What Could Go Right? - podcast cover

What Could Go Right?

Erik Orton + Emily Ortonwww.theawesomefactory.nyc
With little experience and even less money, we moved aboard a sailboat in the Caribbean with our five kids. We spent the next year sailing it back to our home in Manhattan. That changed everything. We wrote all about it in our NYTimes Top 10 Travel Book "Seven at Sea." Here we talk about personal growth and sailing. We want to help you live your best life one adventure at a time.

Episodes

Ep 62 - How We Sold Our Sailboat

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 and all the incredible friendships and memories I made with my family living on a sailboat. Today, ...

Jul 31, 202424 min

Ep 61 - DIY vs Who Not How: Finding Balance

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 your hosts: Erik Orton and Emily Orton. We talk about personal growth and sailing. In 2014, with li...

Jul 25, 202434 min

Ep 60 - Collaborating as a Couple - Writing Our Book

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 little experience and less money, we bootstrapped a year on a sailboat with our five kids and it ch...

Jul 18, 202446 min

Ep 59 - How to Grow the Size of Your Dreams

'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 to the What Could Go Right? Podcast. We’re your hosts: Erik Orton and Emily Orton. We talk ab...

Jul 11, 202422 min

Ep 58 - Declare Your Independence

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 freedom. In this episode, we tell our freedom stories to share the spark so you can declare your independ...

Jul 04, 202428 min

Ep 57 - Personal Growth + Sailing

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 help you go from fear to freedom one adventure at a time. Get your power up today.   Welcome to...

Jun 27, 202421 min

Ep 56 - Our Personal Packing List for Sailing Trips

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 most up-to-date packing list for sailing trips and we talk through every item so you don't have to won...

Jun 20, 202442 min

Ep 55 - Navigating the Empty Nest Transition

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 hosts: Erik Orton and Emily Orton. We talk about personal growth and sailing. In 2014, with little exper...

Jun 13, 202424 min

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

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 little experience and less money, we bootstrapped a year on a sailboat with our five kids and it change...

Jun 06, 20241 hr 15 min

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

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 Could Go Right? Podcast. We’re your hosts: Erik Orton and Emily Orton. We talk about personal growth...

May 30, 202438 min

Ep 52 - Tortillas to $200M - Lisa Binggeli

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 her process and finding similar success.  If real estate is part of your adventure, you can fi...

May 23, 20241 hr 19 min

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

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, family connections, and parenting adult kids. The show is hosted by Erik Orton and Emily Orton, creators...

May 16, 202420 min

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

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, family connections, and parenting adult kids. The show is hosted by Erik Orton and Emily Orton, creat...

May 09, 202418 min

Ep 49 - Darling, Let's Be Adventurers

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 plan, purpose, pitfalls, personal patterns for goal-getting, and perspectives from people with more exp...

May 02, 202450 min

Ep 48 - Books, Beauty Pageants and Politics

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 inspired them to stretch and grow as a family, a couple, and as individuals. In 2024, Tiffany stretc...

Apr 25, 20241 hr 16 min

Ep 47 - We Bought An Eco Resort In Belize

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 already overcome. Bookmark this episode and share it with your friends. This conversation is full o...

Apr 18, 20241 hr 24 min

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

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. People gravitate toward you, eager to collaborate and share resources. Custom made opportunities find...

Apr 11, 202418 min

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

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 for Moms and Dads Who Want to Make Midlife Meaningful featuring personal growth, family connections, ...

Apr 04, 202426 min

Ep 44 - Two Takeaways From Our Forties

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 about aging. Then we'll identify some awesome things ahead – when you're willing to live intentiona...

Mar 28, 202421 min

Ep 43 - How to Stop Worrying and Start Living

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?  is a Life Design Podcast for Moms and Dads Who Want to Make Midlife Meaningful featuring per...

Mar 21, 202430 min

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

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 script and transform excuses into stepping stones. This technique is one of the ingredients in our famil...

Mar 14, 202420 min

Ep 41 - How to Let Your Dreams Come True

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 let your dreams (small and big) come true.   What Could Go Right?  is a Life Design Podcas...

Mar 07, 202423 min

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

 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 power of changing your environment to for mental clarity. Most importantly, when it comes to being&n...

Feb 29, 202430 min

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

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 as a backyard apple party turned into something much, much more ambitious. So ambitious Jared was he...

Feb 22, 20241 hr 10 min

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

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 Podcast for Moms and Dads Who Want to Make Midlife Meaningful featuring personal growth, family connectio...

Feb 15, 20242 hr 32 min

Ep 37 - Vulnerable Valentine's Day

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 for Moms and Dads Who Want to Make Midlife Meaningful featuring personal growth, family connections,...

Feb 08, 202425 min

Ep 36 - Midlife Crisis vs. Midlife Quest

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 in mind. If you're ready to design a life you love –Subscribe and Stay Tuned. LINKS: Learn more abo...

Feb 01, 202418 min

Ep 35 - How Adventures Help You Create Lasting Connections

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 adventures you didn't plan.  What Could Go Right? is a Life Design Podcast for Moms and Dads Who Want to...

Jan 25, 202418 min

Ep 34 - Shifting Your Mindset About Money and Dreams

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? Let’s dive in. What Could Go Right? is a Life Design Podcast for Moms and Dads Who Want to Make Midlif...

Jan 18, 202425 min

Ep 33 - Raising Kids and Chasing Dreams at the Same Time - Dreyson + Shaundi Killpack

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. As it turns out, dreams brought them closer as a couple, as a family, and even deepened their connec...

Jan 11, 20241 hr 7 min