I used to scramble to pay life insurance once a year or car insurance twice, because it wasn't a bill that came due every month. Now I make a list of every bill like that, add up the estimated costs & divide by 12. I save at least that every month to cover those bills.
My list includes: life, home, and car insurance, property taxes, school taxes, estimates of federal, state, & local tax. I add eye-glasses every-other year.
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Many companies send out bills that are due on the 1st & 15th. Like a number of companies, mine PAYS on the 1st & 15th. Sometimes money going into my account wouldn't get in before the bills were due and I'd have a penalty or have to pay more interest. I contacted ALL the people who bill me, including my mortgage company, & they have all agreed to make my bills due on the 5th & 20th. I had to climb a few "Customer Service" ladders, but now my bill paying doesn't cost me penalties or interest.
I keep a small mail holder box hung up near a calendar. When a bill comes, I stick in the box and post the due date on the calendar. I keep the bills in order so that the next bill due is in the front of the box. The calendar gives me a visual aide to remind me when bills are due.
For my family, I make out a monthly budget of all monthly bills (such as mtg, groceries, credit card, utilities, etc). Start by making a monthly template and each month it is easy to stick to what needs to be paid (mtg, child care, car pymts, food, etc) I have found by doing this I have paid down or paid off bills quicker and still have money left over at the end of the week and month. Also make sure you list money placed in savings as a monthly "expense" so you build up your fund.
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