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Stop Automating the Wrong Things

Originally posted on LinkedIn

The automation trap is real: you see a repetitive task, you immediately think “I should automate that,” and three days later you’ve built an elaborate system for something that takes 2 minutes to do manually.

The Automation Paradox

The biggest mistake isn’t failing to automate. It’s automating something that shouldn’t exist in the first place.

Before writing a single line of code, ask: Why does this task exist? Half the time, the answer is “because nobody questioned it.” The task is a workaround for a broken process, a legacy of a tool that was replaced, or a manual step that only exists because two systems don’t talk to each other.

Fix the process first. Automate what remains.

The Decision Framework

When I evaluate whether to automate something, I use a simple scoring system:

Frequency × Time × Error Risk = Automation Priority

  • Frequency: How often does this happen? Daily = high priority. Quarterly = low priority.
  • Time: How long does it take manually? 2 minutes = low priority. 2 hours = high priority.
  • Error Risk: What happens when a human makes a mistake? Typo in a report = low risk. Wrong number in a financial calculation = high risk.

Score each 1-5 and multiply. Anything above 50 is worth automating immediately. Below 20? Leave it manual.

The Five Things to Never Automate

  1. Tasks that require judgment. If the outcome depends on context that changes every time, a script will get it wrong more often than a human.

  2. Tasks that happen once. Writing a script takes longer than just doing it. Don’t build a rocket to cross the street.

  3. Tasks where failure is invisible. If the automation breaks silently and nobody notices for weeks, the damage is worse than the manual effort.

  4. Tasks that are about to change. If the underlying process is being redesigned, your automation will be obsolete before it launches.

  5. Tasks that build relationships. That weekly check-in email you send to clients? Keep doing it yourself. The personal touch matters more than the time saved.

Start With the Quick Wins

The best automation targets are boring, repetitive, and predictable:

  • File organization — sorting downloads, renaming conventions, backup routines
  • Data entry — copying between systems, formatting reports, updating spreadsheets
  • Notifications — alerting you when something changes, summarizing daily activity
  • Scheduling — recurring tasks, reminders, follow-ups

These are the “30 minutes a day” automations that compound into weeks of saved time per year.

The Compound Effect

One 30-minute-per-day automation saves 130 hours per year. That’s over three full work weeks.

Stack five of those and you’ve freed up an entire quarter of productive time. That’s when automation stops being a convenience and starts being a competitive advantage.

But only if you automated the right things.

Originally posted on LinkedIn.