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...

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Episodes

Ep 136 – How to Pack Light: Your Suitcase and Your Life

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,Ā hear how intentional...
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Ep 135 – Magical Mexico: Sea of Cortez

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...
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Ep 134 – From Stuck to Soaring with Curtis and Irene Hill

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...
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Ep 133 – Behind the Scenes: Progress in Real Life

Real growth isn’t a glow-up—it’s a beautiful mess. In this episode, we open up about the transitions, challenges, and quiet wins happening inside our family and business this year. If you’ve been feeling behind, this...
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Ep 132 – Best of The Bahamas

POV: What it’s like to sail the Exumas, part of the Bahamas’ stunning island chain. If you’re curious whether this style of travel fits you—and want a real sense of what a week sailing out of Nassau is like—this...
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Ep 131- When You Can't See Your Progress

Progress isn’t always loud. Sometimes it shows up as tiny improvements you barely register: handling stress better, recovering faster, or responding with more patience than the old you. This episode explores how to...
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Ep 130 - Burnt Out From Giving?

If you’ve spent years giving to everyone else—your kids, your partner, your parents, your job—and now feel emptied out, this episode is for you. You want to give from a place of love, but the burnout is real. In this...
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Ep 129 - If You're NOT Having Fun...

Think success has to be hard? What if having more fun could actually be the key to living a more intentional, fulfilled life? Too many of us chase purpose while forgetting joy. In this episode, we guide you—our...
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Ep 128 - We Talked to 1,000 People: Most Frequently Asked Questions about sailing with us

We’ve spoken with over 1,000 people about our sailing trips, and we’ve gathered the questions you ask most. In this episode, we’re answering the updated FAQ based on what we’ve learned from more trips, more locations,...
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Ep 127 - Courage to Begin

Trying something new always sounds simple… until it’s your turn. Those first steps—whether it’s pressing ā€œsend,ā€ showing up, or saying yes—can feel monumental. Because they are. In this episode, we talk about the...
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Ep 126 - Best of the British Virgin Islands

Our most requested sailing destination is the British Virgin Islands. Today, we’ll share what makes it so special — from secluded snorkeling spots where the fish are the only crowds to playful granite caves — and why...
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Ep 125 - Life is Short. Legacy is Long.

Life is short—no matter how long you live—and facing that reality can actually help you live with more clarity, love, and purpose. This month, we’ve been confronted with death more than usual—funerals for friends, the...
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