What Could Go Right?

Have you ever felt like one forgotten detail could ruin the vacation you've been dreaming about for months? When time off is precious and travel is a big investment, it's easy to let the pressure of getting everything "just right" steal the joy before your adventure even begins.

In this episode, we explore why preparation sometimes turns into perfectionism—and how to leave home with more excitement and less stress. Whether you're planning your first beginner sailing adventure, one of our sailing trips, or your own dream vacation, you'll discover simple ways to quiet the mental load, let go of the impossible standard of a "perfect" trip, and protect the gift of anticipation.

Because the best adventures don't belong to the best planners.

They belong to the people who are willing to live boldly, stay curious, and trust themselves to enjoy whatever unfolds.

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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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The Saronic Islands are of the best regions for a first sailing trip. Discover what makes Greek sailing unique—from calm waters and hidden coves to incredible food, rich history, and beginner-friendly routes. If you’re curious about Greek Isles travel and sailing for beginners, this is a great place to start.

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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

This episode explores how meaningful travel—from sailing trips to impact-driven experiences—can transform not just the places you visit, but who you become. 

Meet Christopher Hill, founder of Hands Up Holidays, who introduces a different kind of travel—one that blends adventure, connection, and meaningful contribution. 

From building homes in South Africa to creating life-changing experiences for families around the world, Christopher shares how travel can go beyond sightseeing and become something transformative.

If you’ve ever considered sailing trips, beginner sailing trips, or simply want a more meaningful way to explore the world, this conversation will expand what’s possible.

Because the best trips don’t just show you new places—they change how you show up in the world.

Hands Up Holidays: https://handsupholidays.com/destinations/

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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

What if the reset you’ve been craving isn’t a life overhaul—but time on the water?
In this episode, we explore the science behind why sailing trips reduce stress, improve sleep, and help you feel like yourself again. Discover how just a few days near the ocean can shift your perspective, calm your mind, and create lasting connection. 

⭐⭐⭐⭐⭐ 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

The first time Erik took the helm of a 47-foot sailboat, he was heading straight for another boat. 

No panic. No yelling. Just a calm voice beside him:
“Maybe turn a few degrees to starboard…”

That voice belonged to Matt Holt—our sailing instructor, and one of our greatest mentors.

In this episode, you'll hear what makes a truly great captain—not just on the water, but in life. From teaching teenagers at sea to building a life in the British Virgin Islands, Matt shares the philosophy that’s shaped thousands of sailors (including us).

You’ll walk away thinking differently about leadership, confidence, and what it really means to guide others. Because sometimes, the most powerful thing you can do… is stay calm.

Stay at Matt Holt's villa on Tortola, British Virgin Islands https://www.seachangebvi.com/

⭐⭐⭐⭐⭐ 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

If you’re dreaming of sailing trips or planning your next adventure, discover the field-tested essentials that help you stay comfortable, protected, and ready for anything—plus where to find their curated favorites at the Awesome Factory shop.

⭐⭐⭐⭐⭐ 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 your biggest milestones are still ahead of you? In this episode of What Could Go Right?, we explore what happens after graduation, after the big life moments, and into midlife transitions—when life opens up in new and unexpected ways. Through real stories from our sailing trips, we talk about personal growth, trying something new, and finding purpose in your next chapter. From learning to sail to building confidence and reimagining what’s possible, these are the milestones that don’t come with a ceremony—but change everything. If you’ve been feeling curious, restless, or ready for more, this episode will help you see that you’re not behind—you might just be getting started.

⭐⭐⭐⭐⭐ 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 your next vacation felt easier… calmer… and more beautiful than you expected? In this episode, you’ll get an inside look at what it’s really like to sail the Abacos in the Bahamas—especially if you’ve never done anything like this before. You’ll hear what makes the water look unreal, why this part of the Bahamas feels so quiet and uncrowded, and what your days could actually look like out there—from sailing and snorkeling to finding hidden beaches and simple island towns. If you’ve ever wondered, “Could I really do something like this?”—this episode will help you picture it. And you might be surprised by the answer.

⭐⭐⭐⭐⭐ 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 planning your adventure felt easier—and a lot more fun—than you expected? In this episode, we’re sharing a few “hidden perks” of our sailing trips to help you feel more confident, flexible, and ready for the experience. You’ll learn how to: Protect your trip with simple travel insurance (including cancel-for-any-reason options) Start learning to sail with beginner-friendly online and on-the-water resources Show up feeling confident—even if you have zero experience Upgrade your trip with our favorite travel and sailing gear We’ll also show you why our approach is different—no pressure, no tests—just real adventure, hands-on learning, and a chance for you to actually enjoy the experience. If you’ve been curious what it’s like to live on a sailboat—or you’re ready to try something new—this episode will help you take that first step. So… what could go right?

⭐⭐⭐⭐⭐ 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’re not stuck because you need to push harder—but because you don’t know how to rest? Explore how growth works more like sailing than constant effort—progress depends on rhythm, not nonstop pushing. Rest isn’t always stopping, but sometimes switching gears. Discover how sailors naturally adjust instead of forcing their way forward. You’ll also learn how to tell the difference between fake rest and the kind of recovery that actually restores clarity and energy.  If you’ve been feeling tired, stuck, or like your effort isn’t paying off, this episode will help you find a more sustainable rhythm for moving forward.

⭐⭐⭐⭐⭐ 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