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SECOND-ACT SIGNIFICANCE II: Erik and Emily Orton #111

Warwick Fairfax

April 13, 2022

We take to the high seas this week with Erik and Emily Orton — which is where they headed in 2014, after Erik’s dream job as a playwright and theatrical producer came to a crashing halt when his off-Broadway show was closed after only a few performances. The failure left him fearful and rudderless – until his curiosity about sailing became his family’s passion for it and they steered their boat’s rudder on a 5,000 mile journey from New York to the Caribbean.

What Erik and Emily learned on the journey, with their five kids sharing the adventure with them, was how to turn worry into wonder and the importance of building confidence, credibility and calm. Those are truths they now teach others through their speaking, writing  and coaching.
To learn more about Erik and Emily Orton’s family adventures and their coaching services, visit www.theawesomefactgory.nyc

Highlights

  • How Erik and Emily grew up … and met (2:41)
  • Moments from their childhoods when they felt proud (4:32)
  • Erik’s theater career and off-Broadway crucible in his first act (10:30)
  • The dark place they faced after his failure (14:25)
  • The appeal of sailing (18:23)
  • Sailing as a family … and overcoming fear (25:24)
  • How the intermission of sailing led to their second act (33:35)
  • The importance of turning worry into wonder (36:27)
  • Writing a book and launching new careers (43:25)
  • The Ortons’ final message of hope (47:25)

Transcript

Warwick F:

Welcome to Beyond the Crucible. I’m Warwick Fairfax, the founder of Crucible Leadership.

Eric O:

I’d go down to this high rise in the financial districts every afternoon and I’d work 3 till midnight. So I would take a dinner break right around sunset, and I would walk along the Hudson River. I would see these sailboats that just carve their way up and down, silhouetted against the sky.

Eric O:

During my dinner break, that’s when Emily and I would get on the phone and we would talk as we try to figure out how to dig ourselves out of this hole that we found ourselves in. I would describe this to her, and she was happy that I would see these boats and that they gave me a sense of peace. As I described it often enough, I realized that there was a sailing school right downstairs from where I worked, and that’s where these boats were coming from. She said, “You should go check it out. Maybe you’d want to learn how to sail.”

Gary S:

Eric Orton ended up taking his wife’s advice, and it changed their family’s livelihood and life. Hi, I’m Gary Schneeberger, co-host of the show. On this episode of our series, Second Act Significance, we take to the high seas with Eric and his wife, Emily. The high seas is where they went in 2014 after Eric’s dream job as a playwright and theatrical producer came to a crashing halt when his off-Broadway show was closed after only a few performances. The failure left him fearful and rudderless, until his curiosity about sailing became his family’s passion for it, and they steered their boat’s rudder on a 5,000 mile journey from New York to the Caribbean.

Gary S:

What Eric and Emily learned on the journey with their five kids sharing the adventure with them was how to turn worry into wonder and the importance of building confidence, credibility, and calm. Those are truths they now teach others through their speaking, writing, and coaching. Eric and Emily Orton have found second act significance and you can, too.

Warwick F:

Well, Eric and Emily, thank you so much for being here. I mean, it’s so exciting what you’re doing with the Seven at Sea book and The Awesome Factory. Just your journey on the sailboat for a year, I mean, that’s just magical that people only dream about but you do advocate for turning dreams into reality.

Warwick F:

Before we get into what the challenges that set up that year on the sailboat, talk a bit about maybe, as they say in the movies, the origin story of Eric and Emily, and maybe not every beat growing up, but just what some of the backstory of who the Ortons are before we get to the rocks, so to speak, with some of the challenges.

Emily O:

Okay. I love this question. So we both grew up with dads in the military. So we moved around a bit and our paths intersected first just outside of DC when we were still in elementary school grades, but we did not meet there. We met later in college. We were in the same school and that’s where we actually met each other, and right away, we didn’t-

Gary S:

Oh, this is going to be good. I can tell they’re laughing before they say what happened.

Emily O:

I’m like, “I don’t want to drift here. I want to navigate.”

Eric O:

Navigate carefully, right?

Emily O:

We didn’t hit it off first thing, but before long, it became apparent to me that Eric was just a genuine good guy, and that really resonated with me, and I was very interested in him, and he’s so forthright. He told me right away as soon as he heard, “Nothing will ever happen between us, but we’ll stay friends.” I can say we’ve been married for 26 years now and we are still friends. So we were both right.

Warwick F:

Yeah, but it sounds like there is something between you now, right? You’re more than just friends. Would that be a fair assumption?

Eric O:

Sure, yeah. With five kids, I would say we’ve moved beyond the friend stage, for sure. So far so good.

Emily O:

I think we were recently each sharing what was a moment from our childhood where we felt proud. As we were sharing those stories, I feel like that really ties into the core being of who we really are. For mine, it was just that my mom and my grandma had taken me to some boring conference, and I had to wear a dress, and I was nine, and I didn’t care about any of that stuff, but at this restaurant we went to afterwards, I was presented with my first slice of cheesecake. I’d never heard of it. Can you imagine hearing of it for the first time? What a weird concept, cake made out of cheese?

Emily O:

So I was trepidatious, but after I had it I was like, “Wow! That was very small,” that slice of cheesecake and I wanted more. My mom said, “Well, if you can pay for it, you can get a second slice.”

