Today marks my 10th year as a self-employed independent creator. I don’t recommend it.
It all started when my boss called me into a conference room. As I followed her down the hall, I noticed she was carrying a manila envelope. I could sense what was coming.
It was a short meeting. She told me I was terminated, and I felt relieved. I got up and thanked her. “July 17, 2007 will be a special day in my life,” I told her, smiling genuinely. I rode the antique elevator and stepped out onto Market Street, walking confidently one more time past the tourists in line for the street car. I descended into the Powell Street BART station.
I felt sure that I’d never work for someone else again. My will to “work” was gone. I cashed out a big chunk of my retirement fund to buy myself some time. After all, I had spent years eating 80-cent Banquet® meals for lunch, saving for this moment.
The next morning, I opened my eyes to vastness. There was nothing but time to be filled, like I was just floating in space. I could do anything I wanted with that vastness — build a startup, write a book, or play Guitar Hero and eat nachos. That was every bit as scary as it was exciting. My mission was to reconnect with my curiosity — that feeling that I had had so many times, alone in my room drawing or reading, the time passing so quickly I’d forget to eat.
I wanted to find that again. If I could just find a little snowball of curiosity, I imagined that I could keep rolling it, it would get bigger and bigger, and it would fill up the vastness. Eventually maybe I’d have my own planet to stand on.
That was ten years ago. I’ve stuck with my mission, but I never imagined it would take this long.
. . . .
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.
. . . .
It’s true that we tend to rationalize things after the fact. It’s quite possible that there’s some parallel universe where I stayed in my hometown with my friends and family, or I somehow mustered the strength to to remain a designer in Silicon Valley. Maybe I’m even happier in those worlds. That’s hard for me to imagine.
I remember early on in my quest, my dad asking me “so, at some point will you decide to get a job?” It’s the kind of question you’d expect from a guy who held onto the same job for 37 years. I thought about it for a minute. A complex web of potential causes and effects unfurled in my mind. Every day, I was learning something new, and each one of those things would branch off into three more things. My answer was a clear “no.”
. . . .
I want to make a living creating. I don’t want creating to be merely a marketing strategy for other things. Is that completely insane?
Link to the rest at Medium