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 willing to try. Takeaways: Make adventure achievable at your own pace Grow emotional intelligence on the journey Balance big goals without losing what matters Include kids of all abilities in your adventures. Find the Osbournes at https://www.osborneadventure.com/

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 sailboat with our five kids and it changed our lives forever. We tell the whole story in our book Seven at Sea. On this podcast, we want to help you go from fear to freedom one adventure at a time.

⭐⭐⭐⭐⭐ 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 For A Life-Changing Year On A Sailboat 

Knock: The Spiritual Journey of a Door-to-Door Salesman

Connect with Erik + Emily:

Email Subscribe to Encouragement

Youtube Like, Comment, Subscribe

Instagram 

Facebook

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 experience and less money, we bootstrapped a year on a sailboat with our five kids and it changed our lives forever. We tell the whole story in our book Seven at Sea. On this podcast, we want to help you go from fear to freedom one adventure at a time.

⭐⭐⭐⭐⭐ Rate. Review. Subscribe.  

Resources:

Find Christina online: macs-explore.com  and on Instagram: @macs_explore 

Our conversation with Christina on her podcast, Your Limitless Life: From Fear to Freedom: How to Big Risks Lead to Big Results

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 For A Life-Changing Year On A Sailboat 

Knock: The Spiritual Journey of a Door-to-Door Salesman

Connect with Erik + Emily:

Email Subscribe to Encouragement

Youtube Like, Comment, Subscribe

Instagram 

Facebook

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 sailboat with our five kids and it changed our lives forever. We tell the whole story in our book Seven at Sea. On this podcast, we want to help you go from fear to freedom one adventure at a time.

⭐⭐⭐⭐⭐ 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 For A Life-Changing Year On A Sailboat 

Knock: The Spiritual Journey of a Door-to-Door Salesman

Connect with Erik + Emily:

Email Subscribe to Encouragement

Youtube Like, Comment, Subscribe

Instagram 

Facebook

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 not alone. We’re exploring how to move through disappointment with grace, flexibility, and just enough hope to keep going. Because even when things don’t go as planned, growth is still possible—and maybe even something better is waiting.

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 sailboat with our five kids and it changed our lives forever. We tell the whole story in our book Seven at Sea. On this podcast, we want to help you go from fear to freedom one adventure at a time.

⭐⭐⭐⭐⭐ 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 For A Life-Changing Year On A Sailboat 

Knock: The Spiritual Journey of a Door-to-Door Salesman

Connect with Erik + Emily:

Email Subscribe to Encouragement

Youtube Like, Comment, Subscribe

Instagram 

Facebook

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 a new culture. Whether you're curious about Croatia or just craving more connection and freedom in your own life, this conversation offers a hopeful reminder that the world is wide—and more possible than you think.

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 sailboat with our five kids and it changed our lives forever. We tell the whole story in our book Seven at Sea. On this podcast, we want to help you go from fear to freedom one adventure at a time.

⭐⭐⭐⭐⭐ 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 For A Life-Changing Year On A Sailboat 

Knock: The Spiritual Journey of a Door-to-Door Salesman

Connect with Erik + Emily:

Email Subscribe to Encouragement

Youtube Like, Comment, Subscribe

Instagram 

Facebook

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 talk about personal growth and sailing. In 2014, with little experience and less money, we bootstrapped a year on a sailboat with our five kids and it changed our lives forever. We tell the whole story in our book Seven at Sea. On this podcast, we want to help you go from fear to freedom one adventure at a time.

⭐⭐⭐⭐⭐ 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 For A Life-Changing Year On A Sailboat 

Knock: The Spiritual Journey of a Door-to-Door Salesman

Connect with Erik + Emily:

Email Subscribe to Encouragement

Youtube Like, Comment, Subscribe

Instagram 

Facebook

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 nudge toward something new, this one’s for you. Let’s take the first step together—and see what could go right.

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 sailboat with our five kids and it changed our lives forever. We tell the whole story in our book Seven at Sea. On this podcast, we want to help you go from fear to freedom one adventure at a time.

⭐⭐⭐⭐⭐ 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 For A Life-Changing Year On A Sailboat 

Knock: The Spiritual Journey of a Door-to-Door Salesman

Connect with Erik + Emily:

Email Subscribe to Encouragement

Youtube Like, Comment, Subscribe

Instagram 

Facebook

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, or the bridge connecting the two, you’re part of a much bigger story. If you’re standing at the edge of something new, this conversation will remind you: you don’t need a map—just the courage to begin.

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 sailboat with our five kids and it changed our lives forever. We tell the whole story in our book Seven at Sea. On this podcast, we want to help you go from fear to freedom one adventure at a time.

⭐⭐⭐⭐⭐ 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 For A Life-Changing Year On A Sailboat 

Knock: The Spiritual Journey of a Door-to-Door Salesman

Connect with Erik + Emily:

Email Subscribe to Encouragement

Youtube Like, Comment, Subscribe

Instagram 

Facebook

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, or the bridge connecting the two, you’re part of a much bigger story. If you’re standing at the edge of something new, this conversation will remind you: you don’t need a map—just the courage to begin.

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 sailboat with our five kids and it changed our lives forever. We tell the whole story in our book Seven at Sea. On this podcast, we want to help you go from fear to freedom one adventure at a time.

⭐⭐⭐⭐⭐ 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 For A Life-Changing Year On A Sailboat 

Knock: The Spiritual Journey of a Door-to-Door Salesman

Connect with Erik + Emily:

Email Subscribe to Encouragement

Youtube Like, Comment, Subscribe

Instagram 

Facebook

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 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 sailboat with our five kids and it changed our lives forever. We tell the whole story in our book Seven at Sea. On this podcast, we want to help you go from fear to freedom one adventure at a time.

⭐⭐⭐⭐⭐ 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 For A Life-Changing Year On A Sailboat 

Knock: The Spiritual Journey of a Door-to-Door Salesman

Connect with Erik + Emily:

Email Subscribe to Encouragement

Youtube Like, Comment, Subscribe

Instagram 

Facebook