I don't think any other kind of situation pops up more in a programmers day to day work than a Tradeoff. Tradeoffs are everywhere and being able to identify and access tradeoffs I think is one thing that makes a great developer.

I don't listen to podcasts regularly - only when I see one that looks interesting, or someone points me to one. My brother Steve pointed me this IT Conversations podcast with Jason Fried of 37 Signals, on Lessons learned while building basecamp.