Overcoming Emotional Barriers in Entrepreneurship
10 Oct 2023 · 28 min
This is a podcast titled "Overcoming Emotional Barriers in Entrepreneurship" recorded in October 2023. It features a conversation between Terry Rice, a business development consultant and staff writer at Entrepreneur Magazine, and Barrett Brooks, a writer and executive coach. They discuss the emotional challenges entrepreneurs face, such as comparison, jealousy, envy, resentment, and anxiety, and explore strategies to overcome these barriers to grow and sustain a business. The episode includes personal stories, coaching insights, and practical advice for entrepreneurs.
Looking to diversify your business portfolio with a high growth opportunity? Discover Mathnasium Learning Centers, the 1 math only education franchise. For more than 20 years, Mathnasium has triumphed in a booming multi billion dollar tutoring industry. With over 1200 centers worldwide. Ranked on entrepreneurs franchise 500 list for 11 consecutive years, Mathnasium is low cost, recession resistant and offers significant growth potential in an expanding market. The demand for math education is skyrocketing driven by declining math scores and the growing need for STEM skills in today's workforce. What makes Mathnasium a smart investment, affordable entry point and quick build out time? High earning centers with seven figure annual revenue and industry leading 30% plus average profit margins and it's a trusted brand with high consumer satisfaction scores. And here's something extra. They're offering a 25% discount on the franchise fee for former teachers and veterans. So whether you're expanding your franchise portfolio or making your first investment, Mathnasium gives you the systems and support you need to succeed. Get your free franchise information kit@mathnasiumfranchise.com or call 888-763-2604. That's mathnasiumfranchise.com, or call 888-763- 2604.
Jack Daniels is proudly served in fine establishments, questionable joints, and everywhere in between. So no matter where you go in every bar, you'll always know someone by name.
Jack Jack and Coke.
Shot at Jack. Jack Daniels, please. Right away. That's what makes Jack Jack.
Please drink responsibly. Responsibility.org Jack Daniels and old number seven are registered trademarks. Copyright 2025 Jack Daniels. Tennessee Whiskey 40% alcohol by volume, 80 proof.
Everything about me, my personality, my family, my livelihood, my mission in life, it's all tied up in being an entrepreneur. And if you think you can avoid the emotional side of that and growing a business, I think you're just kind of kidding yourself, right?
Every entrepreneur encounters setbacks, but embracing them is the first step to overcoming them. And on today's show, we'll delve into the interplay between emotions and business dynamics and how you can leverage this to exceed your expectations. This is the Launch youh Business Podcast because we know starting a business is challenging, but it doesn't have to be confusing. Each week we'll give you the tactical advice and the necessary tools to scale your business without feeling burnt out. I'm Terry Rice, business development consultant and staff writer here at Entrepreneur Magazine. Let's dive in. Here's my goal. I want to help you overcome setbacks Create opportunities and perform at your highest level. And while that may sound great, you might be wondering how I arrived at that commitment. Well, it's because I had to overcome setbacks, create opportunities and perform at a higher level in order to live in the vision that I created for my family. And that vision was drastically altered on May 29, 2017. That's the day I lost my son, T.J. i'm going to share the details at a later time, but. But what I want to focus on now is how I arrived at a spot where I even feel comfortable talking about this in public. I was recently at a mastermind event, and one of the sessions was led by Barrett Brooks, a writer and executive coach. During the session, we focused on deep inner work that challenged our assumptions, revealed blind spots, and empowered us to move forward fearlessly. This was the first time I publicly talked about losing my son.
And.
And I can't thank Barrett enough for providing me with the empowerment and opportunity to do so in a way that would honor his legacy. And what I like about Barrett is he's able to tackle deep topics in a way that doesn't feel as heavy or forced. He has a way of naturally guiding you towards revealing and discovering whatever feels right for you in the moment. Plus, his dry sense of humor keeps you on your toes. And on today's show, we'll discuss common roadblocks entrepreneurs face and how to overcome them. How your emotions express themselves in your business and how you can use that to your advantage. And the difference between jealousy, envy, and resentment, plus how you can rid yourself of those emotions. Let's hop into it right now. Barrett, how are you today?
I'm great, Terry. It's good to see you. Thanks for having me.
Yeah, yeah. I'm glad to chat with you today because we had an amazing experience at craft and commerce thanks to that mastermind that you. That you led. And it was transformational for me. So I'm looking forward to digging in on that soon. But first, how about you just go ahead and introduce yourself?