Emily O:

As a nine year old, I’m not carrying my wallet with me. She was basically just saying no, and I just sat there thinking about cheesecake, and I excused myself ostensibly to go to the restroom, but what I had remembered is that there was a wishing well out front of the restaurant. So I walked out of the restaurant. I stepped into the wishing wall and I filled my skirt with coins, and I brought back a pile of wet money.

Emily O:

My mom was aghast that I had done this in front of everyone. She said, “Those are other people’s wishes,” and my grandma came to bat for me and she said, “I bet they wished for a little girl to have a piece of cheesecake.” I got a second piece of cheesecake, but mostly what I think makes me proud of that moment is that I had nothing and I wanted something, and I just figured out what was in my environment to find a way to make it happen. So I guess as far as background on us, for me, that would be illustrative.

Eric O:

I guess the experience for my part that Emily was talking about, because we were running a retreat this past week and the opening question that we asked everyone was, “What’s a moment from your childhood that you’re proud of?” I was stumped until afterwards I was telling Emily, I was like, “Actually, I played a version of baseball as a kid called coach pitch.” I don’t know if it’s still a thing, but it’s between T-ball and regular baseball where-

Warwick F:

Yeah, yeah, yeah. My boys did coach pitch, so I’m familiar with it. Yeah.

Eric O:

Okay. So coach pitch is where the coach actually throws the ball and some kid stands next to him to field anything that gets hit. So my position was actually right field, where the ball never goes. They put me there because I was no good. The kid that was playing pitcher got injured or couldn’t make it. Anyway, so where could they afford to bring somebody in from? They brought me in from right field and I stood next to the coach who’s pitching it.

Eric O:

Then big Dan on the other team comes to the plate. He’s this big. We’re all eight years old and he looks like a 13 or 15-year-old. He’s just huge. The coach pitches the ball and all the outfielders backed up to get ready for his line drive for the fence. He hits this ball and it’s going straight over my head and I’m like, “Okay.” I just put my hand up and I jumped, and I feel it bounced off the tip of my glove and I come down and I turned around and I looked behind me to see how far, “is it a home run or is it inside the park?” I don’t see the ball.

Eric O:

Of course, I look in my glove and it’s there, and I was stunned. Everyone else was stunned. The place erupts. It’s one of those eight-year-old boys’ dreams. I’m just so glad that I went for it, not even thinking I had a chance, but I went for it. It was fun because they did a little write up in the baseball team newsletter and I became the permanent guy standing next to the pitcher, but really, just sometimes you don’t know if you even stand a chance, but if you go for it, you just might.

Gary S:

As a baseball fan, I have to interject. Just one, one little comment. Guess who played most of his games in right field? That would be Mr. Babe Ruth.

Eric O:

What?

Gary S:

So when people say right field is where the balls never hit and the “not good players” go there, Babe Ruth played right field. Just tell them that.

Eric O:

Wow. I’m making a note of that. Thank you, Gary. I had no idea.

Warwick F:

That is so great. Those are wonderful stories. I got to imagine, Eric, for weeks or more after people were saying, “Eric Orton, that’s the guy who got big Dan out.”

Warwick F:

“No, Big Dan? Are you kidding me?”

Warwick F:

Right? I’m sure you’re a legend. That’s cool.

Eric O:

Pretty much, yeah, as much as you can be as an eight-year-old.

Emily O:

Our family visited Germany before borders closed for the pandemic, and he-

Eric O:

This is where, I was living in Germany at the time.

Emily O:

He was living in Germany and he took us to this baseball field on the military base to show all the kids where it happened. So yeah.

Warwick F:

Wow. It also reminds me of the other movie, Field of Dreams. That was your field of dreams.

Eric O:

With Kevin Costner, yup. Me, Kevin Costner, and Babe Ruth, basically.

Gary S:

Hey, there’s a play in that. There could be a play in that.

Eric O:

Totally. Baseball through the ages.

Gary S:

Yes.

Warwick F:

There you go. So I want to move ahead of it, but what I love about that story is they’re both maybe, I don’t know, origin stories but maybe a vignette of what was to come about two people that just went for it, that went for their dreams. So I want to fast forward here, and unfortunately with the pandemic, it’s been harder to go see shows, but I grew up going to plays, and we live in Annapolis, Maryland. So we actually have seen Wicked on Broadway a number of years ago and like everybody, it’s unbelievable. So the fact that you were involved in there and helping to produce it is just unbelievable.

Warwick F:

That’s a lead up to your challenge, but talk about … You obviously love music and producing and the theater. So talk about some of that background and Wicked, and then you went on to get an Emmy award for Berlin. So talk a bit about that period in your life because you love music and the theater. So I mean, that feels a bit making your dreams come true. I mean, it sounds pretty exciting.

Eric O:

It was pretty exciting. Yeah. I studied music growing up and got into musical theater by accident. My friends signed me up for an audition in high school and I went. Anyway, I started doing theater and studied music and was writing in musicals and just started producing them when I was in college, mostly my own stuff.

Eric O:

Then right out of college, I got a job as a junior manager a Broadway show, and we moved to New York basically straight out of college. We got married while we were at school and we already had our oldest daughter was born while we were students, but we moved there with two kids. Our second daughter was born right before we moved there.

