Get Out Of Your Own Way – Release the Imposter Syndrome with James Robilotta

REW 8 | Imposter Syndrome


Get out of your own way. What is your “I’m not ___ enough?” In this episode, James Robilotta, author and entrepreneur, joins Moneeka Sawyer as he shares his story of authenticity and vulnerability and why you should release the imposter syndrome. James and Moneeka talk about recognizing patterns inside yourself, the way you think about yourself, and how are you effectively shaming yourself. Get to know the fears that are holding you back and are hindering you to take action. Not only does James define the imposter syndrome, but he also talks about how to change the way you speak about yourself and become an advocate for yourself and not just accommodate.

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Get Out Of Your Own Way – Release the Imposter Syndrome with James Robilotta

I am excited to welcome to our show, James Robilotta. He is an author speaker, coach and entrepreneur. His book is titled Leading Imperfectly. He speaks internationally to willing and unwilling attendees about authenticity and vulnerability in leadership and life. His clients include Amex, GE and others. He’s also an experienced stand-up and improv comedian. James is also a personal coach. He loves helping people get out of their own way to live the lives they deserve and be the leaders they are capable of becoming. His clients undergo purposeful life-changing and self-affirming transformations. His clientele ranges from CEOs to college students. James, welcome to the show.

What’s up, Moneeka? How are you?

I’m good. How are you?

I’m chilling. I’m doing well. Thank you. I’m excited to be here.

I’m excited to have you here too. Could you tell us a little bit about who you are? Tell us a little bit about your story.

I’m a born and raised a New Yorker. I am a professional speaker. I travel around the country to talk about authenticity, vulnerability and the stories that we write. That’s what I get to do and I love what I get to do. Interestingly enough, I majored in Marine Biology in college and promptly put that to good use by getting a Master’s in Counseling. Apparently, I was putting too many jokes in my scientific papers. I worked in the field of higher education for a while, developing student leaders and professional leaders on college campuses.

I went to a conference one time and presented a session to share some ideas with my colleagues. Somebody came up to me afterwards and asked me how much I charge. I said, “With all due respect, who are you talking to?” That’s not what I was there for. I got my first paid speech because he bought me lunch and away we went from there. I’ve been on my own since. I started speaking in 2011. It was a side hustle for a few years and then became the main hustle, so we’re out here. That’s what I do now.

I met James at the New Media Summit. I went to this conference and met some amazing speakers. I’m bringing many of them to you. The reason that I was attracted to James was his power on the stage but also his personal power. How is this relevant in real estate? You can imagine that creating that power can help you to move forward in your business. I don’t know if you’ve heard this but when people are at a funeral, most of them would rather be in the casket than giving the eulogy. Public speaking is a scary thing. One of the things to become an effective and powerful speaker like James is to develop the ability to recognize your fear, step past it, and to be your best self no matter what. I feel like he brings that skill to his world and I wanted him to bring that to our world. That’s why I invited him on the show and we’ve got some good stuff to share. Talk to me first about recognizing patterns inside of yourself and how you think about yourself.

You are the person that kicks yourself in the butt, that pushes you off the ledge to figure out if you can do it. Share on X

We as humans are pattern generators. Whether we recognize it or not, our brains are equipped to write patterns over and over again. Think about the patterns that you don’t even have to think about anymore. For example, if I told you that I want you to brush your teeth with your other hand, that would take you way longer and you’d probably drop the toothpaste in the sink. Fortunately, our brain has developed a pattern. We can brush our teeth even in the morning haze and fog. We don’t even have to worry about it. Our brain knows. If I told you to eat your cereal with your other hand and all of these things. We have all these patterns inside of us that we don’t recognize.

We also have patterns of thoughts. A lot of people, myself included, I should on myself a lot. I don’t know if any of you out there should on yourself, “I should do this. I should do that. I should listen to this webinar.” We get caught into it. We’re caught in these patterns of when we should on ourselves, it’s effectively shaming ourselves because we’re saying, “I’m not enough. I should do this.” What are the patterns of thought that you were in that you don’t recognize either or you just trained yourself? Those are the kinds of patterns that I love to explore with people because some of those patterns serve us, but many of them don’t serve us. That’s an interesting thing to explore.

