How to Overcome Insecurity and Live a Powerful Life, Q & A with Sean Stephenson
11 Dec 2025 · 23 min
Sean Stephenson, a therapist and entrepreneur, talks about overcoming comparison and insecurity. He breaks down the shift from fear to confidence through commitment, courage, and competence, and offers two frameworks: GAP (Goals, Appreciations, Preferences) and FED (Fear, Envy, Dislike) to reset your mental focus.
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Hey fastlaners, this is Ryan Daniel Moran. Welcome back to Freedom Fastlane. Today you're going to hear a clip from our December called Freedom Fastlane Live. It was held here in Austin, Texas. And what we try to do at Freedom Fast Lane Live is put the best capitalists, entrepreneurs, brand builders and investors into one place, invite people to join and watch what happens. We just try to create the biggest business up leveling possible. This year's event featured Peter Diamandis, JP Sears, Cameron Herold, the founder of Whole Foods, John Mackey, a panel of people who built million businesses, our investor panel and a bunch more. And in past events we've had billionaire Jeff Hoffman, Pat Flynn, Robert Herjavec, Gary Vaynerchuk and others. So today you're gonna hear a clip from the recent event. We don't release the entire event for obvious reasons, but there are certain clips that we find particularly beneficial that we want to share with you. So that's what you're gonna hear on today's episode. If you want to be on the waiting list for the event in 2017, you can go over to freedomfastlane live.com enter your best email address and you will be on the notification list for when we release the speakers. Until then, enjoy this clip from Freedom Fastlane Live.
Sean, thank you for that.
You're welcome.
I want to ask you a few pointed questions because we as entrepreneurs, well, we're a weird bunch and we have, I think we have, I don't know if we have more mental demons than most, but they're different than most.
Right?
So what have you seen? Because I know you speak at a lot of events, what have you seen come up as like a recurring theme or a recurring insecurity specifically for entrepreneurs who are running companies.
I would say one of the biggest insecurities I deal with as a therapist with my clients because I have a unique practice. I work only with entrepreneurs and as an individual that only works with entrepreneurs, I hear their fears, their complaints, their excuses, their insecurities every day. And when I'm working with a client, I work in a very unique format where I work for 12 hours in a row with the client and then never again. So we like peel back the layers in that 12 hour session. And I think the biggest problem that I see is. And I want you to write this down, please. Is compare leads to despair. You alluded to that in your introduction to this day, that when you compare, you lead to despair.
Every time you think, well, I don't have what that person has, you feel a drain in power. I think what entrepreneurs need to do is they need to put on blinders. And that might sound counterintuitive to put on blinders, but I find that when I listen to my own intuition and I do what I know is going to work based on the research that I've already done, and I just stick to it and I focus on it, and I don't chase the new squirrel or that new shiny object, but I stay on. Where is my sweet spot? Am I the world's greatest copywriter? Am I the world's best speaker? Am I the world's best. Fill in the blank and focus on that and make that my passion and work on it and not compare myself and try to. I had a new skill set that so and so over here just told me about. Man, you get so much done, you feel really good. Insecurities come about when we look at somebody else's stuff and go, oh, should I have that? That's what tears us down. That's what I've seen most.
You alluded at the beginning of your talk about, are you doing what you were born to do, or did you get golden handcuffs, essentially? And I think a lot of entreprene intentionally put golden handcuffs on themselves because they don't know what they were born to do, so they kind of COVID it up with cash flow. And then there's this lingering, I don't know what I'm here for. But at the same time, I also think that the marketplace. I had a professor in college who said, all of you kids who are worried about what God's plan is for your life, he gave you the marketplace, just follow that. And I think there is some truth to that. You do make the greatest difference by following the market. So that doesn't make everyone happy at the same time. So this is a challenge that I think is unique for entrepreneurs of this idea of, am I at my highest and best use all the time? This person looks like they're doing great things. They're doing great things. I don't feel like I'm doing great things. So how do you address that with somebody when they bring that up?
