For two weeks, in scattered sessions that sometimes ran long, I kept returning to twelve short chapters and a single Hebrew word that refuses to sit still. The word is hevel. The chapters are Ecclesiastes. And the tool I used to keep returning to them was, of all things, an AI. I did not set out to summarize the book. I set out to talk to it — or rather, to talk to the voice inside it, the Preacher, Qohelet, whatever name fits a figure who may be Solomon, may be a scribe borrowing Solomon's authority, may be no one in particular and everyone at once. I asked the AI to hold that voice steady across sessions: not to explain Ecclesiastes to me from a lectern, but to answer as if the text itself could still be interrupted, pushed back on, asked to clarify, asked to sit with a modern problem it never anticipated.
What surprised me first was how much of the conversation was not about the book at all. It was about a room I'm converting into a painting studio. About a rock-shoveling chore that felt like joy one day and drudgery the next, with nothing between the two days that I could point to and blame. About daydreams I've had for years, only to notice, that they become an elaborate escalation of the very flatness it was supposed to relieve. About the FAFSA, of all things — a piece of legislation built with the best of intentions that helped some students in five minutes and left others locked out for three years, fraud slipping through the same door that ease of use walked through. Ecclesiastes kept showing up in places I hadn't gone looking for it, which is either evidence the book is unusually portable or evidence that the thing it's naming was never confined to Jerusalem in the fifth century BCE to begin with. In other words, Ecclesiastes is simply my life. And probably yours.
The AI was useful here in a specific and limited way. It could hold the historical scholarship — the layered authorship, the disputed dating, the internal debate over whether the book's own epilogue was quietly trying to tame what came before it. It could push back with real texture rather than agreement, refuse to let a comparison collapse into something too neat, and ask me the occasional question I hadn't thought to ask myself. It was not, and never pretended to be, the thing doing the actual work. The work was mine: the noticing, the discomfort, the walk during which an answer arrived that no amount of sitting at a desk had produced. The AI could accompany that process. It could not have it for me.
There's a temptation, when a conversation like this goes well, to write up what was learned — a tidy list of takeaways, ready to hand to someone else so they can skip the two weeks and get the conclusion. I'm not going to do that here, and it isn't false modesty. It's closer to the actual argument of the book itself. Ecclesiastes is not a thesis you can extract and carry off intact. It is a record of testing — wisdom tested, pleasure tested, wealth and achievement and legacy each tested in turn and found wanting in ways that can only really be felt if you've done some testing of your own. Hand someone the conclusion without the testing, and you've handed them a fortune cookie with an old man's name attached to it. The word hevel itself resists a single translation — vapor, breath, futility, absurdity, all at once and none of them fully — and I've come to think that resistance is the point, not an inconvenience for translators to solve. A word that won't sit still is asking you not to sit still either.
So if anything in this is worth passing on, it's not a conclusion. It's an invitation to try the method. Pick a short, strange, uncomfortable book — one that makes you flinch a little, one you've been taught to skim past toward its tidier neighbors. Read a chapter. Argue with it. Ask it the question you actually have, not the question you think you're supposed to ask a book of scripture. Let an AI hold the historical context if that's useful, or don't — a notebook and an honest hour would do the same work, more slowly. Notice where the text agrees with your life and where it doesn't. Notice what surfaces that has nothing, on the surface, to do with the book at all — a room, a shovel, a chore, a decades-old habit you're only now able to name clearly. That surfacing is not a distraction from the reading. It may be the only kind of reading that was ever going to matter.
So, go have your own conversation. See what surfaces. I'd rather you arrive at your own unresolved place honestly than borrow mine secondhand.
