What Could Go Right?

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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:

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If there’s one thing sailing has taught us, it’s this: the wind doesn’t always do what you expect. And honestly? That’s where the good stuff lives. In this episode, Erik and I talk about the role of flexibility—not 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 you’re 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 g...

If Italy’s 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 –woven 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 vacation–it's a reset. It’s not just a vacation—it’s a reset. And, full transparency: this will likely be our last commercial sailing trip to Italy, as we focus on new adventures ahead. If you’ve been curious… this...

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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...

Real confidence—the kind that sticks—isn’t handed out like a participation ribbon. It’s earned through doing hard things. Stretching past what’s 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!

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Try Sailing for a Week: 

Do you want an experience where you become the kind of person who trusts...

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 reset—a 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.

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Try Sailing for a Week: 

Perfect for rookies who want to test drive the live...

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.

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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 F...

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 chan...

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.

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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 Conventi...

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.

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Resources:

Try Sailing for a Week: 

Perfect for rookies who want to test drive the live-aboard dream. Yes, we let you drive the...