I'm biased here since I know Ray, but I thought this post was super informative & helpful! I love how short & sweet it is yet so chock full of meaningful points. Thanks Ray!
Here's an interesting notion -- that a lot of wisdom is simply bound up in the integral over time of personal life experience.
Thus, the value of wisdom is individual, and non-transferrable -- it can neither be carried "backwards over time", nor handed over to another human via a "brain dump".
The best one can hope for, is to distill personal lessons from our own experience (compute that integral), and invite others to sample it (no guarantees that it'll stick in any way, but their journey might be similar, allowing them to compute their own integrals faster, by seeing our own).