What Could Go Right?
What Could Go Right? is a podcast that encourages listeners to face fear, take meaningful risks, and live a more intentional life. Hosted by lifelong explorers Erik and Emily Orton, founders of The Awesome Factory, the show combines adventure with personal growth. Each episode invites you to trade the question 'what could go wrong?' for the more energizing 'what could go right?' through playful sailing experiences and shared moments of awe.
Episodes
Ep 1 65 Sailing Adventures Build Belonging
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.
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Try Living on a Sai
Ep 164 Travel Like a Beginner: The Curiosity Advantage - Lessons from Finland
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 th
Ep 163 The Hidden Cost of Playing it Safe
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
Ep 162 How to Stop Overthinking Your Next Sailing Trip
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
Ep 161 Why Greece Is Perfect for Your First Sailing Trip
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 W
Ep 160 From Tourist to Contributor: A New Way to Experience Travel with Christopher Hill
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-c
Ep 159 Why Sailing Trips Are the Ultimate Reset (Backed by Science)
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.
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Try Li
Ep 158 He Let a Beginner Sail a 47-Foot Boat – What Great Captains Know with Matt Holt
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 l
Ep 157 Field-Tested Gear for Sailing Trips
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.
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Try Living on a Sailboat for a Week:
No experience required—and yes, you’ll take the helm.
N
Ep 156 Milestones and New Beginnings
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 lea
Ep 155 Sailing the Abacos for the First Time (And Why It Surprised Us)
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
Ep 154 Hidden Perks on our Sailing Trips (+ Travel Insurance, Learning to Sail, and Gear Favorites)
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
Ep 153 Burnout, Productivity, and Why Rest Is the Missing Skill
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 b
Ep 152 The Real Reason Travel Changes You (It’s Not the Destination)
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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Ep 151 Exhaustion vs. Motivation: How to Know When to Push and When to Rest
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
Ep 150 New Growth Over Glory Days: Why Your Best Adventures Are Still Ahead
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
Ep 149 New Favorite Boat? Tour the Leopard 4600
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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Ep 148 The Knock That Changed Everything: Overcoming Fear, Burnout, and Starting Over Midlife
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,
Ep 147 How to Rewire Your Brain for Self-Trust, Resilience, and Joy
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 patt
Ep 146 How to Know When to Persist or Pivot (Overcoming Challenges on Your Personal Growth Journey)
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, a
Ep 145 How to Get Clear on What You Want in Life (The Desire List Practice)
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 possib
Ep 144 Feeling Stuck When You Want Momentum? The Unexpected Gift of Stillness with Ganel-Lyn Condie
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 meaning
Ep 143 From Rural Indiana to Rwanda with Mark Richardson: What Goes Right When You Step Outside Your Comfort Zone
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
Ep 142 - He Retired. Then the Real Adventure Began – Everest, PTSD & Reinvention
What happens when retirement finally arrives… and a perfect lawn isn’t enough? In this episode, Paul Fowler, soft-spoken, thoughtful, and nearing 70—reveals how he became an unlikely world adventurer. From a life-threatening evacuation on Mount Everest to walking the Camino for healing and connection, he shares how travel, courage, and conversations with strangers helped him rebuild confi
Ep 141 - Sailing, Adventure, Transformation: Matt & Julie’s Story
Matt and Julie LeCroix started their sailing adventure with us in Greece—and it sparked a journey that took them to the Bahamas and the U.S. Virgin Islands once Matt became a certified skipper. They share the thrill of exploring new waters, building lasting friendships, and stepping boldly into experiences that change your perspective. If you’ve ever wondered what could go right when you
Ep 140 – Why Celebrating Small Wins Builds Confidence & Lasting Habits
What if you’re succeeding more than you think? Discover how celebrating small wins builds confidence and turns simple actions into habits that stick.
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Resources:
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
Ep 139 – The Amalfi Coast by Sea: Italy's Most Iconic Islands
What if Italy didn’t feel rushed? In this episode, we talk about seeing the Amalfi Coast from the sea — sailing to Procida, Ischia, and Capri, and discovering a slower, more human way to travel. It’s a conversation about choosing a different pace of adventure — one that leaves you feeling connected, nourished, and more alive.
