Scripting as a Habit, Not a Hero Moment
Nobody scripts the first time they do a task. You script the fourth time, usually right after you've caught yourself thinking "didn't I just do this." That instinct, the mild irritation of repeating yourself, is the whole trigger. You don't need a grand automation strategy. You need to notice the fourth time and actually act on it.
The Real Cost of Doing It By Hand
Manual work doesn't feel expensive in the moment because the cost is spread out: five minutes here, three minutes there, easy to justify individually. But it compounds silently, and worse, it's error-prone in a way scripts aren't. Tired hands skip steps, copy-paste the wrong line, forget the flag they used last time. A script does the same tedious thing the same correct way every time, which is worth something even before you factor in the time saved.
What Makes a Good First Script
Small and ugly beats ambitious and unfinished. Your first automation doesn't need error handling, a config file, or a clever name. It needs to replace one specific annoying step, reliably, today. Renaming a batch of files. Pulling the same report. Restarting the same three services in the right order. Polish comes later, if it ever needs to. A script that works and is never touched again already did its job.
Where to Actually Keep Them
The single biggest failure mode isn't writing a bad script. It's writing a good one and losing track of it in some folder you'll never open again. Keep a dedicated scripts directory, under version control, even if it's just you. Give things names you'll actually remember at 4pm on a Friday. A script you can't find is functionally identical to a script you never wrote.
When Automation Isn't Worth It
Not everything earns a script. A one-off task, no matter how tedious, is still cheaper to just do than to automate. The whole point of the ledger above is catching the difference between "annoying once" and "annoying repeatedly." If you're not confident you'll do this task again, do it by hand. You can always script it the second time.