I guess every time I draw myself, I feel different! That’s what it really comes down to. It also depends on what I’m drawing me for- if it’s for a comic, I’d rather go silly or simple, or if it’s for a display picture I try and go a more caricature-like route, and those often display how I’m feeling.
A lot of it also comes down to my improvement of skill. I don’t feel like I could draw myself just one way when I keep learning better ways to draw things. I feel the better I get at drawing, the more my pictures look like me.
Sorry if it’s a weird answer, but it just comes down to feelings I guess!