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Get Over Yourself: Transformational Insights from New York Times Best-Selling Author, Dave Kerpen

In this episode, Dave Kerpen, a serial entrepreneur and New York Times best-selling author, discusses imposter syndrome and the power of delegation. His new book, "Get Over Yourself," delves into how delegation prioritizes what truly matters in our lives. Tune in to learn effective delegation strategies to overcome self-doubt and reclaim time.

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Audio Only

March 27, 2024

Join us as we delve into the insightful world of self-discovery and productivity with serial entrepreneur, global keynote speaker, and New York Times best-selling author, Dave Kerpen.

In this candid conversation, Dave opens up about his personal journey with imposter syndrome and introduces us to his latest gem, "Get Over Yourself," a book that shines a light on the power of delegation in both professional and personal realms. Through heartfelt anecdotes and profound wisdom, Dave reveals how delegation isn't just about lightening your workload – it's about reclaiming time for the things that truly matter. 

Tune in for a dose of inspiration and practical wisdom that promises to elevate your understanding of success and fulfillment.

Dr. Chloe: Dave, congratulations! I absolutely loved the book. I had my orange highlighter. Really enjoyed it.

Dr. Chloe: But just to introduce you, of course, is that Dave, I must say, is an incredibly generous person. He's my mentor, super successful, had an eight-figure exit from one of his businesses, and has built many other various successful businesses in addition, of course, to being a New York Times bestselling author. So I'm super fascinated to know what is going on inside of Dave's head during such a big moment as a book launch because Dave is publishing yet another book, Get Over Yourself, which I think is a great title for a book about delegation.

Dr. Chloe: So, Dave is a New York Times bestselling author, super successful, yet he actually confided to me during one of our mentor sessions where I'm the mentee, that he actually sometimes suffers from imposter syndrome. Of course, as a psychologist and a mentee, this was incredibly surprising for me. 

Dr. Chloe: I'm really excited to ask Dave a few questions about what he said about imposter syndrome, as well as a bunch of questions about his process in writing the book and a bunch of questions and comments about the book itself because it was incredibly inspiring to me. I've actually gotten a million things done since reading this book because it was so inspiring to get things done. So thank you, Dave, for that. 

Dave: Thank you for your wonderful, wonderful intro, Chloe. And thanks for chatting with me here. I appreciate it. And it's so funny because this is very macro, but the book title is Get Over Yourself and it's a double entendre. The first refers to delegation, but also getting out of our own heads when it comes to the issues that we have that keep us from delegating.

Dave: But ironically, I needed to get over myself with respect to my imposter syndrome and sort of get out of my own head with respect to how I was feeling with the book launch. And it's good because I'm staring at the words “Get Over Yourself” all the time. So it's actually very valuable for me in helping me manage things.

Dr. Chloe: Yeah, so I have to ask, obviously it might sound kind of counterintuitive to ask this, but since part of what I do is teach people that, in fact, there's a healthy function to anxiety, which is to stimulate preparation behaviors. I have to ask, do you feel like there's any healthy function to imposter syndrome?

Dr. Chloe: Like, does it help to keep you on your toes? Or maybe even just staying in touch with yourself? Or do you think that there's absolutely no healthy side to imposter syndrome? 

Dave: That's a great question. I mean, you're the psychologist, not I. I think that while there is some doubt, there's positive elements to everything.

Dave: And to your point being in touch with dealing with imposter syndrome is certainly helpful for me in certain ways. While it might seem challenging at the time because it is associated with feelings of self-doubt, self-criticism and anxiety, it also can be kind of humbling, which is nice, right? Also can be a nice reminder for me to focus on what's really important to me. 

Dave: We haven't talked since the launch. We launched a week ago and I had in my head this goal of being in the top 1,000 of all books on Amazon. And I was very clear about that goal. 

Dave: And I didn't hit that goal. We were in the top 6, 000 of all books on Amazon. But not in the top 1,000. So I could, this is after the fact, right? So it's not necessarily imposter syndrome, but I could take that fact and become very self-punishing and self-critical and down on myself.

Dave: Or I can step back, look rationally at the situation, and think, well, top 6,000 of over 2 million books versus top 1,000 of over 2 million books, doesn't really make much of a difference in the grand scheme of things. And why was that a goal anyway? My real goal is impacting people and helping people.