Eric O:

Fast fast forward, I don’t know, eight, 10 years, I was managing the national tours of Wicked. It was a pretty dream job. I love the show. Steven Schwartz, who wrote it, was a hero of mine, so getting to work with him. Before I’d accepted this job on Wicked, I agreed to produce this little show called The Arc, which is about Noah and the arc, but it has a modern take on it.

Eric O:

I felt a deep loyalty to this little project of mine, and so I left this really secure and high profile job on Wicked because a secure job in the theater is a contradiction in terms, but I had that yet I walked away with Emily’s support. It was a pretty exciting time because I’d raised the money, I’d hired the director and the designers, and I booked the deal with the theater, and it was extra exciting because Emily was due to give birth to our fourth child, now our first son, the day that this show was scheduled to open.

Eric O:

The show came and opened up and it was a great time. The audiences loved it and we had a big party afterwards. Then Emily, right on schedule, went into labor and gave birth to our beautiful boy. I said to my producing partner, “Hey, I’m going to take a day, 24 hours. I’m just going to go be with my girls and our new son.”

Eric O:

So I went off radar, and while I was in the hospital, the reviews came out and they weren’t amazing. They weren’t terrible, but my producing partner, who is a generation older than me, was doing her best. Without consulting me, though, she made the decision to post a closing notice for the show, which for her meant one thing because she was an established producer and had all kinds of other revenue streams, and for us as a young dad and as a young family, I don’t think she realized that it was everything.

Eric O:

Basically, when I came out of the hospital and found out that the show was closing, I was broke, I was unemployed, and quite frankly, I felt humiliated at this professional failure, and I ended up as the poster boy for failure because there was a picture of me on this roundup article that they had in Crain’s Business New York. I don’t know how many people read that magazine, but it’s a big broadsheet that they print in New York City, and my face was front and center of why the off-Broadway business model was broken.

Eric O:

So that failure put me in a pretty dark place. I was confused. I was scared. Yet, I still had Emily and our kids and I felt the responsibility of providing for them. So I just went and I got a job, any job, which ended up being temping at a bank in the financial district doing graphics at night. That’s our low point. That was where we got into the crucible that I think was a real pivot point for us.

Warwick F:

So Emily, as this is going on, you probably have a mix of emotions. You have a baby boy that’s just sheer delight and gratitude, and you’ve got a husband that was at the pinnacle of success and now is being branded as a failure by Crain’s Business Journal, which I’m familiar with. It’s a big deal. So what was going through your mind as all this was happening and you’re trying to focus on a new little life there? That must have been a sea of different emotions, I’m guessing.

Emily O:

Well, I always say I will always bet on Eric Orton. I know I married him for a reason. I really believe in him, but he needed this space to feel the grief of being disoriented. I actually think it was a huge blessing that around that same time we were able to have this little baby and we have these three sweet little girls, and Eric would just hold him and look at his eyes and be like, “Oh.” It’s just very centering. As much as it inspires you to feel like, “Oh, I need to take care of my family,” your family being there also is a source of comfort and strength.

Emily O:

I’ve heard Eric say to young men considering marriage to say, “Nothing lights a fire under your butt like having a wife and kids. It makes you pretty ambitious,” but no. He was devastated and it was very challenging. I’m just so grateful that we’re able to just talk and communicate. He actually had this unexpected paternity leave where we spent a couple of weeks just saying, “Oh, my gosh! Let me stop reeling and make a pivot.”

Gary S:

As we’re about to pivot into the next bit of your story, you said something to me, Eric, when we talked offline when I explained the nature of our series, Second Act Significance. You actually indicated, and it’s not surprising at all given your theatrical background, you indicated that you called the period after your show closed and you guys were looking for what that next act was going to be, you called it what?

Eric O:

Intermission.

Gary S:

Right. Right. What follows intermission if it’s the first act that has been intermissioned is what?

Eric O:

The second act, yeah.

Gary S:

Right. Yeah.

Eric O:

So yeah, we’re more than happy to talk some more about that, but yeah, we definitely feel like our life is divided into two parts. There was before the sailboat and before everything that led up to the sailboat and everything after it. So for sure, there’s a two act structure going on here.

Warwick F:

So here you were in this, for what I understand, you’re in this hired office building doing a temp job, and I think, what, during a dinner break, you were looking out the window and it seemed like that look out the window changed your life. So just talk about what happened as you were there in that temp job.

Eric O:

So yeah, I’d go down to this high rise in the financial district every afternoon and I’d work 3 till midnight. So I would take a dinner break right around sunset and I would walk along the Hudson river, and I would see these sailboats that just carved their way up and down silhouetted against the sky. During my dinner break, that’s when Emily and I would get on the phone and we would talk as we tried to figure out how to dig ourselves out of this hole that we found ourselves in.

Eric O:

I would describe this to her. She was happy that I would see the boats and that they gave me a sense of peace. As I described it often enough, I realized that there was a sailing school right downstairs from where I worked, and that’s where these boats were coming from. She said, “You should go check it out. Maybe you’d want to learn how to sail.”

Eric O:

I told her that it wasn’t going to happen because here’s what I knew about sailing is that you had to be rich to sail, you had to be well-connected or you needed to grow up around sailboats and have a pedigree. None of which were true from me. Yet, she persisted because we talked every night and-

Emily O:

I just want to say we had this whole system where he would call me on his cellphone, tell me the number of the payphone, then I would call him back on the payphone so that we wouldn’t use up our minutes during his dinner break. I don’t even know if there are pay phones anymore in Manhattan, but-

Eric O:

That was the very beginning-

Emily O:

That’s how we made it work.