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Try Living on a Sail
Ep 138 – Real Connection is Real Luxury
The very things meant to make your life easier may be quietly making it lonelier. When everything is done for you, connection often disappears. What if shared work—cooking, cleaning, contributing—has become one of the most overlooked luxuries of our time?
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Resources:
Ep.129 If You're Not Having Fun
Ep. 54 Your Guide to Letting Go with Y.E. Young
E
Ep - 137 Bora Bora – Beyond the Postcard
Imagine sailing Bora Bora’s calm lagoons, snorkeling with rays and small sharks, exploring vanilla farms, biking around the island, and dining where the floor is sand. In this episode, you’ll get a first-hand look at French Polynesia beyond the photos — from flat-water sailing and paddleboarding in protected lagoons to immersing yourself in the island’s local culture. Whether you’re plann
Ep 136 – How to Pack Light: Your Suitcase and Your Life
Ever feel like you’re carrying more than you need—just in case? In this episode, Explore how real growth often comes from packing lighter, not adding more. Through stories from life at sea, hear how intentional choices, a growth mindset, and a little boldness can help you move from fear to freedom and step more fully into the journey you’re on right now.
Welcome to the What Could Go
Ep 135 – Magical Mexico: Sea of Cortez
Feeling like life has piled on responsibilities and left little room for joy or adventure? In this episode, we take you to the stunning Sea of Cortez, Mexico, where guests discovered play, wonder, and connection. From walking with stingrays in Balandra Bay to snorkeling with thousands of fish, spotting a gray humpback whale, and even learning to backflip off the boat—after 50—they proved
Ep 134 – From Stuck to Soaring with Curtis and Irene Hill
Curtis had six kids, just lost his job, and wondered if he’d ever get ahead—or live his lifelong dream of flying. Alongside his wife Irene, he navigated big fears, bold risks, and life-changing decisions, from investing in a groundbreaking ed-tech startup to finally buying the small airplane he’d always dreamed of. In this episode, Curtis and Irene share their story of courage, partnershi
Ep 133 – Behind the Scenes: Progress in Real Life
Real growth isn’t a glow-up—it’s a beautiful mess. In this episode, we open up about the transitions, challenges, and quiet wins happening inside our family and business this year. If you’ve been feeling behind, this conversation will remind you you’re not alone—progress is progress, even when it’s slow. And asking What has gone right? might just shift everything.
Welcome to the What Coul
Ep 132 – Best of The Bahamas
POV: What it’s like to sail the Exumas, part of the Bahamas’ stunning island chain. If you’re curious whether this style of travel fits you—and want a real sense of what a week sailing out of Nassau is like—this episode is your guide. Discover the rhythm of life onboard and the joy of exploring uninhabited islands you can only reach by boat. Experience shallow, calm waters, excellent snor
Ep 131- When You Can't See Your Progress
Progress isn’t always loud. Sometimes it shows up as tiny improvements you barely register: handling stress better, recovering faster, or responding with more patience than the old you. This episode explores how to track those gains and trust that forward motion is happening even when it doesn’t feel like it.
Welcome to the What Could Go Right? Podcast. We’re your hosts: Erik Orton
Ep 130 - Burnt Out From Giving?
If you’ve spent years giving to everyone else—your kids, your partner, your parents, your job—and now feel emptied out, this episode is for you. You want to give from a place of love, but the burnout is real. In this conversation, we unpack how to recenter, rediscover what brings you joy, and rebuild a life of meaning that fuels rather than drains.
Welcome to the What Could Go Right? Pod
Ep 129 - If You're NOT Having Fun...
Think success has to be hard? What if having more fun could actually be the key to living a more intentional, fulfilled life? Too many of us chase purpose while forgetting joy. In this episode, we guide you—our hero—toward a life where fun fuels productivity, health, and connection. Through stories from sailing, play, and everyday adventures, you’ll discover how to make work, relationship
Ep 128 - We Talked to 1,000 People: Most Frequently Asked Questions about sailing with us
We’ve spoken with over 1,000 people about our sailing trips, and we’ve gathered the questions you ask most. In this episode, we’re answering the updated FAQ based on what we’ve learned from more trips, more locations, and refining our best practices. From packing tips to life aboard the boat, we’ll help you feel prepared, confident, and excited for adventure. Got a question we haven’t cov
Ep 127 - Courage to Begin
Trying something new always sounds simple… until it’s your turn. Those first steps—whether it’s pressing “send,” showing up, or saying yes—can feel monumental. Because they are. In this episode, we talk about the courage it takes to start when you don’t feel ready, the doubts that show up right on time, and why even a small step can be a big deal. Forward doesn’t have to be flawless—it ju
Ep 126 - Best of the British Virgin Islands
Our most requested sailing destination is the British Virgin Islands. Today, we’ll share what makes it so special — from secluded snorkeling spots where the fish are the only crowds to playful granite caves — and why we keep coming back for more. Correction: The underwater coral archway mentioned in this episode is at The Indians not The Dog Islands
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Ep 125 - Life is Short. Legacy is Long.
