This is a well-written essay even if it's a bit long and somewhat navel-gazing (it is, after all, written for pg himself). However, I was continuously struck by just how ridiculously privileged and serendipitous pg's early life was to the point where I just can't even relate to it. He basically meandered his way from an expensive (today) college to an even more expensive (today) grad school, then to art school becaus…
If there's privilege here (and if we're using that word in something other than a Twitter putdown sense), it seems to me more more intellectual than financial. pg has clearly always been single-minded about doing what he wanted to do / was interested in, and stubborn as hell about not doing what he didn't want to do. That mindset may be part nature and part nurture, but at least his upbringing didn't damage it, as many other people's would have.
To me the key detail is not that pg nagged his father into buying a TRS-80, not that he learned to program with it, but that his father used one of pg's own programs to write an entire book. That's a hell of a success for a kid, and it says something significant about their relationship. Many of us had a similar path to the first two of those steps, but that third step branches somewhere different—perhaps life-changingly different.
Edit: btw, on the matter of luck, I always remember https://news.ycombinator.com/item?id=1621768.