How To Deal With Imposter Syndrome

What's up, everyone? I'm Alex Lieberman. Yo, this is Jesse Pujji. And this is The Crazy Ones. What's up, everyone? This is Alex, and I am back with another journal-style episode of The Crazy Ones. People have been loving this shorter, more personal format of the show. So Jesse and I are keeping it going once a week to start. Maybe we'll increase it in the future. By the way, Jesse and I have been loving getting these emails from literally hundreds of you and getting to know you through the inbox. So if you haven't yet done so, please email us at thecrazyones@morningbrew.com. You can literally just say hi. It's literally 2 letters and we will respond to you. Think about it this way. Would you more regret taking 15 seconds to send that email or not taking 15 seconds to send the email and wondering what a conversation with Jesse and I could have turned into? So shoot us an email now at thecrazyones@morningbrew.com or after you listen to this episode. On this episode, I am going to talk about imposter syndrome, what it is, how it's tormented me for my entire entrepreneurial career, the types of self-doubting thoughts that I have, and what I do to navigate it productively. Let's do this. I am a fraud. I've gotten lucky. I'm not actually that good. All of these thoughts have nagged at me while building Morning Brew over the last 8 years. I've experienced persistent anxiety about my qualifications as a co-founder, former CEO, and now chairman of a growing media business. And guess what? Even after selling Morning Brew and having that win, I experience these doubts as I work on other endeavors, like being a host of this show, The Crazy Ones, or building a backyard game business, which many of you know is called The Plunge. When I first experienced these feelings of doubt, I didn't have the vocabulary to name it. I just guessed what it could be. I chalked up these worries to my age, being 29 years old and being inexperienced relative to other founders. Plus, before Morning Brew, I had no experience in media, and for a while I assumed it was just another manifestation of OCD, which I've suffered from since high school. Basically, I assumed any career anxieties were Alex-specific anxieties. Now, while everything I just mentioned may play a part in the fears that I felt at some point in my entrepreneurial journey, I came to realize my feelings are wildly unoriginal. What I just described is 1,000% imposter syndrome, and it's estimated that 70% of people have had some experience with it. Now, for you history nerds, imposter syndrome was discovered as a psychological phenomenon that 2 Georgia State professors wrote a paper about in 1979. Imposter syndrome manifests in a host of contexts, from relationship to career to life moments like first-time parenting. And what ties all of these different contexts or examples together is the feeling of success due to luck rather than skill. And there's a fear that you'll be outed as a fraud at some point in the near future. The CEO of Atlassian described it best. And by the way, for those of you that don't know, Atlassian is a $42 billion publicly traded B2B SaaS company. He said, let me let you in on a secret. Most days I feel like a fraud, like I don't really know what I'm doing. In the early days, customers would call up asking for accounts payable and I'd think, are they giving us money or asking for it? Interviewing our first HR manager at Atlassian, having never worked anywhere with an HR department, was terrifying. More recently, I attended board meetings where I didn't know all the acronyms being thrown around and had to write them down surreptitiously so I could Wikipedia them later. So next time you feel like you're the only one with imposter syndrome, just remember what I just read to you was written by the founder of a company with nearly 9,000 employees. So that's what imposter syndrome is. And just so you know, when I first put a name to the feelings, It didn't make imposter syndrome go away. It just provided a bit of comfort because I didn't feel crazy or alone for having these thoughts. In a few minutes, I'm going to talk about active techniques that I use to deal with these feelings. But first, I want to show you specifically how imposter syndrome has showed up in my life for years. The first thing you need to know about imposter syndrome is it goes in waves. When it's a 0 out of 10, I'm feeling really confident about the work I'm doing, and I just feel like I have my swagger. When it's a 10 out of 10, I'm feeling self-conscious. It's all I can think about, and I assume I'm a lucky one-hit wonder who will never build something successful again. Here are some of the recurring thoughts that I have when I am closer to that 10 out of 10. First, it feels like there are a few specific things that I'm really good at: public speaking, relationship building, thinking of new big business ideas to build. Then it feels like the rest of things like operational prowess, being organized, project management— I feel like that's where I'm average at best. You could say we all have a few superpowers, but not being best in class at