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.
Totally relate to this evolution—we went from stamps and envelopes to watching real-time alerts pop up on our phones. I remember feeling nervous the first time I paid a bill online. Now it’s second nature. The point about what happens after death is something we don’t think about enough, though. That "death letter" is a smart move. I started a Google Doc for my spouse with logins, payment methods, and what needs to be canceled or updated. Not fun to think about, but it makes things a whole lot easier down the line.
 
Totally relate to this evolution—we went from stamps and envelopes to watching real-time alerts pop up on our phones. I remember feeling nervous the first time I paid a bill online. Now it’s second nature. The point about what happens after death is something we don’t think about enough, though. That "death letter" is a smart move. I started a Google Doc for my spouse with logins, payment methods, and what needs to be canceled or updated. Not fun to think about, but it makes things a whole lot easier down the line.
Other than our mortgage payment, the first auto payment I set up was for water/sewer. Prior to allowing them to make a direct withdrawal, the only options for payments were by mail, dropping it off at city hall or a drop box at a grocery store. Once I saw how well it worked, I started paying CCs online. When monthly bills started accepting CCs for payments, they went on a CC that offered 2% cash back. Now, some of those bills are charging a fee for CC use, so those are going to direct withdrawal.

I think I started my letter 3 times over the last 5 years. My goal is to finish it this year.
 
I love the BofA billpay because they can pay anyone, even an individual. When I get a bill for a one time event, I can add them to billpay. BofA will even send a paper check by snail mail. I assume other billpay systems are comparable but I hate the thought of setting up all my payees in a new billpay system. Over 20 years without a late payment even with snail mail.
 
Way, way back, I could dial-up my credit union at 1200 baud, and it would slowly list, in ascii characters, the last ten checks that cleared.
I call mine if I want to know if something cleared. The automated voice reads it to me. Faster than logging in cause I can multitask. I can listen and do things, I can't type and do things. I rarely care much though it all works out in the end.
 
Quicken tracks all scheduled payments and recurring payments like monthly annually quarterly, some custom. Several like CCs, utilities, change monthly and get updated when emailed the bill - update quicken and bill pay together. So DH and I have a central location for that critical info and it also shows future cash flow by account which is very helpful.

Also going on a long trip (don’t take a laptop anymore) this setup helps me prepay most bills especially CCs so minimal happening while we are gone.
 
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.
Is this continuity for your wife when you are gone? I see that as being a problem for my wife, I do online bill pay, but my wife is basically computer illiterate except for clicking the links I setup for the local grocery store ads.
 
Nah, she's technically capable. And I figure my daughters will come stay for a while too.
 
Well, there's always the bank where the account is, but of course they gouge on the price. The last time I ordered checks (maybe five years ago?) I ordered them from WalMart, which was the cheapest reputable company I could find. I think Amazon also sells checks but I haven't looked lately.
If you use Fidelity, they are free.
 
I have most bills auto charge the CC then I pay the CC bill when due online from checking.
 
My story is somewhat different. When I retired in 2009 (age 55 1/2) we were GONE from home over 50% of the days the first year.
I do NOT like letting people "take" money from our account
I set up an Excel spreadsheet with Hot Links to each payee ( electric, natural gas, c/cards, etc)
It is a little cumbersome but it works for ME. On the first of the month, I open each link and SEND them the money. Right now there are about a dozen. Does not take very long.
The ONLY exceptions, where I ALLOW them to take $$ are: Insurance (Auto, Home & Umbrella) Our CalPERS Long Term Care policy and our HOA dues.
I like haveing the control of what goes out.
 
For continuity when I pass (statistically more likely... sigh) I did a Word document called "Bill Paying Instructions" DW has hard copy and also where it is on the laptop desktop. Has screenshots from every company - from their Home Page clear thru their "Submit" or "Pay Now" button.
A LOT of work, but she is a very methodical woman and feels more comfortable having step-by-step instructions. I update it each year or so - SOME companies just cannot leave their procedures ALONE.
 
My story is somewhat different. When I retired in 2009 (age 55 1/2) we were GONE from home over 50% of the days the first year.
I do NOT like letting people "take" money from our account
I set up an Excel spreadsheet with Hot Links to each payee ( electric, natural gas, c/cards, etc)
It is a little cumbersome but it works for ME. On the first of the month, I open each link and SEND them the money. Right now there are about a dozen. Does not take very long.
The ONLY exceptions, where I ALLOW them to take $$ are: Insurance (Auto, Home & Umbrella) Our CalPERS Long Term Care policy and our HOA dues.
I like haveing the control of what goes out.
It's all about what works for you and what level of control you feel you need. Personally, I find it quite easy to have them charge the credit card and then I pay that bill from checking. The airline miles are just a bonus.
 
