The Fear of Failure

When I wrote Unlearning What Worked, I thought I was writing about failure.

Looking back, I don’t think I was.

I think I was writing about the fear of failure.

For much of my life, I believed the safest decision was to avoid situations where I might fail. If I wasn’t reasonably confident I could succeed, it often felt easier not to try at all. That mindset influenced far more than my career. It affected friendships, leadership opportunities, public speaking, and countless moments where I talked myself out of taking a chance because the possibility of failure felt worse than the certainty of standing still.

One chapter in the book centers around what we called the SPLAT Award at my work. It wasn’t an award anyone wanted to receive. I earned it after a mistake that contributed to a significant outage, and I took it harder than anyone around me probably realized. I walked into my manager’s office embarrassed, frustrated, and honestly fighting back tears. I wasn’t looking for him to tell me it wasn’t my fault. I wanted to understand how I had failed so badly and what I needed to do to make sure it never happened again.

Instead of focusing on the outage itself, he challenged the way I was looking at it.

He told me that if I wanted to guarantee I never received another SPLAT Award, there was a simple solution. Stop taking risks. Do only what was required. Never volunteer for difficult projects. Never stretch beyond what I already knew.

Of course, that wasn’t really his advice.

His point was that the people who occasionally make mistakes are often the same people trying to improve things. They volunteer. They take ownership. They attempt projects that don’t come with guarantees. Sometimes those efforts succeed, and sometimes they don’t. The objective isn’t to eliminate failure altogether. The objective is to learn from it so your next decision is better informed than the last.

That conversation forced me to confront something much bigger than a single outage. I realized fear of failure had quietly become fear of trying. Looking back, I could see it everywhere. I hesitated to speak up because I might sound foolish. I avoided opportunities because I wasn’t sure I was ready. I worried so much about making the wrong decision that sometimes I made no decision at all. The greatest obstacle in my life wasn’t failure. It was allowing fear to convince me not to begin.

A few weeks later, I bought my own donkey trophy, engraved it with the date I had received the original SPLAT Award, and put it on my desk.

People thought I was displaying a failure.

I wasn’t.

I was displaying a reminder.

The trophy wasn’t there because I was proud of making a mistake. It was there because I never wanted to forget what that mistake had taught me. Every time I looked at it, I was reminded that growth doesn’t come from pretending we’ve never failed. It comes from examining our failures honestly, learning from them, and moving forward anyway.

Years later, I found myself telling that same story during a technology conference. Ironically, it wasn’t part of the presentation I had spent weeks preparing. At the last minute, I abandoned my script because I wanted to talk less about Python automation and more about something I thought our community needed to hear.

I’ve been in IT long enough to watch us chase a different silver bullet every few years. At one point, everything had to move to the cloud. Before that, companies rushed to put up websites simply because having a website was supposed to matter, even if it served no real purpose. Today, it’s AI. AI is an incredible tool, but like every technology before it, it isn’t the answer to every problem. The real skill isn’t adopting the newest technology. It’s understanding where it adds value, where it doesn’t, and having the judgment to know the difference. That judgment usually comes from experience, and experience usually includes a few mistakes along the way.

That’s why I believe we need to share our failures as willingly as we share our successes.

Success inspires people.

Failure teaches people.

If all we ever talk about are the moments when everything worked perfectly, we leave everyone else believing they are the only ones struggling, doubting themselves, or learning through mistakes. Some of the most valuable lessons I’ve ever received came from conversations about what went wrong, not what went right.

Looking back now, I understand the title Unlearning What Worked a little better than I did when I wrote it. The habits that once protected me eventually became the habits that held me back. Unlearning them didn’t eliminate my fear of failure, but it helped me realize that fear didn’t have to make my decisions for me.

Sometimes the greatest risk isn’t failing.

Sometimes it’s convincing yourself not to try.

As always, thank you for being part of this journey. If you’d like to read Unlearning What Worked, subscribers can use the link below to receive a 10% discount through the West-James Press store. If you prefer another retailer or reading platform, it’s also available through several major booksellers.

​Buy a copy of Unlearning What Worked​

​

​​​​​