How to deal with imposter syndrome

What's up, everyone? This is Alex, the host of Founders Journal. As you may know, I built Morning Brew from my senior year of college until we sold the business in 2020. And now I'm building a variety of businesses in different spaces and different stages. I'm basically averaging 1 to 2 new businesses per year. And because of that, I have had the opportunity to test a ton of different products and services, ultimately landing on a core software stack that serves as my business operating system whenever I start a new company. I have my go-to banking service. I have my go-to formation service. I have my go-to domain hosting service. But probably the most important of them all is my HR service, Gusto. If you're a longtime Founders Journal listener, you know how much I think about people in the context of business. A business is nothing without its people, which means a platform that helps me manage and take care of my people is invaluable. And that means I've tried every HR platform under the sun, always with the same exact goals in mind. First, I want a product that's intuitive and delightful to use. As a non-HR person, I find the intricacies of payroll, benefits, taxes, compliance, and expenses to be painful. So I just want something that makes my life easier. Second, I want it to be affordable. I'm a bootstrapper at heart. I started Morning Brew with $0 and I started StoryArc with $0 as well, which means I don't have infinite dollars to drop on SaaS products. And third, I want a platform that acts as my one-stop shop for all things people. I want it to handle payroll, benefits, hiring, onboarding, and taxes, all while integrating with all of the other tools in my business stack, whether it be QuickBooks, Slack, or Google Workspace. Well, Gusto hit the trifecta, which is why I am a customer and use it for every single one of my businesses. Yes, this is a paid sponsorship by the amazing team at Gusto, but I would sing their praises even if I wasn't being paid to do so. So if you're looking for a platform that takes the pain out of payroll, benefits, and HR, I highly recommend you check out Gusto. And if you sign up at gusto.com/alex, you will get your first 3 months free. Now onto the episode.

What is up everyone? This is Alex Lieberman, co-founder and CEO of Morning Brew. Welcome back to Founder's Journal, my personal audio diary, where I give you, the business builder, the tools you need to think better in order to build better, whether that's building a business, a team, or a new product. It's time to let you in on a little secret. I spent the weekend looking through the analytics on past Founders Journal episodes and noticed that there were 3 types of episodes in the last 2 months that have performed better than every other. The first type of episode is a timely news hook. So for example, my episode on the rise of Clubhouse did well because it connected strategies for building to trending technologies like consumer social apps. The second type of episode is what I call service content. Episodes like Process for Productivity, where I talked about my way of staying productive. Those episodes do well because they solve a clear problem for the listener and leave them with actionable insights. And the third type of episode I put in the bucket of vulnerability. Founders Journal listeners love to unlock their vulnerability through my own vulnerability. So for example, my episode about losing my dad, it was no surprise that I got far more emails from that episode than any other Founder's Journal episode ever. And while I, I'm going to continue to focus on all 3 of these types of episodes, I want to spend today talking about the 3rd category, vulnerability, and more specifically, one of my biggest anxieties as an entrepreneur. Let's hop into it. 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 5 years. Since going full-time, I've experienced persistent anxiety about my qualifications as a co-founder and the CEO of a growing media business. I chalked up these worries to my age, being a 27-year-old, my lack of experience in media since I had no experience in media, and just another manifestation of my OCD that I suffer from. All that to say, I assumed that any anxieties I had, it was an Alex-specific thing. And while all of these factors may play a part in the fears that I feel at some point in my entrepreneurial journey, I discovered that what I was feeling was wildly unoriginal. I am among 70% of people that experience imposter syndrome, which is a psychological phenomenon that was first published about in 1978 by 2 Georgia State professors. Imposter syndrome manifests in a host of contexts from relationships 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 the fear that you'll be outed as a fraud at some point in the near future. You know, while putting a name to this thing didn't make imposter syndrome go away, it's at least provided me the comfort Knowing that I'm not the only person dealing with it. So I want to, I want to kind of pull you into Morning Brew and share with you what imposter syndrome actually looks like in my world within our business. The first thing with imposter syndrome is it goes in waves. Some days I'm feeling really confident about the work that I'm doing and my ability to build a really big business. And other days I'm feeling self-conscious