The thing is that working as a hacker (white hat) has made me actually less worried about my bad security habits.
It's like real life. If your sane in your habits and stay alert not much is likely to happen.
It's like insurance. You only insure as much as you feel is at potential risk; once the cost of insurance outweighs the risk you (should) stop paying.
Same with your passwords; the risk of losing them is fairly minimal. If someone wants to get them really bad they will do, not a lot you can ultimately do to stop them. Reasonable vigilance should be enough to keep you secure.
(and by that I mean having enough sense that when XYZ site's password database is compromised you change things etc.)