Well, you know, Joseph Campbell said it best, follow your bliss. Right? And sometimes when you think of that, it's like, oh, hey, you know, kumbaya. And, yeah, if you want to follow your bliss, you're going to be unemployed in a very short period of time. You'll run out of cash flow. I think it's follow your bliss, but make good money doing it right. So I love that you own capitalism.com, right, because in my heart, I think the best businesses are the ones that you have a blast getting paid to do what you love. I give the same speech now, same energy, same care, same intellect that I did five years ago. But we charge far more because we've developed the business, we've developed the brand, we've developed the impact and the marketing strategies and all that. But it's the same thing. And 20 years from now, I'm still going to be doing this, even though there will maybe add things, take things out, but at your court, you know, the things that drive you, you know, the things that fill you up. That doesn't mean I don't have challenges. You know, I just got back from Switzerland, right. So I don't know what time zone I'm even in right now, but it doesn't matter because it's morning. What's morning?
It's morning right now. Yeah.
Just so you. Look. So the whole thing for me is, if I died today, did I do something that was on my mission? I mean, if you died today, would you be happy that you were on your mission, that you were here? If you're not supposed to be here on your mission, you really should ask for a refund and leave. I know that doesn't sound good, but it's true. Like, if you're. If this being in this room right now isn't lighting you up and there's nowhere else you'd rather be, then you know you're not in the right room. I mean, I. I'm excited to be here with you because if I die on my plane ride home, I know I was on my miss and that's what makes me fearless. I get scared, but I still act in the face of that fear because I know I'm on my mission. I've never had Ryan in all my years of therapy, a client sit down on my couch and look at me and say, sean, I'm on my mission. I'm making a big difference. I am working on my personal growth and I want to kill myself.
Nobody says that. No, people say, like, I have a bunch of money, I'm really famous, and I hate myself. And you're like, how did you get there? And they're like, well, Because I was tall and I got told I needed to play basketball or, you know, they said I was funny. So I became a comedian. Like, when you have somebody else tell you what to do with your life. That's why I love entrepreneurs. We don't do well when people tell us what to do. That's why we're not employed. Wait, let's be honest. You do not have a job because no one would hire you.
The reason why I'm an entrepreneur is I had no choice. I had no choice. I suck as an employee because I'm going to do what I'm going to do in this life because I look for what's the most efficient, most impactful, best way to get something done and make the biggest rewards. Like, that's the way my brain is wired. And when I tried to get a job in traditional corporate America, I applied when I was in high school and in college for traditional jobs. And they told me over and over and over, sean, you are smart. You have great credentials. But. And then they would tell me their fear about my disability. But, you know, what if the client needs something and you gotta hop into a car and quickly get over there? What if there's something on the top shelf and they blatantly discriminated against me? And you might think, well, Sean, why didn't you just sue that company? Well, because I didn't want to go work for a company I was suing. I don't think that would make a fun first day, right? Hey, I'm the class action guy. No, right? And so for me, I started looking around like, well, I gotta make money.
I love making money. Money is awesome. It does some cool things. I flew home last two nights ago on business class. And when I walked past the. When I saw past in the back behind me, economy class, I'm like, I remember being in economy. I hated that. I'm not lying. It sucks, right? When you're in business, you're laying down, you're eating the better food, get into business class, okay? And so I had to figure out, how do I make the money? And I started telling my story. And when I was in high school, I got hired to speak to another high school about how to get over your fears and what is it like being different and how do you find your gifts? And the business grew out of just sharing with people my life experience. And then we built a business around it, and I became an entrepreneur for survival because it felt like at the time that the traditional lemmings didn't want me. So I want you to think about this for a moment. If there's not an example for you in society of somebody that looks like you, that wants what you want, then that means you need to go be the first person.
You know, when I was at my darkest period trying to find love, thinking, is anybody going to want to love a little man in a wheelchair? I remember reaching out to one of my mentors and I said, you know, there's not a single person on television or movies that lands the main girl that looks anything like me. And he said this incredible piece of advice. He said, then you need to go be that example for the world.
If you're in this woman, as a woman, in this room, as a woman right now, and you feel like, oh, there's not enough women business leaders out there, and that's an example that you need to rise up. No matter what it is that you're going through, if there's not somebody out there that looks like you or has what you've had or gone through, what you've gone through as an example to lead you, that is the call that you need to be that for others.
