“It is not enough to "have" free speech. People must learn to speak freely. Noam Chomsky remarked in the sixties about the short-life ultra-radicals on campus who thought that Marx should have been burning down the British Museum rather than writing and thinking in it. The less political descendants of that faction have now tried to reduce life to a system of empowerment etiquette, and have wasted a lot of their own time and everyone else's in the process. But the real bridle on our tongues is imposed by the everyday lying and jargon, sanctioned and promulgated at the highest levels of media and politics, and not by the awkward handful who imagine themselves revolutionaries.”

On his university experience, in a discussion thread https://www.lesswrong.com/posts/MzfrRhB4Q7YgCW3f6/college-selection-advice#PuZtQ3excyvoPZh42 on LessWrong, March 2011
Context: Here's my experience. I applied to just MIT and my state university (University of Washington). I got on MIT's waiting list but was ultimately not accepted, so went to UW. I would certainly have gone to MIT had I been accepted, but my thinking now is that if I did that, I would not have had enough free time in college to write Crypto++ and think about anonymous protocols, Tegmark's multiverse, anthropic reasoning, etc., and these spare-time efforts have probably done more for my "career" than the MIT name or what I might have learned there.

Source: A History of Economic Thought (1939), Chapter VI, Marx, p. 295

Source: On Writing: A Memoir of the Craft

Source: Glasshouse (2006), Chapter 15, “Recovery” (p. 255)

"Peaceableness Toward Enemies".
Sex, Economy, Freedom & Community (1993)

Source: Sex, Art and American Culture : New Essays (1992), The Rape Debate, Continued, p. 59
Context: I am being vilified by feminists for merely having a common-sense attitude about rape. I loathe this thing about date rape. Have twelve tequilas at a fraternity party and a guy asks you to go up to his room, and then you're surprised when he assaults you? Most women want to be seduced or lured. The more you study literature and art, the more you see it. Listen to Don Giovanni. Read The Faerie Queene. Pursuit and seduction are the essence of sexuality. It’s part of the sizzle. Girls hurl themselves at guitarists, right down to the lowest bar band here. The guys are strutting. If you live in rock and roll, as I do, you see the reality of sex, of male lust and women being aroused by male lust. It attracts women. It doesn't repel them. Women have the right to freely choose and to say yes or no. Everyone should be personally responsible for what happens in life. I see the sexual impulse as egotistical and dominating, and therefore I have no problem understanding rape. Women have to understand this correctly and they'll protect themselves better. If a real rape occurs, it's got to go to the police. The business of having a campus grievance committee decide whether or not a rape is committed is an outrageous infringement of civil liberties. Today, on an Ivy League campus, if a guy tells a girl she's got great tits, she can charge him with sexual harassment. Chickenshit stuff. Is this what strong women do?

2000s, 2003, Remarks on U.S.-British relations and foreign policy (November 2003)