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Bills & deadlines

The dates that cost money when they slip past you.

Deadlines that cost money share a pattern: they are far enough apart that you never build a habit, and the penalty for missing one is out of all proportion to the effort of doing it. A car insurance renewal takes ten minutes and costs a few hundred if you let it auto-renew unchecked.

Email reminders for these arrive weeks early, when there is nothing to do yet, and are then buried by the time it matters. The useful reminder is the one that arrives the day it needs doing, when you can actually act.

These articles cover renewals, tax dates, meter readings, subscriptions you meant to cancel, and the follow-up chasing that refunds and claims always need. Most of them are about timing rather than memory — knowing when to be reminded matters more than being reminded often.

26 articles