This part of the first comment got an audible guffaw out of me:
I think that there's been a failure to inhabit the least convenient possible world°, and the general distribution over possible outcomes, and correspondingly attempt to move to the pareto-frontier of outcomes assuming that distribution.
Unintentional self-parody of the highest order.
I wonder if he's ever applied this advice to himself. Because one could argue that trauma was a significant factor in his obsession with transhumanism and the singularity.
When Yud's younger brother died tragically at age 19, it clearly traumatized him. In this case, X was "the death of my little brother". From this he learned Y: to be angry and fearful of death ("You do not make peace with Death!"). His fascination with the singularity can be seen in this light as a wish to cheat death, while his more recent AI doomerism is the singularity's fatalistic counterpart: an eschatological distortion and acceleration of the reality that death comes for us all.