Life is short—no matter how long you live—and facing that reality can actually help you live with more clarity, love, and purpose. This month, we’ve been confronted with death more than usual—funerals for friends, the passing of public figures, and a book that reminded us none of us can take our stuff with us. It’s left us wondering: what does it really mean to live fully and without regr
Ep 124 - Compass vs. Map: Navigating Life Without Perfect Plans
You know that feeling when you’re trying to follow a map, but it keeps changing and you’re not sure if you’re going the right way? That’s where values come in—they’re your compass, steady and always guiding you, while goals are just helpful maps along the journey. In this episode, we share stories from our sailing adventures and show how trusting your compass helps you make choices that f
Ep 123 - Anchoring: Stable vs Stuck
Are your anchors keeping you grounded… or holding you back? In this episode, we explore the difference between being anchored in stability or stuck in fear. You'll get life lessons from our own sailing adventures so you know when to hold fast—and when to let go.
Welcome to the What Could Go Right? Podcast. We’re your hosts: Erik Orton and Emily Orton. We tal
Ep 122 - Adventure Right Where You Are
You don’t have to cross an ocean to live with more adventure. In this episode, we share simple, creative ways to break out of your daily routine and spark wonder right where you live. From flipping a coin at every corner of your neighborhood walk to finding the global destination spots near you (hint: National Parks) there are endless ways to discover the unfamiliar and wake up your
Ep 121 - Planning Your Private Sailing Trip
esign your dream sailing trip: your people, your destination, your adventure. What if you could choose the destination, curate the guest list, and create a week of laughter and connection at sea? In this episode, we reveal how private sailing trips work—and why you don’t need to be a celebrity to design an unforgettable escape with your favorite people.
Welcome to the What Could Go R
Ep 120 - 2026 Sailing Schedule
What if 2026 could be the year you stop saying “someday” and finally give yourself the gift of adventure? In this episode, we unveil our new sailing season—spanning the British Virgin Islands, the Abacos and Exumas in the Bahamas, La Paz Mexico, Raiatea to Bora Bora in French Polynesia, Norway, Athens, Naples, and Croatia—and share what makes each destination unforgettable. You’ll hear wh
Ep 119 - First Trip To Croatia
Sometimes travel shows us the world is bigger, richer, and more layered than our daily lives let us remember. Croatia did that for us—through pebble beaches, ancient ruins, local cuisine, and connection. This episode is an invitation to discover a new country and rediscover wonder.
Welcome to the What Could Go Right? Podcast. We’re your hosts: Erik Orton and Emily Orton. We talk abou
Ep 118 - Adventure for Everyone with Paul and Val Osborne
What does adventure really mean — and how do you make it possible for every member of your family? Paul and Valerie Osborne share how sailing 37,000+ nautical miles with their kids, including their son with Down syndrome, taught them lessons in emotional intelligence, perspective, and balancing big goals with family life. Their story proves adventure isn’t just for the elite — it’s for an
Ep 117 - Travelpreneur Christina McEvoy on Adventure and Growth
Ever wonder if you could turn your love of travel into something bigger? In this episode of What Could Go Right?, travelpreneur Christina McEvoy shares how adventure, recovery, and clarity can transform not just your trips, but your whole life.
Welcome to the What Could Go Right? Podcast. We’re your hosts: Erik Orton and Emily Orton. We talk about personal growth and sailing. In 2014, wit
Ep 116 - The Readiness Myth
If you’ve been waiting to feel ‘ready’ before chasing a dream or making a change, this episode will show you why readiness is built through action—and how to start right where you are.
