How Courage Leads to Happiness With Scott Simon

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Happiness entrepreneur Scott Simon joins us today as he talks about the connection between courage and happiness. Scott shares the value of doing things that scare you to ultimately bring satisfaction to your life. Scott has also given a TED talk on the topic, as well as authoring a book called Scare Your Soul. Scott has also founded what he calls a Happiness Incubator to help people get the most out of their lives. Tune in to today’s episode and learn how to be brave and happy at the same time.


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How Courage Leads to Happiness With Scott Simon

It is my honor to introduce my guest, Scott Simon. He is a Happiness Entrepreneur, a speaker, and the Founder of Scare Your Soul. It is a movement inspiring individuals to embrace global change through small acts of courage. He has spoken around the world, motivating people at schools and companies. He has given a TED Talk, co-founded happiness incubator, and studied and worked with international thought leaders in the areas of courage and happiness. It's a great combination.

He is a high-performance coach focusing primarily on creating flourishing lives, post-divorce, leads mindfulness meditations, and has served as an officiate of numerous weddings. Scott is the proud father of two children, and when not out fulfilling his sense of wanderlust. He lives in Cleveland, Ohio. Scott, I'm thrilled and honored to have you and welcome you to the show.

Thank you. I appreciate it so much. It’s good to be around the campfire with you.

It's such a beautiful intro in terms of when I look at your bio and get a sense for who you are as an individual. There are many elements of what you are now. I'm looking forward to understanding the journey that got you to where you are.

Journey is the perfect word. We're all on it and mine has been a bit of a rollercoaster. I look forward to discussing it with you.

For a little context, what we do in the show is share people's stories through what's called Flashpoints. These Flashpoints are moments in your life that have revealed your gifts to the world. As you are sharing your Flashpoints, we'll stop along the way and see what themes are showing up. In a moment, I'm going to turn it over to you, and you can start wherever you'd like to start. It could be your childhood or a moment that is more recent, and we can play with time. We can go back and forth whatever feels most comfortable to you. With that, please take it away.

I'll start with a Flashpoint that was critical for me in opening up a door and a path for me that has been the most important in my entire life. That Flashpoint begins in fourth grade. I feel like you and I are sitting around a campfire, and I'm telling you a story. The story is the following. I was a ten-year-old, very shy and short boy. I was bullied by two boys in my school who would spin me around in circles and send me off into the bushes. When I was young, even though I came from a great family, very affirming and wonderful, I wanted to be invisible.

That feeling got even deeper in fourth grade when I was part of a choir practice. I don't know if your readers remember being in a school choir. If you can imagine yourselves walking onto those risers, it was all by height. The tallest people went first, and the shortest people went last. I was the last person. I got on the riser, and we were preparing for our holiday concert. There was an extravaganza.

It was the song Seventy-Six Trombones from The Music Man. My substitute choir teacher had given me this little solo line. I was already shy, quiet, and short. I was on the far left-hand side of this riser. Each time that the choir got around to me, and I was about ready to sing this solo line that he gave me, I choked up. Each time, he looked at me with a glare and then started over again. The entire grade had to start over again just because of me.

On the third time, I literally choked. I could not even get out a syllable. I was turning bright red and he stormed towards me and said, “You have a terrible voice. Why don't you just mouth the words for the rest of the year?” I did not sing again for 35 years. For 35 years, at every concert I went to, I mouthed the words. Every time I was at a party and people were playing music, I mouth the words. He silenced me for 35 years.

Here's my next Flashpoint. After an epiphany I had on an airplane that made me a fear chaser, after meeting a professor at Harvard who taught me the Science of Happiness, I decided that I was going to remove that demon from my shoulder and I was going to sing yet again. After 35 years, I went to a busy restaurant on a Sunday morning.

It's a brunch restaurant that is popular and people are spilling out in front of the front doors they're waiting to get in. I brought an acoustic guitar with me and I sang in front of this group of strangers. It was one of the most terrifying moments of my life. When I started, everyone looked annoyed. They looked, “Who is this guy? Why is he singing? He clearly does not have a good voice,” but somewhere in the middle of it, I found this peace, power, and sense of freedom.

When I finished and they all applauded, I put my guitar back in the case, walked back to my car, and I had a feeling inside of me that I have never felt before. It was this feeling of freedom. I wrote a Facebook post about my experience, encouraging other people to push their comfort zones and to do something the following week that would move them in the way that this moved me.

