The Double-Edged Sword of Being a Perfectionist

What's up everyone, this is Alex Lieberman, co-founder and Executive Chairman 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. Today, I am talking about the double edged sword of being a striver and a perfectionist. Let's hop into it.

So I was actually talking about this with our executive producer this morning, that probably the most cliche interview question on planet earth is "What is your one big weakness?" I feel like everyone asks that in interviews, and oftentimes we say how people just give fake strengths as weaknesses, and probably the most cliche fake strength is when someone says to you, "My big weakness is that I'm a perfectionist." That generally gets the eye roll, the common reaction to that answer is "Come on, that's a fake weakness, tell us what you are actually bad at so that we know what to expect when you come join our company." But what I'll say is the more I go through my career and understand my own psyche and also understand other people that I work with within Morning Brew and outside of the business, the more that I believe being a striver and a perfectionist is actually a legitimate weakness if you don't understand it properly.

Fatal Flaw of Perfectionism #1: Never Being Satisfied

So let's just talk about me for a second. Like many of you, I'm a really competitive person. I take myself seriously, probably too seriously. And I expect perfection and success in everything that I do, from work to life, to my intramural soccer game on Wednesdays. And I've recently spent some time thinking about why this is, why is it that I'm never satisfied? Why is it that I expect perfection in what I do? And oftentimes those expectations, while lofty, are sometimes unrealistic. And I think there's three main reasons.

Why I Expect Perfection: My Upbringing

I think part of it is due to my upbringing. You know, I grew up in a Wall Street household, my dad worked in sales and trading, mom worked in sales and trading, grandpa worked in sales and trading. Emotion wasn't talked a lot about in the household, money was talked about a fair bit. Sales and trading is notoriously known as a highly competitive environment that a lot of athletes, ex athletes, go into. I'd say the other part is just playing sports from a young age. I was a soccer player. I was on the race team for skiing, I played golf competitively. I think all of these things made me put a lot of pressure on myself to succeed and hit my goals and then hit those goals after the next goals. That's part one, is my upbringing.

Why I Expect Perfection: The Love of The Game

I think the second part is I would argue the most authentic or genuine or intrinsically motivated part of my search for perfection, which is the love of the game. The love of the journey of building something. So whether it's a business, my career, there's a part of me that just loves the feeling of activity, of doing things, of solving puzzles and problems. It's funny. I was actually listening yesterday to the Acquired podcast, which is a great podcast, and they had two episodes on the history of Berkshire Hathaway. But the first episode really was about Warren Buffet, his psyche, how he came to be obviously one of the most successful value investors on planet earth.

And one of the things that I just took from that episode is that his just love for analyzing businesses, for figuring out numbers, and his love for honestly, just making money because it's fun rather than like social signaling, I think is what made him so successful. And they talk about in his early life, how he would do everything from, like, literally just counting everything, counting occurrences of letters in newspapers to counting change just as a game, a love and a joy for the numbers and the intellectual challenge. So I would say so much of his success and his drive for perfection came from, kind of, this intrinsic motivator. So that's the second one, we had my upbringing, my love for the journey, love for the game.

Why I Expect Perfection: Need for Validation

And then I would say the third, I would argue that the unhealthiest part of what drives my perfection and my goals for success is my vulnerability to comparison and my need for validation. And if I'm being really honest with you, I really don't like this about myself. I think that my drive for success is partly a function of how it feels to be recognized externally. This is why I also have such a love, hate relationship with things like social media. I love Twitter because it is a great place to learn. It's a great place to connect with people, but I also think it further reinforces my need to be validated by one of my 125,000 followers. It's what makes me feel important, special, and respected.

And if I reflect on, you know, what's happened throughout my life that I need this validation and I need to compare myself to others, I honestly think a lot of it is driven by my own relationships growing up, whether it was in school, whether it was my personal relationships in college, where maybe because I didn't feel nearly validated enough by people who I thought were important and I needed to be validated by, I require this extra level of validation now.

And that's what drives me to be perfect and it's what drives me to be successful. And so when you think about it, being a perfectionist can be a great thing. It can lead you to being obsessed with the work you do, being high achieving, escalating in your career, being compensated a lot, being well-respected. You're always striving, you're striving for promotion, for recognition, for greater compensation, your brain is always asking, "What's next? What else can I do? What more can be done?" But also striving creates suffering. And it's definitely done this for me. It makes it hard, if not impossible, to be satisfied, even when you reach some big goal or the proverbial mountain top of your career, you've already moved mentally on to the next one.

And I've absolutely experienced this with Morning Brew. When I left Morgan Stanley, I just said to myself that I would be happy if we got the business from 30,000 subscribers, which is where we were, to 250,000 subscribers. And then we got to 250,000 subscribers and I wasn't happy or satisfied. And I said, I'd be happy after 500,000 subscribers. We're now 3 million and I'm still not satisfied. And even outside of the subscriber number, let's talk about selling the company. For many people, selling a company is considered the mountaintop of entrepreneurship. But for me, I wasn't even truly happy when we sold Morning Brew. I was just thinking about what more could I achieve within this business and as a professional in general.

