Show Notes
Tyler: In this episode, we're going to talk about impostor syndrome. Do you want to kind of explain what you had in mind here?
Rick: Yeah. So you know this. I left PeopleKeep after 11 years. For most of the time, I was the leader of the company under various titles, most recently CEO. I left in October. So it's been about nine months now.
Rick: One of the big reflections I had was sometimes how I treated people. Sometimes I was super impatient with people and put certain immediate business goals over really trying to make people feel good about what we were doing or where we were going. And I regret those moments because it was so short sighted, right? And so, as I look back and analyze why did I do that? I think a lot of those situations where fear-based. I was scared of missing a short-term goal, or I was scared of what I want to talk to you today about. Feeling like I might be found out as a fraud, as a CEO. And so I want to talk to you about this because I wonder if you ever feel this way? I guess impostor syndrome could be defined as a fear of being found out as a fraud. But I would go a step further and say, do you ever feel like a fraud in your job or catch yourself making decisions not based on what's right but out of fear?
Tyler: Yeah, I mean, okay. So I definitely feel like a fraud all the time. I'm of the opinion that the only people who aren't are sociopaths. Everyone I've ever talked to no matter how accomplished they are, everyone's like, “Oh, I don't belong here. Everyone's smarter than me,” and all that. I definitely feel that way just constantly, yeah. It's surprising to me to hear that you did so much.
Rick: Oh, yeah. Constantly. And I think it caused me to work a lot more than I needed to. That's the fear of failure. It caused me to stress and worry about things that were outside of my control unproductively, and I think it caused me in certain situations to make the wrong decision.
Tyler: Interesting. Yeah. Well, so the reason I was surprised to hear that is because on the surface maybe more than anyone I've ever met you seem like the classic CEO type.
Rick: Are you calling me a sociopath?
Tyler: No, no. What I mean is you're type A personality. Do you agree with that?
Rick: Define a type A personality?
Tyler: Like you... Well, yeah, maybe I don't have the best definition. But I interpret that to mean like, you aren't afraid of conflict. You kind of say what you mean. You're just kind of a person who's in control and likes being in control. And maybe this was me just not seeing what's beneath the surface, but you work really hard. You read a million books, you network, you make connections. To be honest, half my impostor syndrome comes from looking at you and being like, oh, no, that's what a CEO looks like. I'm not doing any of that stuff.
Fear-based decisions and regret
Rick: The interesting thing to me isn't to discuss whether people feel this way because I think everyone does. I think what's scary is... I think what I reflected on was not necessarily that I had this, it's how I dealt with it.
Tyler: Okay.
Rick: And so, I think that, let's assume for purposes of this part of the conversation that everyone has some feelings of impostor syndrome or being fraud. And that's a fear thing. What I think in certain situations I did was, let that dominate my emotions. And that could have resulted in me not being thoughtful about how I was communicating with someone in a moment, or making a decision that was fear-based versus opportunistic. I hypothesize that a lot of decisions leaders make, they make out of fear and maybe those are the decisions that they regret the most. Does that resonate with you?
Tyler: Yeah. I think I have a very different reaction to it than you do. I think that using kind of generic words like fear and regretting a decision, I think those still apply, but like, it takes a very different form for me. But yeah, definitely. I'm trying to think of the worst decisions that I've made.
Tyler: The number one worst one was certainly made out of fear, although I'm not sure it's a fear that was rooted in feeling like an impostor. And that was that I had an employee that I needed to fire. It was obvious to me that I did but I was just like, oh, I'll make it work, this or that. And I just waited for him to quit and he did eventually, thankfully, because it could have dragged on forever. But that's by far when I look back at myself as a leader. That's my weakest moment ever. It was fear-based. I don't think it was impostor syndrome based for me.
Rick: What was the fear?
Tyler: Well, first of all, I just hate confrontation. I guess this is maybe a little different from impostor syndrome. Part of it is that I took a big risk hiring him and I convinced him to take a big risk accepting the offer. And you're admitting you failed is one of the things. Now, I'm normally not too afraid of failure, but when it's really impacting another person's livelihood or something like that, the pressure is really high. And I think I was just afraid to say, I'm putting an end to this. I don't know.
Tyler: I've definitely had other moments though, where... The thing is, I think my reaction to impostor syndrome is to remove all of the things that I feel unconfident about. And so it's less. I think maybe it sounds like you were saying you kind of lash out almost. I do the opposite. I withdraw and say, "Oh, well. I don't think I'm good enough of a leader to do this thing. I'm just not going to do it." The company doesn't do that. That's not in our core competency.