That post went viral. It was shared hundreds of times around the world. That was the beginning of an organization called Scare Your Soul, which I'm now blessed and lucky to be the founder of. It began with an experience of singing badly in front of a busy restaurant because, in my view, it is those moments of stepping into discomfort and fear that end up enlivening our lives. My first Flashpoint for you is that moment in fourth-grade feeling like I couldn't even speak and 35 years later, I found my voice.

It is those moments of stepping into discomfort and fear that end up enlivening our lives.

You're starting us off with a bang here. This is amazing. Those both come well together in the sense that your voice was taken away and it was given back by having that courage to step out there and do it. The message we all need to know is you can't allow people to take anything away from you that you have inside of you, even that courage.

I can feel it viscerally as you were describing that story, the freeing feeling of allowing yourself to get out there and do it. There was 35 years of pent-up oppression in a sense that you felt and then letting that all out. There are many people who are walking around with that sense of holding themselves back for a fear of showing their true selves.

I love that you chose Scare Your Soul because there's a deep soul connection to, “Who am I supposed to be out there in the world and what's holding me in place?” They're beautiful. Going from here, what happened now? I know you started to Scare Your Soul, but tell me before we get there, once you had that realization that you could do this, what happened next? Did you immediately step into action and say, “I'm going to start an organization?” or was it like, “It's interesting. This is happening. Now, what?"

I had already dipped my toe into the world of positive psychology and happiness. I met a wonderful professor who became a mentor of mine. His name is Tal Ben-Shahar. I would recommend him and his books to all of your readers. I want to take a moment to tell you this story because I think this is what life is all about. It's paying attention to those moments when a door opens. Sometimes we don't expect it. We don't plan for it. After I had gotten divorced, I had a 3 and a 5-year-old. It was a very challenging time in my life. The one saving grace for me was yoga.

A friend of mine had invited me to a yoga class. I didn't want to go. When I went, I loved it. The next weekend, I decided to go on a yoga retreat. I felt I had found a spiritual home in a physical home. The retreat that I ended up going to was sold out. They ended up referring me to the front desk of this wonderful retreat center saying, “There's another thing that that's going on this weekend you should pay attention to. If you can't do this yoga retreat, you should go to this.”

It was a Harvard professor talking about the Science of Happiness. I walked into this feeling a little annoyed that I had missed out on my yoga weekend. Within about ten minutes, when Tal started to talk about happiness, flourishing, what can we do, what are the interventions, the studies, and the data behind what makes us happy as human beings, I knew that I had found a new path in my life.

That led me to create a happiness incubator. I did a TED Talk that was an incredible experience about talking about happiness, pleasure, and what lights us up in our lives. That led me to this openness to new experiences because of what I learned in my studies of positive psychology. I'm sure all of your readers are attuned to the concept that growth occurs when we step out of our comfort zone.

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It is part of who we are as humans. It's a little bit of a tension because our bodies and our brains want us to stay safe. They want us to stay in homeostasis and the same as we were before because it allows us to be comfortable, but the challenge is, all of the great things in life happen when we push out of that comfort zone.

I thought to myself, “If I did this, if I sang in front of this restaurant, it would unleash something in me,” and it did. Sharing that with other people allowed me to say, “You all have the opportunity to do everything in your own lives that is going to make yourselves feel courageous.” That, in my mind, is the key. What can we do in our own lives that set us free and set us into a moment where we know that there's something better out there for us?

Something about what you described has me thinking about this connection. We have a fear of moving in a direction or moving beyond our comfort zone then we have this moment of courage that gets us to this place of, “What's the worst that could happen if I move in that direction?” Realizing that on the other side of that is a sense of happiness, fulfillment, and freedom that we experience. The journey you go on is more you're here, “Am I going to do this?” and then all of a sudden, you realize, “I did it. What else is possible? What else can I do now that I've done that?”

Anybody who has done something in their lives where they didn't think that they could do it, and they stepped into that moment of discomfort and something great happened, there's this awareness of, “What could my life look like if I did this more often?” Each week in Scare Your Soul, we put out a free challenge.

Our most classic challenge is to buy a cup of coffee for a stranger and have a conversation with them as you're waiting for your coffee. This is a great example of the work that we can all do, this kind of opportunity that we all have to step in moments of discomfort because we don't know what's going to happen. We're in a moment of service where we're doing something for somebody else. 9 times out of 10, something fantastic happens.

I have done this probably 20 or 30 times since I started Scare Your Soul. Each time I do it, I meet somebody new. We have a conversation I wasn't expecting. They are thrilled. There's a moment of openness and curiosity between us. Scare Your Soul to me is this invitation to step into moments in our own lives where we can push through and achieve those moments of transcendence, curiosity, energy and awe, that we didn't experience before, but when we step in, that's when it happens.

