How to beat perfectionism
Get rid of the imaginary punisher who is supposedly standing behind your shoulders watching all that you do and whipping you for each mistake made.

Perfectionism is not the problem. It's a symptom.
If you do a quick search on how to fix it, you will see duct-tape solutions suppressing the symptom instead of addressing the root cause. Like fever, it's a symptom of many causes. One might have one or many of them. I'll try to address as many as I can think of.
Perfectionism is a symptom of immaturity. As people grow old, the majority of them overcome it. If you listen to advice from 40-60 year olds about how they have changed as they grew old, many share one thing, "care less about other people's opinions". They basically get rid of the imaginary punisher who was supposedly standing behind their shoulders watching all that they do and whipping them for each mistake they make. Sometimes they exist in the real world but they are not even a fraction of the hell bringers as we make them to be.
Seneca said, "There are more things likely to frighten us than there are to crush us; we suffer more often in imagination than in reality".
People fear all sorts of imaginary punishers. Like a boss, peers, family, parents, god, angels, or your own imaginary alter ego that wants you to be 100x better than yourself.
Try to get rid of unnecessary fears. Getting over perfectionism when you are 50 or 60 yo is a bit sad because then it's usually a matter of getting tired of unrealistic expectations and going through an existential crisis. After which people realize, the punisher was just a construct of their imagination and they've lost precious years of their life.
When some people do get rid of the imaginary punishers, sometimes, unfortunately, they get rid of the real versions of it. They rebel too hard. That is swinging the pendulum too far to the other side. That's the worst outcome of not doing anything about the imaginary version. People blame bosses instead of working on themselves. They cut relationships. They blame their parents. They blame God, color their hair purple, become hipsters, or bury themselves in tattoos and whatnot. Do not blame anyone ever.
Naval once said, "The quality of your life is as good as the quality of your mind".
If you are stuck in a rut of perfectionism, identify who do you fear. It could be one or many from the list above or something else. Be honest with yourself for your own sake. When you have identified your nemesis, take a step back and see if the expectations you are trying to fulfill are real or not. What would happen if you didn't do that? Imagine the worst cases and more often than not, the worst case is not catastrophic. Avoid ruinous outcomes and everything else is tolerable.
Talking about bosses, would your CEO care about the 100% test coverage of your code or solving the customer's problem? For jobs, I can tell, no CEO would like to hire a perfectionist. There is no excuse to be one. If you are trying to perfect your code for some real or hypothetical metric, think about what metrics are you chasing. In a job, when you perfect your output, you will impress your manager or people around you but you are not progressing in your career. Think about the Principal-Agent problem. Think like a principal if you want real progress.
If you never miss a shot, you are not levelling up. You are in a rut.
Perfectionism is a symptom of not having a north star. Keep the big picture in mind. Some people don't have a north star and they get stuck in a rut. Rut could be inaction (procrastination), analysis paralysis, waiting for perfect conditions, forever preparing, or learning for the sake of it. Some people do have a north star but they don't have enough conviction about it. They are not 100% "sold" on their north star or don't have clarity about it. In such cases, work on your north star and all the vices I mentioned earlier will take care of themselves. Perfectionism and procrastination very often stem from the same underlying causes. Most people who suffer from perfectionism oscillate between the two. Perfectionism leads to giving up followed by long periods of procrastination.
No one is a perfectionist in all spheres of life. You become one where you fear something. Where you are fearless you have an air of indifference in that area of life. You have no insecurities. Your self-esteem is high in those areas. You don't compare yourself to people. Find those areas in your life and compare them to those where you are too worried about your "image". Do you see a difference? When you get started with something, fear, and anxiety is normal. It helps us to push harder but don't let past fears dictate your future self. Know your worth and do that practice often because humans grow.
Perfectionism is a symptom of not knowing yourself. Run your own race. Some people are talented in certain domains. They have to work less hard than you. If you are 5 feet 4 inches tall, don't waste your energy playing basketball. Play the games that you are suited for, otherwise trying hard won't get you far. Self-discovery takes time. Which is also why age fixes perfectionism. You can expedite that a bit by obsessing over trying to know yourself. Know your intrinsic motivators. Know what you like and dislike. Know your natural tendencies and align your goals with them. Try many things. Try, meditate over it, and repeat.
