Why I Automate Everything

There's a common pattern I see in finance teams: someone builds a spreadsheet, it becomes critical infrastructure, and then everyone is terrified to touch it. Or worse — keeping a flawed process alive becomes one employee's entire job.

The Two-Time Rule

My rule is simple: if I do something more than twice, and it doesn't require much human judgment, I automate it. Not because automation is inherently better — sometimes a manual process is perfectly fine — but because the third repetition is evidence of a pattern worth encoding.

The payoff isn't primarily time. It's reliability. A Python script that pulls data from an API does it the same way every time. A human copying numbers between spreadsheets at 7am on a Monday does not — and a job that consists mostly of repetitious copying erodes morale long before it produces an error big enough to notice.

When NOT to Automate

Automation has costs: building time, maintenance burden, and reduced flexibility. I don't automate when:

• The process is genuinely one-off
• The judgment calls involved are too nuanced to encode
• The time investment to automate exceeds the time saved over a reasonable horizon
• The process is likely to change significantly in the near term

The Sweet Spot

The best automation targets in finance are the "boring middle" tasks — not the creative analysis work, and not the one-off special projects, but the repeatable data gathering, formatting, and distribution work that eats hours every week.

Think: pulling market data, formatting reports, distributing memos, reconciling positions, generating standard charts. These are high-frequency, low-creativity tasks where humans add no unique value.

Where This Actually Gets Tested

The hardest automation I've built is the nightly pipeline behind my equity factor engine: ingest data for 5,500+ stocks, handle corporate actions, detect stale data, recompute factor scores, and have everything ready before the open — unattended. The first version was one long script, and one bad API response at 2am would take down the whole run. The version that works is a chain of small, independent jobs, each of which can fail and retry without dragging the others down.

That rebuild taught me more about automation than any productivity essay: the design question isn't "how do I script this task?" but "what happens at 2am when step four fails?" A process is only automated once nobody has to check on it.

Start Small

You don't need a grand automation platform. Start with a single script that replaces one painful manual step. Get it working, get people to trust it, then expand. The compound effect of many small automations is enormous — and each one frees attention for the work that actually requires judgment, which is the point.