One of the patterns that happen in real estate is we should on ourselves. It happens a lot with me and I’m sure it happens with a lot of the ladies. Also in that, “I should be doing this to improve my business.” Some of that stuff that we end up getting into the pattern of doing is, “I’m going to listen to another podcast. I’m going to get another course. I’m going to listen to another mentor.” We’re in the pattern of learning is action, which it is, but it’s not the action that’s going to move the needle.

Moving our patterns from “I should do this” because that’s not what I want people to do, but to naturally move into, “I know enough and it’s time to take action. This is what I want to do and this is what it looks like so that I can move the needle.” In other words, buy a property or get your financing. Do those things rather than talking, learning, and thinking about it. It’s so much easier to be in the pattern of learning. It’s so much more fun. The pattern of taking further action is another step and it’s sometimes hard to get there. What I would like to do is talk a little bit about fear and how that plays into wanting to take action but not doing it or not taking that next step.

You hit the nail on the head. It was beautifully said because many of your audience, myself included, were entrepreneurs. How long did we have the idea before we did something about it and before we believed that maybe we deserved it or that we earned it? Those kinds of weird things. It’s like, “I’ve taken enough courses. I’ve clicked on enough links.” There’s no magical point where all of a sudden someone hands you a pair of wings and you’re like, “Congratulations. You may now fly, entrepreneur.”

You are the person that kicks yourself in the butt that pushes you off the ledge to figure out if you can do it. Hopefully, you have people around you that love you and care about you. Maybe it also looks like saving that is a net for you to potentially fall and you never fall that far, but you’ve got to fall a little while because this is scary. I love it. There’s a lot of fear of falling and a fear of failing. That’s a big thing. One of the biggest fears that I notice people have said when it comes to going on a new business venture is they say, “Once I get blank, then I can blank.”

We are the people that build those roadblocks. We are the people that say, “This needs to happen before I can do this.” There are very few things that need to happen before you can achieve what you want to achieve. Chances are you put it there, not anyone else. Don’t get me wrong. If you want to be a doctor, I’m going to need you to get your MD first, but that’s not what we’re talking about. There are pieces of information that you need to know, but the barrier of entry is not as high as we make it out to be.

REW 8 | Imposter Syndrome

Imposter Syndrome: They say fake it till you make it but if all you ever do is fake it, you never really make it.


Let’s talk a little bit about that. If you’re want to be a doctor, you need to get your MD. There are millions of doctors out there in the world that got their MD, but there are at least 3, 4, 5 or 10 times that are investing in real estate. Many of those doctors are investing in real estate. This process of real estate is the most intuitive investing you can do on the planet. I say this all the time on my show, “We’ve been doing this since the beginning of the time and the end of time.” In the old days, it used to be the lords that had the land and the peasants that wanted it. We’ve always wanted land. We’ve always wanted a space where we have a footprint that’s our home. We’ve always needed places to live.

This is the single most intuitive, stable, and safe investment you can do. Yet, because of all the classes, the options, and the things you can read and listen to, we complicate it. We turn it into something that is not intuitive and that we need to know a ton about it. There are some things that we need and we can then move forward and learn along the way. That’s how most people do it. It is important to understand that there are pieces you need to learn, but there are huge teams of people out there that can help you. Nothing happens until you take action and you don’t need an MD on this. You don’t need to study for eight years and then go into an internship for this. This is an intuitive strategy that you can plug into your life as is.

Many of us say, “I’m not blank enough. I’m not business savvy enough. I don’t understand finances enough. I’m not a business person. I’m not a head person, I’m a heart person. I’m not this or that.” Whenever we start to do those things of, “I’m not blank enough,” those are the times where we take ourselves out of the game before we even let ourselves play it. We don’t even let ourselves show up at the stadium. A quick story for me, even just a small example. Despite being the charismatic, wonderful, and extroverted man that I am, when I first went to college, I didn’t interact with a lot of people. I was like, “Let me not sit down next to these random groups of people at the dining hall. Let me not sit next to these individuals in the coffee shop that I recognize from class.” I was like, “James, you’re not cool enough. You’re not funny enough. You’re not smart enough. You’re not hot enough. You’re not rich enough.” I missed community building where the places where the audience is telling themselves, “I’m not blank enough,” and they’re not even letting themselves get in the game.

