Fire yourself from the recurring jobs first

    December 2025 · operations

    A founder's week silently fills with recurring jobs: the update, the reconciliation, the chasing, the formatting, the scheduling. Each is small. Together they are the reason the important work happens after ten at night.

    I run ongoing experiments in handing these jobs to AI, and the operating rule that has survived is: before you hire for a recurring job, try to automate it; before you automate it, ask whether it needs doing at all. Every founder-hour reclaimed is distance added per dollar.

    What resists automation is instructive. Judgment, trust, taste, and the conversations where someone needs to be a person — those keep proving to be the actual job. The experiments are not about replacing the founder. They are about finally letting the founder do the founder's work.

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