Any person who has ever endeavored has met with skepticism or even derision. Self doubt is the first impediment, before you can even begin to enjoy the hubris of others.
You either spine up or you don't. If it takes two, or ten, or a hundred, nothing changes except when the act of will comes into being. It doesn't just apply to street photography, but to everything.
For me, it's every morning when my feet hit the floor. I decided that. It just didn't happen. YMMV.
(BTW, I dig the dollar portraits)