Failure and Mistakes Pave the Road to Success: Get comfortable failing.

John Cousins
February 7, 2023
6 min read
Photo by Hayden Walker on Unsplash

The trouble with life is that you get the test first and the lesson later.

Ware constantly put in novel situations and have to make decisions. But it’s only after we reap the consequences of our choices that we get the lesson of what we should have done.

That is life. Life sets us up with situations and allows us to fail regularly.

Life not only allows us to fail but forces us to fail because we only get that lesson if we pause to reflect on what went wrong.

Either we perform an after-action reflection on what went down, or we are doomed to repeat the same mistakes until we do.

So life can be looked at as at best a stumbling forward, stubbing our toe here and bumping our head there and learning from the experiences.

WTF! That’s not the way I was taught in school that life would proceed and progress!

Think Different

I have been thinking a lot lately about mental models. We think in conceptual models. We apply mental models to situations to help us anticipate new situations by relating them to ones we know.

Mental models help the quality of our decisions and provide a structure for understanding our experience and reality. Different models apply to different situations, so we need a toolbox full of them. Then we can grab the right tool for the right job.

One powerful mental model that we can apply to understand the situation outlined above is inversion.


Inversion is looking at something differently. Take an idea or problem, or a belief, and flip it upside down, or turn it inside out.

Inversion puts a spotlight on errors and roadblocks that are not immediately obvious. Inversion challenges us to consider what if the opposite were true. It helps us focus on a different aspect of a situation.

It’s a powerful thinking tool.

Inversion yanks us out of our comfort zone perspective. This reexamination can be immensely helpful because sometimes our beliefs are wrong.

It ain’t what we don’t know that gets us into trouble, but what we know for sure that just ain’t so.

It’s imperative to shed our misconceptions and beliefs that no longer suit us. We have to shed our skin. An adult doesn’t fit into the clothes they wore as a child.

If we keep doing the same things, we can’t expect different results.

If we want to see the world differently, then we must change. The world won’t change to fit our beliefs. Our beliefs must change to meet the world better.

The world is full of magic, waiting for our senses to grow sharper.

-W.B. Yeats

We don’t perceive the world as it is; we see it as we are. If we want to get clearer on how the world is actually operating and how to navigate in it effectively, we must examine our beliefs and refine them to reflect reality with higher fidelity.

It’s always a good idea to take a moment to invert, always invert.

Here is an example of applying inversion to help us get clearer on making our way in the world, progress, and success.


School Daze

In school, we get the lesson first and then the exam.

In school, we are encouraged to learn our lessons and regurgitate the correct answer on the test. Any divergence from the correct answer is met with failure. We learn not to make mistakes.

That is not life. In school, we are encouraged to avoid mistakes and are punished when we make them.

Schooling can teach us to expect a way to progress through the world, which is a formula for frustration.

We need to become comfortable with failure and embrace mistakes.

In school, the smartest people are rewarded for not making mistakes.

In the real world, the smartest people make mistakes, learn, and apply that new knowledge.

Some call this method the School of Hard Knocks. We accumulate its real world knowledge by making mistakes and learning from them.

Fail fast, fail often, fail forward.

Failing forward means learning to adapt favorably to change and to be resilient when confronting adversity.

In school, we should be encouraged to do something where you face the prospect of failing. Every time I have done something in business or had a relationship, I got smarter. Experience makes us smarter.

Authentic learning happens when we go beyond consuming information and commit to playing and making change happen. By playing, we mix it up, experiment, and learn to see things as they truly are.

Calling doing things “play” takes the stigma off failing. If we are playing and experimenting, then mistakes are expected.

We are the most ourselves when we achieve the seriousness of a child at play.

Post-secondary education takes on this attitude.

The highest echelons of schooling invert the lower schooling rules and look more like the real world and the business world of hard knocks. Research work at the doctoral and post-doc level requires embracing failure, making mistakes, and course correcting.

This iterative approach is the basis of the scientific method. We make a hypothesis (a guess), test it, review the results, and adjust our hypothesis based on the results.

Thomas Edison said,

“I didn’t fail. I learned 10,000 ways not to make a light bulb.”

It only takes one right way.

Embrace failure. Not for failure’s sake, but so we can move past what we experience as the immediate failure, and focus on the lesson learned from the experience.

Failing and learning are how we grow. Through growth, we ultimately succeed. Success is really about having higher quality failures.

Success is going from failure to failure and not losing enthusiasm.

-Winston Churchill

When we stop growing and learning, we are diminishing and dying.

Every moment of one’s existence, one is growing into more or retreating into less.” ―Norman Mailer

It is better to begin as a fool and learn from your mistakes than to fake being brilliant and ignore your errors. Ignore a mistake and prepare to repeat it.

Failure teaches us humility.

It’s better to have failures that make us humble than successes that make us arrogant.


I have been reading a book called Extreme Ownership by Jocko Willink and Leif Babin, and it outlines a compelling concept of owning every part of our experience. No blaming. We need to own our mistakes and failures if we hope to move past them and learn from them.

What looks like an obstacle is the way forward.

Obstacles make us tough and creative. Rough seas make good sailors.

You can turn a stumbling block into a stepping-stone or a catastrophe into a catalyst. A stumbling block is a stepping stone wrongly perceived. A catalyst is a catastrophe rightly understood.

We never manage to outgrow making mistakes. Mistakes are part of life. Making mistakes is how we learn.

If a child touches a hot stove once, they don’t do it again, right? Mistake made. Lesson learned.

Maturity is realizing mistakes are not only inevitable but valuable.

Having the wisdom to learn from your mistakes will help you go from victim to victor. You can turbocharge this process by reading and learning from the mistakes of others.

Fools learn from experience. I prefer to learn from the experience of others.

-Otto von Bismarck

To recap:

Use mistakes to propel yourself toward success.

It’s a numbers game.

If you want to increase your success rate, double your failure rate.

One more thing:

Like failure, chaos contains information that can lead to knowledge — even wisdom.

— Toni Morrison

Share this post
John Cousins
Author, Entrepreneur, & Teacher

Receive my 7 day email course

Take your finance skills to the next level with my 7-day corporate finance email course. You'll learn all the essential topics from financial analysis to risk management in a fun, engaging format. Each day, you'll receive an email with practical examples, exercises and resources. Perfect for aspiring finance pros or anyone looking to expand their knowledge. Get ready to transform your finance game!

By clicking Sign Up you're confirming that you agree with our Terms and Conditions.
Thank you! Your submission has been received!
Oops! Something went wrong while submitting the form.

If you like this article. Here are some more articles I think you might like.


The Road to Becoming a Unicorn: A Quick Guide to Startup Funding Rounds

The whole process of funding and developing startups has become more widespread because the cost of getting a product to market has dropped so precipitously in the past couple of decades from millions of dollars to typically anywhere from under $20,000 to $500,000.
John Cousins
December 18, 2023
7 min read

Oh Behave! Behavioral Economics: Why we do what we do.

Behavioral Economics is a method of economic analysis that applies psychological insights into human behavior to explain economic decision making.
John Cousins
December 18, 2023
4 min read
Personal Growth

Professional Development: 3 Types of Skill Sets

To perform effectively in a job and advance to greater responsibilities requires developing a well rounded set of skills. Every job and every industry has its specifics but these skill sets are general and apply across all jobs. Skills are fundamental for turning a job into a career trajectory and this trajectory is part of our personal fulfillment in life.
John Cousins
December 18, 2023
5 min read