Rick: Interesting. So yeah, maybe it kind of gets into fight or flight.
Tyler: Mm-hmm (affirmative).
Rick: I have a fight response, while you have a flight response.
Tyler: Yeah, when you were talking I was thinking exactly that. You're one of those animals that gets real violent when they're backed into a corner.
Rick: Yeah, when I've been under the anesthesia for surgeries before, and I had to learn this, I always forget because I don't get surgeries very often, but I do know this now. Before I go under, I have to tell them when they bring me out of the anesthesia they have to tie me down because…
Tyler: Wow.
Rick: ... I come out and I come out swinging. Which isn't great when you're getting a shoulder surgery.
Tyler: Yeah, seriously. Wow. I didn't even know that was a thing. But yeah, I mean, I don't want to...
Rick: You probably come out going boohoohoo!
Tyler: Yeah, probably crying about something awkward I did in third grade. But yeah, okay. So I think we're saying we experience the same things, but we have very different reactions to them.
Rick: Yeah, but do you regret that reaction? I guess, do you feel like you're missing out on... Are you fleeing from something and making decisions for the company that are fear-based, flight-based that aren't the right decisions?
Tyler: This may be taking this in a direction you didn't intend for it to go. But I've been asking myself this question because basically the situation I'm in now, is I've built a company that I think fits my leadership style really well. It's what I want. And if anyone else looked at it, they'd say, well it's not what it should be. Like it's not as big as it could be. It's not as profitable as it could be and all that stuff. So I think it's like, objectively I've made bad decisions. But I have been asking myself, is that a problem? Maybe I'm fine with the fact that I kind of built this weird environment that I feel safe in and I think the employees here also feel safe in.
Rick: That sounds great. I don't think that's a bad thing at all.
Tyler: Yeah. But I mean, if you looked at it, we could be way bigger than we are. In that sense, they were bad decisions. You know?
Rick: Yeah.
Tyler: There are a lot of times I haven't taken a risk when I could have or something like that.
Rick: What about earlier on when you were more focused on being a high growth company. Do you feel like in those situations you were putting yourself in a more uncomfortable position?
Tyler: Yeah. Okay. That's interesting, because definitely what I did; just for a little background, we started out fully bootstrapped: just me and my brother That part was natural. It's like, I'm just coding, no problem. Then we turned into, okay, it's time to start hiring people and we're growing really fast. And yeah, that's the main part of my life when my impostor syndrome was caused by you, where I was saying like, oh, man, think of all the things Rick would be doing here. He'd be going out and talking to investors. He'd be making contacts to be recruiting. And yeah, probably at that moment. I was like, I need to start acting like Rick.
Tyler: I need to start doing the things you would have done. Or I mean, not just you, I'm using you kind of like a boogie man here. But yeah, I probably made a lot of decisions that were not consistent with my values because I was trying to pretend to be someone I wasn't.
Rick: You're hitting on what I want to talk about. I think that if I look at back what I regret, it's when I allowed [fear] to affect how I behaved in a way that wasn't consistent with the person I want to be. I think that is the point. And it sounds like what you may have experienced that. But instead of changing you, you've actually conformed the business to allow you to be in a safe place so that you can be the person you want to be.
Tyler: Yeah.
Rick: That's cool.
Tyler: I think probably I still need to push myself. I don't want to use this as an excuse to say, oh, just be lazy, don't work hard or any of that. But yeah, the word I'd never thought of it this way that when you say call it impostor syndrome, what that kind of means is that you think you're in a room full of people who are different from you, and that you need to be like them to fit in, right? That's kind of what it's saying. And it's just saying like A, those other people probably aren't these amazing people that you think they are and B, you don't have to conform anyway.
What is impostor syndrome?
Rick: Yeah, we probably should take a step back and say what is impostor syndrome and what do we want to define it for the purpose of this conversation? I would define [impostor syndrome] as feeling like who you are is not good enough for who you are supposed to be in a situation. Who you believe you're supposed to be.
Tyler: I like that. Let me just make a quick disclaimer. My girlfriend is a psychologist. She hates it when people go around making pop science definitions. So let's acknowledge that we're co-opting the term impostor syndrome to mean whatever we want it to. But I agree with that.
