The frustrating fact in technology is that your career is pretty much a lottery. I know people I went to undergrad with who lucked into the right company and are now independently wealthy. Most of the rest of us are still slogging away, having worked for a string of non-rocketships. Nobody at that time (late 90s) knew which company would mean early retirement, and which ones would go bust. It was a total crap shoot.
Try browsing the "Who's hiring" threads here. If you're looking to join a start-up, 99% of them are companies you've never heard of. One of them will be the next Facebook, and if you go work for it, you'll end up set for life--but there's no way to know and chances are you're going to pick one of the many who will go bust or just sputter around without making money for a few years.
Its more about autonomy: after the basics are taken care of, how do I avoid depressing things caused by other people affecting me?
In my opinion all the article is about how he is NOT a "sore lottery loser".
IMHO he is trying to explain how being just a programmer, didn't let him change (in better) the faith of the companies he used to work for.
Also, I know programmers making 50k, more than those making over 100k, but I live in the midwest.
Cant save much, but I can take care of my family and that is what is important to me.