GROUNDWORK

GROUNDWORK

School Bulletin

Everyone (and Everything) Is a Manager Now

Or: what a much-more-technical person taught me about the death of the individual contributor, and the fallout coming for everyone still stuck being one.

Earnest Sweat's avatar
Earnest Sweat
Jul 21, 2026
∙ Paid

A few weeks ago I got on a call with a founder friend of mine who spends most of his waking hours actually building things. He is a universe of technical depth ahead of me, and the whole reason I asked for his time was that my agent setup, which I had cobbled together over the last several quarters, had started to feel clunky in a way I could not diagnose. Too many gears, not enough grip.

About fifteen minutes in, he stopped me and said this:

Friend: So question. Because it’s going to help me identify, like, how I talk to you about this. How technical are you on, like, elements and agents?

Me: I’m just like a self-taught. I’m not that technical. I actually don’t.

Friend: Do you know what a sub-agent is? Do you know what an agent harness is?

Me: No.

Friend: Do you know what a system prompt is?

Me: A system prompt?

Friend: Yeah.

Me: No. What is that? I’m awful. I’m not technical at all.

Friend: Yeah, I know. Yeah, I’m just trying to gauge, like, what terms I can use and not. What about, like, a context window? Tokens?

Me: Yes.

Friend: Okay, damn. So, okay, yeah. So, like, if it’s not in a headline somewhere, you don’t know what it means.

I laughed. He was right. If it was not in an article or a post I was already reading, I did not know it. I am not out here reading technical documents or research papers like Chris Dixon, though I do read the Substack called Technically, and the only reason I made it to that call at all was that I was willing to say so out loud to someone with the vocabulary and the receipts to explain, with a lot of grace, that I had been running my entire operation the wrong way.

I want to talk about what he showed me. But more than that, I want to talk about what it implies for the future of labor. Because I think the individual contributor as a category of worker is about to become endangered, and the people who do not see it coming are going to be the same ones who have spent the last cycle telling themselves they were just a little behind on the technology and would catch up once the disruption settled. They will not catch up. The tools are not the thing. The builder mentality coupled with the (in)organic chart is the thing.

Where I was stuck

I run a small operation with a lot of surface area. I am building a Fund. Two podcasts. A newsletter. Convenings. Consulting. It looks like more than it is because I built agent scaffolding underneath the whole thing to keep action items from falling through the cracks. Every meeting drops a transcript, every transcript gets scraped for to-dos, every to-do gets assigned or drafted or flagged. It runs while I sleep. And when it works, it works well enough that I forget it is running at all.

But it had started to break in the small ways that always add up. Duplicate drafts. Missed follow-ups. Two agents chasing the same task in two different tabs, neither aware of the other. Sand in the gears.

My instinct was to slice the tasks thinner, so I did. One agent for to-dos, one for the partner meeting, one for reengagement, one for intros, each of them polite and focused and operating with a sliver of the picture. Which sounded like discipline, and was actually the opposite. I was treating every agent like an employee I could dispatch, and I was staying in the loop between all of them, checking their work, nudging their progress, rerouting their outputs, playing the role of switchboard operator between a bunch of well-meaning digital ICs who could not see each other.

I was the manager. I had built myself a bullpen of ICs. And I had made myself the bottleneck.

What he actually drew

After I walked him through my misjointed workflows, he stopped me and drew what I should be doing instead. He drew it for me on a whiteboard app while we talked, and I have the screenshots. I keep looking at them because they are the simplest version of a thing I had been failing to see.

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