If the shadow that makes you a perfectionist is your own self who holds you accountable to high standards, understand that your standards come from people and work you look up to. Doing that is perfectly fine but be mindful of the process and circumstances your ideals went through.
Perfectionism is a symptom of extreme ambition when in reality you are a nobody. Don't try to create masterpieces. Become a person for whom making masterpieces is a habit or a side-effect. There's a popular (almost cliched) story of an art teacher who divided a class into two groups. One group was tasked to make 1000 paintings in a year but not worry about quality. The other group was tasked to make only one the entire year but it has to be the absolute best. At the end of the drill the group that was tasked to make 1000 ended up with better-quality paintings. As Naval said, 10,000 iterations over 10,000 hours. 10k iterations might take you the same number of hours but it's a different lens to look at the same problem of achieving mastery. All the top creatives are successful because of their taste. Not because they embrace quality over quantity. They just choose to publish what they find is best. Each one of them is prolific in their domain. There is no rocket science. Science is to conquer yourself. Big goals, small steps.
Ambitious people want to change the world which makes them think that baby steps are for... babies. They are not. Everyone is a little kid in one domain or another. Don't be arrogant about this fact and get over it. For example, if you dislike accounting try not to start big on work/ventures that involve heavy accounting. Likes and dislikes very often stem from what we have done in the past or what we are good at. If you don't like accounting but you do it for many years, over time, you will develop a taste for it. Whatever you like doing, you weren't born liking it. Many people start a career they never wanted to but eventually become good at it. The brain is plastic and molds itself. Most of the time, the only thing it's doing is conserving energy. Understanding that you dislike something is important when getting started with it. Try not to test your willpower by going on a war against it. Slowly and steadily morph yourself and you will become a new person.
You can do anything you want... but not everything.
Start small. Always. Don't try to build the next Google. Try making a personal website and ship it. That won't be a product you are proud of but you will have some tangible output. You will learn trades of building, shipping, marketing, and maintaining a website. Humans need a fine balance of challenge and reward to keep going. If a task is too difficult, you will give up. If a task is too easy, you will get bored. When working, try to orchestrate work in a way that you maintain an optimum level of challenge and reward. When you get comfortable with programming, increase the difficulty. Sooner than later you will be building useful products that you can show to the world.
Perfectionism is a symptom of living up to some label you've put on yourself. Be willing to start from scratch. If you have been a high achiever since high school, have a high-paying, respected position in a corporate company, and want to start a business, you will likely fail in your first attempt. If you are bootstrapped, you will give up. If you are well-funded, you will give up too but call it a pivot. The skills that made you do well in school or job are not the ones that will help you in business or vice versa. Your status as a high achiever will make you stress over and over again about trying to set up the perfect business and take it forward very professionally. That is not how it's done though. You have to be willing to look like a fool again. One could be a master chess player but be pathetic at social skills. If such a person is to venture into a social business, they have to start from zero and come down from the throne of the grand master.
How to beomce a magician?
- 20-29 years become an expert at whatever you do.
- 30-39 years focus on another skill that complements your core skill.
- 40-49 years pick another skill that complements skill # 1 & 2.
At 50 years old you become the grand magus with a hand of Midas.
Payouts compound like hell if you upskill yourself in multiple fields. To do that be willing to start all over again, like a kid, fumbling around. Do not put a label on yourself especially when you have achieved something. Labels will limit you from progressing.
Perfectionism is a symptom of misalignment between your priorities and goals. If you prioritize health and peace of mind over everything else and dream about starting a billion-dollar startup you have a conflict. A conflict between what you prioritize and what you dream about. Go through all your priorities, systems, and actions in your life and compare them with your goals, wants, and wishes. Try to minimize that difference. If you keep that difference too big and for too long, your personality will become bitter. You will blame all sorts of things for your dissatisfaction. Take a pause and think about what you prioritize day to day and what you wish for.
Perfectionist is driven by fear of being ridiculed. Know that very few people care about what you do. Many will root for you, some will mock you, and some will correct you. If you hide behind a shell because of that reason, you stay a fool forever. A fool hidden in plain sight. Come out and dare do what you want to, you will either win or lose. If you win, you learn. If you lose, you learn. If you hide, you get stale.
It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.
