January 31, 2008. Screw partying on New Year’s Eve. All of the glitter and noise and feeling like the party you’re at isn’t cool enough so you’ve gotta go to a different party then another party then at midnight you still feel like there’s somewhere better you should be. It took me a long time to realize what a FOMO-fueled mind-and-wallet-fuck NYE is.
Still, I love New Year’s Eve, and this is probably the best one yet: at home, by myself, contemplating the past and thinking about the future. On my knees, whiteboard on the floor, I drew this diagram:
This was my plan for freedom. As sure as I felt it would work, I had no way of knowing. It did work. I call it “Freedom Stacking.”
I had recently moved to Chicago from Silicon Valley, tail between my legs. Why on earth would an entrepreneur move from Silicon Valley to Chicago?
It took me a few years to realize the VC-backed entrepreneurship game wasn’t my thing. I had an urgent sense of swelling in my brain. I felt sure there was something in there that needed to get out, but I didn’t know what it was.
So, here I was, in an apartment so cold I had to wear long john’s indoors, trying to figure out how to give my brain the freedom to explore.
My “Freedom Stacking” plan consisted of making freedom my main metric for success. Make just enough money to get by, and use whatever time was left to explore my curiosities.
The diagram means this. Oh, crap, you’ve scrolled down too far to see it. Here it is again:
The left side is “$ in,” or, revenue. The right side is “Company Resources,” or rather, my time.
- In the beginning, most of my money would come from “Active” revenue, or freelancing. Time in = money out.
- There would be a small amount of “Passive” revenue. As you can see in the Resources diagram, I’d spend most of my free time on Passive revenue in the beginning.
- Once Passive revenue had grown to give me more freedom, I’d stop spending time on it.
- This would free me up to explore the “Speculative:” things I was sure were in my brain, but that I needed the freedom to discover. Eventually, that Speculative thing would take up my time, and be my main source of revenue.
This plan has more-or-less worked out. I spent 10 hours a week on freelancing, ate lots of canned garbanzo beans and potatoes, and spent the rest of the time on passive revenue. As the passive revenue grew, I explored.
When I finally landed a book deal, my passive revenue streams were enough that I could stop freelancing, and afford to concentrate on the book.
This all took a long-ass time. I had started blogging way back in 2004, while I still had a cubicle job. It wasn’t until 2010 that I got a book deal. This stack-freedom-then-explore-curiosities plan is pretty much my business model now, kind of like how Amazon spends all of their profits on R&D.
Sometimes, the entrepreneurship world reminds me of New Year’s Eve: going from party to party a moment at a time, always with a sick feeling that you’re missing out. But if you take some time to think, and trust your curiosity, you may be surprised where it leads you.