It’s such a good point, “I’m not blank enough.” Ladies, think about that. What is your, “I’m not blank enough?” I will say that I’m not blank enough for me is I’m not smart enough. I went to UC Berkeley but my husband went to Stanford. His whole family thought that Stanford was way superior and let me know about it. My parents thought that Stanford was better. Somehow, this person that was a valedictorian and at the very top of my school with a 4.5 is not smart enough. It’s interesting because it was something that I put so much value on.

Part of what attracted me to my husband was that he was “smarter than me.” In other words, we expanded one another. Suddenly, it became a story for me that I’m not smart enough because I’m not as smart as him, which is not true. He’ll say it all the time but it became my story. I find that even now as I’m talking to many of my guests or I’m looking at other opportunities in the market, I still come up with I’m not smart enough. It is interesting because I’ve been in this business for many years. I know what I’m talking about and I still have that.

For ladies, what is your, “I’m not blank enough?” Let’s figure out how you can readjust that to support yourself more. Let’s also talk a little bit about the imposter syndrome because this is relevant and related. For me, I’m not smart enough but I’m showing up out there in the world as being smart and knowing my stuff. I feel there’s this dichotomy. I’m split because I don’t feel it but I’m acting it. It’s not fully true but that’s how things work for a lot of us. Could you talk a little more about that?

I love to talk about the idea of punching imposter syndrome in the face because it’s something that holds a lot of us back. We don’t even recognize it or name it as such. As an example to help people land the plane a little bit, I had an opportunity to speak to a bunch of doctoral wielding professors at a university. I do not have a doctorate. I’ve been to a doctor but that’s about as close as I’ve gotten. To your Stanford-Cal analogy, I have my Master’s but they have their doctorate. There was this thing when I walked in. I’m like, “I’m not smart enough to talk to these people. I should be the one in the audience and they should be lecturing to me. What are you even doing here? Why are you in this space?”

The barrier to entry is not as high as you make it out to be. Share on X

It’s interesting because we all know the phrase, “Fake it until you make it.” If all you ever do is fake it, you never really make it. There has to be a place in our lives where we recognize that you indeed have something to add. You have a value-add in every room that you walk into. The relationship that you were talking about, Moneeka, what you have added to your husband goes far beyond your already impressive Cal degree. Let’s not slap on Cal. It’s one of the top twenty schools in the world. What you bring to that relationship maybe isn’t measurable by the intelligence standards that we’ve been taught of like SAT scores and things like that. For imposter syndrome, getting over that involves realizing, “I’m bringing something to the room that I could add to these individuals.”

Those professors in my example are smarter than me. They’ve done way more research than me. They probably did better in school than me, but I’m better at engaging people than they are. I’m better at making people realize that sometimes it’s the story behind the facts that makes the fact more sticky, not just the research. It’s that relatability versus credibility argument. There’s a lot of power in relatability and that’s what I brought to the room. That’s what I’m talking about here. We need to punch imposter syndrome in the face because we’re not even letting ourselves get recognized with the beauty that we bring to the table.

I love the way that you say, “The beauty that we bring to the table.” We might have people where their “I’m not” is “I’m not financially savvy enough. I’m not a business person enough.” I understand that those pieces can be learned. Being successful in school is a skill and can be learned. Some of us have a predisposition with talents and stuff that make us better at some things than at others. Because we’re not one thing or we believe one thing, does not mean that that’s something that has to hold you back. It may not even be true. All of those smart people are probably not going to be as engaging on stage, which is why you’re the guy on stage.

One of the things that you said is, “I’m a heart person, not a head person.” In real estate, being a heart person is so valuable because nobody else is out there speaking or negotiating with tenants and landlords from the heart. It’s all about the dollars. It’s hard and clinical. It doesn’t have any feeling to it. If you’re a heart person and you bring that, you can learn that other piece or hire somebody else to do it. Instead of, “I’m not blank enough,” focus more on “I am this or that. That’s what I bring to the table.” How can I now make that the focus of how I’m going to move forward? I want to do my business in a way that highlights that rather than trying to start a business based on what I’m afraid I can’t do.

I completely agree with you and the way that you put it was beautiful. I have a Bachelor of Science in Marine Biology. I have a Master’s in Counseling but I’m an entrepreneur. I’m a businessman or a business human. I consider Shark Tank to be the closest thing to business I know anything about. That’s where I’m getting my “MBA.” Thanks, Mark Cuban, but I still like to tell people I’m in the business of relationships. That’s something that when you hear or think about business, you think about the hard things. You don’t think about the soft and the heart of it. The fact that we are exceptional at making people feel like you’re selling homes to people in real estate. Whether that home is in work like this is a place where you’re trying to build a community to foster the growth of a product and corporate real estate, or a physical home where someone is going to live and grow. What a thing to sell. Isn’t a relationship the best way to sell that?

