Okay, so, as long as you successfully Regain Passion (i.e., become Inspired or Focused instead of Tense), it seems that you do fulfill the Want and overcome the fear, even if you don't go to work with the positive moodlet. It's still a pain when it fails, and you do still have to wait to try again if you don't have the Carefree trait, but it seems that you can do it at any time that fear is there, even if it's not right before work, and your Sim will still have overcome their fear. Of course, it'll always come up again, sometimes as soon as a few days later, but with the knowledge that you don't have to do it *right* before work, it's a little more manageable.
