What Could Go Right? Overcoming Fear with Erik and Emily Orton

Hey Friend!

Ever ask yourself the question, what could go wrong? My hand is raised with you. It is easy to default to fear when stepping out into the big God assignments in our online businesses, especially after facing the first road bump or failure. Could there be another question we could ask ourselves to overcome fear?

Instead of asking what could go wrong, my special guests started asking themselves the question, what could go right? When I met the incredible Erik and Emily Orton at a speaking engagement, the question they asked themselves to overcome fear inspired me. I wanted them to come and share their inspiring story with you. They went from broke to sailing for an entire year with their family of five. Erik is an Emmy Award-winning writer and producer. Emily is an educator, author, and public speaker. They continue to travel the world by charting others on their sailboat.

From their own life’s journey, they create an incredible framework to fight fear that inspired me, and I wanted them to share it with you. If you want to step out of fear and into faith and pursue your big God assignments for your online business, podcast, coaching, or course creation, this conversation is for you.

ERIK AND EMILY ORTON’S STORY

Stef: Let’s start with your story. Tell us who you are and what you do.

Emily: I’m Emily, and this is Erik. We have five children, three of them are adults with one just ready to launch, and a teenage daughter at home. She has Down syndrome and keeps us young. She is into everything and completely fearless. Where our story begins, we had three little girls, a toddler, and a baby who had recently been diagnosed with Down syndrome.

Erik: At the time, I was reeling from a business failure. We lived in New York City when I left working in the theater industry to produce my own show. This show went belly up and I lost it financially.

I was too embarrassed to go back to the theater industry, so I got a temporary job in the financial district of Manhattan. This led us to sailing even though we weren’t sailors before that. After many months, I realized that there was a sailing school downstairs from where I worked.

I had been telling Emily about my evening walks around beautiful sailboats that I would see, and how peaceful it was at this completely turbulent, disruptive, discouraging time in our lives. Sailing to me felt like standing on the outside looking through the glass at a candy store. No matter how much it intrigued me, I felt like I couldn’t do it because I didn’t know anything about sailing.

Even though Emily felt I needed this in my life, I thought sailing was for rich, well-connected people. It couldn’t be for us because we were broke. We didn’t have any money.

Emily still encouraged me, and I finally walked into the sailing school. I said, “Hey. I don’t know anything, but I’m interested. How does this work?” That was the beginning of a really big journey that continues to this day.

OVERCOMING FEAR TIP #1: BE WILLING TO SEE YOURSELF IN A NEW WAY

Emily: I know it was the beginning, but Eric often says it was also the hardest part. Crossing that threshold into being willing to see himself in a new way. And I feel like so often on our journey, whatever it is, a thing that calls to us also scares us.

From there, he asked the entire family to learn how to sail with him which was really scary for me because I was afraid of deep water. It was a huge phobia for me. I didn’t even want to get on the boat; I just wanted it for him.

But the kids were excited! So we did it. We took the class, and then we went out as a family which was a horrible experience. It was a hot mess with our crying toddler and crying baby. It was awful.

From that tumultuous start, a seed was planted. As we got a bit more experience, especially Erik, he continued to sail for a couple of seasons inviting friends to join in. And then he felt ready to bring the rest of us back on board. So we started sailing together as a family in the Long Island Sound. I thought, This is amazing. I’m so adventurous. I’m getting out on the water.

I never got in the water, but sometimes the kids would. It was a great way to connect as a family and get out of the city away from phones. Then one day, Erik said, “I think the seven of us on a sailboat would be enough universe for me.” What he meant was that he wanted to live aboard for a year.

I thought of all the reasons why living abroad on a sailboat wouldn’t work and everything that could go wrong. What about our daughter’s diagnosis, doctors, and our community? We were homeschooling, but I just didn’t know how that was going to work let alone how to pay for it. Not to mention that we didn’t even have the skill set because the boats were big and had engines, electrical systems, and plumbing. It was a whole other level, exponentially more complicated than what we have been doing on these little twenty-foot sailboats in the Long Island Sound.

OVERCOMING FEAR TIP #2: FIND A BIG WHY

Emily: So I said, “When would you want to go?”

Erik: I want to go before our kids leave for college. The window of time that we had with our kids was closing, and it wasn’t coming back. Our oldest was fourteen at the time, and so we figured if we did it by the time she was sixteen, that would be about right. We had an abstract idea that became a thing with a timeline and a really big why.

