What Could Go Right? How One Family Turned Fear Into An Extraordinary Legacy
When was the last time you caught yourself saying "someday"? You know - someday we'll take that big trip, someday we'll start those family traditions, someday we'll document our family stories. For Erik and Emily Orton, "someday" was comfortably far away until their daughter asked a question that changed everything: "Do you really have the guts to do it?"
That simple challenge forced them to confront an uncomfortable truth - they were letting fear write their family's story. Their dream of living on a sailboat with their five children seemed impossible, overwhelming, maybe even irresponsible. But instead of just listing everything that could go wrong (which, trust me, they did), they asked a different question: "What could go right?"
The Power of Possibility
"The negative things are very unlikely to happen. They almost never happen, and it's a huge drain on your energy. But the positive things - so many of those happened, were likely to happen, and sometimes even better than we had ever imagined."
As I listened to Erik and Emily share their journey from Broadway professionals to sailing novices to intentional legacy builders, I couldn't help but think about how many of us let fear keep us from writing the stories we want our descendants to tell. We wait for perfect conditions that never come, forgetting that even in a storm, we always have choices about how to respond.
Choosing Your Direction
"The circumstances in all of our lives are always going to be changing. But if we can choose our destination, if we can be patient and determined and develop some skills... you can still travel in the direction that you want to go. Just like navigating ocean currents, we can't control everything in our lives, but we can choose how we respond and where we ultimately want to arrive."
What started as a seemingly impossible dream - moving their family of seven from a stable life in New York City to living aboard a sailboat - became a masterclass in intentional story crafting. But this isn't just about sailing. It's about the legacy we create when we choose to face our fears and document the journey.
From "What If?" to "What Could Go Right?"
One of the most powerful moments in our conversation came when Emily described their pre-journey process. Like any of us facing a big change, they first listed everything that could go wrong. It got dramatic - financial ruin, family shame, having to separate their children. Sound familiar? It's that same voice that keeps us from starting our family history research, from asking elderly relatives difficult questions, from making changes that might disrupt our comfortable routines.
But then they did something remarkable: they made a list of everything that could go right. This simple shift in perspective changed everything.
"Sometimes we'll literally write out all the excuses that I'm making and then we rewrite the sentence as that's the reason why I should do this."
The Whole Story
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🎧 Listen to the full episode to discover:
- How their daughter's challenge transformed from "someday" into reality
- The night they literally had to turn their boat into a storm to survive
- Why being "comfortable being uncomfortable" became their family motto
- The simple monthly practice they use to document their family's story
- How their children are carrying these lessons into their own families
The Power of One Story
What strikes me most about the Ortons' story isn't the sailing adventure - it's how they've intentionally crafted their family's narrative. Emily shared that one reason they wrote their book was because "when people know that their ancestors were resilient, it helps them be more resilient." They understood that their choices today would become tomorrow's family stories.
Your Story
Think about the story you're writing right now. What would happen if you started asking "what could go right?" instead of just worrying about what could go wrong? Whether it's finally diving into those DNA matches, starting family storytelling traditions, or making a bold life change, you get to choose the narrative.
Story Seeds 🌱
Plant these conversation starters and watch your family stories grow.
- "When you look back on your life so far, what's something you're really glad you had the courage to do, even though it scared you at first?" (Perfect for asking parents or grandparents, helping them share stories of resilience)
- "If we could do anything together as a family next year, without worrying about whether it was practical, what would you want to do?" (Great for asking children or grandchildren, opening up conversations about dreams and possibilities)
- "What's a family tradition you remember from your childhood that made you feel especially connected to our family?" (Ideal for asking aunts, uncles, or older relatives, exploring how traditions create bonds)
- "When you think about telling your grandchildren about this time in our lives someday, what do you hope they'll know about us?" (Wonderful for asking adult children or siblings, encouraging them to think about legacy)
Story Sparks 🔑
Unlock your family's hidden stories with these research techniques.
- Look for instances in your family tree of times when ancestors faced fears and chose to take bold steps or make brave choices. In Ancestry, mark their profile page with a custom MyTreeTag (maybe called “What Went Right”) so you can find them again. And, be sure to look for patterns in families.
- Use the Notes feature in Ancestry to write up a narrative about what happened in your ancestors’ lives. Be sure to record not just what happened but how your ancestors chose to respond to life's challenges.
- Start a monthly family update, following the Ortons' practice of posting a blank paper and letting everyone add memorable moments. Then, snap a photo and upload those to your profile in your Ancestry family tree to preserve them for future generations.
Emily reminded us that "you always have a choice." Whether you're facing literal storms or metaphorical ones, you get to choose how you'll respond. And those choices - both the daily small ones and the occasionally big ones - become the legacy your family will carry forward.
About Erik and Emily:
Erik Orton is an Emmy Award-winning writer and producer. Emily Orton is an educator, author and public speaker. Their life design framework mutes fear and accelerates growth. They are parents to five adult children, including their youngest with Down Syndrome. They raised their family in upper Manhattan for 23 years where Erik worked on such shows as Wicked, Les Miserables and The Phantom of the Opera. When their kids were 6-16 years old, Erik and Emily bootstrapped life aboard a fixer upper sailboat in the Caribbean. They sailed as a family from St. Martin back to New York City. Their memoir about the experience (Seven at Sea) is a New York Times Top 10 Travel book. After life on the boat, they continued to travel the world with their children through Europe, the South Pacific, Africa, and across North and South America in planes, trains, boats and vans. They are the co-founders of The Awesome Factory, a coaching and travel adventure company that leads retreats and sailing adventures all over the world.
Find Erik and Emily at: https://www.theawesomefactory.nyc/
Read their book: Seven at Sea
Listen to their podcast: What Could Go Right
Ready to start asking "what could go right?" with your own family story? Subscribe to Stories That Live In Us wherever you get your podcasts. And if this episode inspired you, please leave us a rating and review - it helps other family story seekers find us.
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