointment, Lessons in Resilience

What do you do when something you were counting on doesn’t come through—and you’re left holding all the plans, hopes, and energy you’d already invested? In this episode of What Could Go Right?, we share the emotional...
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Ep 114 - Croatia Close Up with Jordan + Christinah Mulder

What happens when you put everything in storage, pack up three young kids, and head to Croatia? If you’ve ever dreamed of family travel but wondered how it actually works—especially while juggling remote work—this...
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Ep 113 - Staying Close When Abilities Change

What happens when the way you’ve always connected with your partner—through activity and adventure—suddenly isn’t possible anymore? In this episode of What Could Go Right?, we explore how to stay close when life...
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Ep 112 - Catamaran Tour of Leopard 4500

Ever wondered what it’s really like to live on a sailboat for a week—but felt unsure what to expect (or what to pack)? You’re not alone. In this mini episode, we walk you through life aboard one of our favorite...
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Ep 111 - What if it's Better Than You Imagined?

You thought you'd be more prepared by now—but midlife still feels unfamiliar, like you’ve arrived at a new threshold you didn’t see coming. In this episode of What Could Go Right?, we explore what it means to say yes...
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