This is an interesting question (at least to me) because it causes me to consider changes that I’ve made in my own life in this regard.
Years ago, when paying by check was the normal and expected option, I used to take a particular pleasure (believe it or not) in writing a check for “balance due” on the same day that I received the bill. I just wouldn’t mail the check until a few days before it was actually due. So on the day that the bill arrived I would write the check, post it in my checkbook register, note my copy of the bill with the payment details (check # and date written), ready the payment for mailing – including sealing the envelope and writing the return address – and then writing “date to be mailed” in the corner of the envelope where the stamp would go. Then I would put that envelope in my “time machine” – a collection of payments to be mailed, sorted by date, to be reviewed daily to see if one had to go out today or not. Then I would file my copy of the bill in its proper place: “utility payments”, “loan payments”, “tax payments”, “miscellaneous payments”, etc., including “by year”. I was so damn organized that I can barely recall that person.
Each month I would also reconcile bank statements and balance my checkbook – to the penny – because that was just who I was then. Well, that, and because I used to be a “number dummy” – a field accountant – for the construction division of the company I work for now. I was also very meticulous about posting my paycheck to the account register (even though I’ve had direct deposit for over thirty years), and interest payments each month. I never ever paid late fees or credit card interest.
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After my separation from my wife my habits changed (along with modes of payment, since checks were falling out of fashion). I rely much more upon automatic bill payment (which has to be arranged between the creditor and the bank, since the creditor has to know that the bank will be receiving the payment details, and the bank has to have your authorization to make the payment) or automatic billing to credit card or online payment by credit card for some billers (my water company, for example) who insist on sending out paper bills, but at least have implemented schemes to allow online payment.
And I never – ever – balance my checkbook any more. I haven’t opened an electric bill in a few years now. I know what I pay, since I see the debit from my checking account each month (it’s not that I don’t review my expenditures; I just don’t balance a checkbook register any more), and I “file” things by piling them on tables and chairs until the piles tip over and I put them in boxes. But I still don’t pay late fees or credit card interest. In fact, the only thing that I write in my checkbook register any more is the occasional check that I do write. I don’t record ATM withdrawals, EFT payments, deposits of any kind or interest payments. Just a few checks a year.
I like paying bills by credit card best, because my card gives me points based on what I spend each month, with the points redeemable in cash, and as long as I’m not paying interest on the card, it’s all gravy to me. And much simpler than trying to find a place to write a check nowadays. (Speaking of which, I need to order some new checks, I suppose, for the four or five that I write each year. I have one or two left in my checkbook, and I may need those before the year is out.)