Jay Shirley

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The Daily Practice

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You aren't the hottest girl in the bar.

Published: 19 Jul 2011

Confidence is an interested thing. I’m a man so it’s hard for me to identify with the emotions and thoughts of a cute girl in a bar. I imagine that there really is not a large amount of confidence. I say this because if the girl was so pretty why couldn’t she find Prince Charming already? Where was his white horse? Why is she still here.

Then there are the men. Certain types of men, I mean. The near-criminally confident men who can walk in and secure their position and the get the attention of the most beautiful of girls. They have a different sort of confidence. A confidence very few people have.

Then you have the normal, average fellows. Who sit around and wish for nothing more than the courage to stand up, walk over and introduce themselves.

That was all a metaphor, just to clear that up.

I write about (the software) business. Here is how buying drinks at a bar relates to my world of entrepreneurial floundering.

The pretty girl is the enviable position. You get to relax, elbows up on the bar and simply wait. Good things come to those who wait. There is the time spent prepping yourself. After that it’s clear sailing. Study hard and become desirable to suitors.

The confident guy who everybody really hates are the Zuckerbergs of the world. These guys have done it. They’re usually brilliant and honestly I don’t think care that they’re brilliant. They care about success, but not about succeeding. They care about accomplishing things. They don’t care about failure because it’s not success. They only care about success. Mark Cuban is a good example of this. Why do they not fail? I think because they can pick up on subtle traces of failure and lose interest. Of course, they have to have all the traits someone needs to succeed.

The third is the category nobody really wants to be in. The average guys. They have to spend all the time preparing and getting ready, just like the girl. They don’t feel comfortable, though. They have to then evaluate the scene, decide on a course of action and how to execute. Then they are committed and simply hope they prepared enough. Not having confidence means they don’t act. Or when they do they don’t act with enough confidence. Tunnel vision consumes them and they steadfastedly refuse to back down, after all, it took too much effort to start.

This last category is the type of person most people fall into being (myself included). Networking may land good, ground level startup positions. From an entrepreneurial perspective, that’s different. That means believing in another’s dream, following their direction. The technical cofounder bought by an MBA to make something a reality, where the technical guy just wants to get paid. Then probably start their own thing.

Don’t be the pretty girl. Be the guy buying the drink. That’s the one with the vision. In control and ready to do great things. It takes guts, confidence and a lot of other things I know I don’t fully believe I have. I won’t know until I try. The advice is the same thing people tell you when you are lacking courage to chat up the girl. She says no, big deal.

Just figure out she’s going to say no before she says it. Fail early. Move on to the next one.