deep cut | Creating An Unpredictable Body of Work Using Paradoxical Moves with Michelle Pellizzon Lipsitz

The creative process after 35, being institutionless, & how to make more better things faster

Courtney Romano

and

Michelle Pellizzon Lipsitz

May 01, 2025

Transcript

ALERT THE PRESSES.

You can make a body of work that reveals you to be an unpredictable genius pop star at age 42, if you so choose.

Do you so choose?

If this is the year you want to stop grinding against the rickety machine that someone else built and always breaks down right before you’re supposed to get paid…

and instead you want to heroically hurdle yourself into space at rocket-speed toward your biggest goals like Matt Damon launching himself off Mars in nothing but a spacesuit and a tarp…

Then you’ll need to make a paradoxical move.

What’s a Paradoxical Move?

A paradoxical move is, as

Michelle Pellizzon Lipsitz

explains in this week’s episode, an intentional break in the pattern of your personal thinking. It’s going left when you’d usually go right.

But it’s not a grind. And it’s not random. It’s actually fast and somewhat effortless, super strategic and exceptionally fun.

I wanted to talk with Michelle about this because she introduced me to this concept back in 2021, and there’s literally no one smarter I could ask to explain it to me.

Michelle isn’t just the founder of

Holisticism

or the host of

The Twelfth House

or the creator of

SPACIES

or the brain behind

sublimatrix — a Matrix of Destiny cipher

or a consultant that offers incredible status quo-changing experiences to her clients.

After almost a decade of running a very profitable company, she could sit back and let the hits keep coming. But instead, she’s soon going to UCLA to pursue her PhD.

So truly, there is no one better with whom I could ask about making unknowable, unexpected, and career-intensifying moves than Michelle.

In this episode, we discuss:

The spectrum of age and how it changes your understanding of the creative process
The way independent artists can use institutions as a way to make their body of work at a faster rate
Infinite Games vs. Finite Games (thanks
Yancey Strickler
&
Joshua Citarella
for the inspo there!)
How to discern what you think is cool when you feel indoctrinated by the culture
How to become more unknowable and more unpredictable and evade AI from co-opting your brain
And how to use paradoxical moves in your career to find way more opportunities and get where you want to go much faster