The rule that worked too well.

Ever since I got my first taste of business success back in 2009, I had a very simple way of deciding what I wanted.

More.

I wanted to make more money, take on more (and bigger) responsibility, and find more customers and readers. If something worked well, my goal was to make it work better.

And candidly, for a long time, that was probably the right approach.

The couch years

When I was 28, I had already been fired from a bunch of jobs, was deep in credit card debt, and struggling to survive in NYC. My life had been reduced to sleeping on a couch in my friend’s living room in Brooklyn, next to a rusty old rolling rack that held all of my possessions.

That 28-year-old version of me didn’t need to sit around philosophizing about what “enough” meant. He needed to get his act together and start making some money. More was incredibly important at that point in my life.

When the rule stopped working

The problem with a rule that works is that nobody tells you when to stop following it. More kept delivering, so I kept asking for it, long past the point where each additional win was costing me something I couldn’t see yet.

Cheers,