“A man is great not because he hasn’t failed, a man is great because failure hasn’t stopped him.” -Confucius

Two weeks ago, I had dinner with a friend.

We were catching up over food, laughing about life, and somewhere between the main course and dessert she made a great suggestion.

"I love your newsletter, but I want you to talk about failure more."

Not because failure is something to celebrate for its own sake, but because the fear of failure is one of the top reasons that stops us from realizing our potential. Silence about it creates a false impression.

I agreed.

To be clear: I’ve had countless failures, both personally and professionally.

I’ve been boo’ed on stage while performing stand-up comedy.

I’ve had multiple failed entrepreneurial attempts.
I’ve had failed romantic relationships.
I’ve been fired from a job.


And, I’d be lying to you if I didn’t say those failures chipped at my confidence.

They left some scar tissue.

For many years, I questioned myself.

Do I actually have what it takes?

Am I really an entrepreneur or am I just a wantrapreneur?

Ultimately, I knew, at my core, I had so much more to give the world and I didn’t want to share the same regret of dying.

I knew that mission would never get fulfilled from inside someone else's company, playing it safe, and letting the scar tissue win.

I only had one option.

I had to level up and get better. I had to try again. I had to be willing to fail, again.

The first shift wasn't a decision. It was a reframe.

I’ve read and watched dozen of biographies, and documentaries on successful people.

The more I read the more I realized how common failure was.

I found solace in knowing that:

Oprah was fired from her first job.

Henry Ford had two failed automotive companies before he found success with Ford Motor Company.

Jame’s Dyson failed 5,126 times before creating the worlds best vacuum cleaner.

Think about how you learned to walk.

You didn't read a book about walking. You didn't watch a masterclass. You fell and you got up and you fell again, and again. And again.

Toddlers learning to walk, fall 17 times per hour on average — and they take about 2,368 steps per hour, traveling the equivalent of 7.7 football fields in that time.

By the time they're two, the average toddler falls 38 times per day. So over the full learning-to-walk period — which spans several months, we're talking thousands of falls total.

Failure, in that context, was so obviously the mechanism of learning that nobody even called it failure. We called it growing up.

Somewhere along the way, we forgot that. We started treating failure as evidence of unworthiness rather than evidence of effort.

I kept coming back to Confucius: "A man is great not because he hasn't failed; a man is great because failure hasn't stopped him."

The second shift was about language — specifically, changing the definition I was using, which was incorrect.

Most people don’t know that word failure comes from Old French all the way to Latin — where it simply meant "to fall short" or "to be lacking."

Not a verdict. Not an identity. Just a description of a single moment in time.

Somewhere along the way, we changed that. We turned a word that was always meant to describe an outcome into one that defines a person.

But that was never what the word meant.

Etymologically speaking, failure is temporary and contextual. It describes what happened — not who you are. It measures a result, not a character.

You didn't become a failure. You fell short. Once. In one attempt. On one day.

Those are very different things.

Take a look at the image below.

On the left, someone threw a dart and missed the bullseye.

The dart is in the board — just not in the center.

On the second dartboard, there is no dart at all. The person never threw.

I redefined my definition of failure.

I went from: failure means "not succeeding on the first try." to failure is not trying for something I actually want.

This really crystalized for me when I moved to Mexico City to become conversationally fluent in Spanish.

Every day I had to embarrass myself.

Mispronounced words. Poor grammar. Incorrect accentuation.

It was a humbling experience. There were many days when I felt like giving up.

One day it clicked: “I have to fail my way to fluency. There’s literally no other way.”

Michael Jordan’s iconic Nike commercial finally made sense.

Failure is part of the process. It’s an inevitable part of acheiveing success.

The image below represents this perfectly.

The gem on the right cliff represents fluency.

The blocks represent all my failures.

The gap represents where I am vs. where I want to be.

Failures aren’t obstacles, they’re actually the bridge.

Once I accepted that, everything changed.

The bricks stopped being walls and started being stairs.

The third shift was the deepest — and the one nobody talks about.

I wasn't actually afraid of failure. I was afraid of what I assumed other people would think of me if I failed, and what that would cost me socially.

It’s all based on evolutionary biology and neuroscience.

We’re hard wired for survival, and community is essential to our survival. We evolved in tribal environments where social exclusion wasn't just uncomfortable — it was genuinely life-threatening. Being cast out of the group meant no protection, no food, no chance of survival. Your brain, operating on countless years of evolutionary programming, treats social rejection as a survival threat. It cannot fully distinguish between people thinking less of me and actual danger.

So when I failed at those two ventures, my brain wasn't just processing disappointment. It was running a threat simulation: If I fail, people will think less of me. If they think less of me, my social status drops. If my status drops, my ability to feed myself drops.

All fear is a prediction. And predictions are built on assumptions. The assumption underneath my fear of failure was a chain reaction that ended in isolation — and my brain was treating that assumption as fact.

Once I saw that clearly, I could challenge it. Not with toxic positivity, but with real evidence and tools.

A couple years ago I created a tool called “Sting versus Story.”

Any time I feel a negative emotion, I challenge myself to identify and separate the sting from the story.

The sting is the event itself — the failure, the rejection, the miss. It carries real emotional weight. I don’t pretend it doesn’t exist. I give myself full permission to feel the hurt, the pain, the dissapointment. I honor that emotion and don’t try to dismiss it.

The story is the meaning I attach to the pain. That part is a choice.

The story is what I can control and determines so much of my life’s outlook.

After two failed ventures, the story I had been telling myself was: this is proof I can't do it. I decided to tell a different one. What if I'm ten failures away from the one that works — and I just need to get there faster? What if this is what getting better actually feels like? What if this isn't evidence of my ceiling, but the cost of entry to my next level?

Same sting. Completely different story.

Speaking of stories, one of the most successful story-tellers ever is J.K. Rowling.

She’s the billionaire author of Harry Potter, who was once homeless.

In 2008, while giving the commencement speech at Harvard, she said:

“It’s impossible to live without failing at something, unless you live so cautiously that you might as well not have lived at all. In which case, you fail by default.”

I couldn’t agree more.

Confucius got it right.

The question was never whether I would fail.

The question was whether I'd let it stop me.

Here's your reflection for the week:

This week, I want you to find your story.

Identify one area where fear of failure has been keeping you from trying.

Then ask yourself honestly: what is the actual worst case? And is that story I'm telling myself true — or is it just a prediction my brain made to keep me safe?

Here's your challenge for the week:

Step 1: Pick one person you look up to who has publicly failed.

It could be someone from history — Walt Disney, Henry Ford, Oprah Winfrey, J.K. Rowling. It could be someone in your industry. It could be someone you know personally. The only requirement is that you genuinely respect them and that their failure is documented enough that you can read about it in some detail.

Go read about that failure. Not their success story — the actual failure. The bankruptcy. The rejection. The public embarrassment. Sit with it.

Step 2: Apply the Sting vs. Story framework.

Once you understand what happened, I want you to do something most people never do — get inside their head at the moment of failure and ask:

What was the sting? The sting is the raw event itself. The moment the door closed. The rejection letter. The newspaper headline. The phone call. What actually happened, stripped of all meaning?

What stories did fear probably tell them? This is the voice that shows up first — the one that sounds like logic but is really just self-protection. For your person, it might have sounded like:

Write those down. Really inhabit them.

What were the most empowering stories they could have told — or maybe did tell themselves? Now flip it. What story would a person need to tell themselves to get back up after that? For the same failure, the empowering version might sound like:

Step 3: Use AI to go deeper

Open Claude, ChatGPT, or any AI tool and copy and paste this:

With courage,

Jonathan