I love one of these things that you say, “Move from accommodator to advocate.” Talk to me a little bit more about that. We’re already sort of, “How can I be an advocate for myself?” Much of the time, we are taught to accept ourselves but we’re not taught about how to be an advocate for ourselves. Could you talk to us about that from your own perspective?

I’d even add one step even before accommodator. We have a lot of apologizers out there. We apologize a lot for ourselves, then we become accommodators where we concede a lot, and then we become advocates for ourselves. Unfortunately, because of a lot of societal BS, women are taught to apologize for themselves and that is hot garbage. Where are the places where women can feel more confident to advocate for themselves because their voice is maybe more important at the table? It’s recognizing when you fall asleep at night, you know if you fall asleep proud or ashamed. We all fall asleep on that spectrum at various points.

REW 8 | Imposter Syndrome

Leading Imperfectly: The value of being authentic for leaders, professionals, and human beings

It’s not just because I checked all the boxes on my to-do list. It’s more of like, “I upheld my character. I upheld my value.” When we advocate for ourselves, we recognize that I am smart enough. I am trained enough. I am the right person to be in this space right now. That is a beautiful thing to know. It’s hard to get to but it’s important because when we don’t, instead we accommodate it to others. We let others walk all over us. There are all these contingencies and all these whatever. Having that confidence in, “I know my stuff and I know I’m doing the right thing here by you,” is also important in sales and we know that.

You said something I’ve never heard before, which is a woman saying, “My voice is more important at this table.” A lot of times what you hear in women’s circles and conversation is, “I’m important too. I have a right to speak too.” What about, “I am the smartest person in the room and they need to hear what I have to say?” How many times have we as women heard that? You said it, “I’m important. I am the person that should be speaking.” It’s not just, “I’m important too, but I am the most important.” Not to be egotistical about this, ladies. I’m not saying go out there and start being egotistical. I do think that so much of the time when we are the smartest person in the room, we still will not allow ourselves to be the smartest person in the room. We’re afraid of how it’s going to look.

There are gentle and beautiful ways that we can stand up and be the smartest person in the room without putting anybody else down because I know that’s important to us. It’s recognizing that you are and that’s great and that your voice is important. It’s not just it’s important too, but it is important as it is. It’s important for us to recognize who we are in a room and be honest about it to ourselves. We don’t benefit ourselves, our businesses or the people around us by shrinking back from our own mastery. It’s our mastery that’s going to help to improve the world through our businesses.

When we make ourselves a little bit smaller, we are accommodating to other’s insecurities. I know that this space is male-dominated. Correct me if I’m wrong, I haven’t done all my statistics. In a male-dominated space, male insecurities are not the things that you need to accommodate. In general, our insecurities are always things that we need to be aware of. Being aware is kindness. It allows us to come up with a new approach, but that approach does not have to be accommodating. That approach means we’ve got to try a slightly different size peg to get it in the right hole, but it doesn’t look like you are accommodating.

When I lived in France, it was important for me to say hello in French to get the conversation going. When you notice somebody’s insecurities, starting to speak their language, you’re still going to say what you need to say. Whether I’m speaking in French to the French or in English to the English or in Hindi to the Indians, no matter what language I’m speaking, I still have to say what I want to say. I’m speaking it in a language that they understand because they’re not fluent in English. This is the same thing. You don’t want to necessarily accommodate but you want to be respectful, kind, generous, compassionate and notice. Those are the sort of things but it’s important to not shrink back who you are.

You deserve to be in the space.

Take your space. You’ve got a footprint that was put here on this planet because it belongs here. Own your footprint.

To go back to your too example, “I’m important too. I’m smart too.” When I hear that, I picture a little brother yelling up at an older brother like, “Me too.” It puts levels in place when we do that, but instead, you are on the same level. There’s no too. There’s just is.

“Here I am” and not “Here I am too.” That’s exactly right. I love this conversation, James. I’m excited about what we’re going to be talking about in EXTRA. Ladies, James and I are going to be talking in EXTRA about busy versus productive, and decompression versus inaction, which are important distinctions in how we run our lives. It’s going to be valuable. We’re also going to talk about some of those fear patterns and how we can release them. That’s what’s coming up at EXTRA. I’m excited about it, but before we moved to EXTRA, let’s finish up this show first. Let’s start by telling my ladies how they can get in touch with you, James.