Emily: We had to hustle because if we wanted to get this skill set and get ourselves together and get out before our kids started leaving, we had to move. I was far more inspired by being together as a family and having experiences that would bond us than I was about the actual day-to-day being on a boat or what location we were in.

We set sail when our oldest daughter was sixteen. We got on a boat and we sailed for a year, and it was intensely beautiful, challenging, and refining. Having a really compelling why helps lessen fear.

OVERCOMING FEAR TIP #3: PICTURE YOURSELF AS WHO YOU CAN BECOME

Stef: Wow. The first thing that comes up for me is being open to opportunities that God places before you, such as Erik seeing the sailing shop and wanting to sail while having all the limiting thoughts that we carry around keeping us from taking the first step. You would never be here doing what you do today and taking people on sailing trips if Erik had leaned into the limiting beliefs of I don’t know anything about this. We need money to do it. How did you overcome the stories and the narratives that you had about the opportunity in the first place?

Erik: That’s a tricky one. If you can figure out how to see yourself in a new way, as a successful entrepreneur or podcaster, even though you’re not that person yet, you can overcome limiting beliefs. At the start, everything that feels like a successful entrepreneur are the attributes and qualities and accomplishments of other people. So how do you feel a sense of ownership or have a place at that table without having been there before? That’s the challenge for all of us when we’re trying to do something that feels beyond us.

I remember feeling so defeated when I think back to where we were because it was such a hard thing. Emily was home with the kids. Living on a sailboat was like the equivalent of going to the moon. It felt completely impossible. In hindsight, the thing that I love about it now is that we have to have that big of a vision. When we do, we give God space to show up in our lives.

If we think small, He has a very narrow window to enter and perform miracles for us. But if we have a big vision with no idea how it’s going to happen, He has space to work. He can come rushing in. I was reading self-help books and I was trying to pick myself up and start again from nothing, but I knew that if I was going to grow back up again, I wanted it to be amazing.

Stef: I love that. You said to see yourself in a new way. That’s what I did. I wrote on a piece of paper all the things that I was going be. I had a new vision that was in partnership with God, and it was big. Start to see yourself as that future vision of who you can become and then let God make the how.

I also like that you brought up a seat at the table. We believe that we don’t have a seat at the table just because we haven’t had one there before. It’s such a limiting belief and it’s such a lie. I had someone speak life into me once and say, You have a seat at the table. Pull up a chair.

 
OVERCOMING FEAR TIP #4: DON’T GIVE UP EVEN IN DISASTER

Stef: You told us your first trip was tumultuous. Isn’t that the case when we chase big, audacious, impossible dreams? The first time we try, 99.9% of the time, it’s going to be a mess. How did you not give up after that first disaster? How do you hold on to the dream when the first try fails?

Emily: We learned how to sail, and we had an instructor on the board with us the whole time. This was a scouting trip or a baby step toward our sailing goal. Then we thought, What’s the next step? The next step was to go on the same tiny boat but with no instructor, and see how we did on our own. We did not do great on our own.

Erik: Disaster is the word that usually comes up when we talk about this.

Emily: I often hear people say things like there’s no growth in the comfort zone. I push back just a little bit on that to say that when we go out of our comfort zone, we can’t just immediately survive in that environment forever. We go out. We breathe a little bit of that higher-elevation air, and then we come back to our comfort place and say, What just happened? What do I make of that? Reflect on the experience. We did it. Nobody went overboard. We went out, tootled around, and made it back. It wasn’t pretty in the middle, but we actually did it. Each time we went sailing, we got better and better at it. The more you keep at it, you learn what isn’t working. You make adjustments, and it gets smoother and smoother.

If something goes wrong right out of the gates, you might say, God’s not in this. But I like to think that what you’re willing to overcome shows your character more than what you actually achieve. Sometimes it’s just a little test to see how serious we are. Are you willing to go through hard things for what you hope might be on the other side?

Stef: I can attest to doing the thing, taking the baby step, and then stepping back and evaluating. Then doing it again. Everything in my business has been that way. Try it once, see how it did, evaluate, tweak, and do it again. That’s how any big God dream should go, so thanks for sharing that.

OVERCOMING FEAR TIP #5: KEEP YOUR VISION CLEAR BY TALKING ABOUT IT

Emily: Sailing got better and better for us. Even when Erik brought up the idea of living on a sailboat together as a family, despite my fear, I kept getting a gentle press on my heart like a little Post-It notes that God was saying, This is good. This is going to be good for your family. It’s good that you’re doing this.

