What Could Go Right?

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 opposite directions. Erik and I unpack how to: Balance comfort and adventure Find significance without chasing applause Understand the deeper needs behind our choices If you've ever fel...

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 region stuns with wildlife, turquoise water, and wide-open adventure—with far fewer tourists than you’d expect. You’ll hear why the Sea of Cortez is: A surprisingly easy ge...

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 way of hiking (steady, calm, no burnout), Erik and Emily explore how slowing down can actually get you there faster. Whether you're navigating a big dream, a career pivot, or just tryi...

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 the not-so-fun stuff, this episode’s for you. Welcome to the What Could Go Right? Podcast. We’re your hosts: Erik Orton and Emily Orton. We talk about personal growth and sailing. In 2...

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 life full of passion and purpose. Your next chapter starts here. Welcome to the What Could Go Right? Podcast. We’re your hosts: Erik Orton and Emily Orton. We talk about personal gro...

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 favorites filled with insight, humor, and hope. Whether you’re new or a long-time listener, this retrospective is full of encouragement to live with intention—and ask, What could g...

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 glass of wine at sunset. You will find out what makes Navigator Sailing Trips different—how we built “dry” sailing adventures focused on connection, learning, and presence. ⭐⭐⭐⭐⭐...

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 married, stay in love, stay in business and build a legacy? (That's quite an adventure!)   From factory floors to family dinners, Steve and Donna share&...

🎉 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 tender terrain of transition, offering companionship and insight as you face the bittersweet beauty of letting go. Whether you're saying goodbye to a chapter, a role, or a rhyt...

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 just on the water, but in life. We share stories of plans that went sideways and how those moments became some of our most meaningful memories. Whether you’re dreaming about a sailing t...

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 real stories of lost keys, missed flights, buttery sunsets, barefoot afternoons, and the compelling magic of the Blue Grotto. It's not just a vacation–it's a reset. &n...

⭐⭐⭐⭐⭐ 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 experience as you want with stunning 360-views.   Sail with us. Erik + Emily Memoirs: Seven at Sea: Why a New York City Family Cast Off Convention Fo...

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? For example, there's something you take for granted now that you couldn't even do in the past. In this episode Erik and Emily discuss the relationships between competence, communi...

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 perspective, and realign with what truly matters. Whether you're feeling stuck, craving clarity, or just ready for a fresh start, this episode is your invitation to reset and set sail tow...

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. 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/li...

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, managing tours of Les Misérables, to a boat guy, teaching people to sail all over the world. He recently revisited his theatrical past taking our son, Eli,  to see the Bro...

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 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 sail...

There are a lot of things you don't need on a sailboat in tropical locations - like a parka, ski goggles, or thermal underwear. But some no-go items are less obvious like hair dryers. In this episode of What Could Go Right? We'll share items that are better left at home for electricity management. We also share work arounds for those land luxuries you just can't live without. ⭐⭐⭐⭐⭐ Rate. Revi...

This week's episode is a short discussion of the power of living with love and purpose as described by Paulo Coelho in his well-loved story, The Alchemist. "There was a language in the world that everyone understood, a language the boy had used throughout the time that he was trying to improve things at the shop. It was the language of enthusiasm, of  things accomplished with love and pu...

You're curious about our sailing trips, but you want to know more about the boats we use. This episode is a boat tour - YouTube is the best way to experience this episode. EP 89 on YouTube ⭐⭐⭐⭐⭐ 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 ge...

What did the 5 kids think about living on a sailboat for a year? Our wise and generous firstborn speaks publicly for the first time. You get the pros, the cons, the impact, the personal life lessons, and her counsel for parents of adult kids in Karina's Version. ⭐⭐⭐⭐⭐ Rate. Review. Subscribe.     Resources: Try Sailing for a Week:  Perfect for rookies who want to test driv...

What if you said yes? What holds you back from saying yes to unexpected opportunities? When someone invites you to fly over the Grand Canyon in their small plane, what do you say? That's too much, I couldn't possibly trouble you. OR Thank you. I'd love to! Apparently, a lot of people have said No because his wife said, "Seriously, take him up on it. He loves to do it." Erik had never seen the Gran...

What if you said yes? What holds you back from saying yes to unexpected opportunities?  When someone invites you to fly over the Grand Canyon in their small plane, what do you say? That's too much, I couldn't possibly trouble you. OR Thank you. I'd love to!  Apparently, a lot of people have said No because his wife said, "Seriously, take him up on it.  He loves to do it. "&nbsp...

Maybe, it's not too late. After 17 years of dreaming about the sea (from a landlocked state), Jonathan and Mary Young decided 2024 was the year to turn their dream into reality. Juggling kids, careers, and an ever expanding treehouse project, let's hear how they made it happen. Welcome to the What Could Go Right? Podcast. We’re your hosts: Erik Orton and Emily Orton. We talk about personal gr...

If there is an obstacle between you and the adventure of a lifetime, this episode is for you. "Change is fast but transition is slow and things rarely go as we expect. Three days ago we stuffed our duffles and caught a jet stream to our new floating abode. This unlikely dream journey is already six years old." Fresh takes on 2014 when our family of seven moved aboard s/v Fezywig. Welcome...