Monthly Bill Paying Changes Over Time

Before I even knew what FIRE was, we paid our monthly bills by check or even cash. The internet didn’t exist and most bills and payments were sent via mail. Cash payments were made by going to an office or store and getting a receipt for it.

The next big evolution was a debit card (existed above too, but the main function was for getting cash from an ATM). This occurred when businesses started taking credit cards (beyond their store cards). You really didn’t really use your VISA/Mastercard bank cards because you occasionally carried a balance from that last vacation and who wanted to pay for a tee shirt over time. I clearly remember a time where a grocery store refused a check because we hadn’t used a check in the last 6 months (would have to get re-verified to write checks).

The next big change for us was with the internet. Over time, you could now check your balances on everything and make payments online. During this time, fraud became more of an issue and risking use of a debit card opened your checking account to theft that could cause other bill payments to be denied (written checks carry the same liability). This opened the use of credit cards for paying most all purchases. It’s easy to dispute a CC charge with the only hassle being changing any auto payments made to that card.

So, as it stands now, we make 2 auto ACH monthly payments, mortgage (soon to end), and water/sewer. 1 intermittent ACH payment for heating oil (used to be charged to a CC, but they added a fee for CC use). I make 2 manual payments via our bank’s bill pay feature (it’s free as long as I make 1 payment), for our electricity usage and garbage collection. Our other household bills (internet, cellphones, Netflix, Hulu), are auto charged to a CC. All other purchases (groceries, household, travel, etc.), are made on CC’s which are then manually paid off each month (I have auto pay set up on each card just in case I forget). I make any manual payments as soon as funds are available, to reduce any fraud risk (they can’t steal it if I drain it beforehand).

The main dangers are related to death. Some payments will go on after death and others will stop if bank accounts are frozen. I guess that’s where the death letter, that I’ve been working on for the past few years, comes in. My goal should be to “finish” it this year. Hopefully this post will get me started again.
Your post really struck a chord. I’ve followed a similar financial path—from mailing checks to managing everything online with layered security. Like you, I use credit cards for most things now, mainly for the fraud protection and simplicity with auto-pays.

The point about death planning is so important. I’ve been meaning to update my own “when I’m gone” file and you’ve reminded me why it matters. It’s easy to put off, but a little effort now can save loved ones a lot of stress later. Thanks for the nudge.
 
This was a great walk through the evolution of how we’ve all handled money. I relate to so much of it—especially the shift from checks to credit cards and the constant need to stay ahead of fraud. I’m in the same boat with working on a “death file” for my spouse and kids, and it’s one of those tasks that always feels important but keeps getting pushed off. Thanks for the reminder—I need to get back to it too. These kinds of posts are really helpful.
 
Way back in around 1985 I was using something called "CheckFree" for on-line bill payment. The concept was so new, the screen had an image of a check and you filled in the date, recipient, amount and note just like a regular check.

I remember being very leery such that I only had one recipient at first to make sure it really worked and then added a few more each month. IIRC, you called it up with a DOS prompt.
 
At most we write one cheque per year.

And it is a PIA to actually hunt down our cheque book.

Last time we ordered cheques, at least 9 years or so ago, it was from the same printer that our bank uses.

The only difference was price and delivery. Got them in a week, the cost was exactly half of what the bank would have charged.
 
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I looked at my checkbook the other day and noticed I only had three checks left. I searched to see if I had any more packets of checks but I couldn't find any. Probably threw the box they came in years ago. Guess it's time to order new ones as I might run out in a couple years but have no idea where to go these days.
You can still order checks through Costco. That was where we last ordered, over 10 years ago. I assume it’s still cheaper than ordering directly from the bank.
 
I write a check only when forced, which is why I still have checks from forever ago. Maybe two a year?
 
I still have over a hundred checks from Washington Mutual, which collapsed in 2008. As everyone knows, Chase took them over and (as everyone might not know) kept the routing and account numbers the same. I still use about one or two of these checks each year.
 
It’s been a very long time since I ordered checks, and I still have one checkbook left that may last me over a decade. But I think there was always a decent free set of checks available from the bank so I always ordered those.
 