Welcome to the What Could Go Right? Podcast. We’re your hosts: Erik Orton and Emily Orton. We talk about personal growth and sailing. In 2014, with little experience and less money, we bootstrapped a year o
Ep 115 - Navigating Disappointment, Lessons in Resilience
What do you do when something you were counting on doesn’t come through—and you’re left holding all the plans, hopes, and energy you’d already invested? In this episode of What Could Go Right?, we share the emotional rollercoaster of a business deal that fell apart and the ripple effects it had on our lives. If you’ve ever felt the sting of unmet expectations or the fog of ambiguous loss,
Ep 114 - Croatia Close Up with Jordan + Christinah Mulder
What happens when you put everything in storage, pack up three young kids, and head to Croatia? If you’ve ever dreamed of family travel but wondered how it actually works—especially while juggling remote work—this episode is for you. Christinah and Jordan Mulder join us to share the real story behind their bold move: the beauty, the bumps, and the surprising growth that comes with living
Ep 113 - Staying Close When Abilities Change
What happens when the way you’ve always connected with your partner—through activity and adventure—suddenly isn’t possible anymore? In this episode of What Could Go Right?, we explore how to stay close when life changes your rhythm, and how connection can still grow, even when the old ways fall away.
Welcome to the What Could Go Right? Podcast. We’re your hosts: Erik Orton and Emily Orton
Ep 112 - Catamaran Tour of Leopard 4500
Ever wondered what it’s really like to live on a sailboat for a week—but felt unsure what to expect (or what to pack)? You’re not alone. In this mini episode, we walk you through life aboard one of our favorite catamarans and explore the little surprises—practical and emotional—that make this kind of adventure so unforgettable. If you’ve been craving a different pace, a deeper breath, or
Ep 111 - What if it's Better Than You Imagined?
You thought you'd be more prepared by now—but midlife still feels unfamiliar, like you’ve arrived at a new threshold you didn’t see coming. In this episode of What Could Go Right?, we explore what it means to say yes to that call to adventure—the one that asks you to leave behind what’s comfortable and step into something unknown. Whether you're the h ero chasing a dream, the guide offeri
Ep 110 - This is Your Call to Adventure
You thought you'd be more prepared by now—but midlife still feels unfamiliar, like you’ve arrived at a new threshold you didn’t see coming. In this episode of What Could Go Right?, we explore what it means to say yes to that call to adventure—the one that asks you to leave behind what’s comfortable and step into something unknown. Whether you're the hero chasing a dream, the guide offerin
Ep 109 - Slow Time, Strong Ties
In a world of endless pings and productivity hacks, it’s easy to lose sight of what we actually need to thrive. True freedom comes not just from what we can do—but from knowing what’s worth doing.This episode dives into three core human needs—connection, growth, and contribution—and how tuning into them can change everything from your choices to your relationships.
Welcome to the What Cou
Ep 108 - Sailing the Spectrum of Routine and Risk
Why do we cling to routines—and still crave something new? Why do we want to feel special—but not alone?
In this episode, we’re talking about the paradoxes of being human—and what happens when our needs pull us in opposite directions.
Erik and I unpack how to:
Balance comfort and adventure
Find significance without chasing applause
Understand the deeper needs behind our choices
If
Ep 107 - The Best Sailing Trip You’ve Never Heard Of
In this episode of What Could Go Right?, We share our love for one of the most underrated sailing destinations in the world: the Sea of Cortez. Tucked along the coast of Baja California near La Paz, Mexico, this region stuns with wildlife, turquoise water, and wide-open adventure—with far fewer tourists than you’d expect.
You’ll hear why the Sea of Cortez is:
A surprising
Ep 106 - Steady Swiss Pace
Do you ever feel like your goals are sprinting ahead while you're just trying to catch your breath?
This episode is your reminder: you don’t have to hustle harder—you can pace yourself forward.
Inspired by the Swiss way of hiking (steady, calm, no burnout), Erik and Emily explore how slowing down can actually get you there faster. Whether you're navigating a big dream, a career pivot, or
Ep 104 - "Garbage is Not My Passion"
Taking out the garbage isn’t anyone’s passion — just ask my daughter Lily. We're diving into what to do when your passion doesn’t match the task at hand, but it still needs to get done. If you’ve ever struggled with the not-so-fun stuff, this episode’s for you.