Yeah. Well, my name is Barrett Brooks. I am a writer and executive coach. I work with two groups of entrepreneurs that might seem quite disparate, but they're joined together by my experience. So I work with professional creators who are typically in the six to seven figure range and have either stalled out and can't figure out how to get out of that plateau, or they're growing so fast and can't keep up with it and are finding themselves on the edge of burnout. That's the first group. And Then the second group are climate tech entrepreneurs. So people building startups working to solve the climate crisis. And that's something that's just very personal to me. I find it to be something that I think is the most important issue of our time. And I've been both a creator and a startup exec. And so I've kind of got this like dual purpose career here that I get to practice through my executive coaching.
For this conversation, we'll stick mostly to the creator side. So when you're coaching these creative entrepreneurs, what are some of the common challenges that they come to you with?
So many. So I'll share kind of like the symptoms and then we can get into a little bit of the actual underlying stuff that's going on there. The symptoms are typically, I find there's kind of two profiles of people that think they finally come around to, like, I might need some help here. The first is it's usually a creator who has done really well. They found their audience, they've got a great product or set of services they're doing kind of like, I don't know, it ranges from maybe $300,000 a year all the way up to maybe a million dollars a year in revenue. You know, these are successful entrepreneurs. Like, they've made it in a lot of ways, especially if you're thinking about it from the terms of somebody just getting started. But often what happens is people get to this point and they hit a plateau. A lot of folks who have been in the creator economy for a long time, they've been creators for a long time before that was even a term. They might have been around 10, 12 years by now. And there's this interesting arc. You come out of the gates and you're on fire. You know what your mission is, you know what you're trying to do. You're driven by trying to earn more money, but there's this natural plateau that you can get to. And in startups there's this thing called an S curve. And S curves are really common. They're very common knowledge amongst venture capitalists and startup founders. And it's this idea that certain tactics get you to a certain level of revenue and then in order to break through that and create another kind of like rocket ship style growth curve, you've got to find new tactics, maybe even new products and services to offer that will allow you to get there. So that's kind of the first set of challenges that I see is this like, I'm stuck. I don't know why I can't grow the business anymore. What I used to do isn't working to continue growth. Where do I go? The second group of challenges is there's this other kind of entrepreneur who ends up finding this just like piece of the zeitgeist that they get into. And their business just keeps growing and growing and growing. And whether it's their launch model or the overlap between their product and their market, they just are able to find revenue growth that doesn't seem to stop. And I find that these people tend to be like between 1 and 2 million dollars in revenue. Sometimes over that, but mostly between 1 and 2 million dollars in Revenue. And they come to me and they say, this is incredible. It's better than anything I could have imagined. I honestly didn't think I'd ever be here. But also I am running myself into the ground. I do not know how to stop feeling like I'm chasing my tail and working all the time in service of this business that's now run away. So those are the two kind of groups and that's what it looks like on the surface. And most of the time what people think is like, I just need some tactics like, you know, if I can just figure out some tactical stuff, you know, we'll probably be able to get this, this ship turned. Sometimes they're thinking in terms of changing high level strategy stuff like their pricing or their products or things like that. But mostly it's like I just got to figure out how to get out of this very specific little problem that I've got right now and move on from there. And I find that it's often a lot more complex than that. Which is actually the topic of the workshop that we did in Boise that you were at at Craft and Commerce.
Is your business growing even faster than you expected? For all those growing pains, Comcast Business has what you need. Their network helps run today's fastest growing companies like yours. More orders coming in, you got this. More meetings and emails happening all at once. With a network like this, it's no problem. And with gig speed WI fi, you can power all your connected devices company wide. Plus, Comcast Business delivers 99.9% network reliability. Perfect for a business like yours that's growing and wants to leave nothing to chance. Like security, Comcast's business will help keep you protected with advanced solutions that stop cyber threats. And if that wasn't enough, all their products and services can grow as you grow. So if you need to add more employees, it's easy. Time to open a new location. Go for it. Comcast Business has your back. No wonder they power more businesses than any other provider. All on the next generation 10G network. So is it possible to grow quickly and stay ahead of it with the advanced connectivity, reliability and security of Comcast Business? It's not just possible, it's happening. Comcast Business powering possibilities. You mentioned these are some of the symptoms that people are coming to you with. What are some of the core problems? Because I think for our listeners, just hearing that might help them identify if they have some of those challenges as well.