things that to me are required of a great CEO fuel my feeling of imposter syndrome. It made me feel like I don't actually deserve to be in the position that I was in. Another thought I had throughout building Morning Brew, and I'm sure for those of you that are listening who have a partner or a co-founder, you can relate to this. I would constantly ask myself, am I pulling my weight? While in the day-to-day of the business, I would obsessively wonder if I was contributing as much to the business as my co-founder was. I would catch myself asking, am I doing what I should be doing? Am I doing the right thing for my co-founder? And how am I sure that I'm not just dead weight where the business is pulling me along? Now, the third thought that I have is in the bucket of all of this is just luck. I would tell myself obsessively the same story. The only skill I had was to create a janky PDF newsletter back in 2015 when I was a student at Michigan. That is what literally got the snowball rolling down the hill. But I have demonstrated no skill in keeping it rolling. So the last 8 years can be defined by 1 ounce of skill in 2015, followed by pure luck. Another final fear that is most pronounced right now as I try to build another business outside of The Brew is this idea of being a one-trick pony. That Morning Brew is my only successful venture, and it will always be my only successful venture. It's this thought that makes me fear that I'm not actually a good podcast host, and the content I create will never be successful enough. It's this thought that makes me worry that the Kickstarter campaign for the plunge that I'm doing will be unsuccessful, and it will be further proof that I was just lucky the first time around. And it's this thought that makes me more risk averse than I probably need to be, and view money with a scarcity mindset because I fear that I'll never have a financial success again. So I bet. hoard what I do have right now. But here's the real issue with imposter syndrome. There's the direct effect of feeling anxiety and stress from the stories that I tell myself. But then there's also the indirect effect of that self-doubt impacting the way that I work. I have noticed at points in my career when I'm a 10 out of 10 on the imposter syndrome spectrum, the way that I work changes. First, I lose any semblance of work-life balance. I find myself having to work harder and harder to make up for this feeling that I don't have the right skills or talent. I start to believe the only way I'm going to develop these skills and deserve to be in the position that I'm in is to spend more time working on them. And this has become kind of a tell for me and for my fiancée, whether she's seeing me on my phone while we're watching a TV show or, you know, we get into bed at night and I'll be on my computer working through things. These are all tells about how my behavior changes as a function of this anxiety. The second major impact of imposter syndrome is it's led me to lose appreciation for the entrepreneurial journey at points because I become so obsessed with these feelings of fraudulence, these feelings that I didn't deserve it, that I don't have the right skills, that luck is what's gotten us here. Those all can dull the experience and take me out of the moment of building. And it's a really shitty feeling because one of the best parts about building a business is enjoying All of the little wins along the way. The third effect, and I'd say the most detrimental, is that when I experience imposter syndrome, it makes me lose confidence in doing the things I'm actually really good at. And that's because imposter syndrome doesn't just attack specific skills. It attacks your character. It attacks your identity. And when I feel like my entire identity is attacked, it will make me feel more anxious, not just about the things that I don't think I'm amazing at, but also the things that I think I'm really good at. Whether that's leading meetings or speaking publicly on a podcast or selling big brands on why they should advertise. So where does that leave us? First, I put a name to my feelings, and that name is imposter syndrome. Second, I brought awareness to how imposter syndrome affects my life. Third, and probably the question you're asking yourself is, what do I do once I know I feel this? And to answer that question, and I promise I will answer it, you need to understand why you personally feel imposter syndrome. It's going to be different for everyone, but I've found these to be the 2 major contributors for me. The first is my competitive spirit. I am someone who played sports growing up. I went to a competitive private school and I grew up in a Wall Street family. My way of being is wanting to be great at everything. Now, while I know deep down it is not possible, I don't believe that I really have settled into that reality. And it reminds me of this really profound analogy that my friend Jay Shetty gave me. He said the reason you feel imposter syndrome is because the challenge you're facing exceeds the current skills that you have. And he went on to say that's how he always wants to be in his life. He