Pepperoni turned to pineapple

When I started out in customer support, thousands of people would contact us every day about resetting their password. In order to do so, they would have to answer a security question which they set when they created their account. It was easy to predict which users could answer their question and which would fail and ultimately call us assholes and fascists.

It had nothing to do with the people and everything to do with the question they chose.

In 2007, there were two types of security questions:

  1. Factual: E.g. The name of your third grade teacher, grandmother’s maiden name, etc.
  2. Opinions: E.g. Favorite pizza topping, favorite hobby, name of your best friend, etc.

Factual questions were never a problem. Facts don’t change. You might forget the name of your third grade teacher, but her name is fully independent of your feelings, preferences, and desires. Conversely, opinions are nothing but the shifting sum of our feelings, preferences, and desires. Opinions are the meals we cook with whatever happens to be in the fridge at the time.

Whenever we told a user that no, their favorite pizza topping was not pineapple, they’d go apeshit. “I know what pizza I goddamn like, you dicks, now let me into my account.”

I will repeat, the problem wasn’t the users, it was the questions. We make the mistake of thinking about our preferences as malleable in the past, but stable in the future. People create their account thinking they’ll always love pepperoni, not imagining the possibility that in eight months a pushy date will insist they try Hawaiian pizza and blow their mind.

Our favorites are fickle.

And so is our motivation.

In an ecstatic midnight fit of passion, we bought the domain name, mocked up designs, drafted our blog posts. It went really well. Really well. We got a lot of Likes that first month.

Six weeks in, something changed.The thought of working on our side project didn’t move us like it first did. We wanted to spend Saturday morning testing AdWords, but we just weren’t Feeling It. We wanted to join that new morning running group instead. Or we hadn’t had a good brunch in a while and wanted to hang out with our friends. Pepperoni turned to pineapple.

As marathon runners know, motivation will not get you across the finish line. Motivation won’t get you further than a dozen blocks. We must plan to feel indifferently about the thing we love right now.

My favorite resource on how to develop that plan is Seth Godin’s The Dip.

Of course, it might not be my favorite in a year.