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

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Episodes

Ep 58 - Declare Your Independence 04.07.2024

Listen if you want more freedom. In the Orton home, independence is a family value. Like you, we aspire to more independence in all areas of life. Erik and I literally named our son Independence. (Try writing that in first grade.) Like many people, we've felt stuck. Then, like fireworks on a summer evening, someone shares a story that sparks new possibilities and it feels like freed...

Ep 57 - Personal Growth + Sailing 27.06.2024

You are wired for growth.  That means, worry is your most constant obstacle. This is why you never overdose on encouragement, inspiration, and fresh stories of triumph and possibility. That's why we've refined the focus of the   What Could Go Right?  podcast. New studio, cleaner audio, and clearer vision. Learn how this focus on  personal growth and  sailing can...

Ep 56 - Our Personal Packing List for Sailing Trips 20.06.2024

Avoid the most common travel mistake –– packing too much. Especially when it comes to sailing, you don't want to be caught hundreds (or thousands) of miles from home without something you need. But, if it's your first time, you don't really know what you'll need. This can spell big anxiety. We've got your back. We've been refining our packing lists for over a decade. This week we're sharing our mo...

Ep 55 - Navigating the Empty Nest Transition 13.06.2024

It's graduation season and that means big changes for everyone. When you know what to expect you can be more intentional about this new season. The first step is acknowledging what the changes are and how they affect you. Whether you've launched your last child or your home dynamics are changing in other ways, this episode will help. Welcome to the What Could Go Right? Podcast. We’re your hos...

Ep 54 - Your Guide to Letting Go - with Y.E. Young 06.06.2024

Will letting go actually allow you to receive a more abundant life? Ridiculously OK author, Y.E. Young says it will. In this episode he tells you how. Join us in exploring the dynamic process of letting go again and again throughout your 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, with lit...

Ep 53 - Why Loved Ones Inadvertantly Try to Hold Us Back 30.05.2024

Sometimes the people who love us the most may inadvertently be the ones who hold us back from reaching our full potential. How do you know when to listen to their concern and when to let it go? How can you share your important decisions without inviting negative feedback? On the other side of the coin, how can you encourage others? All this and more as we dive into episode 53. Welcome to the What...

Ep 52 - Tortillas to $200M - Lisa Binggeli 23.05.2024

Stuck. Trapped. Lonely. Searching for something.  If you've ever felt this way, I know you are going to love Lisa Binggeli's true adventure. "I used to count pennies and put groceries back on the shelf."  In 9 years, Lisa went from raising three small kids working as a remote medical biller and selling homemade tortillas on the side to selling over 200 million in real estate. Students of...

Ep 51 - How to Upgrade Your Identity (Part 2) 16.05.2024

Which came first, the belief or the behavior? Erik and Emily revisit Atomic Habits by James Clear and pushback (a little) on what it takes to change a habit and upgrade your identity. If your life has no room for improvement, don't bother with this episode. What Could Go Right?  is a Life Design Podcast for Moms and Dads Who Want to Make Midlife Meaningful featuring personal growth, fami...

Ep 50 - How to Upgrade Your Identity (Part 1) 09.05.2024

Ready to upgrade your identity? Start here. The biggest obstacles to pursuing your dream may be the simplest to solve. What's the biggest obstacle? Your thoughts. Dive into Atomic Habits by James Clear and the role of your thoughts or beliefs in forming new habits. What Could Go Right?  is a Life Design Podcast for Moms and Dads Who Want to Make Midlife Meaningful featuring personal growth, f...

Ep 49 - Darling, Let's Be Adventurers 02.05.2024

Choosing an adventurous life includes deciding where you want to go and how to get there. It's not a well-paved road with solar-powered street lights and giant signs. Every day you make the decision to stick with your plan or adapt. The stakes (and the obstacles) are even higher when it comes to your bigger goals. Join  The Knight Show  hosts (reposted here) and us as we explore your pla...

Ep 48 - Books, Beauty Pageants and Politics 25.04.2024

Which scenario would you find most challenging to do with your spouse? a. Raise four kids in New York City b. Build a thriving family business from scratch c. Renovate a home d. Homeschool e. Complete a Law degree and a Master's program d. Live and travel in a foreign country with four kids Chandler and Tiffany have done all of the above and more. They share how asking, 'What could go right?' has...

Ep 47 - We Bought An Eco Resort In Belize 18.04.2024

Have your dreams ever come true too soon? Lance and Chrissy Walker planned to run an eco resort for wellness as a lifestyle business in their retirement years. Not with four young kids at home. Not in the jungles of Belize. The opportunity showed up sooner than they expected and they jumped. If you think that's a big adventure, listen in to hear the incredible obstacles they've...

Ep 46 - What's Your Credibility Score and Why Does it Matter? 11.04.2024

In This Episode: What’s your credibility score? Not your credit score – Your credibility score. It is the ratio between what you say you will do and what you actually do. Why does it matter? Your credibility score has a bigger impact on your quality of life than your credit score. A high credibility score doesn’t just earn you the trust and confidence of others; it unlocks a cascade of benefits. P...

