What Could Go Right?

Erik Orton + Emily Orton
  • 5.0 (13)
  • SELF-IMPROVEMENT
  • UPDATED WEEKLY
What Could Go Right?

With little experience and even less money, we moved aboard a sailboat in the Caribbean with our five kids. We spent the next year sailing it back to our home in Manhattan. That changed everything. We wrote all about it in our NYTimes Top 10 Travel Book "Seven at Sea." Here we talk about personal growth and sailing. We want to help you live your best life one adventure at a time.

  1. 2 DAYS AGO

    Ep 76 - Sailing in Sardinia

    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

    23 min

  2. OCT 30

    Ep 75 - From First Click to Casting Off

    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

    20 min

  3. OCT 24

    Ep 74 - T-Minus Friday

    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

    22 min

  4. OCT 17

    Ep 73 - Becoming Grandparents

    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

    20 min

  5. OCT 10

    Ep 72 - Not a Scam

    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

    28 min

  6. OCT 3

    Ep 71 - Treat Yourself Like A Person

    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

    23 min

  7. SEP 26

    Ep 70 - Getting Clarity with Stefanie Gass

    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

    32 min

  8. SEP 19

    Ep 69 - RV, Boat, Van - 7 Years of Travel with the Jackson Family

    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

    1h 35m
See All (76)

5
out of 5
13 Ratings

About

With little experience and even less money, we moved aboard a sailboat in the Caribbean with our five kids. We spent the next year sailing it back to our home in Manhattan. That changed everything. We wrote all about it in our NYTimes Top 10 Travel Book "Seven at Sea." Here we talk about personal growth and sailing. We want to help you live your best life one adventure at a time.

Information

  • Creator
    Erik Orton + Emily Orton
  • Years Active
    2023 - 2024
  • Episodes
    76
  • Rating
    Clean
  • Copyright
    © 2023-2024 The Awesome Factory
  • Show Website
    What Could Go Right?

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