This wouldn't be a classic Paul Graham essay without his two great hallmarks -- many passages of provocative valuable insights -- paired with periodic, bewildering attempts to sabotage his own argument.
I'll add some fan mail later if necessary (because I do get value from reading him), but for the moment, here's where I believe he went off course.
1. When he says the best essays are "ineffective," he's chosen the wrong word. They are "premature." They arrive before the world is fully ready to acknowledge their power. But they catch at least a modest following right away. And then their work grows and grows.
2. Essays about new technology can be quite powerful, and that's Graham's wheelhouse, so it's fine for him to talk up this cohort. But any serious survey of legendary essays needs to look wider. The most powerful essays redefine our social, moral, political and religious norms. Here are a few favorites that didn't just win their year; they stood out for centuries.
70 AD: The Gospel of Mark. Chronologically the first book of the New Testament, and look what that unleashed
1778: Common Sense by Thomas Paine. The boldest, fiercest justification for the American Revolution, and one that's still a touchstone today for anyone with a deep interest in the theory or practice of democracy.
1963: Letter From Birmingham Jail by Martin Luther King. Worth being on the list simply for its effect on the U.S. civil rights movement; even more significant as the unbreakable tuning fork for any civil or human rights movement anywhere.
We'll keep inventing new technologies, because that's what humans are good at, and I'm sure many strong essays will ensue. But it's the redefining of our social institutions that's likely to make the future so incredibly different from today. Anyone who can write a prescient reflection about society's new rules will get my vote for "Great Essays."