What Could Go Right?

POV: What it’s like to sail the Exumas, part of the Bahamas’ stunning island chain. If you’re curious whether this style of travel fits you—and want a real sense of what a week sailing out of Nassau is like—this episode is your guide. Discover the rhythm of life onboard and the joy of exploring uninhabited islands you can only reach by boat. Experience shallow, calm waters, excellent snorkeling, quiet beaches and trails, and the simple pleasure of days spent between turquoise seas and brilliant constellations.

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 Living on a Sailboat 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

Progress isn’t always loud. Sometimes it shows up as tiny improvements you barely register: handling stress better, recovering faster, or responding with more patience than the old you. This episode explores how to track those gains and trust that forward motion is happening even when it doesn’t feel like it.

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 Living on a Sailboat 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’ve spent years giving to everyone else—your kids, your partner, your parents, your job—and now feel emptied out, this episode is for you. You want to give from a place of love, but the burnout is real. In this conversation, we unpack how to recenter, rediscover what brings you joy, and rebuild a life of meaning that fuels rather than drains.

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 Living on a Sailboat 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

Think success has to be hard? What if having more fun could actually be the key to living a more intentional, fulfilled life? Too many of us chase purpose while forgetting joy. In this episode, we guide you—our hero—toward a life where fun fuels productivity, health, and connection. Through stories from sailing, play, and everyday adventures, you’ll discover how to make work, relationships, and goals more enjoyable without losing meaning.

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 Living on a Sailboat 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

We’ve spoken with over 1,000 people about our sailing trips, and we’ve gathered the questions you ask most. In this episode, we’re answering the updated FAQ based on what we’ve learned from more trips, more locations, and refining our best practices. From packing tips to life aboard the boat, we’ll help you feel prepared, confident, and excited for adventure. Got a question we haven’t covered yet? Send it our way—every great journey starts with curiosity.

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 Living on a Sailboat 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

Trying something new always sounds simple… until it’s your turn. Those first steps—whether it’s pressing “send,” showing up, or saying yes—can feel monumental. Because they are. In this episode, we talk about the courage it takes to start when you don’t feel ready, the doubts that show up right on time, and why even a small step can be a big deal. Forward doesn’t have to be flawless—it just has to be forward.

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 Living on a Sailboat 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

Our most requested sailing destination is the British Virgin Islands. Today, we’ll share what makes it so special — from secluded snorkeling spots where the fish are the only crowds to playful granite caves — and why we keep coming back for more. Correction: The underwater coral archway mentioned in this episode is at The Indians not The Dog Islands

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 Living on a Sailboat 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

Life is short—no matter how long you live—and facing that reality can actually help you live with more clarity, love, and purpose. This month, we’ve been confronted with death more than usual—funerals for friends, the passing of public figures, and a book that reminded us none of us can take our stuff with us. It’s left us wondering: what does it really mean to live fully and without regrets? These moments have reminded us that we can curate our lives each day around what matters most. From decluttering your stuff to clarifying your actions and values, this episode explores how facing mortality can be a practical and poignant guide to living fully—so that even if your work is incomplete, you don’t leave behind unfinished business.

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 Living on a Sailboat 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 know that feeling when you’re trying to follow a map, but it keeps changing and you’re not sure if you’re going the right way? That’s where values come in—they’re your compass, steady and always guiding you, while goals are just helpful maps along the journey. In this episode, we share stories from our sailing adventures and show how trusting your compass helps you make choices that feel intentional, even when the path ahead isn’t perfectly clear.

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 Living on a Sailboat 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

Are your anchors keeping you grounded… or holding you back? In this episode, we explore the difference between being anchored in stability or stuck in fear. You'll get life lessons from our own sailing adventures so you know when to hold fast—and when to let go. 

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 Living on a Sailboat 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