Erik Orton + Emily Orton

What Could Go Right?

Living Boldly On and Off the WaterWhat if the life you want is waiting on the other side of one brave decision? On What Could Go Right? you’ll discover how to face fear, take meaningful risks, and step into deeper connection, adventure, and a more intentional life. Hosted by lifelong explorers and the founders of The Awesome Factory, we don’t just talk about adventure — we practice it, inviting you into playful, guided sailing experiences around the world, where growth happens through laughter, learning, and shared moments of awe. Each week, we’ll help you trade 'what could go wrong?' for a fa...

Author

Erik Orton + Emily Orton

Category

Education

Podcast website

www.theawesomefactory.nyc

Latest episode

Jul 1, 2026

Where to listen?

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Episodes

Ep 83 - Living Big by Starting Small 26.12.2024

Do you set goals, words, and/or intentions for the new year? Whether you pick an auspicious date like January 1 or start when the notions strikes, this episode is for you. One sure path to big (atomic) change is small (atomic) steady steps. Here's how it works for us. Welcome to the What Could Go Right? Podcast. We’re your hosts: Erik Orton and Emily Orton. We talk about personal growth and sailin...

Ep 82 - The Christmas Tree Chronicles 19.12.2024

Celebrating the season with some light holiday stories about our adventures with Christmas Trees past. Merry Christmas everyone! 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 on a sailboat with our five kids and it changed our lives forever....

Ep 81 - What Surprised Me in Thailand 12.12.2024

  Have you been to Thailand? Or any part of Asia? What stood out to you? Erik recently hosted a boatload of scuba divers on excursion in Phuket, Thailand. This was his first trip to Asia. Get his fresh-eyes take on this idyllic destination. 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...

Ep 80 - Solo vs. Group Travel: The Benefits 05.12.2024

Could solo travel be the secret to self-discovery, or does the magic lie in shared experiences? There's not one right way to travel. Let's explore the benefits of both. 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 on a sailboat with our fiv...

Ep 79 - Why Be Grateful in Adventure 27.11.2024

Whatever your adventures this season, gratitude is essential. In this short holiday episode, let's get grateful. It will increase your stamina for adventure and your enjoyment. 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 on a sailboat with...

Ep 78 - Our Top Travel Trips 20.11.2024

  "I was wondering what secret tips you would have as someone who travels frequently..."  We don't want any of our travel tips to be secret. Today, we share travel tips that have worked for us in 30 countries.   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 les...

Ep 77 - The Company You Keep 13.11.2024

If you're looking to change your life, one of the most powerful ways to do that is to change your environment.   Get in a community that reinforces the identity you want for yourself and learn from them.  Who do you want to be more like? Who is going the direction you want to go?   This is what we call the current – this community normalizes what you aspire to. They make it feel eas...

Ep 76 - Sailing in Sardinia 06.11.2024

Curious about sailing in Sardinia? Emily had lots of questions about Erik's September/October 2024 trip in Sardinia, Italy. Today, Erik shares the experience from shore to snorkeling to sailing. 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...

Ep 75 - From First Click to Casting Off 30.10.2024

What happens – from your perspective – when you click the link to schedule a call about going sailing with us? You may be curious to try living on a sailboat for a week but anxious about hopping on a call. Today, we walk you from first click to casting off. 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,...

Ep 74 - T-Minus Friday 24.10.2024

What does it actually look like to make the leap from the life you're living to something very different? It is likely something similar to what we experienced 10 years ago when Erik quit his job and our family of seven moved aboard an ex-charter fixer-upper catamaran in St. Martin. It's easy to look back and tell a seamless story knowing how it all worked out, but that's not helpful.&nb...

Ep 73 - Becoming Grandparents 17.10.2024

What's your next big adventure? Erik and Emily are  becoming grandparents. Today, they  delve into this big transition.  Whatever your next adventure you can probably relate to this part of the journey.  The part that's exciting, unpredictable, a little bit chaotic, and maybe exhausting but   completely worth it as you grow into the wonderful new versio...

Ep 72 - Not a Scam 10.10.2024

Accused of running a sailing scam on Facebook, we tell about the exchange and respond here. We tell all about our sailing trips, what makes them unique, and why our bespoke sailing experience may be exactly what you're looking for.    Welcome to the What Could Go Right? Podcast. We’re your hosts: Erik Orton and Emily Orton. We talk about personal growth and sailing. I...