Your post really struck a chord. I’ve followed a similar financial path—from mailing checks to managing everything online with layered security. Like you, I use credit cards for most things now, mainly for the fraud protection and simplicity with auto-pays.

The point about death planning is so important. I’ve been meaning to update my own “when I’m gone” file and you’ve reminded me why it matters. It’s easy to put off, but a little effort now can save loved ones a lot of stress later. Thanks for the nudge.
I'm w*rking on my succession plan. Not as easy or straight forward as I'd hoped. YMMV
 
I'm w*rking on my succession plan. Not as easy or straight forward as I'd hoped. YMMV
Likewise - I find the whole process a tad depressing, knowing that people I haven't seen in a long time will just BTD. Will likely add some more charity stuff and may even do some BTD myself.
 
I am almost fully on autopilot, but I get texts and/or emails alerting for most.
 
My "When I Die" notebook is done and DD has it. Now waiting for the kickoff event.

As far as bill paying, I have four CC's:

One for Costco gas and shopping (paid auto withdrawal from my Ally account),
One for only periodic auto charge payments like health ins, fiber line, Apple subscription, etc (paid auto withdrawal from my Ally account),
One for General use (daily purchase items), (paid auto withdrawal from my Ally account),
One for Amazon (Chase 5% off CC), auto paid monthly out of my Chase checking account.

I pay a few services through a Zelle transfer (Chase checking).

All utility bills are on autopay to CC's or my Chase account.

I wrote two checks last year, property tax and HOA payment, but I COULD have used a CC if I wanted to pay a 3% fee. But I am cheap.
 
Pretty much automatic now, a few checks to charities, property tax.
Probably time to review and update our end of life notebook.
 
I have always used an outside vendor when I buy new checks, although that has happened very rarely lately. The last time was back in late 2016 when I bought 150 checks from Designer Checks for $5.50. I still have 33 checks remaining, so that will last me around through the end of 2027.
 
Related story I may have posted before.

My 86 yr old cousin calls me from time to time to take her to the credit union. I try to convince or show her that she can conduct business online but inevitaby she insists she has to “talk to somebody” at the credit union. So I pick her up to go to the credit union. On the drive over she tells me a story about my grandma. Many eons ago grandma asked cousin to drive her to the bank. Cousin agrees and grandma gets “dressed” to go to the bank. They get to the bank and cousin wheels her TransAm into the drive-up teller lane. Now I’m picturing grandma in her business dress and hat in cousin’s TransAm. Grandma says “What are you doing?” Cousin explains the auto teller but grandma says “ Oh No!! I need to go inside and watch them put my money away!” We laugh and I’m thinking deja vu. At what point will I reject the latest banking technology?
 
I thought about making this post a separate thread, but I didn’t think it would be that long.

Taxes.

I’ve always done my own taxes starting from my first summer job. Early on, it was easy because I used the short form for filing. That changed when we bought our first home. Now, we had more deductions to report, so I’d go to the post office and get the needed publications and forms, filling them in manually.

As time moved forward, taxes got more complicated (or our situation changed to make it more complicated), and it became harder to keep up. But then the age of PCs came and we had a program called TurboTax. No more following tax changes, just let the program do it.

Many years I dutifully purchased TurboTax until that year they changed pricing. I jumped ship, landing on H&R Block, which has kept pricing about the same (with discounts). I use the PC version, mainly to keep our data stored locally. I just don’t trust the web/cloud for storing our records.

I foresee doing our taxes until I die. As for DW, she’ll likely hire it out (or won’t file?!!?), or might have our oldest do it, who does his online. Oh, I also do our other kids taxes, but I have tried to get them to do it themselves.
 
I wrote two checks last year, property tax and HOA payment, but I COULD have used a CC if I wanted to pay a 3% fee. But I am cheap.
My annoyance with paying the property tax has gone through several stages. I hate mailing checks for bills and if you want a receipt you have to enclose a self-addressed stamped return envelope. It would take a very long time to process. So I started going to the closest property tax office, not too far, but that involved standing in a long line for the privilege of paying in person. Got fed up with that so for several years I went by a local bank, not far away, that accepted property tax payments for the county, no lines and could even use the drive through. But I even got tired of that once a year errand. So I finally switched to a using high rewards card which covers most of that cc fee and am always really glad I did so. Way easier and instant, no travel. And receipts are available online now even though it takes a couple of weeks to show $0 owed. Also I get email notifications of my property tax bill and retrieve it online.