Yeah. So I find that as business people and just the entrepreneurial mindset, I think, is that we have a problem. And if we can just figure out the knowledge we're lacking and the tactics we don't understand yet and apply them, they'll get solved. And what I find is that mostly entrepreneurs know what they need to be doing. They know they have the knowledge they need in order to get where they're going. And mostly they know the tactics and yet they're still not doing it. And I got really curious about that. Cause that seems backwards, right? It's like, well, if you already have the thing you say you think you need, then what's actually going on here? And that's actually a question I often ask in coaching. So what's really going on here? Given that you know what you should be doing? And what's usually really going on is there's some kind of emotional blocker standing in the way between where they are and where they want to be. And it might be, you know, I kind of have this framework of like these six categories of blockers. And it might be because you're comparing yourself to others and that you're so focused on other people that you can't. You've lost focus on your own business. It might be that you're worried about. You know, you just don't have clarity. It's like something's holding you back, related to you don't know where you want to go from here. You had this vision and it got you to a certain point. And now you don't have vision anymore. Cause you did everything you set out to do. Um, and so there's these different categories of emotional problems. And what I find is that the solution comes from looking at the emotional piece of it, not at the tactical piece of it. And so for something like clarity, a lot of the exercise that we did that I think led to you saying that it was a breakthrough experience for you is loosely based on a therapeutic system actually called internal family systems. It was created by, interestingly, a former college football player turned therapist named Richard Schwartz. And it's this method of therapy that acknowledges that we have parts inside of us. You know, a lot of people think of, like, having multiple personalities as a disorder, and it's not multiple personalities, but there are these pieces of us that get locked in time based on past pain. And I find that a lot of that pain shows up at work, especially for entrepreneurs, because I don't know about you, but for me, there's not really anything more personal than entrepreneurship. Everything about me, my personality, my family, my livelihood, my mission in life, it's all tied up in being an entrepreneur. And if you think you can avoid the emotional side of that and growing a business, I think you're just kind of kidding yourself. Right? So that's a big piece of it, and it's probably longer than we've got to go through every aspect of that, but maybe we could focus on one. Like, problems of comparison could be one that could be fun to jump into a little bit.
Yeah, I think that makes sense, actually. And one quote you gave during that workshop, which I've been recycling ever since, was, you must confront the emotion that holds you back from doing what you know you should do. And I think comparing is a good one to go with, because a lot of our listeners, you know, maybe they had a corporate job for 10 years, and like, you know what? I want to start my own business. I know I can do this stuff. But they're just seeing everyone on LinkedIn. Seems like they're light years ahead of them. Right. Or maybe you're a couple of years into your business and you're wondering, why am I not doing as well as, like. Like Tim or Kelly or something? So I think if we can solve that problem, we could help a lot of people listening right now. So let's. Let's chat about that.
Yeah, it's a super common one, just for people in general, because we're social animals, but especially for entrepreneurs, because, you know, if you're a creator, it means you're online most of the time. You're paying attention to what everyone else is doing, because that's part of how you build your business. You know, you gotta be part of a network, you gotta be creating content, need to be part of the conversation. But that also means that you're subjected to what's going on with everyone else constantly. And usually you're subjected to the very best version of what's going on with everyone else, and none of the struggles that have gone into that. So the way that I find that this pops up is an entrepreneur gets to this point in their business, and this is typically when they've stalled out and they're looking around. They're like, I know 10 other people that have a similar kind of business to me. Maybe they're in a productivity business or something like that, teaching people how to be more productive with their time. And they're looking around, they're saying, well, that person over there, they've got a $5 million business, and that person over there, they've got a $3 million business, and that guy, he doesn't even know what he's talking about, and he's doing 2 million a year. You know, I mean, it's just common. It's like we all have these thoughts. I have these thoughts about other coaches sometimes, and I have to catch my own self saying, like, okay, what's really going on here? And what I find is really going on. There's. There's questions that are kind of help get to the diagnosis of what's actually going on underneath the surface for people in this kind of situation. So problems of comparison are often rooted in feelings of jealousy, envy, and resentment. So jealousy is that person has a thing, and I'm scared by them having the thing. It means it's going to take it away from me. You know, we most commonly think of this in relationships, right? It's like if you're married and you're jealous of something going on with your partner, it's actually because you're scared of losing your partner. Like, that person might take my partner from me. Well, that happens in business, too. You know, it's like, if that person gets all of the clients, then I might not be able to get the clients, and they might take away the very thing that I need to be successful. Envy is they have a thing that I want, and I kind of admire them for it, but also I don't have it, and that sucks. Resentment is that person has a thing I want, and I hate them for it. You know, that's like. That's kind of what's going on there. That's a little bit of a trait way to describe it. But it's funny. So it helps. Depending on what you're feeling, that helps identify what's the question that'll help you get at what's really going on. So let's say you're feeling. You think you might be feeling jealous. Okay? So the question here is, when I'm jealous, what is it that I'm Scared of losing, that I haven't yet admitted to myself. And most people don't even realize they're feeling jealous. And so step one is, oh, maybe I am feeling this category of comparison and it's related to jealousy.
