On New Year’s Eve, as 2008 turned into 2009, I stayed home, alone, in my drafty apartment in Chicago’s Ukrainian Village. After a year on my own, and a failed startup attempt, I had fled Silicon Valley. I felt pressure in my skull, as if my brain were going to hatch. I felt restlessness in my fingertips. I needed a cold winter, cheap rent, and some space to figure out what it was all about.

On my knees on the hardwood floor, on an $11 piece of tileboard from Home Depot, I sketched this plan.

This was how I would bootstrap my way into making a living following my curiosity. The plan was to make as little money as I needed, with as little of my time as possible, and use the rest of the time to discover and pursue what gave me that feeling of “flow” I had experienced as a child.

Since I had spent as much of my savings as I was comfortable with for now, first, I would freelance. My goal was ten billable hours a week.

With the rest of my time, I would explore ways to make passive revenue.

As I made passive revenue, I would reduce freelancing hours, and spend time on whatever I was curious about.

Eventually, what I was curious about would make money. I would use that money to explore the next thing. And, I’d repeat.