To Hell with self-esteem. My mother regularly pulled apart our writing for school and got very angry if we turned it in without letting her see it. I have much better self-esteem because of it because I'm a pretty solid writer. Of course, I come from a family of voracious readers and I spelling has always been easy for me, so I had a leg up on a lot of my classmates.
When I was a sophomore in high school, I had a reputation for being somebody who read "big books"; _Crime and Punishment_, _the Mill on the Floss_, etc. One day, I came to class with _Adam Bede_ and, when my teacher saw it, she said, "Oh, I thought you'd be ready to read something entertaining for once." _Crime and Punishment_ isn't entertaining?!
For the record, whether you physically write it or type it, don't you still have to be able to spell it to make yourself understood?