When Does Confidence Become Cockiness?

Photo by Kevin Quezada on Unsplash

Today, I wanted to share an embarrassing story. People like embarrassing stories, and I like to think the embarrassment is behind me, so here goes.

In spite of dealing with impostor syndrome at various times throughout my career, I’ve always had a lot of confidence in one skill: My writing.

Sometimes, more confidence than was deserved. And that extra, unearned confidence is the confidence that has gotten me in trouble.

So here’s the story

Back in high school, I had an amazing English teacher. She was tough. Her red pen was famous. After hours of slaving away on the longest paper of the term, she handed it back with entire paragraphs crossed out.

Needless to say, by the time I reached college, I felt like I had learned sometime. I majored in English myself.

Now, college was good to me. I won a few writing awards in my department. By some stroke of luck, I was hired as an intern at an advertising agency. As one of the few writers in a company of more technical marketers, I was given a lot of blog articles to write. And I won’t lie—I started to think I was hot sh*t.

So much in fact, that I started to believe that I really didn’t have much left to learn. Sure, maybe I wasn’t super versed in other forms of writing, but I had this blog stuff DOWN.

Maybe you can see where this is going.

It was a classic case of big fish in a little pond.

See, after graduation, I hoped to turn my internship into a full time position. By now, the company had grown to have a full content team (i.e. a much bigger pond). I walked into the interview full of confidence, ready to use my abilities to help their team.

…And I didn’t get the job.

Why? Because apparently my writing wasn’t up to par.

Maybe my writing would have been passable if I had shown that I was eager to learn. But boy, it’s really hard to look like you’re eager to learn when you think there’s not much else to learn.

My ego was bruised. I wish I could say I learned my lesson then, but in truth it only made me indignant. In my head, it wasn’t that my writing was subpar—they just didn’t give me a good enough chance!


I took an admin position at the same company and licked my wounds. A few months later, my opportunity arose again when a member of the content team left and they needed to fill the position quickly. I was hired as the best option given the circumstances.

Hoo boy, I was smug. I never showed it, but I was terribly smug. They finally realized they needed me!

I completed my first few writing assignments and sent them to my boss, the editor. I waited for his response.

He finally emailed the document back with his revisions. Just like in high school, the page was red.

You’ll always be a student

Know this: No matter how high you climb, there will be others who do it better, who have a broader perspective. There will be more you can learn.

It’s important to have confidence in your abilities. It’s important to believe that you can do things when you put your mind to them. But it’s equally important to acknowledge that even if you can turn out a great result, you have plenty of room to grow.

Why this matters

Throughout my career, I’ve played with the delicate balance of believing in oneself and outright “fake it ‘til you make it.” Sometimes, faking confidence you don’t have can push you to do scary things that need doing. But often, it also comes with two side effects:

  1. You discourage people from helping you—even when you might really need it.

The first one clearly happened to me. The second one is even harder to swallow. I wonder how much valuable instruction I’ve missed out on because I was trying so hard to show that I had everything under control.

Being vulnerable with where you’re really at is inspiring. Everyone wants to help the person who says, “I’m not totally sure I know how to do this, but I’ll try my hardest.”

The bottom line? Have confidence in what you can do. But don’t let it blind you to how much you still get to learn.

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