There were no details, no big vision about how it was actually going to work, only You’re moving in the right direction. I feel like we co-created the vision with Him. You know the scripture in Proverbs 29:18 that says where there is no vision, the people perish. I love to say that where there is vision, the people thrive.

We got vision partly by just speaking it and making space for it. Then we started looking for mentors because we wanted to see who else was sailing year-round. While our trip wasn’t going to look like theirs, we started to piece together what it could look like. God was helping us know what it could feel like and what good could come from it.

If you want to take a risk, make it as clear and concrete as you are capable of making it in order to diminish your fear. The clearer your vision, the less you fear.

OVERCOMING FEAR TIP #6: TRUST GOD FOR PROVISION

Stef: Erik lost his job, income wasn’t coming in, and you want to start sailing. Where did provision come from? Did God show up for you financially and provide as you were led in this very interesting direction that probably didn’t make sense to you? How did you support your five children?

Erik: Yes, and I’ll tell you how. It was a long road. I got a temp job that paid enough.

Emily: I want to say that the same day the show opened, I went into labor with our fourth child. While we were in the hospital, the show closed. It was a surprise that Erik’s partner made this decision solo, and we had to deal with that.

Erik: I was feeling the heat, so I got a temp job that was barely enough to cover our needs. However, they liked me and wanted to hire me on full-time. I became a contractor which was great.

As for the selling lessons, we still couldn’t afford them, so I picked up extra work back in the theater industry. I humbled myself and went back to work for one of my former employers to get enough money to pay for the classes since I was paying for four of us. Things worked out. We made investments that sent us money every now and then and it all pieced together.

As for the cost of sailing, I couldn’t afford that either, so I asked friends to chip in $25 to cover the boat, gas, and tolls so I could sail for free. It was a hobby that paid for itself.

Our financial journey from the show closing and being at zero to now living on a boat was an eight year journey (2006 to 2014). It didn’t happen fast, but it did happen. In it all, we felt provided for and our children always had what they needed.

Stef: Exactly. The reason I ask that question is because often the big God dreams don’t make sense financially. We often hold back from doing the big God dreams out of fear that the provision is not going to be there. I wanted people to hear the testament that you were provided for. That’s the goodness of God.

OVERCOMING FEAR TIP #7: ASK YOURSELF WHAT COULD GO RIGHT?

Stef: There was a pivotal question, Emily, that you began asking yourself as you go closer to your first trip out that got your mind ready. That question was What can go right? Talk to us about that because that question has stayed with me. I’ve asked myself the same question since hearing your story, and it’s helped me say yes to opportunities that I would have been afraid of. Where did this question come from, and how did you start bringing it into your life? What has that question meant to you through this journey?

Emily: I believe the question was inspired through the entire journey as much as we would get little feelings or inclinations that this is the right direction. While I felt that sailing could be great for us, I still felt fear. We noticed fear was strong right at the beginning of the journey. As we got closer to actually accomplishing our goal or achieving what we’ve set out to do, fear got intense.

For us, we always moved forward toward sailing, and the whole family was on board. We talked about the vision over and over again. Every time we sat down together as a family for a meal, we talked about it, creating it in our minds. We kept casting the vision. When we got cold feet, the kids talked about it. When they got cold feet, we encouraged them. It was a dream that was far bigger than just us. It was big enough for the whole family. When we started looking at boats and imagining living on one, it was fun and games until we finally got serious and started putting offers on boats.

I remember being so nervous when we put in the first offer. And the greatest thing happened! They refused our offer, and we said, What a relief! We don’t have to do it, but we tried. We tried. But then we made another offer, and it was accepted. That was so terrifying to us. They said yes. It’s all great when you’re doing your part and trying, but when it actually breaks through, now it’s time to be brave.

The finances and all the money it was going to cost was a symbol of our commitment. I know Erik got scared again at that point. We didn’t feel like we could afford to go see the boat so we hired someone local to do a survey for us. And we questioned, Are we really going to wire this money to an offshore account for a boat we’ve never personally seen? How stupid are we? This could be awful. A whole list of everything that could go wrong just came right back in full force.

