What Could Go Right?

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Try Living on a Sailboat for a Week:  

No experience required—and yes, you’ll take the helm.

Not a party charter. Not a certification course.

A small-group, hands-on sailing experience that’s been called the “unicorn of sailing trips.”

See if it’s your kind of adventure: 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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What happens when you trade warm-water sailing for the rugged fjords of northern Norway?

We recently sailed Norway's Lofoten Islands, and it was an adventure full of dramatic mountain scenery, remote fishing villages, steep hikes, cold water, and a few surprises along the way.

In this episode of What Could Go Right?, we share what it was like to sail a monohull in a very different environment from our usual catamaran trips. We talk about exploring Norway from the water, learning about its fishing heritage, adapting when plans changed, and discovering the unexpected joys of stepping into unfamiliar roles.

Emily also shares how taking on new sailing challenges helped build her confidence. And yes, there were freshly caught fish, beach fires, cinnamon rolls, and surprisingly cozy bunks.

Come along for a northern Norway sailing adventure—and consider what might happen when you try something new, too.

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Try Living on a Sailboat for a Week:  

No experience required—and yes, you’ll take the helm.

Not a party charter. Not a certification course.

A small-group, hands-on sailing experience that’s been called the “unicorn of sailing trips.”

See if it’s your kind of adventure: 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

Correction: Iceland is Nordic, but it is not usually included in the narrower definition of Scandinavia alongside Denmark, Norway, and Sweden.

⭐⭐⭐⭐⭐ Rate. Review. Subscribe.  

Try Living on a Sailboat for a Week:  

No experience required—and yes, you’ll take the helm.

Not a party charter. Not a certification course.

A small-group, hands-on sailing experience that’s been called the “unicorn of sailing trips.”

See if it’s your kind of adventure: 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 your vacation say about you? More than you might think. In this episode of What Could Go Right?, Erik and Emily Orton explore Arthur Brooks's observation that where you choose to vacation can reveal what you truly value—and why Americans can be so much better at working than resting.

From a demanding job that crowds out a long-awaited sailing trip to the surprising value of silence, solitude, and play, this conversation explores how to make time for the life you're working so hard to build. You'll discover why rest doesn't have to wait until your to-do list is empty, how to protect time off, and why having fun can be worthwhile even when it doesn't accomplish anything.

Maybe you need a nap. Maybe you need a week away. What could go right if you made room for both?

⭐⭐⭐⭐⭐ Rate. Review. Subscribe.  

Try Living on a Sailboat for a Week:  

No experience required—and yes, you’ll take the helm.

Not a party charter. Not a certification course.

A small-group, hands-on sailing experience that’s been called the “unicorn of sailing trips.”

See if it’s your kind of adventure: 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 if being a beginner again could make you more confident—not less? 

Trying something unfamiliar can be uncomfortable. You don't know the rules, you don't know what you're doing, and suddenly even simple things require your full attention.

But that's exactly what makes new experiences so valuable.

In this episode, explore what travel, adventure, and beginner sailing can teach you about adaptability, confidence, curiosity, and connection. 

You don't have to be a kid to be a beginner. And you don't have to feel ready before you start.

What could go right if you tried something new?

⭐⭐⭐⭐⭐ Rate. Review. Subscribe.  

Try Living on a Sailboat for a Week:  

No experience required—and yes, you’ll take the helm.

Not a party charter. Not a certification course.

A small-group, hands-on sailing experience that’s been called the “unicorn of sailing trips.”

See if it’s your kind of adventure: 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 if the thing you’re avoiding isn’t actually as hard as you think? Sometimes the hardest part of trying something new is the few seconds before you begin. In Finland, Emily discovered this while swimming in a cold lake—something she was convinced she would hate. But once she got past the initial discomfort, she found something surprisingly joyful. That experience became a reminder that the same thing can happen with bigger thresholds: learning to sail, getting in deep water, trying something you’ve never done before, or simply becoming someone who does things you once thought weren’t for you. In this episode, we explore the cold water principle: how anticipation can make an obstacle feel bigger than it really is, and how a simple routine can help you cross the threshold and get to the good part. You don't have to love the leap. You just have to take the next step.

⭐⭐⭐⭐⭐ Rate. Review. Subscribe.  

Try Living on a Sailboat for a Week:  

No experience required—and yes, you’ll take the helm.

Not a party charter. Not a certification course.

A small-group, hands-on sailing experience that’s been called the “unicorn of sailing trips.”

See if it’s your kind of adventure: 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

Where are you chasing more when you might already have enough? This episode explores how to rethink ambition, success, money, freedom, and purpose through the surprising story of George Washington choosing to walk away from power. You’ll consider what you’re really working toward, whether the sacrifices are worth it, and how defining the life you actually want can help you stop chasing arbitrary milestones and start living with more freedom, contentment, and purpose.

⭐⭐⭐⭐⭐ Rate. Review. Subscribe.  

Try Living on a Sailboat for a Week:  

No experience required—and yes, you’ll take the helm.

Not a party charter. Not a certification course.

A small-group, hands-on sailing experience that’s been called the “unicorn of sailing trips.”

See if it’s your kind of adventure: 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 if the thing you’re dreaming about feels unlikely—even impossible—but you decided to go for it anyway? 

We celebrate American independence on the day it was declared, long before anyone knew whether that declaration would actually succeed. 

In this episode, you’ll hear how that idea played out in our own lives, including the unlikely beginning of our family’s year living aboard a sailboat.

If you’re thinking about trying something new, starting an adventure, changing direction, or becoming someone you haven’t quite been yet, this is your reminder: you don’t have to know how it’s going to work before you begin.

Sometimes the most important step is simply deciding—and putting that decision into words.

⭐⭐⭐⭐⭐ Rate. Review. Subscribe.  

Try Living on a Sailboat for a Week:  

No experience required—and yes, you’ll take the helm.

Not a party charter. Not a certification course.

A small-group, hands-on sailing experience that’s been called the “unicorn of sailing trips.”

See if it’s your kind of adventure: 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 The Odyssey, the Striver’s Curse, and sailing can teach us about being present in the journey without losing sight of where we're going. 

Christopher Nolan’s The Odyssey has us thinking about an ancient story with a very modern problem: “I’ll be happy when I get there.” 

We explore the pull toward “what’s next” and what sailing can teach us about moving forward without missing where we are right now.

⭐⭐⭐⭐⭐ Rate. Review. Subscribe.  

Try Living on a Sailboat for a Week:  

No experience required—and yes, you’ll take the helm.

Not a party charter. Not a certification course.

A small-group, hands-on sailing experience that’s been called the “unicorn of sailing trips.”

See if it’s your kind of adventure: 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

Can you really learn to sail on vacation? Our beginner sailing trip in Croatia put it to the test—with first-time sailors learning to sail, explore, and work as a crew. 

On our latest Awesome Factory sailing trip, our crew explored Croatia’s Dalmatian Coast while learning to sail along the way. They weren't just sightseeing. They were catching mooring balls, tacking, and putting their new skills to work—including during an unexpected man-overboard maneuver involving a six-foot cushion.

We also share what we learned returning to Croatia for a second sailing experience, from new anchorages and better provisioning to finding a rhythm that made the trip even better.

If you've ever wondered whether a first sailing trip could really teach you to sail—and whether you could do it—come along.

⭐⭐⭐⭐⭐ Rate. Review. Subscribe.  

Try Living on a Sailboat for a Week:  

No experience required—and yes, you’ll take the helm.

Not a party charter. Not a certification course.

A small-group, hands-on sailing experience that’s been called the “unicorn of sailing trips.”

See if it’s your kind of adventure: 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