What Could Go Right?

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?

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.

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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:

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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.

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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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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

Learn to sail on vacation? Yes. In Greece. We're reporting from our most recent back-to-back sailing trips in Greece. Our first group of beginner sailors sailed out of Athens and explored the archipelago known as the Saronic Islands. Our second group chose to get up close and personal with Corfu, part of the Ionian Islands, a chain of islands off the west coast of Greece in the Ionian Sea. All the history. All the culture. All the gelato. And... learned how to sail.

⭐⭐⭐⭐⭐ 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

Discover why sailing together is such a powerful setting for you to feel that you matter. We'll start with Jennifer Breheny Wallace's new book, Mattering: The Secret to a Life of Deep Connection and Purpose. We'll end up chasing gray whales in Mexico and having peaches on French toast in Croatia. 

⭐⭐⭐⭐⭐ 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 is actually an advantage? This summer in Finland, we've discovered how approaching travel with curiosity—rather than trying to know exactly what we're doing—can lead to better adventures, unexpected surprises, and experiences we never would have planned. From cold lake swimming and Finnish sauna to learning the language and mistaking a plastic swan for the real thing, we're sharing what surprised us, what changed us, and what we're bringing home. We'll also talk about why this beginner mindset is at the heart of the sailing trips and adventure travel we love, from Naples, Athens, Split, and Corfu to the Lofoten Islands of Norway—and why being willing to try something new can make travel so much more rewarding. Come travel like a beginner with us: be curious, expect the unexpected, and let yourself be surprised.

⭐⭐⭐⭐⭐ 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 you've mistaken fear for wisdom? At what point did being "responsible" start meaning you stopped choosing joy? In this episode, we explore the surprising "hassle factor" that stands between you and the life you want—and why the very thing you've been avoiding might be the doorway to more delight, confidence, and connection than you expected. This isn't really about sailing or even Finland. It's about recognizing the stories that quietly keep your world small... and asking what might happen if you chose differently.

⭐⭐⭐⭐⭐ 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