Dave: And so, if I can do that with this book, why do the Amazon rankings really matter? So I do think imposter syndrome as we might define it is helpful as is all psychological challenges if for no other reason to help give us more self-awareness and help us put things better into context.

Dr. Chloe: Yeah. I feel like there's always two sides to every coin, but as far as your goal of impacting people, oh my goodness, I swear this book definitely impacted me. This is actually so funny. My business does not even need to hire someone, but I felt so driven to hire someone after reading this book.

Dr. Chloe: I actually am in the process of hiring someone for my husband's business, because I just started, you know, knowing what was going on in his business and just, you know, it got me in to delegate to someone. 

Dr. Chloe: And that was such a powerful statistic too in this book that I think it was 33% of businesses, that there are 33% more likely to be successful and revenues are so much higher, which, you know, it does make sense. But what I also loved is the way that you connected delegating to true life goals, to true fulfillment, because when we think about delegating, it can sound almost just like this office skill that doesn't connect on a heartfelt level with us. But you shared some stories in this book. 

Dr. Chloe: One was about a woman that was actually feeling like she might not even be able to have children, that she might've missed her fertile window, and she was looking at other options and things. But she was actually saying, wow, if I had delegated, not felt like I had to do everything myself, I might have found some of that time back when I needed it. 

Dr. Chloe: And you talk about delegating as to picking up your kids from school, be with them and having dad Fridays all the time every Friday. So I love the way that you connected it to heartfelt, I know it sounds cheesy, but to heartfelt living, that taking something like delegating and connecting it that way. 

Dave: Yeah. I mean, for me, the stakes are very high and it's so much bigger than building a 10 million dollar business versus a 5 million dollar business, or a 100 million dollar business versus a 50 million dollar business. In the history of the world, the percentage of people on their deathbeds to have said, I wish I had worked more is so, so low. But the percentage of people that have said, I wish I had more time with my family.

Dave: I wish I had more time to pursue travel. I wish I had more time to pursue my passions. I wish I had more time with my close friends. I wish I had more time to write. There are so many things that people regret when that time goes by that we can't get back. And for me, to your point, Chloe, delegation is sort of a key to prioritizing what's important to us in our lives and then making sure that we give that priority.

Dave: Whatever we prioritize. And for many of us, it's our kids, but I try to not be too biased about that because there are people out there that maybe don't have kids or don't want kids. That's fine. But surely there are things that you would, whoever is watching or listening, there are things that you would prioritize if you could better get stuff off of your plate.

Dr. Chloe: Absolutely. Yeah, you made that really clear that, you know, for many people, it happens to be their kids, but for other people, it could be their spouse, or it could be, you know, time to pursue creative passions and things like that. And as you said on one level, we don't often hear about people who on their deathbed say, you know, gee, I wish it worked more.

Dr. Chloe: But I will say as a clinical psychologist, I have worked with geriatric populations, especially in my training. It's not uncommon for people at the end of their lives to wish that they did have greater financial security for the comfort and the choices that they have, if thanks to the work that they did in their younger years.

Dr. Chloe: And what I love about your book and with delegation is that it allows people to have the best of all worlds that, you know, you can be financially productive and building a good nest egg for yourself in those later years, but you also don't have to sacrifice all of the time doing all that work yourself you know, thanks to delegation.

Dr. Chloe: I have to say, your book, literally, guys, it made me laugh out loud. And I don't like just laugh out loud time when I'm reading books necessarily. But truly this book had me laughing out loud. Dave is a really funny person. I think that there was one line in particular where you were like, I can't even change a light bulb. I've had multiple embarrassing experiences, but thankfully I don't have to, because I can delegate. Right. Honestly, it's a really inspiring book. 

Dr. Chloe: I do want to ask you a few questions more on the personal process side about this book. And I love that you also share, by the way, that some of the books that you even got help from AI, which is incredible.

Dr. Chloe: You talk about delegating to AI and how we can do that too. But I'm curious, how long have you been working on this book? When did you start it? When was it just an idea? How many hours a day did you write? I'm just so curious about your process. 