Ep 45 - Our Top Tips on How to Deal with Change 04.04.2024

What’s new? J/K We know something is always changing. Sometimes change is refreshing—as good as a rest. Other times, you want a rest from all the change. Whatever is changing in your life, please enjoy this short conversation where we explore acknowledging change, choosing change, strategically choosing not to change, and more.   What Could Go Right?  is a Life Design Podcast f...

Ep 44 - Two Takeaways From Our Forties 28.03.2024

Dear listeners, I (Erik) botched the microphones on this episode. Sorry about that. If you have trouble understanding anything we're saying, check out the YouTube version with captions. Thanks! In This Episode: Do you celebrate your birthday or try to forget it? Let's revisit Springsteen's vision of "Glory Days". How depressing would it be to peak in high school? Let's dig into misconceptions...

Ep 43 - How to Stop Worrying and Start Living 21.03.2024

In this episode: Worry has a negative effect on your ability to solve problems, on your relationships, your health, and society as a whole.  Worry is on the rise.  If you would like to worry less, this is for you.  We're sharing five strategies to overcome worry, our favorite book about worry, and what we learned about worry while living on a sailboat for a year. What Could Go Right...

Ep 42 - Our Favorite Excuses and What We Did With Them 14.03.2024

In this episode: You know the drill: we've all been guilty of letting excuses hold us back. You say "I'm just being realistic".  But what if excuses are the roadblocks keeping you from more adventure, more connection, and being more who you are truly meant to be? Get ready to reframe and rewrite your excuses into reasons.  Dive into true stories about what opens up when you flip the scri...

Ep 41 - How to Let Your Dreams Come True 07.03.2024

In This Episode:     Studies show that most people give up on their goals. We don't want that for you. Today, w e're discussing one concept Erik's mother taught him that wildly increases your chance of overcoming your fears and taking action. Mom says, Throw your hat over the fence. We share several applications from simple to spectacular so you can start using this one concept today to...

Ep 40 - How Lily Became a Champion and You Can Too + Bonus Song by Erik 29.02.2024

 In this episode: Compared to what? Parents know kids are often your greatest teachers. Here's what we can all learn about "Comparisonitis" from our daughter's state swim competition. This is your friendly invitation to create your own definition of success with a friendly disregard for anyone else's opinion. You'll also get an introduction to the concepts of Blue Ocean Strategy and the...

Ep 39 - Going from Dreamers to Doers - Tiffani + Jared Wingert 22.02.2024

In This Episode:   Do you have an idea that feels so big and unlikely that you don’t even want to tell anyone about it? Maybe you feel dreams that big are for “other people”. If so, you’ll love this episode . Jared and Tiffani Wingert wanted to connect with their neighbors and connect their neighbors to each other. They saw rampant loneliness and wanted to do something about it. What started...

Ep 38 - Finding Your Purpose - with Michael & Erin Allen 15.02.2024

In This Episode:     What would it feel like to find your purpose? To know the theme of your life's work? Erin and Michael share the dark times that helped them discover their purpose and how they are working to help you discover yours. If you believe meaningful conversations are one of life's luxuries, you struck gold with this episode.   What Could Go Right? is a Life Design Podca...

Ep 37 - Vulnerable Valentine's Day 08.02.2024

In This Episode: Who doesn't want to thrive as a partner? But that requires honesty, lots of it. And that can be scary. Tune in for 4 ways to make sharing safer to help you and your spouse open up. Yes, we’re getting Vulnerable for Valentine’s Day. Whatever your relationship status, these tips can help you feel safer and closer with the ones you love. What Could Go Right? is a Life Design Podcast...

Ep 36 - Midlife Crisis vs. Midlife Quest 01.02.2024

What Could Go Right? is a Life Design Podcast for Moms and Dads Who Want to Make Midlife Meaningful featuring personal growth, family connections, and parenting adult kids. The show is hosted by Erik Orton and Emily Orton, creators, travelers, authors, speakers, sailors, rock climbers, and curious parents of five kids (mostly adults). Subscribe to get honest conversations with bold midlife parents...

Ep 35 - How Adventures Help You Create Lasting Connections 25.01.2024

In This Episode: When we go through things together we become close. This may be the single best reason to plan an adventure. Listen in as Erik and Emily reveal a recent adventure surprise that connected three generations. Hear how they strategically planned an epic family adventure to strengthen their relationships and how it transformed them. Try their number one tip for reframing adventure...

Ep 34 - Shifting Your Mindset About Money and Dreams 18.01.2024

What are you going to do with all that money? This may seem counterintuitive but wanting more money might be an obstacle to  making your dreams a reality. In this episode we talk about money! Let’s delve into the common belief that more money is the quickest path to your dreams. It’s not necessarily so. In fact, focusing on money may make your dreams take even longer to achieve. Intrigued? Le...

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