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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 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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Ep 110 - This is Your Call to Adventure

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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Ep 109 - Slow Time, Strong Ties

In a world of endless pings and productivity hacks, it’s easy to lose sight of what we actually need to thrive. True freedom comes not just from what we can do—but from knowing what’s worth doing.This episode dives...
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Ep 108 - Sailing the Spectrum of Routine and Risk

Why do we cling to routines—and still crave something new? Why do we want to feel special—but not alone? In this episode, we’re talking about the paradoxes of being human—and what happens when our needs pull us in...
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Ep 107 - The Best Sailing Trip You’ve Never Heard Of

In this episode of What Could Go Right?, We share our love for one of the most underrated sailing destinations in the world: the Sea of Cortez. Tucked along the coast of Baja California near La Paz, Mexico, this...
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Ep 106 - Steady Swiss Pace

Do you ever feel like your goals are sprinting ahead while you're just trying to catch your breath? This episode is your reminder: you don’t have to hustle harder—you can pace yourself forward. Inspired by the Swiss...
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Ep 104 - "Garbage is Not My Passion"

Taking out the garbage isn’t anyone’s passion — just ask my daughter Lily. We're diving into what to do when your passion doesn’t match the task at hand, but it still needs to get done. If you’ve ever struggled with...
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Ep 105 - From Cubicle to the Alps - Wild Career Pivot with Nicki Preece

Feeling stuck in your routine? You don’t have to stay there. In this episode, discover how Nicki Preece traded her desk job for guiding hiking adventures in the Swiss Alps — and how you can take bold steps to design a...
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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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