The 100-Times Rule

The 100-times rule is the fast tiering for whether recurring work deserves automation: if you’ll do it 100+ times, build the workflow; 10–100 times, write a checklist or a template; 1–10 times, just do it by hand. The numbers are rough; the shape is the point — the build is worth it only when the payoff repeats often enough to dominate the setup and upkeep.

Why it matters: Both directions. People underestimate truly recurring work — the Friday report you “occasionally” do is every Friday for as long as you’re in business, which is fifty a year and hundreds over the life of the workflow. And people build for work that runs twice a year, producing a weekend project that breaks at the next system change and stands as a monument to time you’d want back. There’s one honest exception in the middle tier: a long task at low frequency (forty-plus hours a year) can justify a build the raw count wouldn’t.