How I prevented wasting another 480 hours of my life

Sep 06, 2013
Tim Ferriss4 Hour Workweek introduced a number of life hacks to me. If you haven’t read it, I recommend you do. By the time I was done with it, I had a virtual assistant based in Singapore and a few chapters of my first effort to write a real book complete. It also reminded me that if I'm able to kick ass at my job in fewer hours than is traditionally expected, or accepted, and make productive use of the remaining time, it doesn’t mean I’m lazy.  

The other day I was reminded of another hack it introduced: automating bills with an airline mile rewards card. Some of you may be welcoming me to the 21st century, but I know quite a few people holding out on this little hack and this post is for them.

For context:

  • I’m particularly organized with money. Meticulous even.

  • I consider myself to be a reasonably early adopter of just about anything, especially if it makes my life easier.

  • I can also delegate with the best of them. I’ve managed to delegate so much that life at times feels like a Sims game, in the “fun to play” way because I don’t have to do much myself kind of way.

Taking all that into account, as well as the fact that I go to great extents to avoid manual labor, it stands to reason I would have been using technology to pay bills a long time ago.

But I wasn’t.

And here’s why: I have trust and control issues. There’s a good chance if you’re still manually plowing through bills and paying each individually you do, too.

The idea of giving access of my credit or checking accounts to a third or fourth party just didn’t sit well. That was just too damn risky. And I wanted control and flexibility of when things were paid. After all, what if I wanted to pay the electricity bill the day after it was due? That should be my prerogative.  

The thing is, I always paid my bills and I was giving the payee my banking information anyway.
Not sure about where you live, but my corner 7-Eleven doesn't stock hormone and antibiotic free, grass fed steaks (I’m a bit of a meat snob). So I need to drive to the grocery store and to that, I need to make my car payment. Personally, things like having access to the Internet are pretty important for me. Yes, for work, but how else am I going to feed my addiction to watching meth cooking schoolteachers, pot growing housewives, and hours of stand up comedy on Netflix?

I always paid my bills, and short of a catastrophe, I was going to keep paying them. It really wasn’t worth my time to pay them manually and, worse, pay them without rewards. 

So, over the course of a few weeks I changed every bill to be paid automatically, with the exception of an investment property. Most companies let you set up automatic payment on their website. For every one that allowed me to use a credit card to pay, I used my Citi credit card, which earns American Airlines miles. ( is a great resource to find the best card for you; you can search by cards with rewards.) If the payee didn’t let me use a credit card, I used my checking account. If the payee didn’t offer automatic payments at all, I set it up in my bank’s bill payment function. Then I set the bill payment function to be paid automatically from my bank.

Once a month I look at Quicken, add up the payments made from my credit card, and make a one-time payment to Citi. Case closed.

The first time I sat down to pay bills after I’d changed everything, I got done so fast I felt uncomfortable. Surely I was missing something. It couldn’t be that easy. Surely I hadn’t wasted hours upon hours, month after month, doing this for no reason. But I had. In fact, spending just 4 hours per month on bills, I’ve wasted 480 hours and missed out on hundreds of thousands of free airline miles over the past decade.

My utility company has yet to ransack my account. Neither has anyone else. Even if they did, it’s really not that difficult to fix the situation.

Even better, I’m getting rewarded for not manually paying my bills. My AAdvantage account at American Airlines is racking up miles on autopilot.

You may have legitimate reasons to want to pay things manually. Not having enough money in your account when bills are due is certainly one of them. But if you find yourself manually paying bills every month, generally on time, it’s probably time to make a change and get a piece of your life back. Not to mention, some free airline tickets with the earned miles.

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