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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 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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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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