and self-critical, wondering why it is that I ended up in the success successful position that's been afforded to me. And here are just like specific thoughts that continue to come up, have come up for the last several years and will continue to come up as long as I'm in the business of building businesses. The first thought that comes up a lot is it always feels like there are a few things that I'm really good at. So public speaking, relationship building, thinking of new and creative ways To make business fun. And then it feels like the rest of the things, you know, operational prowess, like being organized, project management, managing people, it feels like those things I'm average at best. And while one could perceive those things as, yeah, you know, we all have a few superpowers and the rest we're not best in class at, that is actually a thought that fuels my feeling of imposter syndrome. Like I actually don't deserve to be in the position that I'm in. Then there's always the recurring thought about, am I pulling my weight? You know, as someone who started a business as a co-founder, a constant fear that I have is, am I pulling my weight? Am I doing what I should be doing to be doing the right thing for my co-founder? How am I sure that I'm not just deadweight where the business is pulling me along? Another thought I have is all of this is just luck. The only lucky thing I didn't do was to create the the janky PDF newsletter back in 2015 when I was a student at Michigan, which is literally just what got the snowball rolling down the hill. But then I've demonstrated no skill in keeping it rolling. So it's like part of my perception is 1 ounce of skill in 2015, followed by the rest, literally just pure luck. And then especially as the business has grown and I've gotten older and my aspirations have gotten bigger, Another common fear is kind of this thought around the one-trick pony. This idea that I'm a one-trick pony, that Morning Brew is my only successful venture. It will only ever be my successful venture. And because this whole thing has been built on kind of a house of cards driven by luck, that there'll be nothing else I do in my career that is nearly as successful. And You know, when I reflect on this and think about why do these things create so much anxiety for me, I think so much of it comes down to the amount of weight that I place in these thoughts. And I think I place so much weight in these thoughts because so much of my identity in my young adult life and so much of my self-worth has been tied to Morning Brew. And I guess it makes sense when you're in the business of building a business, so much of your time is dedicated to your company, to what you're growing. But I do think it's because it's so important to me because it's my identity. Things that from my perspective could jeopardize my identity are really provoking. And the issue with this is it's not just feeling anxiety, right? It's not just like feeling crappy when I feel like an imposter and when I feel like I feel like a fraud. I think the real issue that I experienced from this is that if it gets impactful enough, if the anxiety becomes strong enough, it can actually impact the way that I work. And so I've noticed at points in my career when, you know, I'm a 10 out of 10 on the imposter syndrome spectrum, there are things about how I work that change. The first thing, which I think is the worst from just like a personal life perspective, is I lose any semblance of work-life balance. And while I don't believe that like work-life balance is really a thing when you're building a company, there is definitely kind of this separation of church and state between personal life and work at times. But when I'm in kind of the throes of imposter syndrome, I find myself having to work harder and harder and harder to make up for this feeling like I don't have skills. And the only way I'm going to develop those skills to deserve to be in the position that I'm in Is to spend more time working on them. And I feel like this has become kind of a tell for me, for my girlfriend, where she can tell when I'm most experiencing imposter syndrome because my work time starts to encroach on our personal time, whether she's, you know, 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. There are tells around how my behavior changes as a function of this anxiety. I think the second thing, which is as important and maybe less detrimental externally, but more detrimental internally for me, is I think imposter syndrome can lead me to losing appreciation for the entrepreneurial journey 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. These feelings of anxiety They can dull the experience and take me out of the moment. And it's a really shitty feeling because one of the best parts about building a business is in the moment, enjoying the little wins along the way. And the third, and I would say most detrimental thing from an external perspective, is that when I experience imposter syndrome in the most concentrated way, it makes me lose confidence in doing the things I'm actually really good at. Because imposter syndrome, you know, doesn't just attack specific skills. It attacks your character, 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, like, you know, leading meetings or speaking publicly on a podcast or, you know, selling big brands of