We need more of that now than more than ever, that's what the invitation is. If you're feeling this sense of disconnect or like, “I'm in a rut,” then maybe it's time to explore those moments and see, “How can I expand myself in a way by doing these little things?” It's not like you're asking somebody to put their lives at risk, although that might be what it feels like.

When we think of the word courage, it oftentimes brings to this concept that it's something beyond us. It's something larger that other people do that we don't do. It's this concept of jumping out of airplanes or quitting our jobs and moving to another country. It's beyond us and the truth is, and the data supports that it's all about small changes and small expressions of courage.

It's almost as if you want to place a metaphor around it like you're training for a marathon, but you've never run a marathon before. You don't start out by running the marathon. You get out the front door, strap on your laces, and start out small and each day you get a little stronger. Courage is very much the same way. It can almost be micro shifts in our lives. When we do it consistently, with zest, love and passion, it starts to move the needle. We start to become more courageous in our own lives.

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That's a great way to describe it. It's like that little micro courage steps that we need to take, which is amazing. I feel like we moved quickly into this amazing place, but I want to bring you back to what you were doing before this amazing moment in this place where you started singing. There are two edges to this question. Number 1) What were you doing before you got into this space? Number 2) How have the people in your world reacted to the new Scott?

I will dig back a little bit and say that my life before what I will call my epiphany on an airplane, which I'll tell you about in a second, was very small. It was a time in my life. Some people may identify with this when I wanted to be invisible, shy, concerned about what people thought about me, and feeling of low self-worth. For those of us who have been bullied, you know that a great deal of shame surrounds being bullied. You don't want to share it. It's something oftentimes that we suffer through ourselves.

Honestly, all of my childhood, I felt like I was in that space. I wanted to do everything to stay invisible so I could stay safe. I switched schools, started out at a college, and switched colleges, which didn't help. Nothing helped. I graduated from college with a degree in English Literature and no plan for what I wanted to do in my life.

I was working the alternative music aisle at Camelot Records at 21. If anybody has any questions about early ‘90s alternative music, I am a bit of a resource. That was my life in my early twenties. It was a very small space, then a moment of providence happened. Somebody offered me the opportunity to teach English to Holocaust survivors in a lower-income neighborhood of Tel Aviv.

I honestly thought to myself, “If I don't take this, I will probably stay in this aisle of the alternative music section for the rest of my life.” I took the job and got on an airplane from JFK to Ben Gurion Airport. I bought this little mead spiral notebook that I had in my backpack, and it was under my seat. The plane took off, and I had a panic attack.

I thought to myself, “How could I possibly go to a different country, speak a language that I don't know, live with a family whom I've never met, and teach English to people who have been through things that I can't even fathom?” In a moment of panic, I pulled out my little spiral notebook and wrote eight words. It came through me almost like it was like tumbling through my pen. What I wrote in that notebook that day was, “Do one thing every day that scares you.”

If anybody has the generosity to pick up the book that I've written, I tell the story about what it felt like for the next year to do something every single day for one year that scared me. It changed my life. It taught me, first of all, that I could do it, that I could step into discomfort, that it was okay to be shy, introverted, not know how to interact with other people, or lead this new life that I was leading.

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If I did something every single day that scared me, all of a sudden, amazing things started to happen, relationships, friendships, new experiences, new visions, and new confidence started to arise. I call it an epiphany on an airplane, but it was this moment of understanding that if we push our own comfort zones every single day in these small ways, not big ways, we start to move the needle.

I came back 100% on fire. I had become what I call in the book a fear chaser. I started to look for opportunities to scare and push myself. I want to be very clear, in no way does that mean putting ourselves in something that is unsafe because fear is within us for a reason. Fear is critical to who we are as human beings. It keeps us safe every single day of our lives. There is this part of the fear that is self-created and that holds us back.

My passion is having gone through this and experienced what life could look like, when you push yourself into discomfort every single day, what does that life look like? To me, it looks like flourishing. It looks like love, connection, adventure, and energy. To me, that's the kind of life I want for myself and everyone else.

I can't tell you how grateful I am that we went back, because that story was worth the price of admission. That's amazing. It’s powerful to share that insight with people, to see that doing one thing every day that scares you a little bit even, is what moves us in the right direction. I love the way you preface this idea of fear. It's there for a reason and it's almost like you got to embrace the fear, but don't let it hold you back from the life that you are meant to live. It’s well said. I'm trying to think of where we're going to go next. There are some directions.

