Who's Working on Labor Day at My House?
The first Labor Day was Tuesday, September 5, 1882, in New York City (the Department of Labor has the whole history, including which union takes credit, which is disputed, because of course it is), which means the holiday turns 144 years old today, and I’ve spent a decent fraction of those years (the ones I was alive for, anyway) pointing out that it’s the worst-named holiday we’ve got. Nobody works on it. That’s the whole joke and nobody seems bothered, and nobody explains it to you as a kid, either. You just get a Monday off and a hot dog and you’re expected not to ask questions, and asking questions is kind of my whole thing (it’s the name of the podcast, and Dawn has long since stopped reacting).
So every year around now I announce that I’m going to treat Labor Day Weekend as the hardest-working weekend of the year, and every year I mostly mean it, and this year my website took me at my word, because if you go look at the home page this week you’ll find me in a hi-vis vest driving an excavator, pulling espresso, and climbing out of a manhole. (Edward, you have never once operated an excavator. You rented a floor sander in 2004 and returned it early. Sit down.) The pictures are AI, obviously, and the fedora is the only real thing in them.
The honest answer to who’s actually working at my house this weekend is 10 AI agents and, in a supporting role, me. I’ve written before about how many agents it takes to run a day, and I won’t re-list the whole zoo, but the weekend roster goes like this. On Saturday at 5AM Atlantic, while I was asleep (I’d like to say I was up, I was not up), a scheduled task on the Windows box in my office launched Claude Code, which read a brief I wrote 4 weeks ago, decided on the jobsite theme, wrote every word on the home page, generated 6 pictures of me looking ridiculous, ran the tests, committed the whole thing, and pushed it to GitHub, which built it and put it on the internet before I’d had coffee. That’s one agent. Its best failure, for the record, is the time it hung for 72 hours waiting on a yes-or-no install prompt inside a window I had deliberately made invisible, and I spent 2 of those days assuming GitHub was down.
Then there’s the one I think of as the chief of staff, which sends me a note before 6AM every day about who I’m seeing and why, and then triages roughly 200 messages a day into piles. It has never sent an email on its own and it never will, and that’s a rule I’d hang on the wall if I had wall space left over from Dawn’s paintings. Nothing in the stack has send authority. Every one of them drafts, and a human sends. That sounds like a limitation until you’ve watched an agent brief you thoroughly and confidently on the wrong human being (it’s happened twice, both times someone who shared a name with the person I was actually meeting, both times sorted out during the handshake).
The daily video agent ships something every day of the weekend, holiday or not, and the rule I had to write for it is my favorite rule in the whole system: on a thin news day, make it 90 seconds and say it’s a thin news day. Before that rule it would find a story every single morning, because it was built to find a story, and one morning it produced 3 confident minutes about a funding round that deserved a sentence. The podcast agent, which took over about 90% of a human producer’s job back in June, once cut 4 seconds of silence where a guest was genuinely thinking, which was technically a correct edit and also deleted the best moment in the episode. I put the silence back by hand, and now I make it leave the pauses alone, which has also started leaking into how I sit through meetings.
The Monday one is the funny one for Labor Day specifically. Every Monday morning a pitch engine reads every call-for-speakers page it can find and ranks the ones where I’d fit, and it does not know or care that this Monday is a federal holiday (signed into law June 28, 1894, by Grover Cleveland, who, I assume, worked that day). So at some point Monday morning while I’m down the manhole, it will pitch me for anything with a stage and a microphone, and I’ll come up and pick the 2 or 3 worth writing to, and I put up with it pitching me for panels on topics I’ve never heard of because it has also found me things I’d never have found on my own.
There are more: a research one that comes back with 40 sources when 6 would do, a writing one whose entire job is to disagree with the first draft (the single most useful idea in the stack, honestly, a generator plus a grader that’s allowed to say no), an image one that violates my blue-fedora rule about 1 time in 8 and once gave me 3 hands (3 hands, on a man in a hi-vis vest, which I only noticed after it shipped, and I have thought a lot since about whether a General Grievous joke would land here or just make it worse, and I’ve decided it makes it worse, and I’m leaving it in anyway), and a recruiting one running the reply sweep for the Caribbean AI Summit on October 9-10 that still can’t tell a polite no from a slow yes, so it keeps both. Across the whole collection the honest failure rate is somewhere near 1 in 10, and every published thing gets looked at by me first, because my name’s the one on it. Which brings me to my hours. My timesheet for the weekend, if I’m honest, is a couple of hours Saturday reading what the agents did, a couple more Sunday, and on Monday whatever the excavator allows. Theirs is 72. The most useful thing I learned in August, from an audit I asked an agent to run on the other agents (yes), is that the system was producing about 1,000 documents a month and I was reading about 25 of them, so I deleted 1,319 files in one afternoon and told everything to prefer doing the thing over writing about the thing. That one’s on me, not them.
If you run a finance team, you have a weekend like this one about 12 times a year and it’s called the close, and nobody brings you a hot dog. That’s the talk I give (the fees are published, keynotes from $15,000, and I answer within 1 business day), and it’s the workshop where your team builds the first 2 agents themselves and argues about which one gets send authority (neither).
Anyway. Happy Labor Day, whichever way you’re celebrating it. If you’re in San Juan on Monday, I’ll be the one in the vest. Come say hi, or write me at Edward@Roske.AI and tell me which 2 things you’d hand to an agent first!
Asking good questions, Edward