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Becoming Jobless

I wrote or published 62 blog posts in 2020.

But only a handful of the 62 were easy to write.

I spent most of my time searching for topics that might be of interest to a wide array of individuals.

I tried to niche myself into a space that was interesting and fun. A space where other smart, creative people lived. Something akin to self-improvement and productivity.

Sometimes I found my way there authentically. Other times I tried, and likely just regurgitated something Naval tweeted.

Literally, I spent one weekend “living” a Naval tweet and wrote about it. People read it, even Naval.

But it fizzled out. I couldn’t keep up with scoring myself and my productivity.

I obliterated any and all atomic habits I had built. And I sunk into a largely unproductive shell. I wasn’t writing, reading, or working out.

I wasn’t self-improving and I knew it.

I’m not alone of course. Akratic behavior plagues us all. I wrote about it last year.

And before that I wrote about how much grit I had. The level barely registers.

So it’s no surprise I couldn’t stick with schtick. I’m not a self-improvement guru.

Productivity Twitter is fun but not my home. I’m a degenerate.

I’d love to be Tim Ferriss…but I’m more at home pretending to be Jonathan Bales.

I belong with the sports-betting, daily fantasy sports-playing, CryptoKitty-owning, NBA TopShot-sleuthing members of society.

But that’s not so bad….and embracing that makes this much easier to write.

For a while, I ran from this group, in search of more legitimacy.

But all I realized was that the friends I made while playing and writing about fake sports for money were still the smartest people I knew. And while yeah, they have unconventional jobs…jobs that boomers scoff at, they aren’t so different from the most successful members of any field.

They hunt edges. They view the world probabilistically. They take chances. They understand risk and reward. They read Atomic Habits. They understand compounding returns.

Grown men bickering about the value of digital trading cards might seem silly.

Unkempt, pajama-donning data scientists that simulate basketball games nightly might even look jobless (not you, Dink).

But that type of joblessness is my dream. It’s core of this pursuit. Making a living through unconventional means.

The type of unconventional living that allows me to order as much Thai food as I want.

The type of unconventional living that allows me to wake up wherever I want, whenever I want.

And the type of unconventional living that has my mom begging me to do something “more normal.”

If I find that – I’m right at home.

And hey, leave my mom alone – she just wants what is best for me, but she can barely use an iPhone and thinks everything on the internet is a scam…she’s almost right.

These posts will be the documentation of my journey to jobless, the pursuit of a life fueled by antifragile income streams, ones that might seem silly and unconventional to you.

It’s scary. I’m far from it. But it’s the identity I’m seeking.


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