Not with NaNoWriMo. The secret here is in the volume of words. 50,000 in one month. Rewrites come later, otherwise we'll never make the finish line.
Here's a thought Rosie: Give him a life changing event. Kill off someone he loves, give him a disease or disability to work through. Make the experience change his attitude.
Don't be afraid to let the book follow a different path than what is in your outline.
I like that, Corin. My painting teacher tells me exactly the same thing about my paintings.