Dave: Yeah, sure. So it's about a year and a half total from kind of idea to launch if you will. And that's mostly because bigger publishers have a long process, right? For folks that are watching and listening that want to self-publish, that process can be much faster. 

Dave: But writing is hard. It's one of the harder things. Writing a book is hard. You know, as an author yourself. For me, the way I do it is I add time on my calendar to write every single day. Very short amount of time. So sometimes basically five minutes. And that forces me to focus exclusively on the writing for that five minutes. I will have some days where I sit there and just not feeling productive and sort of sit there for five minutes killing time. And then it's on to the next thing. 

Dave: But of course, I have other days where I write productively for five minutes. And then since I've blocked out essentially a half hour, if I book from nine o'clock to nine o’five for writing, nobody's booking time with me from nine o’five to nine thirty. So it's a little bit of a secret hack because on days where I'm feeling more productive, I just continue to write for 25 more minutes, sometimes an hour, and then, you know, day by day, hour by hour, it starts to get written. 

Dave: It's kind of ironic because I do often work with co-authors and you would think that co-authors would have made sense for a book about delegation. But this one I did write mostly myself, to your point, I did use AI for a couple of chapters and indicated that where we did it. I did have some help from my apprentices who helped me with some of the chapters as well.

Dr. Chloe: Yeah. To which I have to say was amazing too, honestly, from a marketing standpoint. I feel like the audience for this book could be certainly obviously business people who need to delegate within their businesses, but even just in everyday life as well I felt like there was a lot that we could do there. It really inspired me to get a little bit more curious about what AI could take off of my plate. I'm curious, do you write even if you're not under inspired and do you journal? 

Dave: Oh, great question. I wish I could say yes. I don't write books. I guess I do write articles when I'm feeling inspired. But it's not with the same amount of consistency or structure when I don't have deadlines. And that's why for me having a publisher is very valuable because if nothing else it gives, it forces me to have some deadlines. Whereas when I don't, I can go on long periods of time where I'm less productive writing-wise.

Dave: I don't actually know if you know this, Chloe, but going back to the audience for the book it's funny because, and this is an unfortunate aspect of writing for a publisher because when sometimes there are deadlines and sometimes it's too late, after I wrote the whole book, I realized that while of course the business book I did think and do think some of the principles of delegation apply beyond.

Dave: And so I ended up writing a bonus chapter that I published online for parents about delegating. But it was too late to get it in the book. I was so bummed. So the paperback edition will have a chapter on delegating chores at home. But I was like, wow, I actually can use principles of this to help make sure that kids are doing their job around the house and helping out. And what parent wouldn't benefit from that? 

Dr. Chloe: Yes, which is so true. I mean, a lot of those same principles apply as a parent. And as a psychologist, I think, when we give our kids jobs, it boosts their own self-esteem, it has a practical value to the family and it really teaches us how to be part of a team. So I actually read that chapter and I loved it. 

Dr. Chloe: But since you're mentioning as well about the publisher, that touches on to another question that I had for you which is about the actual publishing process. So one is, how did you choose the publisher? How involved were you in negotiating the book deal? How much do you leave that up to your agent, and how has that maybe changed over the years since you've had several books? 

Dave: Yeah. Okay. All great questions. So I went with BenBella for this book. It's a very entrepreneurial publisher. I picked them for three reasons. First, they did Gina Wickman's Traction, which is one of the sort of best, most sought after, looked up to books in entrepreneurship circles.

Dave: Second and this is sort of funny, but it's not untrue. They also did Jenna Fischer's book from The Office and Jenna Fischer, of course, played Pam on The Office, and The Office is one of my all-time favorite shows. I thought it'd be super cool to work alongside her as an author.

Dave: And then third and most important, it was a really interesting entrepreneurial deal. So much more upside than other publishers. And I felt like I got the best of both worlds with respect to working with a major publisher, with major distribution. They work with Random House to distribute the books, which was my publisher for my last book, The Art of People, but with a really creative, more entrepreneurial structure. 

