I pay bills twice a month, on the 1st and the 15th. I keep a buffer amount in checking so that I know that everything can be paid, and I created my own simple cash flow/budget balance sheet to make sure that unexpected expenses don't cut too deeply into that buffer. I can project the entire financial year with it and then plug in actual expenses as they happen to see how they'll affect cash flow going forward. Pretty much all of our bills are payable online, and I have everything I pay bookmarked in the order I pay them each month. (For those few things that aren't payable online, I use my bank's bill pay option, which I can do through online banking, so no paper or stamps required.) I pay out the first half of the month's bills on the 1st and the second half's on the 15th, and I'm done--takes less than half an hour each time.