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 103 - Our Top 10 Most Popular Episodes

To celebrate two years of What Could Go Right?, Erik and Emily Orton count down their top 10 most popular episodes. From reverse-engineering relationship goals to chasing dreams with kids in tow, they revisit listener...
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Ep 102 - Beyond the Booze Cruise

If you’ve ever felt like sailing wasn’t for you because of the drinking culture—or if you’re simply curious about how alcohol-free adventures can go deeper—this episode is for you. You won't get judged for enjoying a...
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Ep 101 - Marriage, Work & Love with Steve & Donna Kuhr

Steve and Donna run a high-volume, precision manufacturing company. If you have ever been grateful for airbags in your car, some of their 300+ employees make those parts for your car. Do you want to know how they stay...
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Ep 100 - A Time to Mourn

🎉 It’s our 100th episode — and we’re celebrating with honesty. If you're navigating a season of change—where joy and sadness sit side by side—this episode is for you. Erik and Emily Orton gently guide you through the...
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Ep 99 - Flexibility Over Frustration

If there’s one thing sailing has taught us, it’s this: the wind doesn’t always do what you expect. And honestly? That’s where the good stuff lives. In this episode, Erik and I talk about the role of flexibility—not...
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Ep 98 - Why Italy Now

If Italy’s been calling you, this might be your last chance to answer. In this personal episode, Erik and Emily share the soul behind their upcoming sailing trip from Naples to Sorrento, Salerno, and Capri –woven with...
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Ep 97 - Then vs Now (Our Sailing Journey)

⭐⭐⭐⭐⭐ Rate. Review. Subscribe.   Resources: Try Sailing 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...
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Ep 96 - How to Grow Your Confidence

Real confidence—the kind that sticks—isn’t handed out like a participation ribbon. It’s earned through doing hard things. Stretching past what’s comfortable, and realizing, Whoa. I just did that. What else can I do?...
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Ep 95 - Spring Cleaning - How to Reset Yourself

Ever feel like you need a reset button for your life? As the seasons shift, so can we. In this episode, Erik and Emily Orton dive into the magic of a spring reset—a chance to clear out mental clutter, shift your...
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Ep 94 - 3 Sailing Stories (Racing)

Do you know when sailboat racing was invented? When the second boat was built. Today we'll share stories about getting there first, getting there last, and what really matters. ⭐⭐⭐⭐⭐ Rate. Review....
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Ep 93 - People Can Change (Les Miserables)

People can change. This is one of the great superpowers of life. Are you changing from good to better? Shifting to something different? Or just parting your hair on the other side? Erik went from a Broadway guy,...
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Ep 92 - Daily Sailing Life - Wifi, Waste & Water

A sailboat is like a micro-city. You manage your own utilities. It's fascinating and very different from life on land. Here's what you can expect on a sailboat.   ⭐⭐⭐⭐⭐ Rate. Review. Subscribe.   Resources: Try...
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