What Could Go Right?

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 conversation will remind you you’re not alone—progress is progress, even when it’s slow. And asking What has gone right? might just shift everything. Welcome to the What Could Go Righ...

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 episode is your guide. Discover the rhythm of life onboard and the joy of exploring uninhabited islands you can only reach by boat. Experience shallow, calm waters, excellent snorkeling, q...

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 track those gains and trust that forward motion is happening even when it doesn’t feel like it.   Welcome to the What Could Go Right? Podcast. We’re your hosts: Erik Orton and Emil...

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 conversation, we unpack how to recenter, rediscover what brings you joy, and rebuild a life of meaning that fuels rather than drains. Welcome to the What Could Go Right? Podcast. We’r...

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 hero—toward a life where fun fuels productivity, health, and connection. Through stories from sailing, play, and everyday adventures, you’ll discover how to make work, relationships, and go...

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, and refining our best practices. From packing tips to life aboard the boat, we’ll help you feel prepared, confident, and excited for adventure. Got a question we haven’t covered yet?...

Trying something new always sounds simple… until it’s your turn. Those first steps—whether it’s pressing “send,” showing up, or saying yes—can feel monumental. Because they are. In this episode, we talk about the courage it takes to start when you don’t feel ready, the doubts that show up right on time, and why even a small step can be a big deal. Forward doesn’t have to be flawless—it just has to...

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 we keep coming back for more. Correction: The underwater coral archway mentioned in this episode is at The Indians not The Dog Islands Welcome to the What Could Go Right? Podcast. We’...

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 passing of public figures, and a book that reminded us none of us can take our stuff with us. It’s left us wondering: what does it really mean to live fully and without regrets? Thes...

You know that feeling when you’re trying to follow a map, but it keeps changing and you’re not sure if you’re going the right way? That’s where values come in—they’re your compass, steady and always guiding you, while goals are just helpful maps along the journey. In this episode, we share stories from our sailing adventures and show how trusting your compass helps you make choices that feel inten...

Are your anchors keeping you grounded… or holding you back? In this episode, we explore the difference between being anchored in stability or stuck in fear. You'll get life lessons from our own sailing adventures so you know when to hold fast—and when to let go.  Welcome to the What Could Go Right? Podcast. We’re your hosts: Erik Orton and Emily Orton. We talk about p...

You don’t have to cross an ocean to live with more adventure. In this episode, we share simple, creative ways to break out of your daily routine and spark wonder right where you live. From flipping a coin at every corner of your neighborhood walk to finding the global destination spots near you (hint: National Parks) there are endless ways to discover the unfamiliar and wake up your sense of...

esign your dream sailing trip: your people, your destination, your adventure.  What if you could choose the destination, curate the guest list, and create a week of laughter and connection at sea? In this episode, we reveal how private sailing trips work—and why you don’t need to be a celebrity to design an unforgettable escape with your favorite people. Welcome to the What Could Go Right? Po...

What if 2026 could be the year you stop saying “someday” and finally give yourself the gift of adventure? In this episode, we unveil our new sailing season—spanning the British Virgin Islands, the Abacos and Exumas in the Bahamas, La Paz Mexico, Raiatea to Bora Bora in French Polynesia, Norway, Athens, Naples, and Croatia—and share what makes each destination unforgettable. You’ll hear why putting...

Sometimes travel shows us the world is bigger, richer, and more layered than our daily lives let us remember. Croatia did that for us—through pebble beaches, ancient ruins, local cuisine, and connection. This episode is an invitation to discover a new country and rediscover wonder. Welcome to the What Could Go Right? Podcast. We’re your hosts: Erik Orton and Emily Orton. We talk about persona...

What does adventure really mean — and how do you make it possible for every member of your family? Paul and Valerie Osborne share how sailing 37,000+ nautical miles with their kids, including their son with Down syndrome, taught them lessons in emotional intelligence, perspective, and balancing big goals with family life. Their story proves adventure isn’t just for the elite — it’s for anyone will...

Ever wonder if you could turn your love of travel into something bigger? In this episode of What Could Go Right? , travelpreneur Christina McEvoy shares how adventure, recovery, and clarity can transform not just your trips, but your whole life. 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 2014, with little...

If you’ve been waiting to feel ‘ready’ before chasing a dream or making a change, this episode will show you why readiness is built through action—and how to start right where you are. 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 2014, with little experience and less money, we bootstrapped a year on a sailb...

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 rollercoaster of a business deal that fell apart and the ripple effects it had on our lives. If you’ve ever felt the sting of unmet expectations or the fog of ambiguous loss, you’re n...

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 episode is for you. Christinah and Jordan Mulder join us to share the real story behind their bold move: the beauty, the bumps, and the surprising growth that comes with living slowly in...

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 changes your rhythm, and how connection can still grow, even when the old ways fall away. Welcome to the What Could Go Right? Podcast. We’re your hosts: Erik Orton and Emily Orton. We tal...

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 catamarans and explore the little surprises—practical and emotional—that make this kind of adventure so unforgettable. If you’ve been craving a different pace, a deeper breath, or just a nu...

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 to that call to adventure—the one that asks you to leave behind what’s comfortable and step into something unknown. Whether you're the h ero chasing a dream, the guide offering wisdom...

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 to that call to adventure—the one that asks you to leave behind what’s comfortable and step into something unknown. Whether you're the hero chasing a dream, the guide offering wisdom...

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 into three core human needs—connection, growth, and contribution—and how tuning into them can change everything from your choices to your relationships. Welcome to the What Could Go Ri...