I confess. In college, I was a bit cocky. Just a bit. I wore a hat every day that read Italian Stallion with big, bold letters and a dashing black horse galloping on the back. Need I say more?

As I left college, I did so, cocky. Diploma in one hand and vine-ripened ego in the other.

How could I not?

Good grades, good athlete, good smile — the acne I was so “blessed” with in high school, a faint memory and photograph ripped up years ago. I left college completely assured I was going to be the pinnacle of success. Make money. Make a difference. Make people jealous, that sort of thing.

God had huge plans for me, this I know. For my cockiness told me so.

So you can imagine the sharp jagged point those first few years of cubicles, call-centers, and quarter-life crisis was on my inflated self-esteem. The big life I was so sure about, quickly turning into a fable worthy of Aesop.

The Cocky Generation

Picture of the Cocky Generation

The GenY/Millennial generation is often knocked for being the self-assured, cocky generation.

And honestly we are.

Or were.

I’m beginning to see that the cockiness GenY has been knocked for, has been knocked right out of  us — The Great Recession hitting us like a 4th grader crushing a pinata without a blindfold. Our hopes and dreams spilling all over the sidewalk. At least it did me.

We wanted it our way, but our way became no way in hell. Which might’ve been the best way after all.

Cocky’s Evil Twin Brother

We often confuse confidence and cockiness as the same thing. But really cockiness and true confidence are opposites. Cockiness is insecurity masquerading as confidence.

Really I wasn’t cocky as I left college. I was insecure.

I entered the real world like a boy afraid to change in the locker room, scared out of my mind that people were going to really see me. The me without the grades, girls, or game-winning hits that I’d been using as fig leaves my whole life. So during those first tough years out of school when all those fig leaves find a way of going up in flames, I began hiding to keep others from seeing my shame.

All the cocky was being amputated.

Becoming Un-Cocky

Having the cocky kicked out of us might’ve been the best thing to happen. When all the cocky-crutches we use to get by on are removed, it finally makes us walk on our own two feet. Ask the hard questions. Figure out what we’re really passionate about.

So yes, I think having the cockiness ripped out of us like the insides of a Thanksgiving turkey might’ve been ideal. Because it left us all with a side of something that we desperately needed.


A vital bridge from cocky to confident. And if GenY and Millennials are truly going to step up as successful leaders —  confidence, not cockiness, is key.

Do you wish to rise? Begin by descending. You plan a tower that will pierce the clouds? Lay first the foundation of humility ~ Saint Augustine


Photo Credit: Armadillo via Creative Commons



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Like advice from a wiser, funnier, older brother Paul's been there, done that, and wants to save you some pain and some trouble.

– Seth Godin, New York Times bestseller and author of The Icarus Deception