Episodes
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Do you set goals, words, and/or intentions for the new year? Whether you pick an auspicious date like January 1 or start when the notions strikes, this episode is for you. One sure path to big (atomic) change is small (atomic) steady steps. Here's how it works for us.
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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Instagram
Facebook
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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:
Email Subscribe to Encouragement
Youtube Like, Comment, Subscribe
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Facebook
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Missing episodes?
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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
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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
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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
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"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
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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
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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
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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
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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
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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
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Accused of running a sailing scam on Facebook, we tell about the exchange and respond here. We tell all about our sailing trips, what makes them unique, and why our bespoke sailing experience may be exactly what you're looking for.
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
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If you find yourself saying Yes to everyone except you, you may like this episode. A meaningful life includes vibrant relationships, learning new skills, contributing in your community. You also need to make space for yourself. That's what we talk about in this episode.
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
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From rock bottom to breakthrough – Stefanie Gass shows how partnering with God can help you overcome career setbacks and bad habits to step into your true calling. Today, she runs a peaceful 7-figure business and hosts a top 20 podcast that empowers Christian women to thrive in online business. If you’ve got a big dream on your heart, especially one that feels just out of reach, let Stefanie’s story be your inspiration. Don’t miss the free gift from Stefanie in the show notes!
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:
Get Clear! Stef's FREE Clarify Your Calling Workshop
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
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If you've ever considered a nomadic life, the Jackson family is pulling back the curtain. Whether your dream is the hit the open road or the open ocean, they have been there. Rob and Tracy started traveling with their three kids seven years ago. They are still on the road in Europe. Today, they speak to your most common fears: cost, remote work, close quarters, daily rhythm, friends, and homeschooling. They don't hide the problems but share why this lifestyle has been totally worth it for them. Spoiler Alert: Tracy says if you're worried about your kids making friends, don't worry. There are kids everywhere!
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
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One of the most basic fears is fear of the unknown. You don't know what is going to happen so your imagination gets to work creating a negative future outcome. That's called worry. If you want to succeed you've got to stop...or at least, cut back on worry. Today you'll learn the process for how to demystify fear of the unknown so you can live and act with clarity 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 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
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Why is it so important to have a good mentor? Finding a mentor can fast track your progress and help you achieve your goals more quickly. Mentors can provide guidance, support, and reference material to help you navigate challenges and learn from their experiences. And so much more. Today, we'll talk about three kinds of mentors and key traits you need to get the most benefit from a mentor.
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
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What were they thinking?! If you want to take a risk but you're not sure what will happen...this one is for you. When someone does the unexpected, unconventional, or intentionally swims upstream, it's only natural to wonder, 'How did they make the leap from thinking to actually doing?' In this episode, Erik and Emily return to the start to reveal what was really going through their minds and hearts when they launched on a life-changing adventure. Let this validate your dreams and help you get started.
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 and Stay Tuned.
Show Notes:
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
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Lily joined us in the studio for an experimental episode of What Could Go Right? A family is a big adventure. Every child teaches us so many lessons. At six months old, Lily was diagnosed with Down syndrome. As this surprise unfolds, we continue to discover Lily is packed with superpowers. Today we're sharing lessons from Lily that have made our lives better. Hopefully, this episode will inspire you to embrace uniqueness, make magic happen, ask for what you want, and so much more.
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 and Stay Tuned.
Show Notes:
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
-
Just because you hear it over and over again doesn't make it true. People often say, "I want to travel and explore before kids because after kids it will be too hard." Today, Erik and I discuss the reasons we love traveling with our kids and the many magical ways kids make travel better.
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 and Stay Tuned.
Show Notes:
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
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