What Could Go Right?

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 curiosity and courage. 

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 help you go from fear to freedom one adventure at a time.

⭐⭐⭐⭐⭐ Rate. Review. Subscribe.  

Resources:

Miracle on 34th Street movie

Vagabonding by Rolf Potts

Rich Dad, Poor Dad by Robert Kiosaki

Try Living on a Sailboat 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

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? 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 Living on a Sailboat 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 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 adventure on the calendar matters, how anticipation itself can be transformative, and how you can claim a special flight credit toward your trip.

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 Living on a Sailboat 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

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 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 Living on a Sailboat 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 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 Living on a Sailboat 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:

Try Living on a Sailboat 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