Doodles and Finished Pieces

[Garamonde]

Hey um I need some like, drawing advice...

Not for a specific thing, but just for general purposes.

When I go to draw something I think to myself that I will just "do it" whether it's crappy or not, but... then when I actually try to "do it" I come back to the same exact problem time after time again: I don't know to go about it or execute it.

ATM I'm trying to learn to use the brush as opposed to the Pen Tool. At first I thought I would try like blocking out shapes and then shaping them later like you do in pixel art, but then I come to the problem of certain parts, like those that overlap, are not defined this way. It's all just a giant depthless blob/block. In an attempt to fix this I draw a black line to define overlapping shapes but as you might expect that looks awful and I can't stand to look at it so I delete it.

I then try to outline it in black as a sketch type thing but that just does not look nice and I was trying to avoid outlines (especially black) for now.

So basically what I'm asking is, how do you guys start your drawings? How do you go about it? I'm just at a loss of how to even do this stuff. This is why I need to start learning and gaining experience...