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
Podcast website
Latest episode
Jul 1, 2026
Where to listen?
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Episodes
Ep 33 - Raising Kids and Chasing Dreams at the Same Time - Dreyson + Shaundi Killpack 11.01.2024 1:06:54
Having kids is does not mean putting fun on hiatus. Some people think you need to have all your fun before your kids come along. It's just not true. In this week's episode of What Could Go Right? Dreyson and Shaundi Kilpack tell us there is another way. They used to think dreams were for other people – people without kids at home – but when they changed their minds, they also changed their lives....
Ep 32 - Pulling Off Their First One Month Family Trip - Brooke + Nathan Schmoe 04.01.2024 59:59
In this episode: Brooke and Nathan Schmoe share their journey of reclaiming life with their four kids through intentional adventures. Inspired by the Orton family's example, they embarked on the first of five road trips to create lasting memories. Despite obstacles like a car accident and health issues, they persevered and experienced the magic of their dream. Through coaching and ac...
Ep 31 - What is a New Year's First? 28.12.2023 16:35
In this episode: Kick off 2024 with a New Year's First. It gives you fresh momentum without all the burden of a long term resolution. A New Year's First is different from a resolution or goal because it is a one-time experience that can't be undone. Listen for examples of our New Year's Firsts, such as attending a yoga class and watching the sunrise in South Carolina. You're invited to...
Ep 30 - 3 Stories About Not Getting What You Want 21.12.2023 10:58
In This Episode: So much of our happiness in life depends upon our expectations. If we're expecting something to happen and it doesn't, we are disappointed. If we are not expecting something to happen and it does, we are surprised, pleasantly surprised. So at a time of year and perhaps at a time of life or a season that is just fraught with expectations, on today's podcast, I want to tell you thre...
Ep 29 - Our 3 Favorite Gift Ideas That Are Not "Stuff" 14.12.2023 34:01
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 28 - What Every Kid Wants to Hear From You Their Whole Life 07.12.2023 23:57
In This Episode: Parenting adults can be tricky. Parents don't always know what adult kids need. Listen to real-life personal parenting stories. Learn one thing every kid (no matter how old) always wants to hear from a parent. 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...
Ep 27 - Why You Shouldn't Have Medium Size Dreams 30.11.2023 21:05
In This Episode: In This Episode: "If your dreams don't scare you, they're not big enough." --Bono. Fresh off a coaching call we're talking about the difference between medium dreams and big dreams. Here's why we advocate for big dreams! What Could Go Right? is a Life Design Podcast for Moms and Dads Who Want to Make Midlife Meaningful featuring personal growth, family connections, a...
Ep 26 - Why We Are Grateful For You 23.11.2023 12:49
In This Episode: In This Episode We're so grateful for you and all the effort you put into living intentionally because we all get to live in a world influenced by you. The peace you are creating in your family relationships is the starting place for peace on earth. What Could Go Right? is a Life Design Podcast for Moms and Dads Who Want to Make Midlife Meaningful featuring personal growth, family...
Ep 25 - How to Play the "I Like" Game 16.11.2023 14:55
In This Episode: Erik and Emily play a speed-round of the "I Like" game to show you how it works. "I Like" is one of the world's easiest games. Emily invented the "I Like" game when our kids were little. We've continued to play "I Like" with our adult kids, corporate clients, dinner guests, and beyond. It's perfect for any time you're with people, you want to have a good time, and you want to lear...
Ep 24 - Why to Not Read Someone's Mind 09.11.2023 17:23
When you think you know what someone else is thinking – that's mindreading. Learn how it can be helpful or harmful in your marriage and other settings depending on what you do with it. Lots of great communication tips here. 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...
Ep 23 - When You And Your Spouse Don't Share the Same Dream 02.11.2023 26:42
In This Episode: "My wife won't let me." "My spouse isn't adventurous." Sad but common comments we hear. What if you and your spouse don't have the same dream? There are so many ways to be your partner's biggest fan. Listen in for ways you can unite around your differences, find more in common, and have each other's backs as a couple doing life together. It's better for you, be...
Ep 22 - The Scary Stories We Tell Ourselves 26.10.2023 18:54
In This Halloween Episode: As parents, we know the scariest stories are the ones we tell ourselves. Have you ever been shut down by the Three-Headed Resource Monster telling you that you don't have the time, money, or skills to pursue a dream or create a braver life? Have you been scared off by The HOWling? The HOWling appears and starts banging on your brain as soon as you have an i...
Ep 21 - 3 Questions to Discover What You Really Want 19.10.2023 20:48
In This Episode: Explore the transformative power of asking "Blue Sky Questions." You'll discover the invaluable insight of challenging societal expectations, paving the way for your authentic self to shine through. As you listen, you'll learn the importance of deliberate self-reflection, helping you connect deeply with your desires. This episode empowers you to take the helm of your own life, mak...
