What Could Go Right?

Celebrating the season with some light holiday stories about our adventures with Christmas Trees past. Merry Christmas everyone!

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:

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 Have you been to Thailand? Or any part of Asia? What stood out to you? Erik recently hosted a boatload of scuba divers on excursion in Phuket, Thailand. This was his first trip to Asia. Get his fresh-eyes take on this idyllic destination.

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 

Could solo travel be the secret to self-discovery, or does the magic lie in shared experiences? There's not one right way to travel. Let's explore the benefits of both.

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 

Whatever your adventures this season, gratitude is essential. In this short holiday episode, let's get grateful. It will increase your stamina for adventure and your enjoyment.

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 

 "I was wondering what secret tips you would have as someone who travels frequently..." We don't want any of our travel tips to be secret. Today, we share travel tips that have worked for us in 30 countries.

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 

If you're looking to change your life, one of the most powerful ways to do that is to change your environment. Get in a community that reinforces the identity you want for yourself and learn from them. Who do you want to be more like? Who is going the direction you want to go? This is what we call the current – this community normalizes what you aspire to. They make it feel easy. Today, we discuss being intentional about the people that are going the direction you want to go. This makes it way easier to end up where you want to be.

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:

Ep 10 Marriage and Midlife Pivots with Y.E. and Jayne Young Pt. 1

Ep 11 Marriage and Midlife Pivots with Y.W. and Jayne Young Pt. 2

Ep 38 Finding Your Purpose with Mike and Erin Allen

Ep 54 Your Guide to Letting Go with Y.E. Young

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 

Curious about sailing in Sardinia? Emily had lots of questions about Erik's September/October 2024 trip in Sardinia, Italy. Today, Erik shares the experience from shore to snorkeling to sailing.

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 – from your perspective – when you click the link to schedule a call about going sailing with us? You may be curious to try living on a sailboat for a week but anxious about hopping on a call. Today, we walk you from first click to casting off.

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 does it actually look like to make the leap from the life you're living to something very different? It is likely something similar to what we experienced 10 years ago when Erik quit his job and our family of seven moved aboard an ex-charter fixer-upper catamaran in St. Martin. It's easy to look back and tell a seamless story knowing how it all worked out, but that's not helpful. Today you get Erik's actual journal/blog entry about his very last day at work. And our last day in the U.S. We break it down what's easy, what's hard, and what matters. And it comes full circle with a cosmic love note.

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:

Knock audiobook by Erik Orton

T-Friday Original blog post

D-Day (Departure) Original blog post and O-lympics video

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's Sailing Memoir:

Seven at Sea: Why a New York City Family Cast Off Convention For A Life-Changing Year On A Sailboat 

Connect with Erik + Emily:

Email Subscribe to Encouragement

Youtube Like, Comment, Subscribe

Instagram 

Facebook 

What's your next big adventure? Erik and Emily are becoming grandparents. Today, they delve into this big transition. Whatever your next adventure you can probably relate to this part of the journey. The part that's exciting, unpredictable, a little bit chaotic, and maybe exhausting but completely worth it as you grow into the wonderful new version of yourself.

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. Relax, explore, and get as much/little sailing experience as you want with stunning 360-views. Sail with us.

Erik + Emily's Sailing Memoir:

Seven at Sea: Why a New York City Family Cast Off Convention For A Life-Changing Year On A Sailboat 

Connect with Erik + Emily:

Email Subscribe to Encouragement

Youtube Like, Comment, Subscribe

Instagram 

Facebook