Yes, this sounds like a mess. No, it has nothing to do with your worth as a person.

I suggest you contact one of the free credit counselors in your area. It's tough to realize that you are in business for yourself and yet failed to factor in taxes everyone must pay. I think you need someone to show you where to cut costs. You must file the paperwork each year, or quarterly as you mentioned, even if you do not have the money to pay. You incur an additional penalty for not filing the paperwork alone.

Each person makes their own choices, but for instance, I don't have cable tv and I haven't gone to DSL because that would cost me $75 a month more. I eliminated my long distance service on my home phone and reduced my bill by $30 a month. There are more ways to save... a credit counselor can not only help you with that, but also with how to pay all your bills including the taxes. Also, it will help you fare better with the IRS if they see you are now attending to your financial problems, rather than dismissing their concerns. TC!