Ep 20 - How to Ruin a Marriage 12.10.2023 22:11
In This Episode: Nobody wants to ruin a marriage but we all know how to do it. Using a design strategy trusted in many industries you can reverse engineer how to make your marriage flourish. Erik and Emily pull back the curtain on their own relationship and share true failures and triumphs you can apply in your own resilient marriage journey. What Could Go Right? is a Life Design Podcas...
Ep 19 - Our Favorite Quote on Parenting 05.10.2023 16:51
In This Episode: Adulting is getting a bad name but it shouldn't be that way. One of the most important parts of parenting is your ongoing self-education. This is great news because it aligns your personal goals and life satisfaction with what is best for your whole family. "Children know the day will come when it’s up to them to live alone and pay the bills. What they also know is that...
Ep 18 - The 100 Year Grid 28.09.2023 18:53
In This Episode: More than 25% of all young adults are estranged from their families. No wonder parents fear losing connection with their adult kids. We’ve talked with hundreds of newly launched adults and they have some concerns about their parents as well. The 100-Year Life Map can help parents of adult kids get intentional about connection. Bonus: it also helps keep your marriage strong. If you...
Ep 17 - What is Life Design? 21.09.2023 21:28
In This Episode: What are the dangers of living by default? Resentment, escapism, addiction, broken relationships, and worse. What are the benefits of living by design? More confidence, more happiness, better health, stronger relationships, and even more money. What is "Life Design?" Listen in and learn how Life Design can save you so much suffering. Stay to the end for a series of quest...
Ep 16 - Family Lessons Being Robbed in Rome - Dan + Natalie Reeves 14.09.2023 26:49
In This Episode: If you’ve ever wondered what it’s really like to sell your house and travel Europe as a family, you’ll find honest unglamorous answers in this revealing interview. Dan and Natalie have been on the road in Europe with their five young kids for about six months. Expect to hear a host of challenges, benefits (like being more in sync as a couple and the transformation in their k...
Ep 15 - How Pursuing Your Dreams Helps Your Kids 07.09.2023 16:52
In This Episode: "I don't just want to give my kids a better life, I want to show them how you live a life that's meaningful." One thing they'll see is what is involved in the journey (it's not always fun) and that it's worth it. If this is you, you'll love today's show on "Double Return Parenting." These are choices that benefit you AND your family. What Could Go Right? is a Life Design Podcast f...
Ep 14 - Why Your Kids Should Be in 2nd Place 31.08.2023 9:50
In This Episode: Why does Dad always get the biggest piece of cake? Because of this advice we got from a couple who was happily married for nearly 60 years! If you're willing to do this, it will make your marriage (and your family) stronger. 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 pa...
Ep 13 - Who Pays for What? (with adult kids) 24.08.2023 31:27
A Life Design Podcast for Moms and Dads Who Want to Make Midlife Meaningful, What Could Go Right? features 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 middle-aged parent...
Ep 12 - How to Help Your Kids Move Out (and In) 17.08.2023 18:09
Your kids are ready to move out, but are they roommate ready? This is an opportunity for adult kids to learn new communication skills. Whether your kids need a little support or a lot, this episode can help. We share our insights gleaned from launching three kids and providing housing for dozens of young adults fresh to the flat-mate dynamic. We outline the successful sharing conversation all room...
Ep 11 - Marriage & Midlife Pivots: Y.E. Young + Jayne Young - Part 2 10.08.2023 24:17
If you’ve ever wondered if your marriage could be better than “fine.” If you’ve ever wondered what a resilient, connected, satisfying marriage looks like from the inside, listen to this. Peek inside the deep, dynamic, sometimes dark, and (in this case) triumphant journey of midlife marriage. Jayne and Y.E., parents of four adult kids, share their journey through major ...
Ep 10 - Marriage & Midlife Pivots: Y.E. Young + Jayne Young - Part 1 03.08.2023 27:39
If you're looking for real talk about midlife shifts, this honest conversation is for you. This courageous couple will help you explore common pitfalls and pivots in a hopeful way. Their kids were moving out. Y.E. Young watched from the grind of his job as his wife, Jayne, had more bandwidth for new ventures. They didn't have as much in common as they did when the kids were small. Their dream...
Ep 9 - Marriage, New In-Laws and Family Culture 27.07.2023 17:25
Do you have kids getting engaged? Or maybe you have kids who will one day get engaged. This season often takes on mythic proportions in their memories. This episode will help you ask good questions and be mindful as you participate in their origin story. We explore family culture, integrating a new person into your family culture, and figuring out how to participate in their family culture.&n...
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