Choose the automation
Describe the repeated task
Turn a vague wish to automate into a trigger, input, transformation, output, success check, and failure boundary.
10 minute lesson
Every automation in this course starts the same way: with a task you already do by hand. Before you open Shortcuts or write a script, describe that task precisely. Most automations fail here, in the description, not in the code.
Start with one task you already perform. Write down six things about it:
- Trigger: what starts the work. A hotkey, a Finder selection, a schedule, a new file appearing in a folder.
- Input: the exact data the task needs. File paths, text, a folder.
- Actions: the ordered steps, the way you would explain them to a colleague.
- Output: what exists afterwards that did not exist before.
- Success check: the evidence that proves it worked.
- Failure boundary: what must never happen.
Here is a real one, written as a small task card:
trigger: I press a hotkey after taking a screenshot
input: the newest PNG on the Desktop
actions: rename to acme-2026-08-03.png, move to ~/Projects/acme/media
output: the renamed file in the media folder
success: file exists at the destination, Desktop copy is gone
never: overwrite an existing file, touch anything that is not a PNG
Compare two candidate descriptions. “When I finish a screenshot, rename it with the project and date, move it into the project media folder, then reveal the new file.” This is testable: you can run it and check every claim. “Organize my Mac” is not. It has no trigger, no defined input, and no way to know when it succeeded.
The failure boundary deserves extra care. Record what must never happen, such as replacing an existing file or processing a folder outside the chosen project. The first time your automation meets unexpected input, that list is the difference between a harmless no-op and lost work.
One more exercise before you build anything: perform the task manually one last time, and narrate every step out loud. You will notice small decisions you make without thinking, like skipping certain files or picking a different name when one is already taken. Each of those decisions becomes an explicit rule in the card, or it becomes a bug later.
Lesson completed