Essays, SPEECHES, ANNUAL LETTERS

“I Have a Dream” and “Letter from Birmingham Jail” by Martin Luther King, Jr. These are powerful and compelling. The work here is far from done.
“This is Water” by David Foster Wallace. DFW, as he was known, lays out a way of thinking about the world that will make you a more empathetic and compassionate person. I also like the method he uses in the speech. Water to fish is used as a device to highlight the thing that is so close and so pervasive that we don't even stop to think about it. This is a useful mental model in other areas as well.
“The Psychology of Human Misjudgment” by Charlie Munger. Charlie Munger, Vice Chairman of Berkshire Hathaway, or Warren Buffett's lesser-known but equally important partner, has a saying: “All I want to know is where I'm going to die so I never go there.” He means: understand the things that lead you astray in business, investing, and life—and then avoid them. For Buffett and Munger, rationality is king. This talk is a list of the ways human psychology leads us astray, causing us to make irrational decisions.
“A Lesson on Elementary Worldly Wisdom” by Charlie Munger. Another saying of Munger's: “It is better to remember the obvious than to grasp the esoteric.” An aspect of this is having a broad set of mental models on which to draw on order to make a decision. This talk lays out what Munger sees as the most important mental models.
“They're Taking Over” by Tim Flannery. I can’t say I expected to love an essay about this jellyfish, but his essay in The New York Review of Books about precisely that topic is mesmerizing and memorable.
“The Child and the Shadow” by Ursula Le Guin (in The Language of the Night: Essays on Fantasy and Science Fiction). The essay begins with a short fairy tale by Hans Christian Anderson called “The Shadow” and then proceeds to Carl Jung's ideas to explain the importance of fantasy. “The great fantasies, myths, and tales are indeed like dreams: they speak from the unconscious to the unconscious, in the language of the unconscious—symbols and archetypes,” says Le Guin. She describes Jung as “the psychologist whose ideas on art are most meaningful to most artists.” The passage describing his concept of the collective unconscious is just amazing. I captured it here.
Amazon Annual Letters by Jeff Bezos. After Brad Stone's book, The Everything Store, Amazon's annual letters are a great way to learn about Bezos's operating principles.
Berkshire Hathaway Annual Letters by Warren Buffett. Beyond the clear, principled thinking captured in these letters, it's fascinating to see Buffett's thinking about economic and business events (e.g., stagflation in the 70s) as they were happening rather than in hindsight.
“Mathematics, Common Sense, and Good Luck: My Life and Careers” by Jim Simons (talk at MIT, 2010). I wrote about this talk here. One statement stuck with me: “Do something new. I love to do something new. I don’t like to run with the pack. For one thing, I’m not such a fast runner. If you’re one of n people working on the same problem in different places, I know if it were me I’d be last. I’m not going to win that race. But if you can think of a new problem or a new way of doing something, that other people aren’t all working on at the same time, maybe that would give you a chance.”
“Why Software Is Eating the World” by Marc Andreessen (2011). This was a seminal article that offered a simple but powerful framework of the dramatic change the world was experiencing—and likely to experience for decades to come. The framework was updated in 2016 in an A16Z podcast titled, “Software Programs the World” (I noted my takeaways from the podcast here.)
“Full Stack Startups” by Balaji Srinivasan, Chris Dixon, and Glenn Kelman. Would you rather: (i) create a new technology and convince companies to buy your technology to improve the widgets they sell to customers (“Buy our technology—you'll make an ROI of 1,000%!”), or (ii) create a company that makes widgets using that technology?
“The ‘Oh, Shit!’ Moment When Growth Stops” by Jeff Jordan. A simple and powerful framework for startup leadership.
“Competition Is for Losers” by Peter Thiel. I don't think Thiel said anything dramatically new here, though he deliver it in a controversial wrapper, which certainly helped spread his idea (and increase sales of his book, Zero to One, which at the time of publishing was new). He's essentially saying that a business should be hard, if not impossible, to copy. This idea has been core to competitive strategy since Michael Porter wrote his seminal books. What I like about the article (and the book) is Thiel's reframing of objectives: be different, don't compete, don't copy, invent. Quite simply, as Thiel states in the first paragraph, you can't just create value—you have to capture value, too.
“Why Chinese Mothers are Superior” by Amy Chua. I don't, of course, think Chinese mothers are necessarily superior. I love two things about this article: (i) its controversial approach as a tactic (you simply can't not read it and talk about it) and (ii) the fact that she is unapologetically subverting conventional wisdom.
“Here is New York” by E.B. White. This is probably the classic well-crafted essay. It flows beautifully, magically transporting you to New York in the 1940s. It also has a chilling passage that eerily foretells the 9/11 attacks.
“The Principle of the Hiding Hand” by Albert Hirschman. The principle of the hiding hand is an inspiring one, albeit one that could make your life very painful for a long time before leading to dramatic success. Hirschman's observation:

“We may be dealing here with a general principle of action. Creativity always comes as a surprise to us; therefore we can never count on it and we dare not believe in it until it has happened. In other words, we would not consciously engage upon tasks whose success clearly requires that creativity be forthcoming. Hence, the only way in which we can bring our creative resources fully into play is by misjudging the nature of the task, by presenting it to ourselves as more routine, simple, undemanding of genuine creativity than it will turn out to be.”
“How America Can Create Jobs” by Andy Grove. Andy Grove was not only an effective manager and company-builder, he also had a profound respect for people. This isn't because Andy Grove is more of a humanist, where others are more practical or value-oriented. In fact, quite the opposite. I believe Grove has a much stronger grasp of the machinery of value creation and the role that people play in it. Consider the following insight:

“A new industry needs an effective ecosystem in which technology knowhow accumulates, experience builds on experience, and close relationships develop between supplier and customer. ... As happened with batteries, abandoning today's 'commodity' manufacturing can lock you out of tomorrow's emerging industry.”
“The Hedgehog and the Fox” by Isaiah Berlin.

Antilibrary:

“Eichmann in Jerusalem: A Report on the Banality of Evil” by Hannah Arendt.