why they should work with The Brew. And so for me, the, The, one of the most important things was understanding first that I wasn't alone in feeling imposter syndrome, but also understanding how it actually impacts the quality of my work. Because I think once I understood that, I understood how, how much higher the stakes were from feeling this thing. And it led me to making a way more concerted effort to work through it. And in the early days of experiencing these feelings, I tried to fight them and I tried to talk back to them. You know, where I would like in my head say, no, I'm really good at these things. No, I, it hasn't been luck. It's been skill. And it's been maybe a little bit of luck. You need luck in anything you do, but we wouldn't have gotten here without some combination of skill and luck. But what I quickly realized is that by talking back to the anxiety, it actually made the waves of anxiety longer and the feelings of fraudulence more pronounced. And so over time, I've learned how to work with imposter syndrome and you'll hear my language. I didn't say work through imposter syndrome because I don't believe it's going anywhere, but I work with it by not trying to fight it, but by trying to understand why it is that I experience it and what things I can do to give it less power when I'm feeling it. So it doesn't impact the way in which I live my life. So just to break down for a second, it's going to be different for everyone. I think there's 3 reasons that I experience imposter syndrome. The first is my competitive spirit. You know, as someone who grew up playing sports, grew up going to a competitive private school, grew up in a Wall Street family, my way of being is wanting to be great at everything. And while I don't, while I know deep down that is not possible, and you know, I always say like, Focus on your strengths, double down on your strengths, hire into your weaknesses. While I believe that, I don't feel settled in that reality. And so I think that is what has led to some anxiety, is concern around the things that I'm not actually skilled at. The other reason around my competitiveness is I want to feel like I can control the trajectory of any business. I want to feel like fully capable to the extent that if I start another company after Morning Brew, 10 years in the future, whatever it is, that I have the full set of tools and capabilities to make it successful again. And because I don't feel that level of confidence yet, that is something that imposter syndrome latches onto. And the third thing around competitiveness is I always want to feel like I'm growing. I always want to feel like I'm leveling up my definition of success and what I'm trying to achieve. And I just have this underlying concern that I've peaked at the age of 27. And I have hopefully many years ahead of me. And if I am concerned that I'm not going to do anything that is more substantive or successful than what I've done at the age of 27, that is incredibly provoking to me. The second thing that I believe 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'd be lying if I didn't do that. So 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, it perpetuates my feelings of fraudulence because from the outside, it looks like all of these different entrepreneurs have their shit together where they have the skills, they have the utmost confidence in what they're doing. And I think that perpetuates this feeling of anxiety. So there's my competitive mindset, there's my comparison to others. And the third and potentially most unique to me is my OCD. I've had OCD since a young age. And just a quick summary for you, for those of you that don't know what OCD is, it's obsessive compulsive disorder. It's a common mental illness in which basically I experience Persistent unwanted thoughts that trigger deep anxieties. So an example for you would be, in the past, I've experienced an obsession that I have a heart defect and that if I train too hard or work out too hard, my heart will give out and I'll die. And when I think about my OCD and I've, you know, worked through my thoughts on it with a therapist for years, I think of it as a double-edged sword. It is a blessing and a curse. It gets my brain working in a frenetic way to make things happen in life, but it also taints my ability to experience things fully because of the crippling anxiety that I feel when I'm in the throes of an obsessive cycle. And what I've learned about all of my manifestations of OCD, whether it's around health, whether it's around relationships, whether it's around work, Is that my unwanted thoughts latch onto things that are one, incredibly important to me, and two, don't have yes or no answers. And I believe that this is a big reason why I have experienced imposter syndrome throughout my career, because Morning Brew is, you know, a top 4 most important thing to me in my life and whether or not my success has come through luck or skill. Is it's not a fully answerable question. I cannot say with 100% certainty whether Morning Brew success has come through 90% skill or 90% luck. And I think that ambiguity is something that has been really hard for me to deal with. And so once I got to this point of understanding why I thought I personally experienced imposter syndrome, all of those things, competitiveness, comparison to others, OCD, I then felt like