In the intro, we didn't mention that you do a book and it's called Scare Your Soul. I will give that endorsement to go out and grab that book. It's going to be something that people will not want to miss. Let's step into the place of what you are up to these days. Tell me what is the thing that is on the edge of where you're growing into. Now that you're in this place of embracing your fear, where is it taking you next?

Part of this is human because we all deal with fears, insecurities, our fear of failure, our fear of what other people are going to think of us, and sometimes even fear of success. What's going to happen if we do something and it goes well? I feel lucky to be in this space where I get to talk about it. Our Scare Your Soul Community, which was created out of this one Facebook post, which went viral, is now thousands of people every week follow our challenges, but also very importantly, take little steps in their lives to push comfort zones in a way that enlivens them and makes their lives a little bit better.

The book itself is worthwhile telling you because it's instructive about when we follow our passions and lives in our lives and we know what lights us up, great things happen. I had started Scare Your Soul out of this Facebook post. I was funding it exclusively myself. It was a wonderful experience for me. All of a sudden, we had 50 ambassadors around the country. We had thousands of participants, and there was much energy behind it.

I was wondering, “Where is this going to go? What's the next step for this movement that we have started, many of us together?” One day, I was about ready to lead a meditation online. It was December 2020, another Flashpoint for you. In the dark days of COVID, if you remember those days, I decided that I was going to start to lead some loving kindness meditations online for people who were having a harder confusing time.

I was in a dark yoga studio ready to lead a Zoom for 80 or 90 people and an email arrived on my phone. It was from a publisher of the second-largest publishing house in the entire world, saying, “I found your website. I love the message you're putting out in the world. Would you like to write a book?” I deleted the message because I thought to myself at that moment, “What publisher reaches out to somebody saying, ‘I want you to write a book?’”

I only know the story of people. I have wonderful author friends who are talented and strive for years to find agents and publishers to put their work out in the world. Three days later, I thought about it and I pulled that email out of my trash folder. I responded. That led to an amazing partnership with Hachette, which I consider to be one of the greatest publishing houses in the world.

They gave me seven months to write 70,000 words. I put everything I possibly had inside of me in that book, which I hope is a roadmap for people around the world to begin the process of taking control of their own lives, of expressing courage in small ways and in practical ways so that they can begin to lead the lives that they were destined to lead.

The book itself, to me, is almost like a miracle. I can't believe it happened, but it is on the shelves around the world. I'm proud of it. Many people are a part of it. The key thing is it's a partnership between me and the reader. There are writing prompts, exercises, challenges, and ways for the reader to engage with me as the author in ways that are going to immediately start creating change within their own lives.

I love this almost-did-not-happen moment, which is interesting. What I also love is how you shared this idea that it's not just about the reader going on their own. It's a collaboration. When people read a book like this, not every book is like this, but it's about them seeing you as a partner in their journey when they read along. That's what makes it magical. I honor you for that. We can see the book as something more than just written words. That's well said.

There's a part of the ending of the book that was inspired by a mentor of mine, Maria Sirois, who talks about our choir. She talks about the group of people in our lives who are the ones that support us no matter what. They're the people that are there for us in the good times and the bad. I was deciding how to end this book. I go through all of the different ways that people can express courage in their own lives and their relationships and work with their own sense of gratitude and expressions of forgiveness.

I decided it was all about our allies or the choir, as Maria talks about it. How can we engage those people who care the most about us to be our partners, supporters, and accountability partners as we proceed down a path of leading an audacious life? That became important to me. I almost felt like I was channeling all those people that have been supportive of me over the years. I do think that one of the beauties of Scare Your Soul is that we're not in this alone.

We're all human beings struggling with the same fears and challenges. When we connect with each other, we're vulnerable, and we're honest about what we're struggling with, we support each other. We rally around each other. That provides this incredible sense of energy, security, and vitality around leading better lives and more vivacious lives. Honestly, that makes the world a better place.

We're not in this alone. We're all human beings struggling with the same fears and challenges. We must be honest with our struggles and support each other.

I resonate with what you're saying so much. There's a sense of borrow from the idea of the choir. When you're allies and you are celebrating your triumphs together, their voices lift you up. You lift your voices together, and it becomes something that's worth celebrating. When we have a personal victory, it's great, but when you have people around you who you can celebrate, it becomes even more powerful. It becomes amplified. That is something that you're tapping into here, which is to say, don't go it alone. Find people who are allies and who can help you to become even more empowered to do what you want to do.