Dave: So I got a very small advance on this deal. I will share that my offer from another major publisher, I don't think I should share which one, but another major very well-known publisher offered me in advance, which was five times bigger and very tempting. My agent probably wanted me to take that deal. Because they get paid more upfront on that, right? But the reason I went with BenBella was I really liked that overall upside and the entrepreneurial look at that. And at the end of the day, while I have written five books now, I'm more of an entrepreneur than an author. I just sort of thinking about the deal structure ultimately made me think I got to go for this. 

Dr. Chloe: Can you share any particulars of that deal structure that made it that much more attractive just for those of us who are interested in the business side of books? 

Dave: Yeah, I mean, the royalties are just much, much higher. So it's a much smaller advance than major publishers would offer me at this point in my career. But the upside is so much greater, the royalties are so much bigger, that ultimately I want to be rewarded for book sales and for the success of the book. I'd rather do that and have bigger checks hopefully years from now. Than a big check up front and then, you know, nothing ever again. A lot of authors don't earn out of their advances basically ever. 

Dave: And to me, I want to be motivated to sell books for the rest of my life, right? I try to write books that are as evergreen as possible and certain principles, certain things. I'm sure that what AI can do, for instance, will change and get better and better, right? But the idea of delegating to others and delegating to AI hopefully will be really evergreen. 

Dr. Chloe: Definitely. And again, I love that we got to hear a little bit about your approach on the business terms of the book, because that's another area where I swear, just, you know, you have this amazing combination of creativity and drive.

Dr. Chloe: If anyone's ever heard the phrase, like a happy warrior, I just feel like that is you because, you know, there's this really tough New Yorker that's able to go after things from a business perspective, but then so much just genuine care and compassion for people. It's really an unusual combination, but that's another thing. 

Dr. Chloe: I actually learned even just business ideas because Dave shares, he mentors so many people and he shares some of the journeys that people went on through delegation. One of the things I read that I was surprised and intrigued by is one of your mentees hired, it sounds like a C-suite marketing officer or something like that for a hundred percent equity, like through LinkedIn.

Dr. Chloe: So they were getting presumably good professional talent, but the person was under a real cash crunch. And so he hired for a hundred percent equity. Did I read that correctly? 

Dave: 50 percent, yeah, splitting. I think one of the biggest roadblocks in people's heads around hiring somebody very high level is I can't afford to hire somebody very high level.

Dave: And to them, I always answer, well, if you think about it differently and bring in a partner instead of hiring somebody, well, then you can afford talent. Now you have to be able to say, okay, I'm willing to give up, you know, 50%. I don't need a 100%. I'm willing to give up 50%, 75%. But in my view, it's just so much better to have a smaller piece of a much bigger pie and have great help and talent along the way to help us build our businesses.

Dave: I think unfortunately a lot of people think very myopically about this and they want to hold on to 100% of their business. But what's 100% of a business that can't really scale because there aren't real C level kind of rock stars driving the business.

Dr. Chloe: Right. So I didn't mean to suggest that I thought he hired by giving away a hundred percent of his equity, but if I read correctly, it looked like he hired somebody whose compensation was a hundred percent based on equity. 

Dave: Yeah exactly. That's a true partner. Basically finding, bringing people on that are true equity, sweat equity partners. Yeah, he did that. Again, if I'm an entrepreneur and I really believe in something and you can catch me at the right time, yeah, I'd be willing to invest my time in something that I think can produce really significant results. That's essentially the definition of co-founders, right?

Dave: Ultimately, that's what co-founders are. So many, many folks are good at one element of a business, but through co-founders, through partners, they can bring in other, you know, really, really great talent. 

Dr. Chloe: Yeah. It was it was amazing. I will say as has some incredible interview questions, right? So for anyone, if you're like even thinking about delegating, or even if there's just work in your life that you don't feel like doing, this book will help you figure out how to delegate it. And again, I loved the list of interview questions that you shared to really tap into people that are going to be able to be creative and take ownership of the work.

Dr. Chloe: One other thing I just want to share that I found very inspiring that I think is a challenge that a lot of people can hopefully relate to is to be able to take an extended vacation, that Dave has this challenge that he puts out to people to say, you know, could you disconnect from your business?

Dr. Chloe: For say 10 days, which I have to admit, even to me feels very daunting to be able to disconnect for 10 days and just be able to trust that your delegation team has got things under control. I mean, that's pretty amazing. When did you reach that point? Did you struggle originally to let go? I know you talked about that a little bit in the book.

