I think many of us just want to skip the slower progression of heeling progress and jump right into 4-5" stilettos! I surely did, and suffered all the usual pains and emotional set backs. Right now, I spend alot of time in my 3" block heeled ankle boots, which I feel keeps my muscles somewhat stretched in the right fashion....So, when I am lucky enough to be able to wear my stiletto boots, there is little or no pain/discomfort/lack of skill.
I hear ya for sure, wearing my boots is a bit of a "double edge sword". I don't want to be to "over the top" drawing too much attention (perhaps negative attention). But, at the same time, I really do want others to notice, and approve. Sure, one of the benefits of my advanced age is not caring about what others think, to some degree. But, there is still a part of me that wants other to approve, perhaps be a bit envious..