Ep 71 - Treat Yourself Like A Person 03.10.2024

If you find yourself saying Yes to everyone except you, you may like this episode. A meaningful life includes vibrant relationships, learning new skills, contributing in your community. You also need to make space for yourself. That's what we talk about in this episode. 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 70 - Getting Clarity with Stefanie Gass 26.09.2024

From rock bottom to breakthrough – Stefanie Gass shows how partnering with God can help you overcome career setbacks and bad habits to step into your true calling. Today, she runs a peaceful 7-figure business and hosts a top 20 podcast that empowers Christian women to thrive in online business. If you’ve got a big dream on your heart, especially one that feels just out of reach, let Stefanie’s sto...

Ep 69 - RV, Boat, Van - 7 Years of Travel with the Jackson Family 19.09.2024

If you've ever considered a nomadic life, the Jackson family is pulling back the curtain.  Whether your dream is the hit the open road or the open ocean, they have been there.  Rob and Tracy started traveling with their three kids seven years ago.  They are still on the road in Europe.  Today, they speak to your most common fears: cost, remote work, close quarters, da...

Ep 68 - Overcoming Fear of the Unknown 12.09.2024

One of the most basic fears is fear of the unknown. You don't know what is going to happen so your imagination gets to work creating a negative future outcome. That's called worry. If you want to succeed you've got to stop...or at least, cut back on worry. Today you'll learn the process for how to demystify fear of the unknown so you can live and act with clarity and courage.&n...

Ep 67 - The Mentor Advantage 05.09.2024

Why is it so important to have a good mentor? Finding a mentor can fast track your progress and help you achieve your goals more quickly. Mentors can provide guidance, support, and reference material to help you navigate challenges and learn from their experiences. And so much more. Today, we'll talk about three kinds of mentors and key traits you need to get the most benefit from a mentor. Welcom...

Ep 66 - Getting Started - The First Big Adventure (FAQ) 29.08.2024

What were they thinking?! If you want to take a risk but you're not sure what will happen...this one is for you. When someone does the unexpected, unconventional, or intentionally swims upstream, it's only natural to wonder, 'How did they make the leap from thinking to actually doing?' In this episode, Erik and Emily return to the start to reveal what was really going through their minds and heart...

Ep 65 - Lessons from Lily 22.08.2024

Lily joined us in the studio for an experimental episode of What Could Go Right? A family is a big adventure. Every child teaches us so many lessons. At six months old, Lily was diagnosed with Down syndrome. As this surprise unfolds, we continue to discover Lily is packed with superpowers. Today we're sharing lessons from Lily that have made our lives better. Hopefully, this episode will inspire y...

Ep 64 - What We Love About Traveling With Kids 15.08.2024

Just because you hear it over and over again doesn't make it true. People often say, "I want to travel and explore before kids because after kids it will be too hard." Today, Erik and I discuss the reasons we love traveling with our kids and the many magical ways kids make travel better.   Welcome to the What Could Go Right? Podcast. We’re your hosts: Erik Orton and Emily Orton. We talk about...

Ep 63 - Decluttering - Make Space For Your Dream Life 07.08.2024

If you've ever felt overwhelmed, this one is for you. One of the biggest lessons we learned living as a family of seven in New York City is: Less is more. Or you could say: Less but better. Today, we share how to apply this concept to curate your calendar, your habits, and every other area of your intentional life. Welcome to the What Could Go Right? Podcast. We’re your hosts: Erik Orton and...

Ep 62 - How We Sold Our Sailboat 31.07.2024

It is commonly said that the two best days in a boat owner's life are the day you buy your boat and the day you sell your boat. That may or may not be true. We know three things: 1. Most sailboats do not sell quickly 2. A major part of our plan to live aboard affordably was to sell our boat afterward   3. I was emotionally attached to our floating home because of how much we grew individually...

Ep 61 - DIY vs Who Not How: Finding Balance 25.07.2024

Erik and I are trying something new. We started out as scrappy DIY people. We were raised with this noble ethos. We've passed it on to our children. Now, we're trying another approach proposed in Dan Sullivan's book, Who Not How. We're finding 'who' can be more efficient than DIY when it comes to time, energy, money, and even relationships.   Welcome to the What Could Go Right? Podcast. We’re...

Ep 60 - Collaborating as a Couple - Writing Our Book 18.07.2024

What is the thing that you want to do in your life with the person you care about? What are you afraid of? What is the value of figuring that out? Erik and Emily dive into the rarely shared highs, lows, and surprises of collaborating as a couple.  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...

Ep 59 - How to Grow the Size of Your Dreams 11.07.2024

'Thinking about my dreams seems like a waste of time because I can't do anything about them.'If you've ever said this to yourself, this conversation is for you. We've heard this from clients over and over. Whether this statement resonates for you or you're just ready to dream bigger, this episode shares a straightforward approach you can start today to grow your vision of what's possible. Welcome...

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