Need help! Feeling defeated...

This is my second child, but first real attempt at breastfeeding.  With my first I pumped and formula/breast milk fed.  He will be 2 weeks on Wednesday and I've pumped a handful of times.  Do I need to pump on a daily basis or only as I feel full?  He's gotten to the point where I can only feed on one side during a feeding because he falls asleep.  Then I start on the other side the next.  Is that ok?  What kind of pumping schedule do I need to be on once returning to work?  When do I start pumping/preparing for that? Any help is greatly appreciated!!!!