Photo by Eugene Lim on Unsplash

How to Fail (And Why You Have to)

Why everyone is afraid of failing

People are scared of looking less than what they want to project to the world.

Aside from highly competitive people who are very focused on what they want, most walk on a treadmill of self-doubt. We don’t believe we can. We don’t believe we are good enough. So we cling to any small victory we have to project how great we are. We compensate and supplicate to our parents, our colleagues, our friends, our lovers because of the belief that we are not good enough for abundance, for love, for good friendships, for success.

And when you take that feeling and add a couple of mocking comments about how you failed two years ago in your relationship, you think to yourself “man, I will never, ever fail again”. So you settle for what will never put you in the position of failing again. You settle with personal mediocrity out of fear of looking stupid. “Thay guy failed again, what a loser.” You don’t want to hear that. Nobody wants that.

Those who criticize and mock you for failing are cynics. They see themselves in you, they see their fruitless attempts in yours and try to bring you down to their level to justify their own reality; that in which the world is too scary to accommodate their needs. The cynics say “I will project that the world is so bad and I am such a victim that my failures will be justified”.

People are afraid of failing because they don’t want to project to the world that they are less than what they would like to be seen as.

How the environment teaches us that failure is bad

Before learning how to ride a bicycle, your Grandfather shows you a blackboard. He gives you a bunch of books on the anatomy of a bicycle, how does the wind impact the motion of the wheels, the right positions to ride and common mechanical issues of the bicycle. Then he gives you the first lesson: origins of the word bicycle and forces you to write the word bicycle until your hand goes numb.

Finally, at the end of the session, you have to write a 100-word essay about the importance of bicycles. your first exam is at the end of the year. Next year you have Applied Physics in the Context of Bicycles. Your parents are so proud of you. After finally getting the exam, after long stressful nights full of caffeine and Instagram, your Grandfather proudly shows you a bicycle. You can finally ride it. You are accredited to sit your butt on the bicycle.

But now here is the issue: you are scared. You are scared because, after a year of studying the anatomy of the bicycle, something might go wrong. Maybe the wheels will stop. You head is full of scenarios of kids who suffered incredible injuries and *how* to specifically avoid them. You are scared of your Mom seeing you fall off the bicycle. You don’t want to look like a failure in the eyes of your Dad. You brush the bicycle off and tell your Grandfather “I will take 3 more years of Master, Grandad”.

Fortunately for you (and me), Grandad put you on the bicycle and told you to ride. And you had to fly, otherwise you would fall off. So after 100 tries and 10 bruises, you could safely assume that you were able to ride the damn bicycle, and the joy of confronting the chaos and coming up as a winner was so great that you decided to include the story in an essay about failure.

Unfortunately for you, almost everything labeled as “education” is practiced exactly like the fantasy above. Books, exams, blackboards and numb hands, all of which fuel your sense of not being good enough because you grow up to see all the kids who are better at Applied Geometry than you and your Mom asks about your grades and when you say “5” you obviously feel dumb. You also develop the habit of rationalizing waiting to go for what you want for exactly the same reason; your fear of failure, sustained by years of social conditioning.

One of the problems with education is that it conditions children to think failure is the opposite of success.

You can’t even pass the class if you don’t have the minimum grade, regardless of your interest in the subject. This teaches you that failure is not an option even if you hate what you re doing, when in fact, if there is something every successful person knows is that failure is just as much of a component of success like any other one.

Why failure is essential

There is a systematic order of learning anything. Firstly, you have to learn the tools of the trade, then the principles behind it, then you practice deliberately, then you become a master who develops the most effective systems, then you mentor others.

Learning the tools of the trade first means two things:

1) No design mentor will teach you Adobe Illustrator. No public speaking mentor will teach you grammar. No art mentor will teach you how to draw a square.

2) In order to get to the principles, you need context to apply them. You need to know Adobe Illustrator before learning how to be effective in Adobe Illustrator. You need to know how to hammer a nail before learning the physics of hammering a nail. To some of you who did particularly well in school (I know because I’ve been good in school too), this might sound counter-intuitive. What do you mean I have to learn to hammer a nail before learning the first Newtonian Principle? Screw Newton and his principles. If you want to hammer nails, you need to learn to use the hammer.

What all of these means, paradoxically, is that you need to teach yourself the tools. The tools are the most basic, fundamental components of the mastery of certain subjects. You need words to write, speech to speak, hierarchy and grids to design, ability to care for others to lead properly.

And because there is no teacher who will teach you these basic things (not even in schools, mind you), you will have to be your own mentor. And the only way to do that is by trial, error, and extraction of interpretations, formulating a thesis and trying to validate it until you arrive at a suitable model of execution.

Sounds complicated. But this is what you subconsciously do when you learn to ride a bicycle. You calibrate until you get it and the world responds to you in the manner you want it to respond. This is proper learning. Sitting in your (class)room, reading tons of material on the subject before attempting to teach yourself the tools by trial and error *is not* proper learning.

At the end of the learning curve lies your ability to decide whether or not you can proudly pursue a career in cycling because you’ve mastered a basic tool only by trial and error. That only will give you confidence and self-esteem.

