Sorry for going all Fiona Apple on you with the long title. (I’m also sorry for the vague Fiona Apple reference that only myself and maybe two other sad people in the world will get without clicking the link)

Like everyone who has bills to pay each month, I am frustrated. My reason for frustration is not because I don’t have enough money to pay all my bills (although it feels that way sometimes). It’s not because I am late on payments due to forgetfulness (I’m forgetful, but not when it pertains to money). It’s not even because a little part of me dies inside every time money leaves my bank account.

No, I’m frustrated because there doesn’t seem to be one perfect, easy, stress-free method for tracking and paying all of my bills. Instead, there are three decent, imperfect methods I have to use each and every month.

The ol’ Envelope and Stamp Method

This is my (and possibly your) parents’ preferred method for paying bills. Until a few years ago, it was my primary method as well. Paper bills come to your mailbox each month. The dates you receive them and their due dates vary from bill to bill. Depending on how organized you are you either pay all of the bills for the month in one or two sittings, or you sit down and pay your bills randomly throughout the month (hoping none of them are late). If you’re lucky, there is an envelope included with your billing statement you can use to mail your payment. In that pristine scenario, all you have to do to make a payment is get your checkbook, a pen, a stamp, and some saliva.

This method, clearly, is riddled with holes the size of Alec Baldwin’s head.

Online Bill Pay

The modern method for paying bills. It is the method I primarily use. You log into your banking institution’s website, choose who you want to make payments to, fill in the payment amount and date for payment, and submit. No envelopes, no checkbooks, no stamps, and no saliva. It’s pretty easy.

However, it’s not perfect. You still have to track your bills and physically sit down and make the payments. If all of your bills came to you on the 15th of every month and were all due on the 1st, this would be easy. But if you’re like me and you have ten different bills coming to you on ten different days and they’re due on ten different days, this is a hassle.

Online bill pay does allow you to make recurring, scheduled payments (if your cable bill is $60 every month and it is due the 24th of every month, recurring payments are ideal). But what if the amount due for a bill changes from month to month? My electric bill is never the same one month to the next. Neither are the last two credit cards I’m working hard to pay off this year.

Automatic Debit

Many payees offer the capability of automatic debit bill payment. If you give them your bank information, each month on their respective bill due dates they will take the amounts due out of your checking/savings account.

This is as “hands off” as you can get and it has many advantages. You’ll never have to worry about forgetting or being late with a payment, and you don’t have to worry about accidentally paying the wrong amount.

That said, depending on your preferences and situation, it has drawbacks too. Unless you always have enough funds in the bank to cover expenses, you’ll still need to keep tabs on when your bills are due. If a $300 car payment is going to be automatically taken out of your checking account on the 16th of every month, you need to be aware of this fact if you’re the kind of person who has a checking account balance that floats between $100 and $800 from one week to the next. Also, the notion of giving a big company access to your bank account is a bit much for some people.

Conclusions

So what’s the perfect method? Sadly, I don’t know of one that works in all situations for all people (much less one that works for me). In my situation, only half my bills are eligible for automatic debit. If my preference was to use this method (and it is), I couldn’t use it for all my bills. Five of my bills would have to be paid via online bill pay. And one bill, as hard as it is for me to grasp since we live in the year 2007, can only be paid via paper check.

What about all of you? Is there a method I forgot? How do you handle the mind-numbing chore that is paying bills each month?

While it originally debuted on my blog, this article was revised and later published at Associated Content on July 13, 2007. You can go read it here.