And.
And then you get into, all right, well, what are you scared of losing? And that's when you can arrive at, well, I'm scared because that person's a coach also working with climate tech entrepreneurs, that there's not going to be space for me. It's like, oh, that's interesting. Okay, well, let's dive in there. Why do you think that you might not have a business if they have a good business, yada, yada yada. The other one that I think is really informative though, is resentment, because this one is in some ways the most toxic if it's not addressed, because resentment that builds becomes anger, and anger that builds that doesn't get addressed becomes embodied pain. And so with resentment, this question always catches people off guard, but the question I always ask is, what does that person have that you haven't yet admitted to yourself that you want? And when we're judging someone or we're resenting them and we're like, I hate that person for whatever reason, it's often a sign that they've got something we want. A second question that can sometimes uncover this is, what about that person? So this would be more of like a. You find yourself judging someone just for, like, you think that they're a jerk, or you think that they're self promotional or something like this. What in that person might be true about you that you don't like about yourself? And I find that when we start to dig into these deeper questions, we're starting to really get to the root of what's actually going on, right? So it's like, well, I don't like that person because every day they're on Twitter promoting their business and it's working. And I actually wish that I could be that bold because I think I'm better at what I do than they are. And that may or may not be true, that I'm better at what I do, but. But then what that tells me is, okay, well, why don't you feel the confidence to go out and promote yourself in the same way? What's going on there? And oftentimes this stuff is rooted in past pain that we've experienced in our life. Might be from family life, might be from past jobs, it might be from being bullied in high school. There's all kinds of different Things that can add up to us kind of subconsciously organizing our lives to avoid feeling that same pain again. And that often holds us back.
You kind of dropped the mic there. I want to share my own experience with comparison because I think that is an issue that plagues us. There was this one person that I would see often on LinkedIn who appeared to be a successful public speaker. Every clip is this person speaking. And then I saw what was on the slides that he was presenting one time, and it said, companies that use the Internet will grow much faster than companies that don't use the Internet. Like, what's that even mean?
Oh, my gosh. Right?
But his post had all these likes and shares and comments, and I'm like, really? And I was comparing myself and I was annoyed because I'm like, how's this guy getting props for that? Like, did you guys read the slide? But to your point, I was upset because I didn't promote myself enough. Getting over that block of comparison and just joining in instead of, you know, being upset that he was getting attention helped and actually helped us form a friendship.
Yeah. It's like the transformation is, why is that working from him to, oh, that's all it takes. Like, I just need to start at the beginning and teach everything that I've learned along the way. And basic things like being on the Internet will help you be more successful than not can get likes. And that doesn't mean you go do exactly what you're seeing that person do. Doing it means you figure out your version of it. Right. There's this principle in teaching that I've always tried to abide by, and that I think is really valuable for creators, and that is to teach to the beginning, but assume the desire to become an expert. So you're not treating people like they're dumb. You're not treating people like they're not capable. But you're starting at the beginning, because if someone's in the middle, they can skip the beginning part. Fine. But if someone's at the beginning and you start in the middle, you're going to make them feel stupid. And I think if you can start at the beginning and teach towards the desire for expertise, you realize why so much stuff that seems basic when you've built expertise over years and years still matters to a lot of people because there's like, literally billions of people who don't know what you know. That's why it works.
You may be familiar with Fiverr, the talent marketplace that connects freelancers to companies all over the world. What you may not know is that Fiverr has a business friendly offering called Fiverr Pro. Gain access to the very best freelancers for your projects through Fiverr Pro's curated catalog of exceptional talent. Streamline your workflow with their user friendly dashboard where you can organize projects, track progress, save talent lists and collaborate effortlessly with your entire team. Designed to handle projects of any size, Fiverr Pro is the ultimate freelance solution for your business. And the best part, there are no hidden membership or subscription fees. To get started, find help with your next project by heading to pro fiverr.com that's pro.f I v e r r.com well, one thing I've been appreciating about your content even recently is you've been coaching for about six months and you're sharing that you just want to be the best coach out there. And you took this, this assessment called the Highlands Ability Battery. Do you mind sharing what that is and how that helps you just help people more effectively?