Rick: What should we call this? Let's call it something different, if it's not impostor syndrome.
Tyler: No, I mean, everybody's co-opting it. At this point, I don't think anyone's using it correctly. So I think this is fine. I just want to acknowledge this not like a scientific definition here.
Rick: No, this is Rick and Tyler's “how we choose to interpret impostor syndrome for purposes of this discussion.”
Tyler: Right. So you said it's when the person you are isn't as good as the person you think you need to be to achieve your goals basically?
Rick: In a situation.
Tyler: In a certain situation.
Rick: Yeah.
Tyler: Yeah, I buy that. And I think that matches with a little anecdote I talked about during the high growth mode, I didn't feel any impostor syndrome before that. Because I thought in that situation what I need to be as a product person writing some code, and that's what I was doing. Is that I thought who I needed to be changed when my situation changed.
Rick: Mm-hmm (affirmative).
Tyler: So let's talk about you because I'm really interested in this because you have a business background. I think a lot of more business stuff comes naturally to you and the role you were filling was CEO. So it seems you are more naturally aligned with the role. What were the ways in which who you are varied from what you thought you needed to be?
Rick: So I think one particular example is that I'm very much a customer experience-first person. When I start companies, the dollars aren't the number one thing for me early on. I don't want to try to grow something and get people's money until I can promise them and deliver on a customer experience that they're not going to regret. And that takes time. When you're starting a company, that takes time to build. And you kind of see this, when you are a product company or a customer experience company, a lot of times it takes longer to reach those big hockey stick growth moments. But when they come, they're much steeper, right? And I'm very much the person who is willing to delay gratification on the revenue, to have the best product, best customer experience, and then have that asset that I unleash on the world and on the competition later. This was not my partners and investors mentality. So when I was in the boardroom and I was reporting our numbers, who they wanted me to be was a sales-driven CEO. They wanted me to focus on sales and I did not. I wanted to focus on customer experience and sales later.
Tyler: So one could argue, though, that that's not impostor syndrome. In that sense, you actually weren't the person they wanted you to be. This wasn't some made up problem in your head.It's funny to me, because what you're talking about is the delayed gratification. That's the whole point of raising money. If you were to talk to Paul Graham, or a Silicon Valley investor, they'd be like, of course, that's what you're supposed to do. So it's so funny that the thing you feel naturally doing is what a venture backed CEO is supposed to do. That's just not what the situation called for right there.
Rick: In my opinion, the situation called for it. And that's how I would have run the company if I controlled it, but that was... The CEO that the board wanted me to be and that I felt pressured to be, was not the CEO I wanted to be nor was it the CEO, I thought was best for the success of their own capital.
Tyler: Yeah.
Rick: And I don't know, I guess I felt extreme pressure to hit short-term goals from that situation, which led me to kind of be two different people. I'm starting to realize I was actually probably Jekyll and Hyde, a lot of times, and very confusing to my team members when I would represent the CEO of the board wanted out of one side of my mouth and then represent what I thought was best at the other side of the mouth and never actually taking the time to draw a line and say, "I can't be the CEO. This is not for me unless you can align around this different strategy and who I am."
Tyler: Yeah.
Rick: But I never did that.
Tyler: So yeah, this sounds really interesting. And I don't want to invalidate the point of this topic here. That doesn't sound like impostor syndrome to me.
Rick: Fear of failure?
Tyler: Fear-based decision making is at the core. And I agree that it sounds like you were making fear-based decisions. But this was not some internal mistake. The thing about impostor syndrome is (because I mentor a lot of younger people, interns in this coding fellowship thing we have), everyone feels this way. And my advice to them is always like, “I'm oversimplifying it here, but get over it. Everybody feels this way. You're not an impostor. There's not a problem. It's all in your head.” But in your case, there was a problem and it wasn't in your head. Like there was actually a real conflict between who you were and what the board wanted you to be.
Fear and Values
Rick: Yeah, and I guess what that caused me to violate some of my values. But why did I do that? Because I was scared of losing the respect of the board. I was scared of losing my job in some situations, losing the opportunity to build what I was building. And that caused... Yeah, I guess it's really fear... when you are threatened personally, as an individual, as a leader, it can cause you to make some really bad decisions that you regret. And I don't know, I guess I wonder how many CEOs and entrepreneurs out there feel like they sometimes make those decisions out of fear.