Eric O:

Yeah, because we had one cellphone between us and it only had a few hundred minutes and we were just so poor, but then yeah, eventually, we got a phone and so I was able to do these for river walks. It was realizing that there was this school down there and that I could learn about this. That was really the beginning of sailing as a family because we knew nothing. We started from zero, I would say.

Warwick F:

So it wasn’t like, “Oh, I see the sailboat. Let’s go to the Caribbean,” and the vision just happened. It was like a Mount Olympus kind of deal. Yeah. It’s funny because we just did a podcast recently that talks about how visions don’t always happen overnight. There can be little steps. So why sailing? I mean, there’s a lot of things you could do. I mean, why even go to a sailing school? Why even play around with sailboats?

Eric O:

Well, I think, for me, it symbolized the peacefulness, and I guess I’ve always … I used to deliver newspapers as a kid. I don’t know if people remember newspapers, but I used to throw them on people’s doorsteps before the sun came up. So I got to look at the stars a lot. It was this cosmic philosophical time, not every day, but every now and then I would just contemplate my place in the universe, and I always thought about people over the centuries that navigated by the stars. I had this romanticized view of it.

Eric O:

So that plus seeing these boats on the river I just thought, “I need to get to a bigger place where I see things in a bigger perspective and so that my problems will seem smaller.” I think that’s where the idea of sailing…that’s what drew me in emotionally.

Eric O:

I think another important piece was a friend of ours was starting up a life coaching business and we agreed to be her guinea pigs. She sent us these questions that we call blue sky questions. We actually share these questions now when we take people sailing or we do retreats and things like that. Some of them are, “What would you do if you weren’t afraid? What would you if money were no object? What would you do if you knew you would succeed?” and there’s a few others, but I took some time to answer all these questions.

Eric O:

The point of them is to really just to pause fear and to mute it because so often, those feelings work that we have after these failures, they can crush us and they can take out any hope or ability to dream. So we have to just set those aside momentarily when we have no idea how we’re going to pull things off, we don’t have the money, we don’t know if we’ll succeed, and just say, “Set that aside. What would I like to do? What calls to me?”

Eric O:

So when I answered these questions, I wrote down a hundred things, over a hundred. One of them was to sail for a year as a family in, I think, it was in the Mediterranean was where I…spend a year on a boat in the Mediterranean. We won’t get into that right now, but basically, that was the first time I spoke it into the universe by writing it down. Then yeah, it grew gradually from there.

Emily O:

Well, he didn’t tell me that he wrote that in his journal, and I didn’t know he was thinking about it in those terms. I just thought he’s been so devastated and he needs something that’s just fun, some new skill to learn or something like that. So that’s why I was really pushing for it, but he went in and he asked, “So what does it take?” The people were really nice, “Yeah, no problem. We can set you up with the class,” but because of the hours he worked, they didn’t have classes at that time. So he was going to have to bring the class with him, basically.

Emily O:

So he started asking all his friends and coworkers and who else, whoever, if they wanted to … He only needed to find three people, right? There’s eight million people in New York City. So he’s asking around for a couple of weeks and he’s not finding anybody. Then he comes out with this great idea. He goes, “Why don’t you and our two oldest kids take this class with me?” The kids are nine and 11. They’re very excited. They think this is the greatest thing they’ve ever heard, but I don’t really see how this works budgetwise because then now the class is four times the expense and we still have three kids that need a babysitter.

Emily O:

So I tried to play that card first and like, “Well, I don’t really know how we’ll afford it.”

Emily O:

He was like, “I will get a second job.”

Emily O:

Then I finally had to admit to my own fears that I am really scared of deep water. It hasn’t really come to a head up to now. Even though we live on Manhattan island, it just hasn’t been an issue, and I was pretty scared about it. He said, “Look,” he twisted it around and sent it back to me like this, he goes, “You know what? That’s perfect. That’s exactly why you should learn how to sail because then you never have to go in the water.”

Emily O:

I feel like I’ve been had, but no. The kids were excited. At that point, we had started homeschooling our kids, which is a whole different journey, but I cared very much about them having hands-on experiences and concrete experiences. So we went for it. He got the second job. We all went down and we took this class and we learned how to tack and jive and do all that stuff on this tiny little sailboat.

Emily O:

The main thing we learned is that we all get seasick. So that was an obstacle throughout our journey. Then after that class, Eric said, “I thought we’re good,” and he’s like, “Well, we don’t really know if we can do it until we go with no instructor.” So we go with no instructor, but we don’t just say like, “Let’s the four of us go with no instructor.” We bring the whole family. So now we’re adding a six-year-old, a two-year-old and a baby who can’t sit up on her own, and we decide we’re going to try this for the first time in Tom’s River, New Jersey.

Emily O:

As you might expect, we were a spectacle, and other boaters were pointing at us and laughing. Every time we tipped a little, the kids would cry or scream. I’m trying to nurse a baby through two life jackets. The best part of the day is when we were back on land throwing rocks in the water. That was the part we’re like, “Oh, my gosh! We’re never going to do this again. That was rough,” but Eric continued sailing for a couple of seasons with just gathering up friends, whoever wants to chip in we’ll do this.

