The Last Mile Assistant

The most underrated job in the next five years is not prompt engineer.

It is the human who runs errands for someone else’s AI.

I noticed this watching my own setup. My agents handle email triage, calendar holds, research, drafting, CRM updates, follow-ups. They can do the cognitive 90% of an assistant’s job, sometimes better than the assistant could.

What they cannot do is pick up the dry cleaning. Sign for a package. Walk a passport into the consulate. Test that a Slack app actually reinstalled cleanly. Drive a check to the lawyer. Touch a thing in the physical world.

So the assistant role inverts. The AI does the planning, the writing, the reasoning. The human does the in-person follow-through. The agent says “this needs to happen by Friday” and the human is the one who physically makes it happen.

That is a new job category. Not “assistant to a CEO.” Assistant to a CEO’s agent.

The pay model also flips. Today an EA’s value is mostly judgment, prioritization, and writing on your behalf. Tomorrow that value sits in the agents. The premium shifts to the people who can execute reliably in the real world on behalf of the agent, with the trust and discretion to act on the AI’s call without supervision.

It sounds dystopian if you read it cold. It is not, really. It is just specialization catching up to the tools. We already do this with logistics, with Instacart shoppers, with TaskRabbit. The new version is a dedicated person whose entire week is shaped by what your AI needs from the physical world.

The companies that figure this out first will not hire it as “assistant.” They will hire it as a service. A team of operators on retainer, dispatched by your agent, doing the things software cannot reach.

The next assistant job is not less human. It is more human, and less cognitive. The brain is the agent. The hands are the person.

That is the shape of the next five years.