You know, I work in tech but I have never attempted to have a Career in Tech. I definitely don't own a whiteboard and I'm sure I'd never get past the resume stage. (I've only actively applied for a couple of jobs in my life and all in the past year, purely because I thought I should REALLY get some experience with applying for jobs. I actually just had an interview and bombed it so much, omg, at one point I claimed not to know JavaScript! :D I don't think it's for me.)
But out of the rareified circles of HN, I've not found any of the career stuff talked up on here to be necessary anyway. There's more code that needs writing than coders to write it and so long as that's true there'll be work going. I work a few days a week for a company and the rest for myself. I have fun and write code and invent things and people generally give me enough money to pay my bills so I'm happy with that. It's a pretty sweet deal! Before I was a coder I was an unpaid family caregiver (hence no school or credentials or career) so compared to that I can't really imagine a programming job that could really genuinely be BAD. They are all simply gradations of sweet.
My brother (who did massively go to school) works at Google and loves it. I drop in and hang out with him there sometimes and it does seem great for a certain kind of person. And they have so many resources and work on loads of fun games and obviously it would be great to be rich as well. I think it's really clear why it's so attractive. If you think you have a shot then go for it!
But if you know you don't have a shot, why break your heart over it, is my view. It's not a bad thing to be clear eyed about your prospects in life.
I wonder whether their approach has been alienating entire large categories of people, and what diversity of ideas and influences they're missing as a result.