doesn't want his skills to exceed his challenges because then he won't grow. And I found that to be such a comforting thought because, of course, if you're competitive, if you're growth-minded, you're going to create difficult challenges for yourself and you're going to want to gain new skills in life. And when you do that, your challenges will most likely exceed your skills. Now, the second thing that creates imposter syndrome for me is comparison. As much as I wish that I didn't care what others think about me, and as much as I wish I didn't anchor myself to others and their achievements and their characteristics, I would be lying if I said I didn't do that. The fact that I use other founders and entrepreneurs as a reference for the skills that I need to build a business and the emotions that I need to have while growing a company All of those things perpetuate my feelings of fraudulence. And by the way, I fully acknowledge this is one of the downsides of social media because it's a constant reminder of others' skills and achievements versus my own. So those are my whys. Here is what the hell I do about it. First, I've reframed my perception of this experience that is imposter syndrome to be a good thing. As I mentioned, I'm competitive. I have constant concerns about not being skilled enough to be in the position that I'm in, and the idea that it's been driven by luck is really provoking to me. So an activity I've been doing is actually welcoming the anxiety, welcoming the imposter syndrome, and telling myself it's a fear of failure, that my fear of fraudulence is what is actually driving me to get better. And so I've started to kind of become friends with imposter syndrome, telling myself that it's actually this great, helpful biological tool that is pushing me throughout life to never be complacent. The second thing that I do is I've normalized the experience by drawing comparison to other really successful individuals that experience imposter syndrome as well. And so the way I thought about this is if external validation is inevitably a part of my psyche, why not use it to my advantage? The way that I did that was by discovering all of these world-class professionals that suffer from imposter syndrome as well. So I literally just ran a Google search on imposter syndrome and it was like successful businessperson, successful novelist, successful public speaker, one after the other. talking about their experience with imposter syndrome. 2 quick examples for you. The first is Maya Angelou. After writing 11 books and winning dozens of awards, she said, and I quote, I've run a game on everybody and they're going to find me out. This woman literally was one of the most successful and prolific writers ever in the history of writing. Yet she felt imposter syndrome after dozens of successes. The second example is Sheryl Sandberg. The former COO of Meta. In her book Lean In, she says, and every time I didn't embarrass myself or even excelled, I believed that I had fooled everyone yet again. One day soon, the jig would be up. On top of that, I also mentioned Mike Cannon-Brookes, the CEO of Atlassian, earlier, and the list just goes on and on. And then there's one other thing that I do to navigate imposter syndrome. I talk back to it. One of the most powerful methods for working through OCD is called exposure therapy or ERP. It's a tactic where you expose yourself to the fear that you're experiencing in order to normalize the anxiety. For example, let's say you had clean OCD. That's when you constantly feel whenever you're touching things, your hands and body are getting dirty. It's a super common OCD, and a form of exposure therapy for clean OCD would be touching door handles and not washing your hands for 30 minutes. In order to normalize the experience of being dirty. In the context of imposter syndrome, that looks like me writing a script that accepts the fear that I'm enduring. So the script could include a line like, I have exclusively ended up where I am because of luck. I am dead weight and I've peaked in life and I will never do something nearly as impressive. It may sound strange, it may sound provoking, but the idea is that if I repeat this enough times out loud to myself, It will allow me to sit with provoking thoughts of imposter syndrome without obsessing about them over and over in a way that impacts my ability to perform. And that, my friends, is my experience with imposter syndrome. There was a lot to this episode, but if you take one thing from this, it is that feelings of fraudulence or fear of luck over skill are incredibly normal to your career and to your life. I feel them. Sheryl Sandberg feels them. The CEO of Atlassian feels them, and so many others do as well. Now, I would love to hear from you. Have you experienced imposter syndrome before in your career? Tell me about it and tell me how you've tried to work through it on your own before hearing this episode. And even if you haven't felt imposter syndrome, reach out and say what up. Shoot me an email to thecrazyones@morningbrew.com and I'll get back to you. Thanks again for listening, and I'll catch you next episode.