You have a value add in every room that you walk into. Share on X

First of all, thank you so much for letting me be a part of your community. It is indeed an honor. I appreciate you for believing in me too. You can reach me @JamesTRobo on all social media platforms. and [email protected] for my email. Let’s hang out. Your boy looking fresh on Instagram and dropping some meaningful nuggets. I would love to keep in touch with you.

I know that you’ve got a special gift for my ladies. Could you tell us about that?

I wrote a book called Leading Imperfectly and it is about authentic leadership. I would love to give you the first three chapters of that book. If you like it, you can pick it up elsewhere. If you don’t, it was free so who cares.

I assure you they will love it. Are you ready for our three rapid-fire questions?

Here we go.

James, tell us one super tip in getting started in real estate investing.

Get out of your own way. You are ready right now to do it and you have to believe it. The only thing in your way is you. It is not your knowledge, your background, your past or anything you’ve been through. You are the only thing in your own way so it’s time to keep moving.

Give us one strategy on being successful in real estate investing.

REW 8 | Imposter Syndrome

Imposter Syndrome: Get out of your own way. You are ready to do it.


Being successful involves building great relationships and where are the places that you are using those relationships to both learn more and give more in that place. That’s the biggest thing. Our network’s net worth is bigger than our net worth, and so those relationships are super important. I know that’s cliché and it’s cheesy but I love cheese.

What would you say is one daily practice that you do that contributes to your success?

Every day I dream and I live my life based on what I want to be said in my eulogy. The way that I have conversations with people and myself, I think about, how do I want to be remembered and how am I building towards that?

James, it’s been amazing everything that you’ve shared. Thank you so much for sharing that great stuff on this portion of the show.

Thanks for having me.

Ladies, thank you so much for joining James and me for this portion of the show. We’ve got more coming up in EXTRA. If you are subscribed, stay tuned. I’m excited about what we’re going to share. If you’re not subscribed to EXTRA but would like to be, go to I’ve been doing EXTRA for years. I have to say that is my true gift to you. It’s a place where my amazing guests who do a great job on the first part of the show do an even better job later. This is where they shine. This is where they give you their deep and amazing nuggets that will change your life.

If you’re not subscribed, please come and check it out. You get the first seven days free. You can listen to a lot of them and decide if it’s even relevant or anything you want to pursue. If you do decide to subscribe, it’s $4.99 a month. It’s a complete steal for all of this information and for the way that it will improve your life and your business. Please check that out. For those of you that are leaving us, thank you so much for joining us for this portion of the show. I look forward to seeing you next time and until then, remember goals without action are just dreams. Get out there, take action, and create the life your heart deeply desires. I’ll see you next time.


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About James Robilotta

REW 8 | Imposter SyndromeJames is an author, speaker, coach, & entrepreneur. His book is titled: Leading Imperfectly. He speaks internationally to willing & unwilling attendees about authenticity & vulnerability in leadership & life. His clients include AMEX, GE, & others. He’s also an experienced stand-up & improv comedian.

James is also a personal coach. He loves helping people get out of their own way to live the lives they deserve and be the leaders they are capable of becoming. James’ clients undergo purposeful life-changing and self-affirming transformations. His clientele ranges from CEOs to college students. Visit his website:



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Moneeka Sawyer

Moneeka Sawyer is often described as one of the most blissful people you will ever meet.   She has been investing in Real Estate for over 20 years, so has been through all the different cycles of the market.  Still, she has turned $10,000 into over $5,000,000, working only 5-10 hours per MONTH with very little stress. While building her multi-million dollar business, she has traveled to over 55 countries, dances every single day, supports causes that are important to her, and spends lots of time with her husband of over 20 years. She is the international best-selling author of the multiple award-winning books "Choose Bliss: The Power and Practice of Joy and Contentment" and “Real Estate Investing for Women: Expert Conversations to Increase Wealth and Happiness the Blissful Way.” Moneeka has been featured on stages including Carnegie Hall and Nasdaq, radio, podcasts such as Achieve Your Goals with Hal Elrod,  and TV stations including ABC, CBS, FOX, and the CW, impacting over 150 million people.