Yeah. So I first took the Highlands Ability Battery back in 2009 as a part of a leadership development program I was in in college. It was almost like a minor in organizational leadership that the university introduced in the business school. And as in the first year of that program, it's really focused on going inside, learning about yourself, who you are, what you're made of, what you want from life, what your vision is for your career. And the Highlands is a series of 19 cognitive ability work samples. So I think of them almost like brain games. And there's no like, good result, there's no bad result. It's really measuring your natural cognitive abilities and how that plays out in the workplace. The strength of this one is most assessments ask you to reflect on your own experience of going through life and then answer a question like, do you enjoy being around people and does it give you energy, yes or no? This assessment asks you to perform tasks that are work like and then tells you what that means about how your brain works. And I love that because it's very rooted in science. It's strictly objective, it's not about your subjective experience of life. And it maps to the kinds of work environments and the kinds of work responsibilities that can be really fulfilling to you. So the place that I find this to be most valuable, there's a few of them, but one of them is if you've been in work environments in the past, or if you're in one right now, or even if you're a creator or an entrepreneur who's feeling frustration with your work and you've had these, you just have this underlying like sense of restlessness, frustration. You don't know why the work doesn't quite fix it seems like it's aligned to what you believe about the world. A lot of times it's because what are called driving abilities. So there's these five core abilities that really shape how we approach the world. If you're very high in one of them and you're not having a chance to express that at work, it often feels like frustration that you can't find the root of. So that's one area that I really love this assessment for. But where that plays out is how do you shape your work as an entrepreneur and creator so that it caters to your natural abilities and strengths? How do you, how do you build a team around you that has complimentary strengths and abilities so that they can take the things that you don't want to do and excel in them and enjoy their work? And three, how can you help people develop over time that might work for you so that they're using their natural abilities and using that to kind of skyrocket their career over time? And I find that just any, this is not the answer. I think there's many assessments that can be highly valuable, but this is one way to build a lot more self awareness and help people develop in their careers.
Barrett, you have so many great tools and frameworks and prompts and that's one thing I really do appreciate about you. So before we go, is there another one you would recommend? Say someone's feeling like frustrated, they're having a bad day. Is there any kind of like one minute exercise they can do to turn things around?
I have one in for anxiety and that's because I'm well versed in anxiety. I find that a lot of entrepreneurs experience quite a bit of anxiety. So the exercise related to anxiety that I always do is if you're, if you find yourself in a moment of rumination, which is often a sign of anxiety, so it's reflecting on the past and kind of freaking out about something or feeling lost in your body. Ask yourself, right before I started feeling anxious, what was going on in my life? And then the secondary question to that is, given that that's what was going on, what am I feeling that I haven't acknowledged that I'm feeling? And what I find is not all anxiety, but a lot of anxiety comes from unacknowledged, difficult feelings related to what's going on in life. And rather than stare at those feelings, we start getting in these loops about other things we should be worried about because it allows us to kind of stay heightened in our nervous system and that feeds our body with hormones, basically. That allows us to continue to ignore the thing that's really going on underneath the surface. So that's another good one.
That's another great one. So, Barrett, thank you so much for this, and I'm sure our listeners want to learn more about you. So what's the best way for them to do that?
Yeah, barrettbrooks.com is where I do all of my writing. You can find out about my coaching there. If you're interested in working together through executive coaching, Barrettbrooks.com coaching is the place to go.
Thanks, Barrett. I appreciate it.
Thanks, Terry.
And that's our show for today. You can learn more about barrett by visiting barrettbrooks.com I'll spell that B A R R E T T B R o o k s.com and give them a follow on Twitter or X or whatever you're calling it these days. Arooks and look, if you got value from this episode, help us spread the word by sharing on social and leaving a review. Thanks again for listening and I'll catch up with you next time. Apply what you've learned on today's show. You'll find the show notes and more resources at Terryrice Co. Podcast. Again, that's TerryRice Co podcast, and the best way to support this podcast is by subscribing, telling a friend, and leaving a review. Also, you can get more tips by following me on Instagram terryrice or follow me on LinkedIn. This episode was produced by Josh Wilcox of Brooklyn Podcasting Studio and edited by Dan Lardy. Special thanks to my wife, Dominique for keeping our kids relatively quiet as I recorded. Thanks again for listening. I'll see you next time.