The Regret Minimization Framework.

Today marks a full week in the city of Chicago and it’s official. I am in love.

Which is a huge relief, because looking back I was incredibly nervous about moving here when we first decided — even though I wouldn’t admit it to myself.

Big City. Away from small town home. New friends. New routines. Complete change.

(Plus everything your parents tell you about what they hear about big cities like Chicago from Fox News or whatever).

I spent a few hours before we moved combing through every online database I could find about Chicago. Hoodmaps. Crime Rates. Cost of Living. Weather. Happiness Index.

Tried to see if there was any data that could convince me to reconsider. To avoid the risk and keep the safer bet.

But now that we are HERE, I couldn’t be more happy. There’s exuberance, there’s enthusiasm, there’s ambition everywhere. Everything is shiny, everyone is in shape, the buildings are beautiful, the night life reminds me of movies from when I was a kid.

And tbh the groceries cost less than I expected and there’s been way less crime and homeless people than even my previous home in Minnesota.

Parking is expensive and commuting is harder but for a guy who works from home or coffee shops that’s an easy penalty to weigh.

This whole experience of moving has taught me a really valuable lesson. That often times, the best decisions are the scariest. And in many ways, they should be.

An old saying has stuck with me for years.

“There is no comfort in the growth zone, and no growth in the comfort zone”

And I think about it often in times like this. Or even in the micro-experiences of uncomfortable or inconvenient daily tasks — getting up early, going for a run, sending cold emails — in many ways the creature comfort accoutrements of modern life have made us soft.

We rarely do anything hard anymore. When the real purpose of life is to take the difficult thing by the horns and bend reality to your will.

That is what starting a business is about. Or running a marathon. Or getting married or moving to the big city or whatever that big scary goal staring you in the face really is.

One of my favorite videos is from Jeff Bezos. He talks about his Regret Minimization Framework as a tool for making big scary decisions in your life.

The premise is this: when tasked with choosing between to big giant alternatives, you should choose the option that you will regret least when you’re looking back from your 85 year-old bed.

Here’s the video — try to watch it once a year: