What Could Go Right?

By Erik Orton + Emily Orton

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... more

Download on the App Store

Download on the App Store

Get it on Google Play

FAQs about What Could Go Right?:

How many episodes does What Could Go Right? have?

The podcast currently has 99 episodes available.

What Could Go Right? episodes:

February 22, 2024 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 hesitant to say it out loud even to Tiffani. He had no idea how to make it happen. They signed up for The Navigator Framework Private Coaching in the beginning stages. Today they unveil their epic journey to bring an entire town together including their inspiration, small steps, obstacles, and miracles. Along the way, they reveal how big dreams – whatever your dreams are – come together.
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:
For community building ideas follow Jared and Tiffani Instagram at @neighboring__well
Limited Time Offer - March 20, 2024:
Just $1 for 1 day You get 24 hours of unfettered access to The Navigator Framework on-demand video series we only share with our private coaching clients. Whether you browse or binge, we hope you find some tools to help you live intentionally. For best results, pair with private coaching.
Books:
Seven at Sea: Why a New York City Family Cast Off Convention For A Life-Changing Year On A Sailboat (affiliate link) by Erik + Emily Orton
Knock: The Spiritual Journey of a Door-To-Door Salesman by Erik Orton
Coaching:
Ready to break free from midlife drift and embrace a more intentional journey? Coach with us in 2024. Schedule your complimentary Discovery Call
Adventure:
Warm turquoise water and gentle breezes, Sail with us in 2024
Submit your deposit before March 15, 2024 and get $500 OFF
Connect with us:
Email Subscribe to Encouragement
Youtube Like, Comment, Subscribe
Instagram
Facebook
...more
1h 11min
February 15, 2024 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 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 about Erin and Michael's purpose work The Light In Us here and The Heare Brotherhood here.
Warm turquoise water and gentle breezes, Sail with us in 2024
Submit your deposit before March 15, 2024 and get $500 OFF
Ready to break free from midlife drift and embrace a more intentional journey? Coach with us in 2024. Schedule your complimentary Discovery Call

