Expired documents are always discovered at the worst moment
Nobody checks a passport in January. They check it in July, at the airport, or while booking flights for a trip three weeks away, which is exactly too late for most renewal queues. The same script plays out with insurance discovered lapsed after the water damage, and with the lease that auto-renewed the week before you meant to renegotiate it.
The fix is not discipline, it is removing the manual step. When a document enters your vault, its dates are read straight from the page: passport and ID expiry, policy periods, contract end dates. You never type a date, so there is no date you can mistype or forget to enter.
One question, checked against everything
Because the dates live in one place, the useful question is not only "when does X expire" but "what expires soon", asked against every document at once. Before booking travel, ask about the passports of everyone flying. At the start of the year, ask what needs renewal this year and put the answers in your planning instead of your worries.
Renewal paperwork is also less painful with the toolkit next door: photograph the new documents into PDFs with JPG to PDF, translate foreign certificates with Translate PDF, and fill the renewal forms with Fill PDF Form.