Tyler: Yeah, well, I mean, I can say just observing, I'm not like super connected to a bunch of different startups and stuff. But I'd say, maybe more than the typical person. I talk to other founders and stuff like that. And yeah, across the board, you see people, it's always the case. To an outsider, decisions seem pretty clear. You're doing this thing for the wrong reason, basically. But yeah, you see this all the time that people have some kind of, either they're attached to the business more than they should be, or they're indebted to investors or whatever. That yeah, they're desperate and they're making bad decisions as a result of that.
Rick: Which is bad for them, and for the company, right?
Tyler: Yeah although an investor might say, if it wasn't going to work, I want it to fail quickly. Every single podcast we do Rick, I'm going to bring it back to bootstrapping. If you're bootstrapped, you have the luxury of saying, well, no, I'm going to do this slower. I'm not going to push for those sales right away. You may not have that option when you have investors, and maybe it's not bad for them if you fail quickly.
Rick: Yeah, but this fear of failure may cause you to make decisions that actually extend the life of the company when failing would be better.
Tyler: Okay, that's fair. Do you think that happened for you?
Rick: Absolutely.
Tyler: The company would have failed if you hadn't done that stuff.
Rick: Oh, yeah.
Tyler: Okay. Well, that's a whole different layer on top of this then.
Rick: Yeah.
Tyler: Interesting. Yeah.
Rick: I think there's two parts of it: 1) do we accept that this is just the reality of being a leader, having moments of fear; and 2) do we accept that as a leader when you act and make decisions out of fear it's often times the wrong decision.
Tyler: Yes, I think it's natural for people to experience that fear. And I would even go so far as to say that what it means to be a leader or at least one of the primary responsibilities of a leader is to shield everyone else from that. Because an organization where everyone is experiencing that fear is dysfunctional, and a leader is kind of opting into saying, I'm going to experience this and hopefully protect everyone else from having to feel that too.
Rick: Okay, I agree with that.
Tyler: Okay. Anyway, that’s not to disagree with anything you're saying. But…
Rick: It's an extension, and I think as CEO, you are the dam preventing fear from entering the organization and that can take a toll, right? And it's real, it means that you are going to be scared sometimes. And you actually have some very important barriers. You have limitations on how you can express that fear to begin with. I think a lot of leaders, myself included sometimes maybe they don't express the fear directly, but they make decisions based on that fear. Decisions that when they look back on, they will regret and realize that there was a better decision to be made. That's bad. Like having fear isn't bad. Making decisions based on fear is bad. I think.
Tyler: So. Okay. I get where you're going. In nature, things like fear and pain exist to provide you with better decision making, right? If you're running too much and your knee starts to hurt. That's your body telling you, hey, stop running, and you should react to that. Or if you're afraid, it's like evolution saying people who were afraid in this situation ran away and lived, the people who weren't afraid, got eaten by a bear. Do you think just like evolution is not helping and we've evolved, we've grown beyond that, or are there situations where fear is helpful?
Rick: Listen. For purposes of this conversation. I don't think we're talking about basic needs that our cavemen relatives are dealing with, right?
Tyler: Yeah.
Rick: And so this is civilized. We have basic needs met. You're in a leadership position at a company, meaning you probably are not worried. I'm assuming if you have the ability to start a company, you probably are not worried about where you're going to sleep.
Tyler: Right. But that's not what your fear was. Your fear was that the company would fail, not that you would starve.
Rick: ... Exactly. And I would say that's not what that natural response is designed to deal with.
Tyler: So there should be no fear?Or you should never use that to inform decision making?
Rick: ... I think [fear] should inform decision making, but it should absolutely not drive decision making. And it drove decision making for me in certain situations. And I regret... I can't think of a situation in which I made a decision out of fear that I don't regret the way I handled that decision or the decision that I made.
Tyler: Mm-hmm (affirmative).
Rick: And so the third thing, I guess where I want to go with this is how do you... If you're scared and you got to make a decision, and you got all these pressures, how do you make a good decision when you're scared as shit?
Tyler: I think a lot of people could probably either prevent the fear in the first place, or leave themselves with more options when it happens. So for example, committing to really ridiculous milestones. This is one version of this. I think that deadlines drive people to do stupid things, introduce bugs in a code and all that.
Tyler: So if you have the deadline, I don't have a good answer for what to do. But like you could have in advance said, "Hey, I've identified that that's a dumb thing to have."