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Fatal Flaw of Perfectionism #2: Neglecting Your Purpose

So obviously one of the fatal flaws of perfectionism is never being truly happy or satisfied despite accomplishing so many things. But beyond that, striving can also make you blind to everything else in your life that may be important to you, but is not what the striving or the perfectionism is focused on.

So Kat Cole, who is the former president of Focus Brands who owns Auntie Annes, Cinnabon, Jamba Juice, she talks about this concept of purpose portfolio all the time, which is basically all of the things in your life that give you purpose. But what happens is when you are a perfectionist and you're obsessed with career, if you don't moderate yourself through reflection and through having the right perspective, your purpose portfolio may run the risk of being far too concentrated on career and professional life when there are other things that matter to you just as much like relationship, family, religion, hobby, and you inadvertently neglect them because you're a perfectionist in one thing.

Fatal Flaw of Perfectionism #3: Reactivity

So beyond never being satisfied and potentially neglecting other things that bring you purpose in your life and your career, the third fatal flaw of perfectionism and being a striver is that it can make you reactive and feel attached to things happening in a certain way, and if they don't happen that way, you're not able to handle it well. The issue is when you get so married to an outcome, like a promotion or hiring that incredible candidate that your company needs and that you've been working to recruit for the last several months, or building a successful business that needs to have a hundred million dollar outcome. If anything deviates from the plan to reach that outcome, you easily get rattled and find yourself making decisions emotionally versus objectively. But being a striver or a perfectionist also gets more nuance than this.

This is the general risk of defaulting to perfection, not being satisfied, neglecting your portfolio of other things that give you purpose in your life, and being more reactive to things if they don't happen your way. But there are also different forms of perfectionism, and depending on these forms, you can experience specific challenges. And that's why it can be really valuable to identify what type of perfectionist you are. If you are a striver and a perfectionist. So there are five types that psychologists have broken down.

Type #1 of Perfectionism: Self Oriented Perfectionism

The first is what's called self-oriented perfectionism. Basically these are people who have high personal standards. They are intrinsically motivated to have the expectation to be perfect, and they are highly self-critical if they fail to meet these high expectations. This I would argue is the most well studied and common form of perfectionism.

Type #2 of Perfectionism: Socially Prescribed Perfectionism

Then the second one is what's called socially prescribed perfectionism, socially-prescribed perfectionists believe that other people expect them to be perfect and that these other people will be highly critical of them if they fail to meet expectations. I believe that socially prescribed perfectionism is oftentimes driven by FOMO and comparison. Obviously, a lot of the things I was talking about for myself earlier.

Type #3 of Perfectionism: Other-Oriented Perfectionism

The third type of perfectionism is other-oriented perfectionism and other-oriented perfectionists are those people who expect others to be perfect. And they are highly critical of those who fail to meet their impossibly high standards. The way I think about other-oriented perfectionism is everyone has worked with an un-empathetic boss or person in the office who just has unreasonable expectations, and they can't see from your point of view. I find that other oriented perfectionism is a really tough trait to have, if you want to have a successful career and work well with other people.

Type #4 of Perfectionism: Overt Perfectionism

Two more types of perfectionism. The fourth is overt perfectionism, and these are people who have a very strong preference for order and show increased anxiety when they don't have order around them. I'd say these are the people who like having a plan checklist every day, their calendar is time-boxed for every single minute and it's all accounted for. The person who has a project plan and has a project plan for the project plan. This is generally the highly type A personality who is the fast climber within a company.

Type #5 of Perfectionism: Covert Perfectionism

And then the fifth, and I would say the least studied type of perfectionism is covert perfectionism. These are closeted perfectionists, and they can sometimes be hard to identify because their actions don't always match the perfectionistic thoughts in our heads. So covert perfectionists tend to have low expectations of those around them and will outwardly say they prefer being average or laid back, but inside they secretly want to succeed. And this is almost a coping mechanism because they don't want to deal with the pressure to succeed or the competition with those who may be better at an activity.

TL;DR

And so, as I reflect on these five personality traits, the self-oriented the socially prescribed, the other oriented, the overt and the covert, I would actually say I'm most similar to the descriptions of the socially prescribed perfectionist and the covert perfectionist. On one hand, that means I still have the tools to be an empathetic and fair leader and manager and someone who has a growth mindset versus a fixed mindset. But it also means that likely too much of my fulfillment and my purpose in career and work is driven by others through validation and comparison versus my own intrinsic sense of self.

I Want to Hear From You

Now, I want to spend all next episode talking about one of the ways in which you can create a more balanced diversion of perfectionism, where you can be a striver and a high achiever without a lot of the baggage that comes with it. But first I want to hear from you, let's start with, are you a perfectionist? And if so, which type of perfectionism do you most identify with of the five that I listed? Also, how do you find this to be a hindrance in life and work, and do you do anything about it to try to navigate the challenges created by your own specific type of perfectionism? I want to hear your whole story with being a perfectionist and I want us to talk through it. Send an email to alex@morningbrew.com or DM m on Twitter @BusinessBarista with any thoughts or questions you have about this episode. And finally, if you enjoyed the show, please share it with a friend that you think would love to use Founder's Journal as a tool for thinking better in order to build better. Thanks for listening and I'll catch you next episode.