We live in a world I think is worsened now by social media because we're all looking at what everybody else is projecting. I feel like I've grown up with it, but I feel like it must be worse than it has ever been just because it's so in our face all the time. So this strategy, or the example, if you will, what is normal is just plastered in our brain all of the time. And there's almost like an expectation of, I need to be this, I need to be that. And then they end up finding you and saying, I'm not happy. So what is the shift that you start to work with someone? Because there is a gap of what the world tells me I should do and. Or what I need to do to get successful, or what I need to do to get the money or build the business or become the basketball player. And then on the other hand, there is what lights me up and what I want, that can be a massive gap. So it's not like you can just drop out. And now I'm bliss and happy and rainbows and unicorns. So what do you do to fill the gap? How do you pull somebody from one end of the spectrum to the other?
Well, it doesn't matter whether they want to become entrepreneurs or not. I use the same formula. I want to share with you, and I want you to write this down because I want you to share it with Your children, your spouse. See, because I can't rid the world of insecurity on my own, I'm going to need all of your help. And this formula is going to answer that question. And I want you to share it with people. G A P gap. G A P.
Versus Fed. Fed, Fed.
And what you need to do to get the power to continue heading towards the unicorns pooping rainbow thing you were saying. Yeah. So is you need to be focused on the gap. And the gap stands for your goals, your appreciations, and your preferences. Your goals, your appreciations and your preferences. Leaders in business that are crushing it, that are achieving incredible quality of life, not just good numbers. These people are focused on their gap. What do they want, what do they have, and what do they like? When you're happy, I guarantee you every time you're happy and you're feeling like you're on your bliss, you're focused on what you want, have or like, or all three. So what do you want in your life?
What do you have that you're just maybe overlooking?
And your preferences are what do you like? And as entrepreneurs, there's so many things that we like to do, but we think we're too busy to go do them. I was out with a dear friend of mine and this other guy who we just met at this coffee shop. And my buddy is a very successful entrepreneur. He's one of my mentors. And we're talking about this great, great movie we just watched. And this third person that joined us said, oh, who has time for movies? And my mentor says, happy people.
Happy people have time for movies. And it's so easy to get caught in the trap of thinking that the answer to being successful is hustle 24 7. I know the hustle gurus. I'm friends with them.
It works for them. Great. It'll kill me. Hustling 247 is not living in the gap necessarily for most people. If you feel it, it's about pushing the accelerator all the way to the floor and never letting up. You got a high chance of burnout. That's not popular to say because right now hustle's the shit in entrepreneurialism. But I'm just going to say, wait, Wait for it. I'm predicting the predictors. And I'm going to tell you there's going to be a swing, that pretty soon it's going to go back and it's going to be talking about quality of life and peace. And do you like who you are and do you know who your children are? Is your health good? And so the Fed. The Fed is where you want to stay out of. This is where all these people get stuck. They get into suicidal thoughts. They want to quit their businesses and throw everything away. The F stands for fear. That's what you don't want. That's all your anxiety driven thoughts. I don't want this to happen. I don't want to look bad, I don't want to make a mistake. What if I launch this book and it's not a New York Times bestseller? And the E stands for envy. We've been talking about this the whole time. That's focused on what you don't have. When you are in a space of envy, you cannot create success. Maybe you'll get all the trappings, but you won't feel it's enough. And the D stands for dislike. Another way of saying it is complaints. But Fed is easier to remember than fec, so I go with dislikes. When you're focused on what you don't want, don't have, don't like, you'll be miserable every time. When I am on the road, when I'm at home, when I'm working with my team, anytime I'm miserable. I know why now. It's because I'm focused on what I don't want, don't have, don't like. And so when I sit down with people and we're talking about their bliss, I'm like, you have to have the bliss now before you're going to have all the trappings. So I got to shift people's focus because we have control over our focus. We don't have control over these external forces. If you think you can control the weather, go outside. Right now, we're in Texas. You don't control the weather, you don't control the economy. You control your, your internal weather. You control your internal economy. And so when I'm working with people, I'm getting their focus to be right. In that 12 hour period. I'm pulling out with their help. Like, what are the belief systems they have that feel like it's not in the cards for them to enjoy a good life? I pull out the cards because at the end of the day, 80%, I believe at least 80% of our quality of life is mental. It's mental. Only the 20% is the little tiny little strategic things. Would you say that in business as well? 80% of it, if your mind's not right, you could screw up over and over and over.