I could come up with a game plan to cope with it. By facing the very things that were causing it. And so here is how I have coped with imposter syndrome for the last few years. And I hope it gives, you know, you some tactics to grab onto as you work through it yourself. The first thing I've tried to reframe my perception of this experience to be a good thing. As I mentioned, I'm competitive. So I have constant concerns about not being skilled enough to be in the position that I'm in and more it's been driven by luck. And that's really provoking to me. And so an activity I began doing is actually welcoming the anxiety, welcoming the imposter syndrome and telling myself it's this fear of failure, this fear of fraudulence that is actually driving me to get better. And so I've started to kind of like become friends with imposter syndrome where I've told myself and I've I've told imposter syndrome that it's actually this biological tool that is pushing me throughout life to never be complacent. So that's the first thing I've done is reframing. The second thing I've done is normalizing the experience by drawing comparison to other really successful individuals that experience imposter syndrome as well. And so, you know, I think there's absolutely merit to this idea that you can't be truly happy and fulfilled in life As long as you compare yourself to others, without a doubt, that is my ultimate goal in life. But I think that's a lofty aspiration that takes years to accomplish. And so, as I think about working with imposter syndrome today in the short term, I had to think about how, how do I use comparison to my advantage? If I know I'm going to do it, how do I actually make it a positive for me? And the way that I did that was by discovering all of these world-class professionals that suffer from imposter syndrome. I literally just ran a Google search. On imposter syndrome. It was like successful business person, successful novelist, you know, successful public speaker, one after the other, talking about their experience with imposter syndrome. So just 2 quick examples. The first is Maya Angelou. After writing 11 books and winning dozens of awards, there's this quote of her saying that I've run a game on everybody and they're going to find me out. She literally is 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 the CEO of Atlassian. Atlassian is a super successful software company, publicly traded, $1.6 billion in revenue last year, 5,000 employees. The co-CEOs have been running the company since 2002, and he did this TED Talk where he talked about being in a board meeting on several occasions, and he would be in a t-shirt surrounded by all of these other board members in suits, and he would hear these acronyms that these different board members would throw around, and he would have his notebook and quietly be jotting down in his notebook all these acronyms he had never heard of around business or strategy, and he would go home and look it up on Wikipedia later. And what he described is that literally since 2002, he has had imposter syndrome. He's had this feeling of being well out of his depth of knowledge, but being entrenched in a situation where you have to get out of it. And he had this great nuance in how he described imposter syndrome, where he said, you know, it's not a fear of failure. It's a sensation of getting away with something and someone figuring it out. And that stuck with me so much because To me, so much of this is like someone knocking on my door and literally being like, hey, you've actually been in the wrong role. You haven't done any of the things. We're going to need you to leave. And that's literally how he talked about his experience is like waiting for someone to open the door and say, you're in the wrong seat. So that was the second thing I did was using comparison to my advantage and seeing world-class individuals who are going through the same sort of cycles that I do. And then the third thing Is I've talked back to imposter syndrome, just like I've talked back to my other obsessions. One of the most powerful methods for working through OCD is called exposure therapy. It's a tactic where you expose yourself to the fear that you're experiencing in order to normalize the anxiety. So for example, let's say you had clean OCD, where when you, you constantly feel like you're getting dirty and when you touch things, your hands and body are getting dirty. That's a very common OCD. A form of exposure therapy could be you touching door handles and not washing your hands for 30 minutes after to normalize the experience of being dirty. In the context of imposter syndrome, that exact thing 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 again. It sounds strange, strange. It sounds 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 as a professional. And that, my friends, has been 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 am just one living example of the persistent battle that many of us experience.

That is it for today's Founders Journal.

As always, thank you so much for listening to the pod, and I will catch you next episode. And if you have any questions, you want to say what's up, or you want to recommend a future episode or topic I should talk about, shoot me an email to alex@storyarb.com. That is alex@storyarb.com. Thanks for listening.

Catch you next time.