Answer: You cannot measure what one person experiences and then use the measurements to measure another person who has never had those experiences, learned in different ways, and run their lives and learned their lessons in harder or easier ways. For instance:
Bobby has lived his life as the owner of a body shop(if you don't know, this is a place where people work on cars) Bobby dropped out of school at 15 to help his dad with said shop, and has been living a happy life, now 56 with two kids in high school and a lovely wife.
Now you have Craig, who from kindergarden up was a straight A student and now holds a gavel as one of the best judges in the United States. He went to Harvard, where he met his first girlfriend who dumped him two minutes before he walked on stage to graduate from Harvard. Craig now also 56 lives a happy life with no kids and a new girlfriend who he sees every Saturday.
Both men are successful and happy, but they got to where they are in very different ways. No you cannot measure that.