Emily O:

After a couple seasons, he was a little more confident anticipating what might need to be done and being able to give instructions and just be a really present captain. He said, “You know what? Let’s try it again.” We joined a little sailing club in New Rochelle and we started going out as a family. It was this really beautiful season where every kid had a turn at the tiller, and it’s very different when a kid gets to put their hand on the tiller, the experience that they have. We didn’t get any cell service. So we’re just looking at each other’s eyes and when we’d sing together, we’d talk, we’d just lay around in the sun or read a lot of books.

Emily O:

We did this two, three times a month. I thought we were at the perfect amount of adventure. I never had to get in the water. It was close to home. All that was working out great for me.

Emily O:

Then one day, Eric put his arm around me in our little apartment and he said, “I think the seven of us on a sailboat would be enough universe for me.”

Emily O:

I was like, “Really?” because he has so many interests. He said he wrote down over a hundred things. He’s like, “Yeah. That’s all I want, just the seven of us on a sailboat.” I had all these questions going off in my head about like, “Well, that requires a much bigger boat, a much higher skill level. There’s engines and electricity and water. What if we would get injured or hurt or get in a storm or what about leaving our communities, our school communities or our friend communities?” All of that stuff just it made a traffic jam in my head, but at that time, I didn’t say any of that stuff. I just said, “When would you want to go?” He had an answer he knew because he said, “Emily, we have this really short window of time with our kids and it’s closing, and I would want to do something like this as a whole family before our oldest one leaves for college.” I think she was around 14 at the time.

Emily O:

Maybe living on a sailboat wasn’t the biggest dream of my heart. I was actually pretty scared about it, but what I did feel good about what I heard him saying was our children will have me around 24/7. They’ll have that influence and they’ll get to be with their dad all the time, and I couldn’t think of a greater gift, and then that just dovetails in with, yes, hands-on experience, try new things together, create memories.

Emily O:

I really have this belief that memories are the best investment that we can make because they always increase in value. So we just proceeded from there. For me to just real quickly to face that fear about deep water, we were taking a class in the Caribbean to help us know how to sail these larger boats, and I knew we needed this for just basic safety and survival. In my mind this was not a vacation at all even though it was in the beautiful, British Virgin islands.

Emily O:

The instructor every day would invite the students to go snorkeling at night or in the morning. So when I am sitting there in the cockpit and everyone has gone off and they flippered away to the reef and I’m just there thinking, “Do I really think I can live on a sailboat for a year without getting in the water? What example am I really setting for my kids? I’m telling them one thing about how they can overcome their fears and then I’m sitting here in the cockpit. Who do I really want to be in this world?”

Emily O:

So I just put on a mask and flippers and my heart was racing like crazy, but I jumped in and I just started kicking as fast as I could. I saw this large shape just came across from my right periphery to my left periphery before I could even register what it was.

Eric O:

Jaws was her deepest fear.

Emily O:

Yeah. I know. Sharks. So anyway, I saw it. First, I just saw a shape and a color and then I was like, “Wait. That is a sea turtle. That’s fine,” and then immediately the next thought right behind it was like, “What eats sea turtles?” It turns out I actually could swim faster than I thought originally, and I made it all the way to the reef. It was incredible like Finding Nemo. It was so much different than watching it on TV and being fully immersed in that experience and in that world was such a surprise to me. I was so fascinated that I forgot to be afraid.

Emily O:

So the two takeaways for me were that this was going to be a lot more fun than I thought, that, yeah, we could maybe really do this thing and that I could live in the water like this. The second one was that it changed the relationship that I felt like I had with fear because I thought that was a very sturdy fear. I’d been living that way for three decades, and I just thought it was real. When I kicked the tires like that, it just disintegrated.

Emily O:

So I had to reevaluate all the other fears that I already had. Every time a new fear comes up, I have to say really what other favorites are hiding behind those fears. So for me, that was a real turning point.

Warwick F:

That’s huge. I mean, if you can conquer one of your deepest fears, the fear of deep water, it’s like, “Okay. I conquered my deepest fear. I’m ready for the next one. What could be worse than that?” You had to, I’m sure, face fear economically. It’s like, “Well, how do we afford the boat? In a year, how are we going to get income?” I’m sure you solved all those problems, came up with a plan, and off you went.

Warwick F:

I mean, people listening to this are like, “That’s incredible. I mean, they knew nothing about sailing. They learned about sailing. They learned about how to sail in the Caribbean and take a year off sailing in the Caribbean.” Most people dream about those things, but they never do it. They’re sitting on their deathbed thinking, “Wouldn’t it be fun if …”

Warwick F:

I think of that quote that I’m sure you probably heard of by Thoreau, “They live lives of quiet desperation.” That encompasses most of humanity. They have dreams and they never do it, but you did. So talk about, because that leads into what you do now, how did that year with your family change your life because that intermission, it fundamentally changed the direction of your life in ways you probably never could have imagined.

Eric O:

For sure. I often get asked what the hardest part of the journey was. I think the hardest part was actually when I was taking those walks along the Hudson and Emily said, “You should go check this out.” The moment I stepped across the threshold into the sailing school and said, “Hey, I’m interested in learning how to sail. How does this work?” That was the hardest part. Yes, there would be storms and there would be logistics and there would be all kinds of other problems down the road that we would have to solve, but I think the hardest part of these things is seeing ourselves differently because you’re talking about living lives of quiet desperation.

