I've never signed up for an all-in-one bill paying service (yeah, yeah, I know), but I do prefer to pay online, which means "your statement is ready" emails from different vendors scattered throughout the month. Some of them are very good at following up with "we have scheduled your payment" and "we have received your payment" emails; others -- not so much. And while I've tried to make a habit of scheduling the payments right away, I'm much less good at remembering a couple of weeks later whether I really did or not. And sure, in theory, I don't archive the statements until I've scheduled a payment, but in reality, the ADD demons archive the unpaid ones for me every now and again...

So this morning, it finally struck me in that "why didn't I think of this ages ago" way -- having set up the payment, I forward it to myself with a quick note at the top (e.g. "scheduled payment for 11/25 for full amt") before archiving as usual. Since it's Gmail, the annotation becomes part of the same conversation when it comes to tags, searches, etc.

It still feels like more steps than I'd like, and I'd love to automate parts of it. But as a start, it beats banging my head against "but I was sure I did pay that one!"