Class of '87 here.
Most valuable takeaway is that you can read almost _anything_ directly or in translation. You don't need to read a summary of Hegel, you can read Hegel. You don't need to read an article about a Supreme Court case like Marbury v. Madison, you can read the case itself.
When you go into technology, you're then willing to dive into the guts of the actual docs instead of waiting for a book or blog post about it.
Another way it prepares you for tech-- understanding philosophy is the skill of drawing incredibly fine distinctions between things. Designing software is also the skill of drawing incredibly fine distinctions between things. Having years of experience in arguing these incredibly fine distinctions was a huge leg up fr me when I was getting started, and remains useful to this day.
I think that the careers of my graduating class are primarily in software, law, academia, and medicine.
Funny things about it - there are a lot of places where your undergrad experience just doesn't overlap with that of people who didn't go there. Everyone studies the same thing at SJC, so if I meet a Johnny who went there years after me or years before, I can tell them what I did for my senior thesis and they'll have a similar reaction - why the hell did you do that?
It's also _extremely_ small, so if they went there during the same years I did, I almost certainly know them.
The original-works thing works gangbusters on philosophy, science, and literature, and breaks down a little in math. You spend a frustrating amount of time doing Ptolemaic astronomy, because it's an excellent classical treatment of trigonometry. You study Newton for calculus, but you don't actually learn anything that the modern world thinks of as calculus from Newton, so you study supplemental materials that teach you derivatives and integrals over algebraic expressions.
It's culturally pretty liberal on the inside, although it's bizarrely worshipped by some right-wingers who didn't go there because of the curriculum's focus on works from the European tradition.