Someone says to me once in a blue moon "I wish I could do that" re: my hair and the big secret is: you can! And it's fairly easy! Even upkeep! If your hair is medium brown or lighter you don't even need to lift it if your goal is a deep, saturated cool color like forest green. I spend maybe $60 2-3 times a year on supplies and an afternoon or two a month on upkeep. Note I am also a very infrequent shampooer and don't get too fussy about roots, which again if your hair is in the brown-dark blonde area of the spectrum and you're not lifting your hair first will blend in fairly subtly.
But more on the "taking the leap" side of "I wish I could do that" re: bold choices with your appearance: after like, a week you get used to yourself and forget that you're doing anything "weird" until a stranger either a. compliments you or b. gives you the stink-eye in a rural Texas grocery store. Which, btw, the ratio of A:B is about 30:1 if not higher.
Same thing with the undercut, tho that was a very gradual transition that started with a pixie cut. I just kept getting the top longer and the sides shorter at every haircut for a year or two until I fully committed sometime around 2016.