Dave: Yeah. A little, I wish I could say I struggled more because it would make for a better story. But unfortunately, or fortunately for me here, this is something that I have been pretty good at. I think that the vacation test is a really good one. And sometimes we're forced into it. I mean, the story I told in the book is about somebody I was mentoring who didn't want to go on vacation, but it got to the point where his wife was basically going to leave him if he did not go on a vacation.

Dave: And so he had to say, I got to do this, Dave, what am I going to do? And I said, you're going to delegate and it's going to be fine. And guess what? He delegated and it was funny and had a wonderful vacation and, you know, years later has a great marriage. And so, you know, it is very important, but it can be very hard, especially if we're used to being around and being present.

Dave: I think all of us, and you're the psychologist here, but all of us like some sense of control over things. When we delegate, we are essentially letting go of some of that control and that can be hard. So when we're if we're really, fully disconnecting and going vacation, it's really surrendering control, which again can be very hard, but ultimately, I think, is a good lesson.

Dr. Chloe: Yeah, I like it because the book really talks about how to do it, right? Delegation, as Brian Tracy says, delegation is not abdication. The book really talks about for Type-A functionist people that they understand, like they painstakingly built this business and their reputation is on the line. They don't want to just to randomly hand someone the keys to that beautiful car that they've built and let that person just crash it.

Dr. Chloe: So I really like the stair stepper type of approach of how to get comfortable with that. I know you shared as well in Choose Apprentice, in this business that you built really, that helps entrepreneurs to learn how to delegate that on one level, Choose Apprentice is providing the person for them to delegate to. But on the other hand, it's almost like you're like a delegation therapist as if, you know, you're kind of meeting with the business owners. And helping them to work through their anxieties about delegating. And then also how to make sure that they don't just override their anxieties, because, you know, again, for me, I'm always saying the healthy function of anxiety is to stimulate preparation behavior.

Dr. Chloe: So we don't want to just say like, Oh, well, I'm really scared about this delegating, but whatever, I'll just do it. We instead want to say, well, I'm nervous about delegating. So, therefore, how can I set up, you know, some checks and balances? I love the schedules of different types of, you know, frequencies and manners that you could in with people. I'm surprised that you had to say it, but checking in by text does not count. 

Dr. Chloe: So for people that really want like a good. How to guide that will also make them laugh out loud. I definitely recommend Get Over Yourself. It was such a funny book. I mean, funny, but also extremely helpful. I actually really enjoyed it very much.

Dr. Chloe: And as I said, it inspired me. In fact, my husband owes you a thank you because I'm really working on finding him the perfect new financial person for his team. 

Dave: Wonderful, so you've got more time with him. 

Dr. Chloe: Yeah. So Dave, is there anything that I have not asked you about that you wanted to share that didn't come up?

Dave: Well, you know, thank you. It's funny because as much as I love chatting with you about the book and delegation, I guess the fan of therapy in me will flip the script a bit and ask you to help me go a little bit deeper about this imposter syndrome, becauseto me, I wonder if success, if more successful people are more likely to struggle with imposter syndrome. It seems to me that, you know, I'm almost a victim of my own success in as much as, you know, like, yes, I'm very, very honored and proud to have hit the New York Times bestseller list.

Dave: But it's like, once I hit that, now I want to hit it again. It's like, and you know, once I've hit a certain level of success that impacts, you know, well, I need to remain at this level and I need to have these certain ego driven markers of success. So, A.) I wonder if you could share whether my thesis is correct, that more successful people are more likely to struggle with this and B.) more important in your experience, what is the best, I know I wrote a little bit on how I'm managing it in terms of my own, I've learned from you, how in terms of managing anxiety, how to give myself some rest and some breathing and some reprioritization and contextualization. I'm wondering if you have any other thoughts on managing imposter syndrome for listeners and viewers. 

Dr. Chloe: Yeah, that's interesting. Thanks for that though. I think that really driven people, that there could be a connection there with imposter syndrome.

Dr. Chloe: That's actually why I was even curious if there was some kind of a healthy function to it, because, you know, imposter syndrome has become such a colloquial, you know, pop psychology term, but I do just still think it would be helpful to clarify exactly what we're about when we use that term.

