Each Monday I send a letter (yes a handwritten letter) to Jenna at Miami (Oxford, Ohio). Included is a Monday Miami Memory (now on #15) typewritten that describes my decisions 38 years ago as a freshman at Miami. Some were good - some were bad and some took 38 years to determine the outcome - some still remain unresolved.
Wisdom is really just the time to look back and see the outcome of past decisions. Can that wisdom be passed on to another generation? The optimist in me - says "yes". The practical me says - "very little". What might have been a good decision 38 years ago is a function of too many variables - the environment of the time, the practices of the time, the pressures of the time ...... the list is endless.
I've always said in business that any decision can be made successful with enough time and money. The relative correctness of the business decision then becomes a measure of the efficiency of time and money. Life decisions are similar (viewed through the lens of time and money) but not quantifiable.
And - my decision today may not have 38 years of incubation left. Not enough time available to make course corrections. So now it's time to get the decisions correct - maybe that is Wisdom.