The quarterly HOA fee is paid via bank billpay. I think it is the only one where my bank still mails a check, although maybe the city water/garbage collection still does too.
 
We were homeless for one year in 2011. Kept an accommodation address at our son's home for those docs that could not be sent by email. There were only a few. And even those eventually moved to the web by the originating orgs.

We were forced to move everything possible to the web. That included moving all expenses, home and travel, to a combo of either bank autopay or credit card charges.

It was a PIA to do it but we have certainly reaped the convenience benefits ever since.
 
Yes, we went through the same thing in 2005-2010 when we were living in our RV and traveling full time. We set up a mail service with Escapees, a TX based organization supporting full time RVers. Used USPS general delivery when we stopped somewhere long enough. Moved everything possible online. And we had worked so hard to eliminate as much mail as possible there was little to send. Overall it worked out great. We still maintain that mail service address for longer trips >30 days.
 
We did the same in the 90s, ha ha!
Me too. And I have a faint recollection of using a bill pay service that Quicken offered that was a fixed monthly fee for up to 25 checks and 25 cents per check. It was easier and cheaper than buying check stock, printing and mailing checks. When free bank bill pay came along I jettisoned that service.

About 10 years ago I sat down one New Year's Day and put everything possible on bill pay... to my 2% rebate credit card if possible with no fee and otherwise to checking. I've never had a problem with a bill pay.

Today, the vast majority of our bills are auto pay, some I order a check sent from our bank and every once in a while we write a check.(about 20 last year and that was an unusually big year with our move and all).
 
I have a 1-page yearly summary sheet of bills and payments on my desk. There are columns for close, due, and pay by dates. It's printed out at the beginning of the year, for 12 months.

After paying/confirming payments (some auto, some manual) I enter the amount in the correct space. This helps me track various things manually. And if someone needs to take over tomorrow, this is their quick start.
 
One other benefit to being homeless for a year, moving, and transferring everything possible to the web was the huge decrease in hard copy junk mail from our previous residence.

So easy with email. Unsubscribe, block, or hit the delete key. Or empty the spam file.
 
One other benefit to being homeless for a year, moving, and transferring everything possible to the web was the huge decrease in hard copy junk mail from our previous residence.

So easy with email. Unsubscribe, block, or hit the delete key. Or empty the spam file.
I still get way too much snail mail and have everything e-delivery /e-payments.
 
I don't know exactly, but roughly 1979 my bank had an ATM card, called "Treasurer." I found that a great tool when low on cash, for example, on a Sunday. Likewise, I was one of the early Direct Deposit users for my paycheck. I had to ask my bank and Payroll department, but the process was easy. Like others here, nearly all of my bills are auto-paid by credit card. And all of my credit cards have closing dates near the end of the month, so come the first of the month we pay all of the bills, and don't have to think about it again until the enxt month.
 
I recently put all the bills in my wife's brokerage cash management account, and pay everything through that. My wife could pay bills through the mobile app (I taught her how to do it, and remind her she "knows how", occasionally), but I pay them (manually, none are auto-pay). My personal finance software has a list of what's due, so if a paper or email bill gets lost, I still have a reminder that I need to manage that payment. The exceptions are vendors that allow no-fee credit card payments (can't give up 2% on a $400 heating bill). And I don't allow ACH pulls except for when there's a good discount (like 4% on the Medigap).

As to continuity, I've put a camera on my head and started a screen recorder, recorded myself paying bills, etc. Then I edited the head-cam and screen recording together so it would be easy to see where the paper files are as well as what I do on the screen. All the passwords are in a vault, and the master password is in a known location, on paper.

But given that the only constant is change, I'll need to re-record the process again in the future. That would be easier than trying to elucidate edits on the old process.
 
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