Kaj Sotala said:
[I]f you punish yourself for trying and failing, you stop wanting to try in the first place, as it becomes associated with the negative emotions. Also, accepting and being okay with the occasional failure makes you treat it as a genuine choice where you have agency, not something that you're forced to do against your will.
So maybe we should celebrate failed attempts more often ... I for one can't think of anything I've failed at recently, which is probably a sign that I'm not trying enough new things.
So, what specific things have you failed at recently?
I did not achieve a certain milestone at work that I had planned to reach by the end of the week. This means I have failed at estimating how much time I needed to reach it. This is bad because it happens fairly often, and the converse (finishing sooner than expected) happens rarely. Despite everything I know about fallacies and biases with predicting schedules, I keep predicting less work than is really required.
My work is programming. It is notoriously hard to quantify (or the managers could make predictions themselves without asking me). If I can't modify the intuitions I feel, I may have to try just multiplying my feelings by a factor - e.g. adding 100% time to each estimate.
You could measure your estimated time and real time, and calculate the factor from that data. Of course this works best if your bias is consistent, but the data would tell you how consistent it is.