Going Dark

I have been a blonde for over a (couple) decade(s) now.   My real hair is something like this I think, well at least that was what I was born with:

SO not cute...  I think I took my fashion cues from Sophia on the Golden Girls: I had to go way back to find a photo before I started messing with my color  (I discovered peroxide in 6th grade).
Honestly I am scared shitless to go brown,  but it is exhausting maintaining the blonde. Especially since I went platinum a few months ago. (current day, roots are wallet killer$)
Both my sisters rock their brown, why can't I?
So I think I am ready to take the leap and fade out.
This is what got me started down this road: I pinned the coat first, but then was all "I kinda like the hair- I can do that I think" and of course then I was all delusional like "I can grow it and ombre it an look just like Jessica"
 "or maybe ombre what I have now to transition myself"...
 and then I went back to growing it to look like her ...
F U Pinterest for screwing with my head.
Anyhow.  Hair is kind of like paint in my book.  I can't be scared to change it,  it grows (slowly) and I can always color it if I don't like.
How about you guys, anyone doing anything drastic lately to their head?