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In a world of endless pings and productivity hacks, itâs easy to lose sight of what we actually need to thrive. True freedom comes not just from what we can doâbut from knowing whatâs worth doing.This episode dives into three core human needsâconnection, growth, and contributionâand how tuning into them can change everything from your choices to your relationships.
Welcome to the What Could Go Right? Podcast. Weâre 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.
âââââ 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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Why do we cling to routinesâand still crave something new?
Why do we want to feel specialâbut not alone?In this episode, weâre talking about the paradoxes of being humanâand 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. Weâre 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.
âââââ 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
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Facebook
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Fehlende Folgen?
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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 adventureâwith far fewer tourists than youâd expect.
Youâll hear why the Sea of Cortez is:
A surprisingly easy getaway (yes, even from the U.S.)
A wildlife loverâs dreamâwith 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. Weâre 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.
âââââ 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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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 donât have to hustle harderâyou 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 oneâs here to encourage you.
Small steps. Real progress. Persistence beats perfection every time.
Welcome to the What Could Go Right? Podcast. Weâre 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.
âââââ 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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Taking out the garbage isnât anyoneâs passion â just ask my daughter Lily. We're diving into what to do when your passion doesnât match the task at hand, but it still needs to get done. If youâve ever struggled with the not-so-fun stuff, this episodeâs for you.
Welcome to the What Could Go Right? Podcast. Weâre 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.
âââââ 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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Feeling stuck in your routine? You donât have to stay there. In this episode, discover how Nicki Preece traded her desk job for guiding hiking adventures in the Swiss Alps â 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. Weâre 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.
âââââ 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
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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 youâre new or a long-time listener, this retrospective is full of encouragement to live with intentionâand 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
âââââ 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 youâve ever felt like sailing wasnât for you because of the drinking cultureâor if youâre simply curious about how alcohol-free adventures can go deeperâthis episode is for you. You won't get judged for enjoying a glass of wine at sunset. You will find out what makes Navigator Sailing Trips differentâhow we built âdryâ sailing adventures focused on connection, learning, and presence.
âââââ 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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Steve and Donna run a high-volume, precision manufacturing company. If you have ever been grateful for airbags in your car, some of their 300+ employees make those parts for your car. Do you want to know how they stay married, stay in love, stay in business and build a legacy? (That's quite an adventure!) From factory floors to family dinners, Steve and Donna share applicable wisdom on teamwork, emotional intelligence, and the underrated life lessons found in everyday experiences. If youâve ever wondered how to lead with purpose at home and at work, this conversation will leave you inspired to focus on what could go right.
âââââ 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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đ Itâs our 100th episode â and weâre celebrating with honesty. If you're navigating a season of changeâwhere joy and sadness sit side by sideâthis episode is for you. Erik and Emily Orton gently guide you through the tender terrain of transition, offering companionship and insight as you face the bittersweet beauty of letting go. Whether you're saying goodbye to a chapter, a role, or a rhythm that once defined you, you're not alone. In this heartfelt conversation, you're invited to be the hero of your own unfolding story, while Erik and Emily walk alongside you as thoughtful, hopeful guidesâreminding you that every ending carries the quiet promise of something new.
âââââ 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 thereâs one thing sailing has taught us, itâs this: the wind doesnât always do what you expect. And honestly? Thatâs where the good stuff lives. In this episode, Erik and I talk about the role of flexibilityânot just on the water, but in life. We share stories of plans that went sideways and how those moments became some of our most meaningful memories. Whether youâre dreaming about a sailing trip or just trying to navigate your everyday, we hope this conversation leaves you feeling encouraged, open to discovery, and ready to ask, what could go right?
âââââ 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 Italyâs been calling you, this might be your last chance to answer. In this personal episode, Erik and Emily share the soul behind their upcoming sailing trip from Naples to Sorrento, Salerno, and Capri âwoven with real stories of lost keys, missed flights, buttery sunsets, barefoot afternoons, and the compelling magic of the Blue Grotto. It's not just a vacationâit's a reset. Itâs not just a vacationâitâs a reset. And, full transparency: this will likely be our last commercial sailing trip to Italy, as we focus on new adventures ahead. If youâve been curious⊠this is the one to listen to.
âââââ 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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âââââ 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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Real confidenceâthe kind that sticksâisnât handed out like a participation ribbon. Itâs earned through doing hard things. Stretching past whatâs comfortable, and realizing, Whoa. I just did that. What else can I do? For example, there's something you take for granted now that you couldn't even do in the past. In this episode Erik and Emily discuss the relationships between competence, community, and growing confidence. Enjoy!
âââââ Rate. Review. Subscribe.
Resources:
Try Sailing for a Week:
Do you want an experience where you become the kind of person who trusts yourself moreâbecause you did something that proved you could? Come 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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Ever feel like you need a reset button for your life? As the seasons shift, so can we. In this episode, Erik and Emily Orton dive into the magic of a spring resetâa chance to clear out mental clutter, shift your perspective, and realign with what truly matters. Whether you're feeling stuck, craving clarity, or just ready for a fresh start, this episode is your invitation to reset and set sail toward something amazing.
âââââ 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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Do you know when sailboat racing was invented? When the second boat was built. Today we'll share stories about getting there first, getting there last, and what really matters.
âââââ 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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People can change. This is one of the great superpowers of life. Are you changing from good to better? Shifting to something different? Or just parting your hair on the other side? Erik went from a Broadway guy, managing tours of Les Misérables, to a boat guy, teaching people to sail all over the world. He recently revisited his theatrical past taking our son, Eli, to see the Broadway tour of Les Misérables. In this episode, explore the cathartic, redemptive, beautiful message of change in Les Misérables and pour it on your own life. However you are changing, it's healthy to stay open, flexible and pliable at every age.
What do you want to keep the same?
What do you want to change?
âââââ 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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A sailboat is like a micro-city. You manage your own utilities. It's fascinating and very different from life on land. Here's what you can expect on a sailboat.
âââââ 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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There are a lot of things you don't need on a sailboat in tropical locations - like a parka, ski goggles, or thermal underwear. But some no-go items are less obvious like hair dryers. In this episode of What Could Go Right? We'll share items that are better left at home for electricity management. We also share work arounds for those land luxuries you just can't live without.
âââââ 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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This week's episode is a short discussion of the power of living with love and purpose as described by Paulo Coelho in his well-loved story, The Alchemist. "There was a language in the world that everyone understood, a language the boy had used throughout the time that he was trying to improve things at the shop. It was the language of enthusiasm, of things accomplished with love and purpose, and as part of a search for something believed in and desired." Here's to living with love and purpose.
âââââ 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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