Email Subscribe to Encouragement
Youtube Like, Comment, Subscribe
Book Seven at Sea: Why a New York City Family Cast Off Convention for a Life-Changing Year on a Sailboat (affiliate link)
Instagram
Facebook
...more
1h 32min
February 08, 2024 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, 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:
Warm turquoise water and gentle breezes, Sail with us in 2024
Submit your deposit before March 15, 2024 and get $500 OFF
Ready to break free from midlife drift and embrace a more intentional journey? Coach with us in 2024. Schedule your complimentary Discovery Call
Download Your Free 100-Year Grid (PDF)
3 Ways to Travel Big as a Family Without Breaking the Bank (FREE PDF)
Email Subscribe to Encouragement
Youtube Like, Comment, Subscribe
Book Seven at Sea: Why a New York City Family Cast Off Convention for a Life-Changing Year on a Sailboat (affiliate link)
Instagram
Facebook
...more
25min
February 01, 2024 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 about sailing with us in 2024.
Submit your deposit before March 15, 2024 and get $500 OFF
Want to create your own family adventure?
Schedule a call to Discover what's possible for you)
FREE Discovery Call
Download Your Free 100-Year Grid (PDF)
3 Ways to Travel Big as a Family Without Breaking the Bank (FREE PDF)
Email Subscribe to Encouragement
Youtube Like, Comment, Subscribe
Book Seven at Sea: Why a New York City Family Cast Off Convention for a Life-Changing Year on a Sailboat (affiliate link)
Instagram
Facebook
...more
19min
January 25, 2024 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 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 about sailing with us in 2024.
Submit your deposit before March 15, 2024 and get $500 OFF
Want to create your own family adventure?
Schedule a call to Discover what's possible for you)
FREE Discovery Call
Download Your Free 100-Year Grid (PDF)
3 Ways to Travel Big as a Family Without Breaking the Bank (FREE PDF)
Email Subscribe to Encouragement
Youtube Like, Comment, Subscribe
Book Seven at Sea: Why a New York City Family Cast Off Convention for a Life-Changing Year on a Sailboat (affiliate link)
Instagram
Facebook
...more
19min
January 18, 2024 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 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 about sailing with us in 2024.
Submit your deposit before March 15, 2024 and get $500 OFF
Want to create your own family adventure?
Schedule a call to Discover what's possible for you)
FREE Discovery Call
Download Your Free 100-Year Grid (PDF)
3 Ways to Travel Big as a Family Without Breaking the Bank (FREE PDF)
Email Subscribe to Encouragement
Youtube Like, Comment, Subscribe
Book Seven at Sea: Why a New York City Family Cast Off Convention for a Life-Changing Year on a Sailboat (affiliate link)
Instagram
Facebook
...more
26min
January 11, 2024 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 connections with extended family.
*Plot Spoilers*
Everything did not go exactly as planned. There were obstacles, tears, and discomfort. In the end, it was more than worth it. What started as an adventure became a new way of life. I think you'll agree this podcast is more than worth a listen. I can't wait for you to meet the Killpacks. Please let me know your favorite takeaways. 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 about sailing with us in 2024.
Submit your deposit before March 15, 2024 and get $500 OFF
Want to create your own family adventure?
Schedule a call to Discover what's possible for you)
FREE Discovery Call
Download Your Free 100-Year Grid (PDF)
3 Ways to Travel Big as a Family Without Breaking the Bank (FREE PDF)
Email Subscribe to Encouragement
Youtube Like, Comment, Subscribe
Book Seven at Sea: Why a New York City Family Cast Off Convention for a Life-Changing Year on a Sailboat (affiliate link)
Instagram
Facebook
...more
1h 7min
January 04, 2024Ep 32 - Pulling Off Their First One Month Family Trip - Brooke + Nathan Schmoe
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 accountability, they navigated challenges and found joy in the journey. They discuss the process of navigating time away from work and paying for the trip, plus the pay off's of how they created new connections with their kids and each other. Brooke says, "We gave ourselves permission to be great."
TAKEAWAYS:
Sharing your dreams and goals with others can create a network of support and opportunities.
Writing down your dreams and referring to them regularly helps keep them alive and guides your actions.
Obstacles and setbacks can become reasons to pursue your dreams even more passionately.
Creating intentional adventures with your family can strengthen relationships and create lasting memories.
Taking risks and pursuing adventures can strengthen family bonds and create lasting memories.
Living intentionally and dreaming big can lead to a more fulfilling and purposeful life.  Creating traditions and making time for family experiences can have a profound impact on relationships.
CHAPTERS:  (time stamps are approximate)
00:00 Introduction and Inspiration
08:15 Setting the Dream in Motion
21:52 Coaching and Overcoming Obstacles
37:12 Embarking on the Epic Trip
41:27 Magical Moments and Personal Growth
42:51 Adventure in a Yosemite Water Slide
45:14 Becoming a Hero to Stella
49:18 Quitting (sort of) the Job to Make the Trip Happen
56:05 Living Intentionally and Dreaming Big
59:08 Future Adventures and Hopes
LINKS:
Learn more about sailing with us in 2024.
Submit your deposit before March 15, 2024 and get $500 OFF
Want to create your own family adventure?
Schedule a call to Discover what's possible for you)
FREE Discovery Call
Download Your Free 100-Year Grid (PDF)
3 Ways to Travel Big as a Family Without Breaking the Bank (FREE PDF)
Email Subscribe to Encouragement
Youtube Like, Comment, Subscribe
Book Seven at Sea: Why a New York City Family Cast Off Convention for a Life-Changing Year on a Sailboat (affiliate link)
Instagram
Facebook
...more
1h
December 28, 2023 Ep 31 - What is a New Year's First?
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 try a new tradition and participate in a New Year's First. If you've never joined us for a free discovery call to turn your "impossible" goals into "inevitable" realities, this could be your New Year's First. After all, what could go right?
Chapters
00:00Introduction to New Year's First
02:23What is a New Year's First?
04:19 Advantages of a New Year's First 05:18Examples of New Year's First
10:55 Invitation to a New Year's First
11:53 Explanation of Discovery Call
13:18 Benefits of a Discovery Call
SAIL WITH US IN 2024 To learn about being crew on one of our upcoming sailing trips, email: [email protected] and tell us which trip(s) you're interested in.
Bahamas (Abacos) - Feb. 12-16. Want to go somewhere warm this winter? Here's a last minute adventure to get you out of the cold and warm the heart of your favorite person. Spend Valentine's Day on a boat in the turquoise waters of the Bahamas. Your special someone will thank you. (8 people max for this trip)
British Virgin Islands - Mar 11-16 - celebrate the end of winter in the warm, lush waters of the British Virgin Islands. The sailing capital of the world, this protected area offers world-class sailing due to the steady trade winds, plus gorgeous water for crystal clear swimming, snorkeling and diving. (8 people max for this trip)
La Paz, Mexico - April 8-13. Want to go sailing AND see the solar eclipse? Come join us in the Sea of Cortez. Watch the solar eclipse on the first day and enjoy crystal clear water and skies for swimming and stargazing the rest of the week. (8 people max for this trip)
Athens, Greece - July 15-20 Explore the ancient world from the water. This trip will sail out of Athens and explore the nearby islands of historic Greece. This trip is almost sold out (1 cabin remaining). (8 people max for this trip)
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 about sailing with us in 2024.
Want to create your own family adventure?
Schedule a call to Discover what's possible for you) FREE Discovery Call
Mentioned in the Podcast: Episode 13 Who Pays For What? (With Adult Kids)
Download Your Free 100-Year Grid (PDF)
3 Ways to Travel Big as a Family Without Breaking the Bank (FREE PDF)
Email Subscribe to Encouragement
Youtube Like, Comment, Subscribe
Book Seven at Sea: Why a New York City Family Cast Off Convention for a Life-Changing Year on a Sailboat (affiliate link)
Instagram
Facebook
...more
17min
December 21, 2023 Ep 30 - 3 Stories About Not Getting What You Want
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 three stories about not getting what you want.

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 about sailing with us in 2024.
Want to create your own family adventure?
Schedule a call to Discover what's possible for you) FREE Discovery Call
Mentioned in the Podcast: Episode 13 Who Pays For What? (With Adult Kids)
Download Your Free 100-Year Grid (PDF)
3 Ways to Travel Big as a Family Without Breaking the Bank (FREE PDF)
Email Subscribe to Encouragement
Youtube Like, Comment, Subscribe
Book Seven at Sea: Why a New York City Family Cast Off Convention for a Life-Changing Year on a Sailboat (affiliate link)
Instagram
Facebook
...more
11min

FAQs about What Could Go Right?:

How many episodes does What Could Go Right? have?

The podcast currently has 99 episodes available.