Failure is essential because overcoming it is quintessential for your self-confidence and learning curve. The sooner you fail, the sooner you can learn the tools.

How to fail

It is weird that in a culture obsessed with success we don’t have enough teachers telling us about failures. We need a counter-culture that studies failure and examines all its underlying processes. We need to have books and lectures on the principles of failures. Let’s forget for a moment about Elon Musk while he takes a bath in billions of dollars.

Let’s examine the process of failing, from point A (trying) to point B (arriving pathetically on your ass after being knocked down by a bicycle, or an essay, or a design, or a girl/ boy). You’ve enthusiastically exercised your curiosity. You wanted to try. You felt like the thing/ person had potential. You projected a vision of you winning. You formulated a thesis based on your current understanding of how the world works and proceeded to develop a plan to execute the vision. Your initial thesis was faulty, so the plan was incomplete. Your actions were empty of substance or simply wrong.

Maybe you barked at the wrong tree, but now you are a bit more clued in about the nature of the world.

Everyone knows how to fail, but because they are so scared of it, they try to compensate by over-learning how to succeed. We all know someone who is so trapped in his head that the only thing he can do is to read theory but never apply it. We all know someone who is so trapped in his lack of self-agency that is always looking for the next quick money-making scheme. Then they waste their entire lives completing Lotto tickets because that’s their model of reality.

Two types of Failure

The first type of failure is the procedural failure. You fail by being stupid. You fail by having an incomplete model of reality and developing an inconsistent plan for achieving your vision.

The second type of failure is the big-picture failure. You fail by trying not to look stupid. You fail by staying in your comfort zone, in which you never try to fail again- thus you never try to complete your model of reality out of fear of looking stupid. In consequence, your model of reality looks the same for the rest of your life.

The first type of failure is a teacher. The second type of failure is a cage. It is up to you to embrace whichever failure seems most useful and appealing. However, you cannot avoid it.

You either fail by being stupid, or by trying not to look stupid.

Keys to Power

In this context, it is essential to learn a few coordinates that will aid us in the process of failing. This next section is (Exclusively) for people who decided to embrace the first type of failure as a go-to, not because it is cool, but because it is the only way to achieve a model of understanding reality that can give them all the ideas they need to execute on their visions.

The first coordinate is proactivity. Maybe the biggest monster we have to face on a daily basis is inertia. Aside from us feeling like we are not good enough to have good things happening to us and us sabotaging our attempts to be less pathetic, our brain also works in the direction of nothingness. For the reptilian brain, comfort is the opposite of danger, not the aid for growth. The way to grow is to constantly push your comfort zone by deliberate choice, i.e., by being proactive in every endeavor. In layman’s terms, you need to deliberately search for opportunities to knock your head against reality and find out how deep the rabbit’s hole goes. As Stephen Covey put it in The 7 Habits of Effective People:

“Your life doesn’t just “happen.” Whether you know it or not, it is carefully designed by you. The choices, after all, are yours. You choose happiness. You choose sadness. You choose decisiveness. You choose ambivalence. You choose success. You choose failure. You choose courage. You choose fear. Just remember that every moment, every situation, provides a new choice. And in doing so, it gives you a perfect opportunity to do things differently to produce more positive results.”

The second coordinate is speed. You need to learn to fail faster. The faster you fail, the faster you learn. To do this properly, you want the quick iterations you are making to be analyzed in depth. You want to have a failed date and extract everything out of it. The other part of speed is that the sooner you start failing, the more people will call you a “natural” or “talented” later in life, which you can use in your own advantage to seem mysterious and mystical.

The third coordinate is enthusiasm. When you are in the trenches after years of conditioning that failure is bad, your brain will generate self-deprecating thoughts at an amazingly fast pace. You will bleed self-doubt and resistance, for which I highly recommend Steven Pressfield’s The War of Art. To keep myself going, I find it really good to infuse enthusiasm and positivity in order to make myself enjoy every little ounce of progress. I have something I call The Winning Method, in which after I do something that requires willpower to confront resistance, I go to the bathroom, look in the mirror and scream “WINNING!”. It works :D.

The fourth coordinate is objectivity. Buddhism teaches us that the root of all suffering is attachment. The attachment of your ego to specific outcomes clouds your ability to objectively analyze the situations that led to your failure. You are impeding your progress by investing your emotions in what should be purely an exercise in learning. This is not to say “don’t care”, but it is to say “don’t invest your emotions in things that have no other meaning but to get you further down the road of mastery”. The key is more to enjoy the process, not the outcome, and the only way to do this is to strip away all the subjectivity you place upon the outcome and be fiercely realistic and objective.

Notes to the Wise

It is essential to realize this: your process of failing deliberately should not stop after you’ve placed on yourself the label of “master”. The best case scenario is when you love the process so much that you don’t care whether or not you fail or win, but simply enjoy the process of whatever it is you are trying to do.


You want to fail until the concept of failure becomes irrelevant. You have to fail by procedure because if you don’t, the price you pay is a failure of life. You fail effectively by being proactive, fast, enthusiastic and objective.

This story is published in The Startup, Medium’s largest entrepreneurship publication followed by 311,685+ people.

Subscribe to receive our top stories here.