I've decided I want to finally dye my hair a fun color, but I'M SCARED!!!!!!

My hair is naturally medium brown and I've only ever dyed it with semi-perment dye to super dark brown or this color:

And yes, it was 100% because I wanted to be Angela Chase (although mine was more a natural red like this picture than what I imagine "Crimson Glow" would look like).

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At first I was thinking about dying the underside, but I think that might be too big a leap, so now I think I'll start with just a streak. I also can't decide what color. I'm leaning towards turquoise or purple.

I also have no idea what I'm doing. Any tips? Dye recommendations? Vote for a color?