Fear of failure is a big problem in my life right now. Its why I don't have a job, since I'm silly and am afraid of being rejected. This reframed something I think I already knew, but I'm sure it will help anyway. Time to really get on to things now.
Job-hunting fits very well with the model in "Don't Fear Failure": the downside risk is zero. The worst case is accepting a bad job. Assuming you're a USian, jobs are at-will, so just leave then, and you're no worse off.
As a job-hunter, I've learned to model the probability of getting any one job as infinitesimal, so I don't get too hung up on any one application. Let them do the rejecting.
Followup to: Don't Fear Failure
In the same theme as the last article, I think that failure is actually pretty important in learning. Rationality needs data, and trying is a good source of it.
When you're trying to do something new, you probably won't be able to do it right the first time. Even if you obsess over it. Jeff Atwood is a programmer who says Quantity Always Trumps Quality
The people who tried more did better, even though they failed more too. Of course you shouldn't try to fail, but you shouldn't let the fear of it stop you from tyring.
I wouldn't go as far as to say that quantity always trumps quality, but where the cost of failure is low lots of failures that you pay attention to is a pretty good way of learning. You should hold off on proposing solutions, but you also need to get around to actually trying the proposed solution.
I'm normed such that I'll spend more time talking about if something will work than trying it out to see if it works. The problem is that if you don't know about something already, your thoughts about what will work aren't going to be particularly accurate. Trying something will very conclusively demonstrate if something works or not.
Note:
I originally had this as part of Don't Fear Failure, but that post got too long.