What Could Go Right?

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

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 felt torn between sticking with what you know and reaching for something more, this episode is for you. Because sometimes, understanding why we need what we need… is what sets us free.

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 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 getaway (yes, even from the U.S.)

A wildlife lover’s dream—with dolphins, whales, and more

Full of pristine, remote beaches and tranquil sailing routes

Whether you're craving nature, adventure, or a total reset, this may be your next great escape.

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

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 trying to stay motivated through the messy middle, this one’s here to encourage you.

Small steps. Real progress. Persistence beats perfection every time.

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

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 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

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 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:

Alpenwild Tours

Mountain Connections Private European Hiking Tours

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

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 go right?

 Top 10 Episodes

10 Episode 81 What Surprised Me in Thailand

 9 Episode 18 The 100 Year Grid

 8 Episode 20 How to Ruin a Marriage

 7 Episode 2 How to Get Your Kids to Take Your Advice

 6 Episode 21 Three Questions to Discover What You Really Want

 5 Episode 32 Pulling Off Their First One-Month Family Trip with Brooke and Nathan Schmoe

 4 Episode 33 Raising Kids and Chasing Dreams at the Same Time with Dreyson and Shaundi Killpack

 3 Episode 39 Going From Dreamers to Doers with Tiffani and Jared Wingert

 2 Episode 10 Marriage and Midlife Pivots with Y.E. and Jayne Young

1 Episode 1 The One Question That Can Immediately Improve Your Life

⭐⭐⭐⭐⭐ 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