Eric O:

It’s because I think we often get trapped in our own stories, our narrative of how we think our life is going to play out, and the ability to crack that open and allow other possibilities to come in, and to awaken ourselves to our divine potential, to who we really are in the bigger scheme of things, that’s the hardest part.

Eric O:

For all the day-to-day stuff about what happened on this trip, read the book, we won’t get into all that now, but when we came back, first of all, we’d lived to tell the tale. The thing that got us out there was we had this list of worries that Emily had mentioned initially. They’re logical. They’re reasonable, money, health, safety, community, all that sort of stuff, and walking away from that at least temporarily.

Emily O:

Even our two youngest kids didn’t know how to swim and our youngest daughter has down syndrome and she had all this therapy we were leaving behind, I mean, they were legitimate responsibilities we were taking into consideration.

Eric O:

Yeah. I’m not trying to minimize them.

Emily O:

Yeah. Absolutely.

Eric O:

Yet when we looked at all the things that could go right, there’s the what could go wrong category, and we looked at all the things that could go right, and we thought, “We could see beautiful places. We could gain new skills. We could make amazing new friends,” and that list just went on and on and on. The finite unlikely list of what could go wrong balanced against the ever-expanding and likely list of what could go right. At a certain point, it made it an easy decision because we knew that none of this stuff would actually go right unless we did it.

Eric O:

So we gave up our fear of what could go wrong and were able to step into what could go right. Then to come back from the trip, I was worried about financial ruin, but I had a job waiting for me before we got back because I thought my fear was, “Oh, when you leave and you have a gap in your resume, you don’t ever get hired again.” So I’m going to be lucky to get whatever work I have. My old job wanted me right back. People were actually calling me saying, “Hey, are you looking for work now that you’re back?”

Eric O:

So none of those fears came to pass and it opened my mind to all kinds of stuff in a new way. I actually tripled my income after I came home just because I thought about I moved through the world in a different way. I was less afraid. Really, that mindset shift has led to that period of coming home. Then basically, we worked for a few years to get some money back in the coffers and we were able to find inventive ways, not expensive ways, but very inventive ways and travel the world with our kids for the next five years and basically until COVID stopped all that. So I attribute that change to the mindset shift that happened when we went on this trip, and I’m forever grateful for it.

Eric O:

So to Gary’s point, that’s why the boat was intermission and it just took us into a whole new act where we’ve lived in a new way since, and I’m so grateful for that, that failure, that crucible moment, to use your language, that crucible moment that helped us transform into something that we didn’t think was possible for us.

Gary S:

You’ve talked a lot about worry in what you just said. We have guests fill out a form so that we have the ability to ask smart questions when we interview you. One of the questions that we ask every guest is, “What is a critical action you believe people can take to find hope and healing after a setback?” Your answer to that question hinges a bit on worry. You said turn worry into what?

Eric O:

Wonder.

Emily O:

Wonder.

Gary S:

Right. Why is that so important, in general, for anybody who’s gone through a crucible?

Eric O:

So going back to what we were saying about this what could go wrong question, that’s the worry question, and we all go there. It’s being prepared. It’s preparing for contingencies. It’s the responsible thing that we do as adults and parents and business owners or whatever role we might be in as we prepare for what could go wrong. Yet that’s only half the equation.

Eric O:

If we never ask the question, “What can go right?” I feel like there’s a little bit of intellectual dishonesty there to only ask one of those questions. Both of them are valid. When we ask the what can go right question, we then start to take that same imagination, that same mindset that can spin off into a deeper and deeper dark hole of worry and we say, “Well, what could go right?” and that’s the same process of imagining and vision casting, whatever you want to call it, where you start to contemplate all the positive outcomes, and it’s the same skillset that your mind does where you’re imagining a future and you can use it in a negative direction or you can imagine it in a positive direction.

Eric O:

When we can take that mental ability to worry and we flip it towards the positive, then we’re really able to create in our minds and in our spirits the things that we want to bring into being. I think that was really the shift that happened for us. I don’t know if I’m saying it the way that or if you have anything you want to add.

Emily O:

Well, it’s a more complete picture when you balance that. I think as we were nearing home on this trip, we asked our kids, when we left, they were six through 16, and as we approached home, the older two had turned 15 and 17, they’re wise, and we always counsel with them and we like to see how things are going and get their feedback. So we asked them, “How has this changed you or what are you taking away from this trip?”

Emily O:

Our 17-year-old said, “It hasn’t changed me. It’s made me more myself.” I think that’s what we talk about in the crucible experience. It burns off everything. When you have an intense experience, it burns everything that isn’t really you, that doesn’t really matter, and it shows your true colors more vibrantly.

Emily O:

Then the 15-year-old said to us, “This trip has made me comfortable being uncomfortable.”

Emily O:

Just piggybacking off what our children had said, I said, “You know what, Eric? I think what we’re really taking away from this experience, the real treasure here is three kinds of confidence.” It organically grows out of competence. When you learn a new skill, you’re like, “Wow! I did a new thing,” and then it expands what you think you’re capable of doing, and we did this thing and we learned a whole bunch of new skills and that grew our confidence.