Often, we are afraid of what people on social media or coworkers are going to think of us. The truth is, many people are focused on what is happening in their own lives. If we can rely on our own innate sense of courage and on those people who truly care about, love, and support us to be there for us as our foundation, it's almost limitless what we can accomplish.

To me, why would we want to lead a life anything but that? We have such a blessing to be on this Earth. It is rare that we are all together at this moment alive, breathing, and leading these journeys that we are on. Why should we limit ourselves based on self-created fears that stop us from being this vivacious, vibrant person that is inside each one of us?

Not that I want to steal your thunder here, but it's not only are you limiting yourself if you're holding yourself back, but you're limiting all of us by not putting your best self out there because we need your gifts.

There were great studies done a number of years ago by Nicholas Christakis who was at Harvard, now he's at Yale, about the connection point between when we get happier and more courageous in our lives, what happens to the people in our social networks, our family members, children, parents, or coworkers. When we start adopting experiences of positivity, happiness, and courage, it impacts them, which means that the more people who get involved in this type of work, we start to change families, workplaces, and communities. I honestly believe we start to change the world.

We're coming to the end of our time together. Although, I don't want that to be the case. I do have one last question to ask you. What are 1 or 2 books that have had an impact on you and why?

I can give you a 100, but I will limit it to 2. These are directly in my soul. One is a book called Man’s Search for Meaning, which is Viktor Frankl's book, that many people have read, but to me is powerful because he wrote it after a period of time in his life when he had experienced the Holocaust. He had experienced the most degradation that is possible in human life, and he was able to find a space within himself of power and of choice.

Something that many of us forget. Regardless of how challenging our situations are around us, we have the power to control our own perspective and create our own attitude and reality. If you're like me and I've got clients, readers, and people that I interact with, they know me to be uber-optimistic and uber-positive. That's the way that I lead my life. Honestly, regardless of my circumstances, I'm always going to feel that way because it's my choice. I think that that is incredibly empowering. The second is a book, and all you have to say about this is the title. I feel like the title says it all. The book is brilliant. It's Susan Jeffers's book, Feel The Fear…And Do It Anyway.

Regardless of how challenging our situations are, we have the power to control our own perspective, create our own attitude, and craft our own reality.

The reality is fear is going to be with us every day of our lives. It is a primal human emotion like love is. If we can make fear our friend, dance partner, part of our daily lives, and still move into action, that leads us into these brilliant moments of accomplishment, connection, love, innovation, and creativity that lead to a wonderful, flourishing, vivacious life. Those are the books that, in my mind, when I go back to them, they're the foundation. They're my wellspring.

We can make fear our friend – part of our daily lives – and still move into action that leads us into brilliant moments of accomplishment. That will lead to a wonderful, flourishing, vivacious life.

Both of them are great choices, but there's something that you said that I've heard before, but sometimes you hear it and it gets amplified. It is, “Your attitude is a choice. It's a choice that you make. Once you make that choice and you commit to moving forward with it, there's a sense of you get to create your world around that. You are almost deciding, 'What attitude do I want to take in life?'" Thank you so much for sharing and for bringing all of your stories and insights into this space. Your presence alone is something that uplifts the world. Keep on doing the amazing work you're doing. Thank you for being here.

Thank you. Continue the work that you're doing. It is uplifting the world as well. It's been such a pleasure being with you.

Before I let you go, I want to make sure people know where they can find out more about you and interact. Tell me where's the best place to reach you. is where they will find everything. It has information about our community. They can access our free challenges. They come out every Wednesday. They can find out information about the book and plug in. They can also find out about our Ambassador Program, which is growing. I am thrilled with the number of people that we have and am always open to people joining our Ambassador Program, people who are passionate about helping other people push their own comfort zones. I'd be thrilled to interact with anybody who wants to learn more.

Thank you, readers, for coming on the journey. Go out and grab a copy of Scott's book. Come consume this community and get involved. This is truly fantastic.

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About Scott Simon

Graphics - Scott Simon Headshot - VCP 198 Scott Simon less than 100kbScott Simon is a sought-after author, speaker and founder of the Scare Your Soul movement. Scott’s passion lies in connecting people to their own sense of courage in a deeply fearful world.  

He has spoken around the world, motivated people at schools and companies, given a TEDx Talk, co-founded a happiness incubator, and studied and worked with international thought leaders in the areas of courage and happiness. 

Aside from Scare Your Soul, Scott is a coach focusing primarily on creating flourishing post-divorce lives, leads online Metta mindfulness meditations, has led retreats around the world, officiated countless weddings, and scares his soul every single day. 

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