I typically am not a mean person. It's in my genes to be a people pleaser. I blame my mother (or I should probably thank her).
Don't get me wrong, I've had my moments of being kind of ... (cough, cough), but I usually feel guilty about it and apologize afterwards.
I've been working on my current WIP and I got to 15K and realized something. I'm not being mean enough. I'm not throwing enough obstacles at my main character. I've made her life too easy.
So instead of doing a full NaNo, I'm going to do a half, because I'm going to start again and throw as many darts at my character as I can. They might not all stick, but I need to continually make her life harder, at least until the end.
How about you? Do you have a hard time putting your character is bad or awkward situations?