Emily O:

Then the second is credibility. When we do what we say we’ll do, even if we only tell ourself we’re going to do it, it grows our trust and we have learned that there’s a ratio relationship there between the credibility that we have with ourself and how big our dreams are. So we came to trust ourselves more. Our kids believed us that we would do what we said we would do. Other people believed us. I think that’s why Eric was getting those calls like, “Hey, do you want to come work for us? This is a guy who gets things done.”

Emily O:

Then calm, for me, was the most transformative because I come from a line of professional warriors and always trying to put in all the possible contingencies, and what about this variable, and what would we do in that case. This helped me see. As we literally move from island to island to island to island all the way up this chain from St. Martin to Manhattan, 2,500 miles, we did this process over and over again where we’d never been there before, we didn’t know exactly what it was going to be like, and as we got closer and closer, palm trees would emerge. We’d see where we were going to anchor the boat. We’d find the grocery store, see if we needed to change money, all those, the details would fill in as we got closer.

Emily O:

So that gave me this sense of calm like I don’t have to know all the answers before I take off. I don’t even have to know all the questions, but as I move in the direction I want to go, the details will fill in, the path or the answers will emerge, and it’s going to be okay. So we’ve done this so many times now that I believe going forward we will figure it out. So that is really everything under that umbrella of turning worry into wonder is like, “Let’s just get curious about this for a minute,” and I think, grateful.

Warwick F:

Yeah. I want listeners to listen to what Emily and Eric are saying. I mean, this concept of turning worry into wonder, not just looking at the column that says what could go wrong, what could go right, and as you start taking steps of faith, however you want to express it in your inner self or the divine, whatever paradigm you want to look at, but as you trust yourself and you make those steps, it increases your belief. It increases your ability to take a bigger step and another step.

Warwick F:

So one of the things you said, Emily, I believe, I love, and this is all part of the wonder muscle, I think, is I think you said something like this. You develop a friendly disregard for others’ opinions. When you live a life you love, everyone wins. I mean, getting other people’s input is good, but you kind of know when to switch it off and it’s not serving you. So talk about how all of those experiences, all of that wonder muscle exercise led to, obviously, you wrote a book, Seven at Sea, but The Awesome Factory. Talk about how all that dovetailed into your second act.

Emily O:

So as we wrote this book, we came home and everyone was like, “When are you going to write the book? When are you going to write the book?” I’m like, “That wasn’t our intent. We weren’t doing some kind of gimmick trick that we could then write a book about,” but we do know we’re both life long journalers. Obviously, Eric’s written plays, and when I was teaching in public schools, I was an English teacher and we both feel deeply about the power of writing and the power of story.

Emily O:

So we thought, “We’re not really going to have completed this trip until we’ve written about it and processed it and gleaned our takeaways.” So we hoped that we could solidify that, have something to pass on to our children, and if anyone else wanted to read it and it could encourage them to live more deliberately, live a little more boldly, then we were all about that.

Emily O:

So what we didn’t expect as we wrote it was that we were going to reverse engineer this process, which we now call the navigator framework for facing disruption, whether you’re causing it or it’s coming to you. We used all sailing metaphors. That was our experience and that’s what the book is about. So we pulled out those of choosing your own island, having your destination, and there are clues and exploratory time prior to the choosing, chart your course, cast off, navigate out of the harbor, set your autopilot, trust your compass, and then drop anchor, and there are some important parts in dropping anchor as well to rest, reflect, and celebrate on what just happened before you start the cycle all over again, but we recognized it and now we had this map.

Emily O:

So as new opportunities would arise, we would identify them. We’d know where we were. We know where the fear was going to come in, and we’d have our strategies of we need more information so we have a bigger vision, so we’re able to release what we’re clinging to or things like that. We just used it as our own secret sauce to do all these things.

Emily O:

Gary was mentioning at the top of the show traveling around the world. Eric climbed El Cap. We got scuba-certified. We lived in New Zealand for a hundred days just farmsitting and traveling around by RV. We were just so curious. We wanted to take this idea of, “I want to see for myself. I want to go there. I want to touch it. I want to taste it. I want to smell it,” have these experiences with our kids.

Emily O:

Then when COVID hit, we realized this is uncertainty on a massive scale. People aren’t used to facing disruption. We’ve become accustomed to this dance, and we have developed a lot of strategies, and we just didn’t feel like we could just keep these to ourselves and only pass them to our children anymore. We thought we want to start sharing and helping, and just what you said at the beginning, to go from drifting to navigating, just taking this, I think everyone’s having this big shift of saying, “Wait a minute. Am I really where I want to be, and where am I actually going?”

Emily O:

I was like, “This is the perfect moment to just step in and talk about these strategies for being at the helm in your own life, being the navigator in your own life,” and that doesn’t mean you always all the circumstances, but it means you’re always deliberate about the choices that you’re making and which direction you’re trying to head.

Gary S:

You used the phrase drop anchor a little while ago, a few minutes back. We’ve reached the time in the show where I normally say, “The captain’s turned on the fasten seatbelt sign. We’re going to have to land the plane soon,” but come on, we’re talking to people who sail the boat 3,000 miles and a guy who produced plays. So we’re going to either drop the anchor in a bit or we’re going to drop the curtain in a bit. We’re going to do one of those two things, but before we do, I would be remiss in my duties as a co-host if I did not give you, Emily and Eric, the opportunity to let folks know how they can find out more about out the book and more about The Awesome Factory online. How can they reach you guys, find out what you do, and maybe engage with you?

