I think you would have done better to have linked directly to your blog, rather than making this a self post. If you really feel that a tl;dr is necessary, that's what a comment is for.

Anyway, here's my own brief response to both PG and your response:

1) "Nerd" and "Jock" are stereotypes. Given a large enough sample size, of course there will be popular nerds and intelligent jocks, and every shade of gray in between.

2) What about a "jock" who deviates from the accepted wisdom and take chances? For every high school football star who goes on to become an NFL star as an adult, I'm sure there will be a dozen has-been football stars who end up giving up football and find a boring job. I'd argue that there's not much difference between nerds and jocks when it comes to the probability of success.

3) In my interpretation, PG's central insight is not that the real world places a higher value on intelligence than American schools do. The central idea of the essay, which PG repeats several times throughout the piece, is that school is a prison. When you graduate from that prison, you are finally free to find like-minded nerds and do interesting things together with them. Of course, as you said, the whole world might be just another prison that demands compliance with the status quo. But since this prison is several orders of magnitude larger than a typical high school, there are many more opportunities to do interesting things inside of it.

First of all, thank you for your comment. I didn't realize that linking directly to the blog post and adding the tl;dr as a comment would have been a better format. I'll remember that for the future. I do believe the tl;dr is necessary because I didn't want anyone to feel they'd wasted their time reading my entire post without having a preview.

1) You're very right. PG has likely seen more diversity than I have. However, I think his bias, when discussing the real world environment in the essay, leans toward culture that values the properties most nerds have. My bias probably leans the opposite way. So neither of us even considered a large enough environment sample as we generalized "Nerds" and "Jocks." Or perhaps PG did consider it, and that is why he alluded to the sense of greater freedom in real life.

2) This is an important idea in the essence of my post (perhaps inaccurately conveyed). Even though I considered myself a nerd, my status in high school was primarily "Jock." After high school, I was primarily a "Nerd." For me, deviating from the standard path to popularity was so much easier as a jock in high school, than as a nerd in real life. As for success after high school, I do believe nerds have a better probability overall, but anyone who disobeys the status quo in real life should expect plenty of headwinds.

3) I agree with you. My experience within a small sample of what the world offers in its entirety likely constricts my perception of the relative freedom between secondary school and real life. I only know what it's like struggling in the real world in a small farm town in MT, in a medium college-town with a population of a few hundred thousand, in Los Angeles, and in a large city in Brazil. I know what it's like to be financially successful only in that medium-sized town and in Brazil. I do believe that the lower you find yourself on the hierarchical ladder, the more imprisoned you will feel in both high school and real life.

Thank you for your insight and for both taking the time to read my blog and respond to it.

Here's my response: nerds focus on long-term optimization whereas jocks focus on premature optimization (in computer science speak, think "Big O" values for 10,000n vs 2^n).

As a result, nerds are seen as low value at the present and subconsciously remind jocks that their maximum values are relatively low in the long term.