Some short essays/posts/articles which I think make for good use of reading time. The test for inclusion is whether I would've been happy to find the link from someone else's list. I highlighted in orange those that I think are particularly good, and in blue those that I felt stood out from the rest.

• The Relativity of Wrong (Isaac Asimov)
• Mathematics on a Distant Planet (Richard Hamming)
  • Related
  • The Unreasonable Effectiveness of Mathematics (Richard Hamming)
  • The Unreasonable Effectiveness of Mathematics in the Natural Sciences (Eugene Wigner)
  • On Proof and Progress in Mathematics (William Thurston)
  • "Theoretical mathematics": Toward a cultural synthesis of mathematics and theoretical physics (Arthur Jaffe and Frank Quinn)
  • What Is Good Mathematics? (Terence Tao)
• The Inner Ring (C.S. Lewis)
  • Related
  • Machiavelli, Morals, and You (Martha Lagace / Joseph Badaracco)
• Cargo Cult Science (Richard Feynman)
• The Psychology of Human Misjudgment (Charlie Munger)
• Gospel of Wealth (Andrew Carnegie)
• Do Not Remain Nameless to Yourself (Richard Feynman)
• The Mundanity of Excellence (Daniel Chambliss)
• You and Your Research (Richard Hamming)
  • Related
  • Advice to a Young Mathematician (Michael Atiyah)
  • Advice For Graduate Students in Statistics (Michael Steele)
• Statistical Science Conversations
• Statistical Modeling: The Two Cultures (Leo Breiman)
• Abraham Wald's Work on Aircraft Survivability (Marc Mangel and Francisco Samaniego)
• The Blind Men and the Elephant (as retold by John Saxe)
• The Two Cultures of Mathematics (Timothy Gowers)
  • Related
  • PDE As a Unified Subject (Sergiu Klainerman)
  • Structure and Randomness in Fourier Analysis and Number Theory (Terence Tao)
• The Use of Knowledge in Society (Friedrich Hayek)
  • Related
  • Taking a Fence Down (G.K. Chesterton, in essence)
• Warning Signs in Experimental Design and Interpretation (Peter Norvig)
  • Related
  • Ten Signs a Claimed Mathematical Breakthrough is Wrong (Scott Aaronson)
• 20 Years, 20 Lessons, Part I (Part II) (Part III) (Mark Rosewater)
• A Map of the Limits of Statistics (Nassim Taleb)
  • Related
  • Standard deviation (Nassim Taleb)
  • A Philosophical Notebook (Nassim Taleb)
• Taste for Makers (Paul Graham)
• What You'll Wish You'd Known (Paul Graham)
• Mathematical Problems (David Hilbert)
  • Related
  • Mathematics in the 20th Century (Michael Atiyah)
• How to Write Mathematics (Paul Halmos)
• Practical Thought About Practical Thought (Paraphrasing Charlie Munger)
• Unhappy Meals (Michael Pollan)
• The Strengths of the Academic Enterprise (Edsger Dijkstra)
• Craft in Operations Research (Hugh Miser)
• The Cryptographic Mathematics of Enigma (Ray Miller, NSA)
• The Future of Operational Research Is Past (Russell Ackoff)
• Negative Probability (Richard Feynman)
• Negative Expertise (Marvin Minsky)
• The "No Self-Defeating Object" Argument (Terence Tao)
• The Importance of Stupidity in Scientific Research (Martin Schwartz)
• The Shapes of Stories (video, Kurt Vonnegut)
• Who was Ramanujan? (Stephen Wolfram)
• Salary Negotiation (Patrick McKenzie)
• Interview with Michael Atiyah
• AlphaFold @ CASP13: “What just happened?” (Mohammed AlQuraishi)
• Transcript of Surreptitiously Taped Conversations among German Nuclear Physicists at Farm Hall
• Who Can Name The Bigger Number? (Scott Aaronson)