Eric O:

Sure. The book is Seven at Sea. You can buy it anywhere that good books are sold. Theawesomefactory.nyc is our website and there’s information about us, the book, and social media, and all that there. So theawesomefactory.nyc is the best place to connect with us.

Gary S:

That’s awesome. I would say, Warwick, Warwick, you have the last question or two.

Warwick F:

So Eric and Emily, I mean, I just find this fascinating, your story, and your journey, and a couple thoughts in my mind. One is that quote of Thoreau. So many people live lives of quiet desperation. I’m wondering, if you had to re-engineer that quote as people that love English and theater, what would that be? I don’t know if that’s the right approach. I mean, that’s certainly one tack and another would be what’s the message of hope and encouragement you can give to people that are maybe living life in the gray, maybe they’re in that cubicle, maybe they’ve had that financial failure or physical failure or however you want to answer that. What’s a message of hope or a life that’s not a life of quiet desperation, but what’s your hope and dream for people that maybe they’re not fulfilling life, they’re sad, depressed, feel like life is just not the way they thought it was going to be?

Eric O:

I think that’s a very beautiful and compassionate question, Warwick, and I’ll try to do it justice. I’ve been that guy in the gray cubicle as you know, and I’ve been that guy who’s felt just crushed and not feeling like anything that I want in life is happening. I would say this. As Emily and I are fond of saying, “When you live a life you love, everybody wins.” That’s nice if you can get there. How do you get there? I think it starts with what Emily was talking about earlier, which is how do we build these three kinds of confidence in ourselves? It starts with little things.

Eric O:

If I say, “I’m going to go for a walk every day,” and then I get it up and I put my shoes on and I go for a walk every day, I’m going to feel better about myself, and when I start to feel better about myself, I’m going to start to make better decisions. I’m going to start to see the world differently, and it can be as some something as simple as I’m going to go for a walk every day or I’m going to eat an apple instead of a candy bar, whatever it may be, but if you do it, your confidence grows and your light starts to brighten.

Eric O:

I think what I was saying earlier, which is the hardest part of this journey for me was seeing myself differently, if we can invite light in in all these different ways and illuminate our view of ourselves, and the world, and God, whatever that means to you, if we can invite that light in and have that fresh perspective, that’s what ultimately leads to living a life that we love, and when we do that, everybody wins. We win, our spouse wins, our colleagues win, our kids, everybody. So it starts with seeing ourselves differently.

Emily O:

I would just add to that making space, like Eric said, for the light. He was talking to a coworker once when he was in the gray cubicle place, and this other guy, he was in a similar place in his own life. This was for him also a holding pattern after a fail. He was telling about all the things he’d done in his past and Eric said, “What are you doing here?” That really woke him up to his capacities, and he just realized, “I’ve been in sleeper mode here, and I have stopped taking responsibility, and I’ve stopped even listening to my own thoughts.”

Emily O:

So the single change that he made is that he stopped listening to music while he has a default mode to just put something in his ears to distract his brain, and he started giving himself some quiet so he could listen to his own thoughts. Lo and behold, he started having all kinds of ideas.

Emily O:

We would be remiss if we didn’t actually say that for us, when you’re in that place where you just feel stuck, we’ve found gratitude to be transformational, and when we first got engaged, Eric mentioned we were pretty young, but the first thing we did is we got a piece of paper and we wrote a list of all the things that we would always have control of no matter what our external circumstances were.

Emily O:

One of the things that we put on that list is that we could always be grateful. We decided early on that if we tried gratitude and that didn’t help, then we would know we were in real trouble. We’ve been married for 26 years now and so far, gratitude has always helped us get a little inch up and get a better perspective on what’s going on and helped us see, “Yeah, we have more to play with here than we originally thought we did.”

Gary S:

I have been in the communications business long enough to know when the last word on a subject has been spoken. So the anchor is down, the curtain’s down. You can get off the boat or you can leave the theater, however that works for you, listener.

Gary S:

Before we go, I have to tell you, Eric and Emily, I love reading the things that you wrote in the form that we had you fill out. I love looking at The Awesome Factory website. I love talking to you beforehand and here because I’ve written a bunch of notes down. Listening to you guys speak about what you’ve been through is like following around and grabbing paper and stuffing it in your pockets because you have so many good perspectives and the way that you phrase them can be so compelling and so beautiful.

Gary S:

There’s one thing that you said that I want to leave our listeners with, not just listeners to Beyond the Crucible, but for this series on Second Act Significance because you said this, which I think could be my background in entertainment comes from the movie business. So the log line for this series could be this. How can you live deliberately doing what you care about most with the people you care about most? That’s something that you said. I’ll say it again, listener, and as you look to move beyond your intermission to your second act, have this question in your mind, “How can you live deliberately doing what you care about most with the people you care about most?” because that is a recipe for second act significance.

Gary S:

Until we’re together the next time on Beyond the Crucible, listener, thank you for spending this time with us, and please remember that while your crucible experiences are difficult and painful, we know that, the Ortons certainly know that, Warwick certainly knows that, those crucible experiences are not the end of your story. In fact, if you learn the lessons of them, if you recognize they’re not things that happen to you but things that for you, you can begin a journey. Doesn’t have to be on a sailboat, but it can be. You can begin a journey that leads to a better end to your story, a better place for your compass to point you because where that takes you is to a life of significance.