Welcome to the What Could Go Right? Podcast. We’re your hosts: Erik Orton and Emily Orton. We talk about personal growth and sail
Ep 105 - From Cubicle to the Alps - Wild Career Pivot with Nicki Preece
Feeling stuck in your routine? You don’t have to stay there. In this episode, discover how Nicki Preece traded her desk job for guiding hiking adventures in the Swiss Alps — and how you can take bold steps to design a life full of passion and purpose. Your next chapter starts here.
Welcome to the What Could Go Right? Podcast. We’re your hosts: Erik Orton and Emily Orton. We talk about per
Ep 103 - Our Top 10 Most Popular Episodes
To celebrate two years of What Could Go Right?, Erik and Emily Orton count down their top 10 most popular episodes. From reverse-engineering relationship goals to chasing dreams with kids in tow, they revisit listener favorites filled with insight, humor, and hope. Whether you’re new or a long-time listener, this retrospective is full of encouragement to live with intention—and ask, What
Ep 102 - Beyond the Booze Cruise
If you’ve ever felt like sailing wasn’t for you because of the drinking culture—or if you’re simply curious about how alcohol-free adventures can go deeper—this episode is for you. You won't get judged for enjoying a glass of wine at sunset. You will find out what makes Navigator Sailing Trips different—how we built “dry” sailing adventures focused on connection, learning, and presence.
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Ep 101 - Marriage, Work & Love with Steve & Donna Kuhr
Steve and Donna run a high-volume, precision manufacturing company. If you have ever been grateful for airbags in your car, some of their 300+ employees make those parts for your car. Do you want to know how they stay married, stay in love, stay in business and build a legacy? (That's quite an adventure!) From factory floors to family dinners, Steve and Donn
Ep 100 - A Time to Mourn
🎉 It’s our 100th episode — and we’re celebrating with honesty. If you're navigating a season of change—where joy and sadness sit side by side—this episode is for you. Erik and Emily Orton gently guide you through the tender terrain of transition, offering companionship and insight as you face the bittersweet beauty of letting go. Whether you're saying goodbye to a chapter, a role, or
Ep 99 - Flexibility Over Frustration
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
Ep 98 - Why Italy Now
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
Ep 97 - Then vs Now (Our Sailing Journey)
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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 Fo
Ep 96 - How to Grow Your Confidence
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
Ep 95 - Spring Cleaning - How to Reset Yourself
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
Ep 94 - 3 Sailing Stories (Racing)
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/
Ep 93 - People Can Change (Les Miserables)
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
Ep 92 - Daily Sailing Life - Wifi, Waste & Water
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 sa
Ep 91 - Daily Sailing Life - What NOT to Pack: Managing Electricity
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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Ep 90 - The Language of the Universe
This week's episode is a short discussion of the power of living with love and purpose as described by Paulo Coelho in his well-loved story, The Alchemist. "There was a language in the world that everyone understood, a language the boy had used throughout the time that he was trying to improve things at the shop. It was the language of enthusiasm, of things accomplished with lov
Ep 89 - Boat Tour - Lagoon 52 Catamaran
You're curious about our sailing trips, but you want to know more about the boats we use. This episode is a boat tour - YouTube is the best way to experience this episode. EP 89 on YouTube
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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
Ep 88 - Seven at Sea Revisited (Karina's Version)
What did the 5 kids think about living on a sailboat for a year? Our wise and generous firstborn speaks publicly for the first time. You get the pros, the cons, the impact, the personal life lessons, and her counsel for parents of adult kids in Karina's Version.
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Resources:
Try Sailing for a Week:
Perfect for rookies who want to test dr
Ep 87 - Cruise Ship or Custom Sailing Trip – Side by Side Comparison
What if you said yes? What holds you back from saying yes to unexpected opportunities? When someone invites you to fly over the Grand Canyon in their small plane, what do you say? That's too much, I couldn't possibly trouble you. OR Thank you. I'd love to! Apparently, a lot of people have said No because his wife said, "Seriously, take him up on it. He loves to do it." Erik had never seen
Ep 86 - Saying Yes: Flying Over the Grand Canyon
What if you said yes? What holds you back from saying yes to unexpected opportunities? When someone invites you to fly over the Grand Canyon in their small plane, what do you say? That's too much, I couldn't possibly trouble you. OR Thank you. I'd love to! Apparently, a lot of people have said No because his wife said, "Seriously, take him up on it. He loves to do it."
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