There are two main ways to set up bill paying - the old fashioned way with
Pros - faster, usually, since accounts can be credited the same day, especially if using the account website (Capital One, for example) versus your bank's online bill pay option
Cons - for us poors, you might need a day or two to make sure you have enough cash in your account to cover the bills
Pro - some banks, like my awesome one, offer rewards for using the online bill pay
Con - it is easy to forget when a bill is due and/or record the transaction in your register
Pro - a paper trail is created should you ever need to verify a payment or fight an unfair charge
Con - you have to make sure you always have checks on hand and stamps
Pro - some accounts, like medical bills, still usually only accept paper checks
Con - some poor account representative will have to try and decipher your serial killer handwriting
I do about 90% of bill paying online. I have alerts set up on my computer and smartphone to remind me to pay bills on time. I also have my bill checklist to help remember as well as a daily planner. My bank offers a mobile banking app, so I can pay bills anywhere, anytime. And I get those rewards I mentioned above. All and all, it's pretty sweet.
For the other 10% of bills, ones that need actual checks in the mail, I like to sit down once a week, usually on Thursday since that's shitty TV night, and write all the checks and enter the transactions into the register. Then I stamp them bitches and put them in the outgoing mail slot for a trip to the mailbox on Friday morning.
Organize along with me in The Good Wife's Weekly Organization Challenges