What Could Go Right?

You can plan the perfect trip—but the moments that change you rarely go according to plan. You’ll hear how unexpected detours, uncomfortable moments, and off-script experiences became the stories that mattered most. If you’ve ever wondered why some trips stay with you long after you return… this will change how you see travel. 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:

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Explore the tension every thoughtful adult faces: How do you keep stepping up… without burning out? How do you honor your drive… while protecting your most important asset—your physical and mental well-being? This isn’t about doing less. It’s about learning when to push… and when to protect what you’ve built. Because the goal isn’t to squeeze more out of life—it’s to have the capacity to actually experience it.

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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

If you've been wondering whether your best days are behind you, this conversation might shift everything. Explore why clinging to past achievements can drain your vitality and what real thriving looks like. With a controversial take on Bruce Springsteen's "Glory Days," we dig into the dangerous myth that humans peak early. You still have adventures ahead—and the courage to chase them. The best is yet to come.

Resources: Erik playing techno accordion on Instagram @erikorton 

Essentialism by Greg McKeown (affiliate link)

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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

Step aboard one of the newest models we’ve been exploring—the Leopard 4600. We share some of our favorite features from past boats (including Lagoon and Bali models), and what we’ve learned after years of living, sailing, and hosting guests at sea. Then we dive into what makes this boat different… Captain might have found a new favorite.

WATCH on YouTube

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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

Considering a midlife career change or searching for more purpose, money, and freedom?
This episode reveals what it really takes to reinvent your life—and push through fear to do it.

After a life-changing sailing sabbatical, one man (who also hosts this podcast) returns to his cubicle… and knows he can’t stay. What follows is a raw journey into door-to-door sales, where rejection, doubt, and discomfort forge something deeper: confidence, clarity, and purpose.

We unpack the breaking points, the unexpected rewards, and a wild final chapter that somehow blends a summer theatre and a sales office into one life.

A conversation about courage, reinvention—and what’s waiting on the other side of the knock.

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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

Feeling stuck in negative thought loops or like your mindset keeps pulling you down? This episode explores how savoring positive moments can literally rewire your brain for resilience, emotional well-being, and self-trust—without ignoring life’s hard realities. Learn the science-backed practices behind gratitude, mindfulness, and visualization inspired by experts to shift your mental patterns and create more uplifting, empowering states in everyday life.

(As an Amazon affiliate, The Awesome Factory earns from qualifying purchases)

Rick Hansen – Hardwiring Happiness: The New Brain Science of Calm, Contentment, and Confidence

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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

Ever feel stuck facing obstacles and unsure whether to keep going or pivot? This episode helps you overcome challenges, make better decisions, and grow personally by showing how to trust your instincts and navigate life’s toughest moments. You’ll discover practical ways to turn obstacles into opportunities, evaluate fear versus new information, and move forward with clarity, confidence, and intention.

⭐⭐⭐⭐⭐ Rate. Review. Subscribe.  

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

 Do you actually know what you want in life right now? Not what you should want—what you truly want. In this episode, explore why getting clear about your desires is a powerful form of self-discovery. When you ignore what you want, life can start to feel reactive—and resentment is often the first signal. Tune in for practical tips that can help retrain your brain to notice new possibilities and move toward a more fulfilling life.

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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

Feeling stuck, lost, or in a season of stillness? In this episode of What Could Go Right?, Emily and Erik Orton talk with Ganel-Lyn Condie about navigating life transitions, including identity shifts, empty nesting, and unexpected pauses. They explore trust, vulnerability, and personal growth, uncovering how quiet seasons — even unwanted ones — can lead to insight, resilience, and meaningful change.

Connect with Ganel-Lyn on Instagram or get your copy of Sourdough and the Savior

⭐⭐⭐⭐⭐ Rate. Review. Subscribe.  

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 don’t have to move to Rwanda to change your life — but you might have to do something that scares you. In this episode of What Could Go Right?, Mark shares how travel took him from rural Indiana to teaching coding in Rwanda, fully immersed in local community life. We explore how stepping outside your comfort zone through cultural immersion and long-term travel can spark deep personal growth. If you’ve been wondering what could happen if you finally said yes to the adventure, this conversation will expand what feels possible.

⭐⭐⭐⭐⭐ Rate. Review. Subscribe.  

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