“Can I Automate That?”

Life Hacks for Simpler Lives

John Doherty
4 min readApr 15, 2014


I read Tim Ferriss’s The 4 Hour Work Week when I was 24 years old. It actually ruined my life (in a good way) as I read it alongside watching Office Space, because I realized what my life had become. Six months later I was on an airplane back to Switzerland to pursue a new life. Six years later I live in San Francisco.

But this story isn’t about that. One of the biggest takeaways I had from The 4 Hour Work Week was how Tim automated a lot of his life so that he could focus on what Seth Godin calls “the big work”.

As soon as I read the points about automation, I immediately signed into all my utilities and other recurring monthly payments and automated them. I never want to become like my father was once per month, sitting down at his desk with a sad look on his face to pay bills manually, one at a time. Instead, I’ve automated all of the following (and soon to figure out more):

  • Car payments
  • Car insurance
  • All utilities (electric, cable, Internet, you name it)
  • Cell phone bills
  • Gym memberships
  • My apartment search in San Francisco (I work for HotPads.com where we allow people to do this)
  • Birthday reminders (but not gifts)
  • New car search (using IFTTT triggers)
  • Posting Rebecca Black’s “Friday” onto my Facebook wall every Friday to troll my friends.
  • Puppy search (using IFTTT triggers)
Example of an automated Craigslist email using IFTTT

A coworker who uses Bank of America told me that she’s automated her rent by using BofA to send a check from her account to her landlord on the 28th of each month, ensuring that it arrives at the correct time. Smart!

Not everything should be automated, though. Let’s unpack that a bit.

What Else Can I Automate?

You can automate most things including both serious and non-serious tasks that a) remove the need to remember to do them, and b) bring joy to your life.

I work in marketing where one of the popular themes of the day is “marketing automation”. According to this VentureBeat article, marketing automation still has a long ways to go and is a huge market. I do believe in automating the processes of collecting data and moving them into the correct places. I don’t believe that we should automate any human interactions unless we have thought them through carefully and are willing to test and change them as we receive feedback. So, we can (and should) automate email marketing, but not without consistent oversight.

What Else SHOULD I Automate

Some things should not be automated. I mention above that I’ve automated birthday reminders, but not birthday gifts (some online flower companies will alert you when a birthday is coming up the next year. Super smart). I think my approach to automation can boil down to this:

Automate anything that you hate to do, but never automate relationships.

By this I mean that automation of menial tasks like bills is a value add to your life. However, relationships are of high importance so we should not try to automate or optimize our way through relationships. (Side note: I severely disliked this post about how a guy did it). You can automate reminders that you’re supposed to hang out with a friend this evening, though.

When you try to control relationships too tightly, you lose out on the serendipity of relationships (this is also my issue with “productivity nuts” who try to optimize their whole life). Serendipity is part of what makes human-to-human interaction so powerful. Rand Fishkin wrote a great post about manufacturing serendipity that you should read.

When you start thinking about automation through the lens of relationship, clarity begins to emerge. For instance, don’t only automate your Twitter feed. Yes, use tools like Buffer to schedule your tweets, but if you just tweet everything you come across your feed becomes noise and you miss out on opportunities to connect with others. Take Guy Kawasaki’s Twitter feed:

Tweets posted automatically every 5 minutes. No human interaction.

What have you automated in your life? What have you automated that you later rethought? Where do you disagree? Tweet me — @dohertyjf



John Doherty

Founder & CEO of Credo (getcredo.com). Veteran digital marketer in Denver. Entrepreneur. Traveler. Skier. Other sites: johnfdoherty.com and singlegeared.com