Why Are We Always The Ugly Girl At The Dance?

Information Security, as many of you may or may not know, is a tough job.  Why is it so tough you ask?  Because people don't realize the importance of a sound security program until something happens.  In addition they are so busy keeping the lights on and dealing with IT / storage issues they don't *make* the time and budget for security.  Much like how I don't *make* the time to eat healthy, work out, etc.

This results in a situation where security initiatives end up being the Ugly Girl At The Dance.  As The Ugly Girl At The Dance- you really want the business to dance with you; you hope they will spend money on you; you have done *everything* to look pretty for them and give them the best you can; you *know* for a fact that if they do give you just a little bit more they will be so happy in the end; but the reality is you are afraid to ask for the money, and when you do you feel uncomfortable with the amount of attention you are requesting.

When you do ask for the money you are worried you are expecting too much.  What if he doesn't like me enough?  What if I ask for too much?  You are worried that perhaps they would rather spend money on the prettier girl, the one that provides you with storage WHICH THEY NEED MUCH MORE THAN YOU.

So, how did we become the Ugly Girl At the Dance, and how do we avoid this?  More confidence?  More FUD?  Less FUD?  More Nike-Just Do It???