At what point do you stop asking for permission?

I have always been brought up to say my "please" and "thank you's". Another big life lesson my parents bestowed on me was to always ask for what I want vs. assuming I'm going to get it. Case in point:
Me at 16 - "Mom I'm going to take the car to Rachel's house."
Mom - "You mean, CAN I please take the car to Rachel's house?"

Asking for permission has become a common practice of mine. I don't consider it a bad thing, but the fact I still carry that habit around for years has almost succumbed me to using it when not necessary. Is it because I consider it common courtesy...or because it's just habitual?

Someone got me thinking about this the other day. I was talking about a vacation I am planning on taking and I was trying to figure out what days I wanted to ask off. When I approached my boss asking if I could take a vacation day on X day, he smirked and said, "You don't need to ask for permission, you can do what you want with those days!" After thinking about it, it was quite silly, they are my vacation days, that I earned. I shouldn't feel a need to ask to use them. But, I still feel that need to just ask. To me it always felt like I was being respectful, but now after looking at who I am now and all I have accomplished in my life, I feel like I don't always need to be doing that. Does the fact that I ask for permission on most things make me look weak, or even worse...unsure of myself?

I experimented with this yesterday by telling one of my consulting clients that I am going to go into some of her sites and do some work - no permission asked. I was straight forward and told her I was going to do it. The response, "Great - thanks! Do what you need to do!" This was a great feeling. I felt trusted, worthy and still respected. It made me value the relationship I have with my client even more.

I still don't know if there will ever be a point for me where I'm comfortable just doing what I want without someone giving me a thumbs up or an approval. I guess I'll just take the opportunities when I can.

At what point do you stop asking for permission? Does a point exist even if you are wealthy, powerful, understood and respected?