Rick: Say for example, the guy or gal who you wish you had parted ways with, that you mentioned earlier. I mean, you were scared. How could you go back in time and make a better decision? How could you remove that fear and made the right decision?
Tyler: Yeah, that's a good question. So first of all, I'm not saying I should have done this, but I took a huge risk hiring him and he took a huge risk. Taking huge risks is a good way to end up in a situation where you're afraid. So one option would have been to realize there's too much uncertainty, let's just not even do this in the first place. That's hard to say though. I wish I'd gone back in time and said, if six months from now, these three things are true. You should leave. It's not me firing you. It's not you quitting. It's us agreeing in advance that it's not working.
Rick: I really liked what you said at the beginning of that the higher the risk, the higher the opportunity for you to be scared and find yourself in a situation where fear is driving you.
Tyler: But that doesn't mean don't take risk, right? Because that's what we do.
Rick: Yeah. So maybe it's about how you approach high risk, high stakes bets from the beginning. Maybe it's just the mentality of saying, listen, when I take high risks, it means there's going to be failure, and I have to be OK with it. I guess that just comes with the territory. Being a leader is high risk.
Tyler: Yeah, although it is different. So I was much more comfortable taking risk when it was just my co-founder and I because we were both prepared. First of all, we both accepted the risk. And second of all, we had great safety nets. So if something went wrong, no problem. As soon as we started hiring people who are counting on us, A, the fear went up and, B, the risk tolerance went down, which is probably healthy.
Tyler: It's healthy to say, you know what, if it were just me, I'd be cutting it right on the edge of like constantly almost going out of business to grow faster. But now there's another person here, we're going to have a little more money in the bank, we're going to move a little slower. So that's one thing you can do to mitigate the fear, I guess.
Rick: But in that situation, are you making a decision not to grow out of fear?
Tyler: I don't want to be constantly feeling like everything might fall apart. And so we've made the decision. Like I've told you before, we're now calling ourselves a small business instead of the startup. Because that gives us permission to say, yeah, we're going to trade off a little bit of growth for a little bit of stability.
Rick: I like what you just said. I'm scared of being scared.
Tyler: Yeah.
Rick: I'm a bad person when I am scared. I think that's what I'm scared of too. I'm scared of being scared.
Takeaways
Rick: So it's really about trying to create situations where you minimize your own fear. And then there's going to be situations where you do have to deal with it. Number one, minimize those times and two, I guess what I'm trying to get to is, when you find yourself in that situation, I guess you’ve got to figure out how to get out of that state of fear and think rationally. Do not have any frameworks for decision making like that?
Tyler: No, I don't know if any frameworks... Like while we've been talking, I've been thinking about my own experiences. So I can speculate on that. But I don't know if someone has proposed a solution to this.
Rick: The only one that comes to mind for me is Jeff Bezos. He has a concept called the regret minimization framework. I'm not sure if he coined it or not. Logically, if the things I regret the most are the things that I have decided to do or done based out of fear, then if I could figure out how to make decisions while minimizing regret, it could offset that fear. So I can kind of see... I don't know a ton about the framework. But that comes to mind is something I should look into as a way to combat it.
Rick: First of all, avoid situations where you're scared as a leader because that makes you a bad leader. Or it set you up to be a bad leader and then have frameworks in place, if they exist out there to help you make a good decision when you're scared and it sounds like this regret minimization framework actually, I need to look into it. I just read about it a few weeks ago, it could be a good framework for this.
Tyler: Yeah. Let me know if you do look into that, what it says. I'm just... I know we need to wrap it up here. But I'm thinking on my end, the situations where I've done well with fear are ones where I was really excited. There's like fear that you said earlier, you're much more interested in user experience than money. So you might be more interested in taking on a high pressure, high fear situation that is taking a big shot at making the user experience great, versus taking a big shot at making the money great. So maybe that's one way you can do it to say, am I excited about this? Is this exhilarating? Or am I just cowering at this?
Rick: Yeah, it comes down to who you are and what you value. If you're doing things that you value. I'm willing to bet big on being me. And doubling down on situations that allow me to be even more me. It's the situations where I'm being asked to be someone I don't want to be. I'm not saying don't become a better person. I'm saying don't become a worse person in your own eyes because that sucks.
Tyler: Yeah.
Rick: This all comes back to culture and putting yourself in a situation where the people around you share your values and allow you to make decisions together or as a leader to put yourself in a situation to be the best leader you can be. Interesting.