So then I thought, What if we think about what could go right? So we made a column of what could go wrong and a column of what could go right. The column of what could go right got longer and longer with incredible and amazing things such as: the experiences we were going to have, how we were going to grow as a family, the confidence we would build, the places we would see, and everything that we would do together. This what could go right list made us feel like we could not afford to miss it.

Had we only made a what could go wrong list, it would have been dishonest because it was only looking at half the picture. Not only that, as we read scriptures, the Lord says to not fear. We felt chastised because we were not keeping that commandment. We were scared and not of good cheer. Making a list of what could go right helped us move into a cheerful mindset. It was hopeful and gave us stamina to move forward.

Erik: I’ll just add that once we knew that if we didn’t go sailing and if we didn’t buy the boat, everything on the what could go right list was for sure not going to happen. We would definitely miss out on that. That’s when we said, “We have to go because it would be silly not to.” That’s what asking what can go right did for us.

Stef: Answering the question what could go right on your paper with all the things you wrote down, I would bet money that after you guys did this and you came home, there was more things that went right than what you even projected. I bet there was more connection and deeper relationships with your kids and in your marriage, more friendships, more breakthroughs, and growth in your abilities within yourselves. I bet it was infinitely greater because you took that faith forward risk.

Erik: Absolutely. It has turned out way better than we imagined. We are still in touch with the friends we met ten years ago which was not on my list of what could go right.

Emily: Our what could go right list gave us new vision and took blinders off because suddenly we started seeing that opportunities were constantly flowing. We just had to reach out and pick them up. It truly was life changing. It also completely changed our relationship to fear.

OVERCOMING FEAR TIP #8: BE BRAVE FOR FIVE MINUTES

Emily: I think of how I overcame my fear of deep water. In one of our sailing classes on a larger boat, I was only there to learn how to not die when we went sailing as a family. I was a supportive wife but really didn’t want to die.

Every morning, the instructor took the other students out snorkeling. One day, we anchored in a lagoon and everyone went snorkeling over to the reef while I sat evaluating Who do I think I am? Is this the kind of example I want to set for my kids? They see their mom never getting in the water because she is too scared. So I decided to try to be brave for a few minutes, not forever, but brave for five minutes. I put on a snorkel mask and flippers and got into the water. I started swimming, and the first thing I saw was a huge shape that went right past me! Of course, my brain immediately thought it was a shark. But it was just a green sea turtle. It was really cool and beautiful.

I got scared again. So I swam as fast as I could, singing myself little Sunday school songs on the way, and I arrived at the reef. Immediately, a rainbow fish was smiling at me, and I became so fascinated. It was just like being in Finding Nemo with the colorful fins, different colored coral, all the fish, the sun, and the little sounds the fish make underwater when they’re tapping away at the coral. Everything about this experience was so unexpected and beautiful and enchanting that I forgot to be afraid. When Erik tapped me on the shoulder and asked if I wanted to swim back, I said, “No. This is my new favorite thing.”

I started asking what other favorites are hiding behind my fears? What you are afraid may be calling to you because there is a new favorite hiding behind the fear. Now I was so much more excited to go on this trip. I was a much better leader unified with Erik ready for the journey. Now when things scare me, I think of it as a flag letting me know there’s something here for me. I need to push into it a little bit.

Stef: That story is the biggest thing that hit me when I first met you. I want to highlight that you said you got brave for five minutes. I think that’s so it. How can we tell ourselves that we can do hard things for five minutes? What we often find is we forget to be afraid.

I also love that you said there is a favorite behind your fear. I love that so much. And what could go right? Ask yourself that question anytime resistance comes up. What could go right? And maybe there’s a favorite in here.

HOW TO FOLLOW ERIK AND EMILY ORTON

Stef: This has been fantastic. I love your story. I’m so excited for you that you get to do what you love as your work now. God is moving through both of you in such incredible, mighty ways, so keep sharing and showing up for the work that you do. If people want to learn more from you tell where they can come connect with you.

Emily: Our book called Seven at Sea, Why a New York City Family Cast Off Convention for a Life-Changing Year on a Sailboat can be purchases on Amazon and at Barnes and Noble.

Erik: Our website is Awesome Factory. We are on social media and our podcast is called What Could Go Right? I just have to say, we resisted podcasting for a long, time and now it’s a favorite thing that was hiding behind our fear. We started a little over a year ago and have sixty-seven episodes. Emily and I have a lot of fun with the podcast.

Stef: I love it. You guys are awesome. Thanks for being here.

I pray this blesses you!

Xo,

Stef

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