"User-friendly" accounting software (such as QuickBooks) tends to obscure the fundamental simplicity of double-entry accounting.

If you want to actually understand your books, use something simple and powerful like John Wiegley's ledger:

https://github.com/jwiegley/ledger/

Wow, that's a slanted view of the world!

Outside of the software industry, which is a tiny (~1%) portion of the economy, what has changed since 1995? Suppose you're an investment banker, and you hate your boss, as most investment bankers do. Want to start your own investment bank? How? You need to have connections to upper management at lots and lots of companies, so you can arrange deals. And very few people have that.

Or, suppose you're an accountant. Can you start your own accounting practice? Sure, maybe, it's not a crazy idea. But is it really any different than it was 15 years ago? You still need to get a reputation, build up a client list, market yourself well, etc. Not much has really changed.

Or, even, suppose that you're in another, non-software tech industry, like pharmaceuticals. That's way harder than it was 15 years ago, because of tighter FDA regulation. Just try getting a drug to market with less than $100,000,000 in capital, and very few people can raise that kind of capital.

"I believe my generation will overthrow the arbitrary and brutal authority of corporate capitalism and bigoted conservatism in favor of rationalistic, libertarian socialism driven by a scientific approach and a concern for universal social justice."

That's what my generation believed. And my parents' generation. And their parents....read some literature from 100 years ago, for example by the Fabians or other socialist writers. This little blasted thing called human nature always seems to screw things up....

Regarding the main point of the OP, I have a counterexample. I have a friend whose career has never taken off, who usually gets fired after a few months, and has never acquired any useful skills beyond blustering self-confidence. Why ? His father is a multi-millionaire who has arranged every job he's had, and bailed him out of every financial difficulty. He's never had to work a day in his life and has absolutely no ambition or drive.

That's not saying all rich kids suffer from what you might call the George W. Bush syndrome - but taking away the need to make money can also make people over-confident and lazy.