Dr. Chloe: So imposter syndrome and it's purist form would be, if a clinical psychologist would sit with people for a therapy session, I would honestly feel as if I had no right to be there, no sense of belonging. They're completely doubting, you know, my own obvious credentials, right? I'm sure that that's not obviously healthy, but.

Dr. Chloe: I do think that maybe there's this other side to it where when it's in a very more mild form, it might be that there is a silver lining to it. Just like with anxiety, it's not productive to become so anxious that we're just, you know, frozen in fear. But on the other hand, a little bit of anxiety helps stimulate us to look ahead and say, Hey, what could go wrong in the future? How can I right now take some steps to safeguard and to prepare for that?

Dr. Chloe: And so healthy side of imposter syndrome, again, using the term somewhat colloquially, but to be able to say, you know, I don't take it for granted, Dave, like in your case, like I don't take it for granted that every book I write is going to be a success.

Dr. Chloe: And there's this very successful people tend to be high on conscientiousness, which is their tendency to look at themselves and to say, you know, where am I falling short? What could I improve here? And we don't want to become obsessive about that. But many people need to learn how to self-reflect and, and to say, you know, on what level have I put out a certain face to the world that I know inside, I'm not really meeting that standard.

Dr. Chloe: And then I think the important question is what do we do with it? If we then just beat ourselves up with that awareness, it's not productive. But if we use that awareness to say, well, how could I get there? You know, then I do think that there can be a healthy side to it. So I hope that answers your question. But maybe not. 

Dave: No, I think it does. I think for me. It's the most valuable aspect of this book launch and dealing with, you know, again, to your point, using it perhaps more colloquially imposter syndrome has been the self-reflection and self-awareness of why I'm doing this. I am not doing this to hit the New York Times bestseller list.

Dave: And at the end of the day, I'm really not doing this to sell as many books as I can. Although of course those are wonderful outcomes. I'm doing this because I really believe that I can help people, and people can help themselves if they can better delegate. And that at the end of the day, if I can do that with this book, then that's an amazing blessing and just something that I can be something that I can be proud of.

Dave: So that for me, imposter syndrome is about maybe checking my ego at the door a little bit and focusing on what it is that I'm really looking to do. I love your suggestion that perhaps I index pretty well on conscientiousness because that's something that I definitely am focused on being very aware of and working on.

Dr. Chloe: Yeah, again, but I love the sense of humor that you have about it, like even the name of the book, Get Over Yourself. Because again, when we're delegating, we do have a little bit of a sense of self-awareness, self-importance. And so finding that balance is amazing.

Dr. Chloe: So Dave, I'm sure you’re in the middle of a book launch and running all of your multiple, multiple businesses and whatnot, I'm sure you have a million things to do. So I won't keep you all day, but where can people find you and where can they find the book? What's the best way? 

Dave: Thanks for asking. The book is available in bookstores everywhere and online on Amazon. We have a site, that has a free chapter for parents, and you can click on any of those links to buy the book. And then I'm available on social media. One of my core values is responsiveness. So anyone that reaches out on social, I respond to, and I also offer a pro bono office hours every Thursday afternoon.

Dave: So anyone that ever wants to chat with me about writing a book or building a business or delegating better or anything that you got, you all want to talk about you go to and I'm happy to spend my Thursday afternoons with anyone that wants to share a few minutes with me.

Dr. Chloe: Such a gift, you guys! Honestly, I cannot imagine like any other situation in life where you would have a guide, like a man who has hadeight figure exits, multiple, huge successful businesses, New York Times bestselling author. And he just says I want to pay it forward. I want to make myself available to help people.

Dr. Chloe: I'll tell you all personally, I've been signing up for those sessions now for several years, and it changed my life. So I encourage everyone to check out Get Over Yourself to get inspired in a helpful and practical way. And definitely to follow Dave because you can't go wrong. Thanks so much again, Dave, for taking the time today.

Dave: Thank you, Chloe. You're the best. 

Dr. Chloe: Take care. Bye.

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The High Functioning Hotspot Podcast is hosted and produced by Dr. Chloe Carmichael, PhD. For more information, visit

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