John Hodgman has done something quite nice in his new book Vacationland: True Stories from Painful Beaches: he's infused memoir and humor together to create an affecting piece of writing that centers on the idea that all anyone is trying to do is their best.
He doesn't say this explicitly in the book, but it comes through in numerous scenes. He spends an afternoon with a friend, stoned, at a river in western Massachusetts (a lovely area) building rock stacks. He discusses his mother's death in a way that is touching and vulnerable as well as authentic and flavored by the notion that his mother, like he, did her best to be a good parent.
There is also his humble ownership of his life as a minor celebrity and the wealth and ease of life it's brought him--not to mention his father sold him a house in the Berkshires for a dollar. He does not claim to have been masterful and strategic. He only claims to have worked at his craft--writing and being funny--and being lucky to have been called by Jon Stewart to appear on The Daily Show, which gave his career a huge assist. And then the Apple commercials didn't hurt his bottom line. In all, he just says he did his best and with some luck (which is the intersection of preparedness and opportunity) he's built a nice life.
It is hard not to at least be a little envious of his life. Aspiring and striving writers (I place myself among the striving) will see a path that could open to them and hopefully someday will. With this may come a little why him and not me. Few of us can buy a house for a dollar.
But he does have talent--Vacationland proves that--and he does have humility.
He only claims to be doing his best, which is what we all are doing.
So, please read his book and enjoy it as I'm sure you will.