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We're living on Easy Street! How to use automation to pay bills on time, find free time, most of the time

Updated: Oct 23, 2025

We're living on Easy Street!


If you have read my blog on Free Money! then you recall that one of the most important things is to pay off all credit cards in full each month. First, this prevents you from spending (and living) beyond your means. Second, this is going to help you get to "Easy Street" by using automation.

Amber Rudd is right.
Amber Rudd is right.

Automation does drive the decline of repetitive tasks. So how can we automate to pay bills on time, find free time, most of the time?


First, let's start with your regular bills and savings goals. Car payment? Rent? Vacation Savings? Great, you have these identified.

Next, work with your bank and lenders to autopay these bills on a set date each month.

Then set a reoccurring reminder on your electronic calendar to remind you when bills are paid each month and the amount. (enter an average amount if the monthly total varies) At first, the reminders will remind you to confirm that your auto-payment went out and the lender received the payment. As time goes on, it's a great way to see your minimum monthly personal spending.

You're off to a Great Start!

Let's take this further. What about the bills that won't accept auto-payment? What about expenses that change amounts all the time? Well, my friend, this is where the magic happens! Let's go back to Free Money! where you did your homework and found a credit card that offers an awesome cashback program. Now, take that card and set up payment for the variable expenses. You know the ones, grocery delivery, Amazon Subscribe & Save for dishwasher detergent, pet treats, and the macaroni & cheese that keeps disappearing.

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