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The Chief of Staff as an LLM prompt

Notes from six months of running my work and life through agents.

July 2026 · 3 min read

I'm grateful to be a millennial. We've been part of two worlds, analog and digital.

Record players and dial-up phones. VCRs and LaserDiscs, then CDs, then the MP3. We built our own computers, then bought them off the shelf. Cash, then crypto. Dial-up, internet, mobile, SaaS. And now the frontier is intelligence.

My dad made a meager salary at the restaurant. My mom worked mostly on tips. But when I wanted the latest and greatest gadget, they said yes, sometimes at the cost of months of their wages. I look back with gratitude, and I tried not to waste it. Their sacrifice bought me the privilege of learning by playing.

Through every one of those waves, hands-on was the only way I ever learned. Playing with the technology, working with it, breaking it a little. So when this wave arrived, I did the same thing. I started running my work and my life through an AI.

What it actually does

Six months in, my Chief of Staff runs project management and meeting briefings. It reviews my calendar. It ingests big dumps of tasks and half-thoughts and organizes them into an executable plan. It acts as a thought partner: iterating drafts before they go to the team, doing research, helping me get clear on my own thinking.

It handles enough of the routine that typing is starting to feel like using a typewriter. We're close to not needing the keyboard at all. Just dictation, with execution.

The line

Here's what I don't hand over. The writing. The sends. The publishing. Private data. Anything that needs judgment, taste, or structure.

What I do instead is guide. There's a fair amount of reiterating, of building systems and documentation that get a first pass to 70, 80, 90 percent. Then I work like a chef, tasting the food as it moves through the kitchen the way I grew up watching my family do it, making sure the quality stays high.

Six months of honest notes

The good: I can watch the models improving, the quality improving, month over month.

The bad: it's still verbose. And it drifts. It can take over the message and turn it a degree or two off the point, and a degree or two, held long enough, puts you very far from the original destination. So I guide it the way a tower guides planes. Small corrections, constantly.

The surprise is what it changed in me. I find myself thinking about systems, steps, the entire process, instead of getting lost in the manual typing and researching.

My friend Emmett tells me to aim higher, that it's capable of so much more. My friend Hiten says to just give it more and see where it goes. More is more.

We'll see. I'm hoping more is less. Less knowledge work, more human impact.

Less time proving I can do everything myself. More time on what it means to be human. Money is just fuel; it's what we build that matters. Intelligence should help, and we should have fun along the way. Learning. Exploring.

And hugs. More time for hugs.