You started to allude to something at the Beginning, I think, a mutual friend of ours, Dan Sullivan, talks about his four Cs, which he says, you start to talk about courage wouldn't be great or confidence. Wouldn't it be great if we all had more confidence?
Sure.
And most people think that the confidence shows up, which allows you to be courageous and make commitments.
But the order is the opposite.
Absolutely.
First you have to make the commitment, and then there's a period of courage which does not feel good. We think courage feels good.
We think it's Brad Pitt and Troy that's courageous, but it's actually really scary and really uncomfortable.
No. Courage is filling your pants and asking for help. Courage is saying, I need to go to the nurse's station and get help. Courage is telling your neighbor at a conference that you just met, hey, I'm dealing with this challenge. But the reason why it's a courageous act is because you were scared. Courage is anytime you feel scared to do something. But I found that every time you take an act of courage, you get stronger. You get more confident on the other side.
Yeah. It's the confidence that comes on the back of the competence you get during that period of courage. It's the final stage in the process. And once you get that confidence, then it's just time to make another commitment. And what made me think of that is when you're looking at this gap.
There'S often this period, especially those of us who are entrepreneurs, who, we know where we are, we know where we want to go, but that chasm seems impossible, and it requires that period of courage to just take risk.
It better be fun to you. You better add more fun in your life. I married a very serious woman. My wife is a badass. You would not want to mess with my wife, okay? She is a focused entrepreneur. She's serious, and then she marries a big goofball, right? And we teach each other. She shows me how to use my head all the time. She's like, sean, you might want to think that one through a little bit more. And I show her how to use her heart, how to use the emotions. So you might want to feel that more. And when you surround yourself with people that have fun, that's critical. If you're not having a fun as a high priority, I bet you're burned out or you're burning out. Like, I ask myself every day, what can I do today that would be fun getting this activity done. So that gap between here's where I want to be and here's where I am, if I'm having Fun. I don't care how long it takes. You know, I have fun with people constantly. I will. I will go in an elevator, complete strangers, and ask them, you know, how long is this meeting gonna take? You know, I just have fun with pedestrians. This crowd needs to have a little bit more fun. You get that? Can you feel that? Seriously, you guys need to loosen up.
So I want you to write this question down. Here's how you add more fun to your life. Write down what's funny about this. When you're looking for what's funny about a scenario, your life will just get better and better because the people that laugh, they interpret that things are funny and enjoyable. And that life, look, none of us get out of life. You're gonna die.
Death is coming for you. Have a good day.
No, but seriously, I'm not really that motivational. I'm a realistic optimist. I look at what's coming for me and I say, how can I have fun in the process? Because I don't know. I mean, I faced death about five times now. And you know, in that moment when you think you're going to die, you don't think to yourself, like, I wish I would have screwed over more people and made more money. You don't think to yourself, like, oh, I wish I would have spent more time working on, like, did I leave any money on the table? No. You know what? You worry about the people you leave behind. The impact you make have a profound difference. I say, don't leave any love on the table. You're going to regret leaving love on the table. And when you put your heart behind things and you have a blast, that enthusiasm is contagious. People love to buy products and services from people who love their life. Think about it. When you meet somebody, you're going to buy a car from them, and you could tell that person would like to kill themselves that morning. Is that going to be a fun sales conversation? No. You're gonna be like, holy cow, I need to get out of here. But if you can tell that person loves you and they're like, hey, whether we can get you into this car or not, that's up to you. But can I tell you all about how this is going to be awesome for your family, for your life? Can I show you around? And all of a sudden, you can feel the salesperson is having fun with you and they love their life. You're like, shit, I want to buy this car just so I can see this person again. Right? Because you want to be around people who are alive. So many people out in this world are walking around dead. They don't even care anymore. They're disconnected from their joy. And when you get around people that are alive, you're like, wow, I want some of what he's having.
So I say, look for what's fun. That's what's going to spark that joy in you.
Sean, thank you for being here and for being an inspiration. We appreciate you. We love you. Let's give it up for Sean Stephenson one more time.


