Perfectionism is the Enemy of Startups
It’s been 14 years since I started my first company and along the way, mostly due to Technori, I have had the opportunity to have thousands of coffee and beer meetings with entrepreneurs. For a spur of the moment research project in 2015 I sat down for two days and combed my email and calendar and placed the number around 3,000(ish) individual coffee/beer conversations.
The majority of those were between 2010–2013, in a period of my life where I desperately craved conversation. Like so many other founders, I wanted to collect stories. I wanted to know what made these people tick. I find most business interviews to be shallow and worthless from a content standpoint. It’s amazing how you can read a 1,600 word interview and walk away having learned nothing about that person. So, when I met with founders I’d ask about their childhood, school life, family, hobbies, passions, religion, politics, fears, failures, etc… I wanted to know about the content of their character, not their business successes or the latest feature in their app. Sure, we would get to that as well, but it was always an afterthought.
From the notebooks I have filled with thoughts on these conversations, one theme emerged over and over. It felt bigger than a common trait or a some sort of coincidental anecdote. It was pervasive and dangerous. It seemed to have the symptoms of anger, depression, drug abuse, anxiety, shame, panic attacks, and for some the edges of suicide.
There is a constant battle between perfectionism and reality in the daily life of founders and it behaves like a disease.
Being aware of that you may be a perfectionist is the first step in addressing it. My guess is that some of you already are. For the rest, you might be surprised as to what some of the classic symptoms of perfectionism are. Procrastination and perfectionism are closely linked. All or nothing attitudes. A strong desire to appeal to and appease others. Obsessing over little mistakes. Feelings of guilt around your work. Being highly judgemental and critical of peers. A feeling of always being “just at the edge” of where you need to be, but you never seem to reach that edge no matter what. The list goes on and on and by no means are these guaranteed signs of finding a perfectionist, but they are common symptoms.
A founder reached out to me last year in a melancholy state. He had found a good amount of success in his life, but was constantly dogged with anxiety and feelings of inadequacy surrounding his startup. Even though his current startup is doing quite well, every competitor announcement, funding round, TechCrunch article about their space, etc… felt like a slash with a knife. He felt an unending pressure to be better, faster, leaner, smarter… If they weren’t the best at all of these things, it was a total loss to even exist as a startup. If he could just grow “this” much faster, just launch that new feature, then everything would be good. Everything could be perfect.
And at one point in his email, he wrote:
“I’m a perfectionist with a lot of anxiety, but it’s also why I feel like I’ve been successful. But I get depressed when things aren’t working. The anxiety becomes too much.”
This the life of quiet desperation that most founders live.
(Stealing that line from Thoreau. Though he was most likely a huge asshole and hated people, so maybe not the best reference. Moving on…)
As founders we are expected to be always be “crushing it” and not show weakness. To ship on time, every time. To be charismatic leaders, but humble. To lead effortlessly, even on days where we want to curl up in the corner with some headphones and pretend the world doesn’t exist. We are expected to wow a room of investors with our latest pitch and take their feedback with a smile. To come across super passionate, but totally in control. Patient and calculated, yet appear to be sprinting at the same time. To be everything anyone needs us to be at that moment, every day.
However, every single thing I just mentioned is self-induced. They are all artificial pressures we put on ourselves, with the expectation that we are required to be something other than being human.
Founders are just people. The greatest founders in recorded history still dealt with the mental and physical constraints that apply to everyone else. People mess up, they are vulnerable, and occasionally weak. People get tired and have days when they want to quit. People tend to be irrational, sometimes making their problems worse. This is not unusual, it’s a typical Tuesday in the world of being people.
Perfectionism is not human. To chase it is to try to make yourself something not human. Something that is not possible and that no one has ever been in history. As if that wasn’t bad enough, perfectionism demands that you hold your lack of perfection against yourself when you don’t reach that insane goal. That you are a failure somehow because you couldn’t attain the impossible.
Luckily, there is plethora of advice to address founder perfectionism, most a Google search away like this and this. Additionally, Brene Brown has written an amazing trio of books that address perfectionism among many other powerful topics. I would start with The Gifts of Imperfection.
Personally, I offer up a slightly different view. One that I find quite beautiful, but won’t appeal to everyone. Rather than chasing “perfect”, can you fall in love with chasing the imperfect instead? I didn’t think so until I stumbled upon a beautiful life view called Wabi-sabi that has helped me deal with perfectionism.
Wabi-sabi is the art of embracing the imperfect, the incomplete, the impermanent. It’s accepting that chasing perfection is moving away from being human and the natural world. We are surrounded by people & things that we love, that we embrace completely, and see each day that are imperfect. Yet we love them regardless. Many times it’s specifically because they are imperfect that we appreciate them ever more. Wabi-sabi is embracing being human.
However you go about it, I hope you rid yourself perfectionism and the desire to leave humanity. We need more people deeply in touch with their shared humanity now than ever before.
