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)
 Related
 Special Issue: Commentaries on Breiman's Two Cultures paper (Observational Studies, Volume 7, Issue 1, 2021)
 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)

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)
 Taste for Makers (Paul Graham)
 What You'll Wish You'd Known (Paul Graham)
 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 SelfDefeating Object" Argument (Terence Tao)
 The Importance of Stupidity in Scientific Research (Martin Schwartz)
 The Shapes of Stories (video, Kurt Vonnegut)
 Interview with Michael Atiyah
 Who Can Name The Bigger Number? (Scott Aaronson)
 AlphaFold @ CASP13: “What just happened?” (Mohammed AlQuraishi)
 A History of Insurance (Swiss Re)