It's all about what works for you and what level of control you feel you need. Personally, I find it quite easy to have them charge the credit card and then I pay that bill from checking. The airline miles are just a bonus.
Curious, are you charged a fee when you pay on your credit card when paying your monthly bills?
I ask because I would like simplify my bill paying, but the possible added fee's stop me at the moment.
 
Curious, are you charged a fee when you pay on your credit card when paying your monthly bills?
I ask because I would like simplify my bill paying, but the possible added fee's stop me at the moment.
No - I have never been charged a fee by anyone I pay that way. I would think it would save them some time and money as they don't have to send out an email or paper bill and then have someone followup when the payment is finally received. I think some of the cell providers prefer you to use auto pay and charge you more if you don't.
 
I use Schwab Bill Pay for most payments. AFIK they either send a check or pay the vendor electronically. No credit cards involved. I have a few vendors (internet service at the lake home, for example) that do not directly participate in the Bill Pay program, but their billing ($66/mo IIRC) is regular so I just have Bill Pay set up to send them a monthly check in that amount. So ... friction free. Since virtually everything is in Bill Pay, on my demise DW will have no difficulty in taking things over.

Re checks I write two types: Checks to the wine store (sole proprietorship) to save him the discount whack. Schwab has also sent me a book of checks that I use to pay QCDs, so a bit anachronistic but effective.
 
Curious, are you charged a fee when you pay on your credit card when paying your monthly bills?
I ask because I would like simplify my bill paying, but the possible added fee's stop me at the moment.
My credit card reward is 2% cashback. As long as the fee is less than 2% I still use my card. Most of the fees are a flat amount $2 or less. My utility company charges 3.50 I think so sometimes I pay two months at once. Things like monthly insurance payments have hefty fees but no fee if you pay the full premium plus 2% cashback
 
Quicken tracks all scheduled payments and recurring payments like monthly annually quarterly, some custom. Several like CCs, utilities, change monthly and get updated when emailed the bill - update quicken and bill pay together. So DH and I have a central location for that critical info and it also shows future cash flow by account which is very helpful.

Also going on a long trip (don’t take a laptop anymore) this setup helps me prepay most bills especially CCs so minimal happening while we are gone.
I pay my two CC balances twice a month whether I'm at home or traveling, using their apps on my smartphone...
 
...I do NOT like letting people "take" money from our account

...The ONLY exceptions, where I ALLOW them to take $$ are: Insurance (Auto, Home & Umbrella) Our CalPERS Long Term Care policy and our HOA dues.
I like haveing the control of what goes out.
You should consider getting over your phobia. I've had autopay a long time and have NEVER had a problem.
 
Curious, are you charged a fee when you pay on your credit card when paying your monthly bills?
I ask because I would like simplify my bill paying, but the possible added fee's stop me at the moment.
IME it varies. If there is no fee, I autoay to the credit card for get the 2% rebate the my credit card pays me. If there is a fee then I have them withdraw from my bank account since there usually is not a fee for that.
 
Recently, 2 vendors offered incentives for not using CCs for paying their bills. One was going to place a 3% surcharge and another offered a discount for not using CCs. So they’re both set up for direct withdrawals.
 
Recently, 2 vendors offered incentives for not using CCs for paying their bills. One was going to place a 3% surcharge and another offered a discount for not using CCs. So they’re both set up for direct withdrawals.
In one those cases, T-Mobile, I added their Money checking account and move cash there every 6 months to cover the phone bills.

Most other vendors get sent a check from my bank or if they allow auto pay by credit card with no fee I choose that first.

Health insurance premiums and income tax payments are direct debited.
 
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For bills that I can’t pay by CC, but can pay via a withdrawal initiated by others, I have a special checking account with a local credit union. I periodically make a deposit to it that will cover the expected withdrawals. My main account where things like the SS money gets deposited is not used to let others pull money from it. I do use BILL PAY in my main account when I initiate a payment to those I owe money.
 
Curious, are you charged a fee when you pay on your credit card when paying your monthly bills?
I ask because I would like simplify my bill paying, but the possible added fee's stop me at the moment.
I like to pay all my bills with my airline AMEX card and I have not been charged any fees for that. In fact, a couple give a negligible discount for setting up the automatic payment.

My electric utility won't allow me to setup automatic payments with a credit card as they require ACH from my bank account. As I live in Atlanta with not insignificant electric bills (air conditioning), I do get quite a few airline miles/MQDs from paying with my CC. So I set the account up to ACH with my bank and then pay it off monthly using PayPal which then charges my AMEX CC. No fees and just a minor inconvenience. The ACH is setup in case I forget to use PayPal so the bill will get paid anyway. Interesting that I can do one time payments with PayPal or my CC but not recurring payments.
 
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