Do I fight management to get the two weeks I'll need to write feature X correctly, or just take the obvious shortcuts to get it done in 1 week?
Of course my laziness shows through because I haven't been in management's ear for long enough beforehand that they decided to give me one week without consulting with me ;)
I display this "lack of bottom-up management" failure mode consistently, I'm more interested in writing code :\
As for my OOD teachers, I've had mountains of bad Perl and PHP code to wade through, and the benefit of Stack Overflow and the Django Project to guide my thinking on the matter.
Type systems do provide some compiler-level assistance in the march towards coherent, well designed software, but they won't solve problems like
def position_sprite( top_left: point, sprite: sprite)
When you provide the top_left of the wrong element (e.g.: confusing the top left of the drawing space with the top left of the window or display area.