Learning, out there, in the arena, by doing, is many times faster than learning in the shadows. As Sahil puts it, "Start, then learn".
Another reason is traditions. People who grow up in strictly religious or traditional households stress over the tiniest of details and follow the traditions too strictly. Religion in many cases becomes a set of rituals at max and loses its essence. I think the essence is of more importance and rituals should follow that. You can't just eliminate rituals like you shouldn't remove Chesterton's Fence. If you make it all about rituals, you will start stressing too much over them and almost develop an OCD.
Perfectionism is a symptom of childhood traumas. If parents are too controlling, the child grows up in fear instead of love. That fear becomes a part of their personality and they live a life engulfed by all sorts of fears. They see the world as a thorny hell, with a pessimistic point of view, with ambushes and traps laid all over the place and each specie conspiring against them. Those who grow on love see it as a garden with sunshine, abundance, and opportunities. Identify your childhood traumas and work through them. They are the hardest to recognize and fix. Unlearn what your parents taught you. Unlearn how they think about the world and reimagine a new world through a fresh lens with a child-like curiosity. Protect yourself from negativity. If you couldn't heal yourself and have children, learn from your children. Learn from your toddlers. See how they do not worry about perfectionism or consequences and when they set their eyes on something, they expend all they can to get to that thing. Bright-eyed, with relentless optimism, energy, and force. All they can muster.
Good parenting is not raising your children well. It's more about raising yourself.
Perfectionism is a knee-jerk reaction to risk. Understand your risk appetite. Most people don't do this or they don't do it very often. Your risk appetite is the amount of risk you can take at any point in time with little to no downside. When you were a kid in college, you had a very different risk appetite than when you were out of college making money full-time. Previously you could risk your time as you had an abundance of that and now you can't. Now you have money which you didn't have back then. Your risk appetite when you just started a job vs. when you are at mid-level is also very different. At each point in life, recalibrate on what you can risk that has little to no downside but a high upside. Quite often you can take a lot more risk than you are taking at the moment and a primary reason is that you don't even understand that you can take a lot more risk. Whatever is surplus, put it to use. It could be time, money, status, or white hair.
School makes some of us perfectionists. We couldn't risk thinking independently out of fear of beating or low grades. We conformed. When out of school our risk appetite needs reevaluation. You don't have to think linearly anymore. There are no right or wrong answers in life. In school, it was risky to think independently or make an attempt without preparation. In life, that's not a problem anymore. Life is not 6 months of learning and 1 hour of performing (in the exam). In school, we had to prepare, prepare, and eventually nail the exam. We carry that notion way too far into life. Life is almost the opposite of that. It's a contiguous performance. In the first performance, you get 1 out of 100. After hundreds of performances, you get 90+/100. It's also a reason why I hate the entire education system. Who likes being schooled anyway?
In life, take exams early and often. Ship often. Publish often. Take more risk. Don't work for 6 months and then ship. Try to ship ASAP, get feedback from the real world, and iterate. Don't be afraid of getting started because the circumstances are not perfect. In school, you know you are going to get it right if you are at it for months. In real life, the chances are slim because there are no right answers. To get to those right answers you have to start and iterate a lot. If there is something that has to be worked on for years, that shouldn't be your first project. Start and start small.
School is predictable; life is not. School can be aced with a plan and preparation. Life will hurl your homework and cheat sheet in your face at the very first step. Think in probabilities instead of thinking linearly. Life is not all or nothing. It has a lot more nuance to it. Nothing is perfect and will ever be except the system of the universe that we live in.
Mark of maturity is the ability to entertain nuance.
Many smart people strategize too much thinking of life as a game of chess. Life is not chess. It's poker. Chess has no randomness and all moves can be predicted. In poker, you are dealt a hand randomly at every turn. You have to do your best with the cards you are dealt.
Perfectionism is not all that bad. Some people need to be more perfectionists, more thorough, more thoughtful, careful, and meditative but that's a different story for different people.
I am not too fond of how this post turned out to be. I am not a good writer. The post has a lot of information but a lot is missing that I couldn't formalize and put in words. I tried to address the root cause. Since the post is not well written, reading multiple times spaced out by months might help. If there is something I couldn't explain well, let me know and I can build on it. What did I miss? Reply by email or comments.