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Fail Intelligently

By Jason Bilyeu

Lazy Creativity features innovative and creative thinkers, makers, and doers. As part of our guest blogging series we aim to give platform to diverse thinking, ideas, and topics.

More than One Form of Correct

For many designers and creators, our fear and aversion to failure stems from a school system that encouraged “correctness” above all else. Understanding the basics of math and science is critical, at least as a starting point. Answers are right or wrong when it comes to long division and multiplication. A word is either spelled correctly or incorrectly. Yet, when every homework assignment, pop quiz, and final exam values only one thing, correctness, how does one push themselves beyond the curriculum and common knowledge to create something unique and new to the world?

The requirement of being correct doesn’t incentivize risk taking or adventure, but rather a careful, cautious, almost robotic regurgitation of information. To build a culture of creativity and innovation we must incentivize something different. We must allow, or rather encourage, different ways of thinking, new perspectives and methods for looking at and understanding the world around us. When learning, a student shouldn’t be paralyzed by the fear of getting the wrong answer but rather invigorated by the adventure of building a hypothesis and designing a test to prove it right or wrong, learning and growing from either result, often more so from being wrong. We must all learn how to fail and, more importantly, how to fail intelligently.

None of this is meant to disparage educational systems or the teachers who have dedicated their lives to educating students. I am incredibly thankful for the education I received as it provided me with knowledge on many topics and a wide breadth of different skills, abilities, and competencies. This is not meant as a diatribe in any way, as the value and the opportunity delivered by a well-rounded education is undeniable. However, all things can be improved and we cannot improve without understanding the problem.

The Problem

So, here is the problem: regurgitation of information is not a replacement for critical thinking and creativity. Being evaluated purely on correctness with permanent grades on the line encourages caution and timidity. The adventure of designing and creating something new is vitalized and invigorated by failure if one has the desire to learn from it and the fortitude to keep moving forward.

Personally, much of my educational journey was spent studying to ensure I could reiterate the “correct answer” and never risking the ever terrifying bad grade. Grades were the goal. Grades meant more opportunity, got you accepted into top level universities, and paved the way for scholarships. They set you up well for life. They also provided many of us, myself included, with an easy way to compare ourselves to others and feel superior. In my experience it was all about the grade and I went all in on getting the best grades I could.

Yet, my drive towards perfection of this kind did not develop a confidence in my abilities to solve problems and think critically, but rather created a cautionary attitude as I was not willing to risk failure.

In fact, I avoided risk all together. Risk meant the possibility of failure and failure wasn’t an option.

This mindset took a strong hold in my mind and in my actions for many years. In high school I consciously chose not to take an AP English course even though it would have qualified me to be Valedictorian or Salutatorian of my class. But I was terrified of giving a speech in front of my class, the school, and all of the parents. What if I messed up? What if I stumbled on my words and said something stupid? What if I wasn’t able to give a perfect or “correct” speech? My striving for an appearance of perfection actually inhibited my success and ability to achieve my goals. I was crippled by fear. A fear that had benefited me in many ways throughout my educational career. It drove me to study, to practice, and to memorize the correct answer so that I did not have to face the shame of failure. But it did not prepare me to confront the unknown, situations where there isn’t a right answer, where it takes courage to simply give it a shot and see what happens. This unknown and uncontrollable outcome was something I was not prepared to handle and so I avoided it. I sabotaged myself due to my fear of failure.

Brain Rewiring

It has taken many years to rewire my brain and learn to embrace both failure and risk. Although it remains a constant daily struggle, I’ve come to believe in two statements which have proven themselves true over and over again in my experience:

  1. Risk is inherent in creativity and innovation.

  2. You will always fail on a truly creative path but the relentless do not let that stop them.

Failure is a complicated thing. There are many ways one can fail. There are those who make irrational and rash decisions and fail due to a lack of forethought and planning. Some spend all of their energy planning but never have the courage to post, sell, or release. Time eventually passes them by and they miss their window. Still others shrink and withdraw at the first sign of struggle, not willing to feel the stinging pain of failure.

Then there are those who have a vision and a passion to do something new, create something that has never existed, or to put forth a new perspective that will be beneficial to the world. They plan meticulously, create a strategy, and then implement it. They take action. Often they fail but the failure never stops them. They learn from it, having understood the likelihood of it occurring they are ready to assess what went wrong and try again. These are the relentless few who are capable of creating true art as well as new innovative technologies.

Fail Intelligently

This is what it means to fail intelligently:

  • You are under no illusions of the difficulty and likelihood of failure.

  • You plan ahead, build a strategy, and pay careful attention to results.

  • When struggle inevitably comes, you analyze it and learn from it.

  • You are passionate and planned, realistic yet relentless.

In the end, we will all face failure at some point. We must accept that but not let it deter us. Creative and innovative people thrive off failure because they understand how to use it to make themselves better. Failing intelligently not only improves the depth of our understanding but also allows for creative insight; all the while building a spirit of endurance and relentlessness.

It is time to move past the restrictive nature of perfectionism, embrace the risk, and pursue the adventure of creating something new.

Jason can be found on Instagram and through his Substack.


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