DAY 12: The paradox that has haunted me

Friday, February 3, 2023

WFIW of the Day: Going on an impromptu jog with my husband. Nice and slow. Admired the neighborhoods, moved my body, connected with him. It was fantastic.


I did not tiptoe into meditation. I was dropped into the deep end like a kid in an 80’s swim class.

It was 2010. I had graduated from NYU Law School and was working my ass off as a corporate lawyer in Times Square. When I wasn’t working or sleeping… I hardly knew what to do with myself. I remember going to a lot of kickboxing classes because it felt like a productive use of my time. I did that, and a lot of meaningless shopping. I lived with my boyfriend, but we hardly ever connected on a deep and honest level, because we didn’t know how to tell ourselves the truth, let alone each other.

In short, underneath a fragile shell of successful busy-ness, I felt completely hollow.

So when my friend Julie told me about meditation and how it helped her to feel more at peace… my ears perked up.

And one Sunday, I found myself sitting on a cushion in a spare, high-ceilinged room full of windows, somewhere in Brooklyn, staring at a piece of the white wall in complete silence thinking,

“Hooooly hell, what madness have I gotten myself into?”

I think we were 6 minutes into a 45-minute silent meditation.

Deep end.


The weird thing is, I kept going back. There was something about being forced into silence, just breathing and listening to my own brain, amongst all these other people who did seem much more “zen” than your typical harried corporate lawyer…

~~~And I’ve had a lusciously fulfilling meditation practice ever since~~~

HAHA… NO I HAVEN’T.

But my chronic difficulty with sit-down meditation is a story for another day.

Today, I want to hash out the seeming PARADOX that haunted me as soon as I learned about the possibility of a more peaceful, contented existence.

>>>What is the difference between CONTENTMENT and COMPLACENCY?

I mean, if we all became completely serene and unbothered by life, wouldn’t we stop progressing as a species? Wasn’t sitting on a rock in contemplation the very opposite of forward motion?


My whole life, I had operated under the belief that good things came from hard work, even (and especially) if you didn’t want to do it. If you could push yourself past the point where everyone else gave up, you’d get the edge… you’d be the best.

I got a LOT of praise and validation for being the best.

And we celebrate the WINNERS in life, especially here in the good ol’ U.S.:

  1. The athletes who train so hard they have to plunge themselves into ice baths to recover.

  2. The CEOs who crush all the competition (and who really cares if they thought of the idea or stole it, as long as they’re bringing that new convenience to the masses).

  3. The valedictorians, the “employees of the month”, the Ivy League, the artists whose pieces sell for the most millions.

Not that there’s anything wrong with celebrating excellence.

But when the stories all seem to imply that this excellence is born out of desperate striving, Steve Jobs-level assholery, bodies pushed until they break, tortured creatives who eventually kill themselves.

When we think that excellence only comes from exquisite pain… what’s up with that?


I think that was the source of the seeming PARADOX I was wrestling with.

Because what I realize now is that CONTENTMENT vs. COMPLACENCY is a false binary.

It assumes that:

  • Contentment and peace look the same for everyone (i.e. sitting still for most hours of the day, not consuming much).

  • Feeling peaceful erases the desire to change things about the world.

  • Moving forward, progressing, creating new revenue streams… those are what we SHOULD be doing at all cost.

It was a “paradox” that flattened out the delicious curves of human existence and made some seriously stupid assumptions.

But it felt REAL to me back in 2010. I could not get my mind around it.

Because I wanted to hold onto the system that had gotten me so far in life. Because I WAS the valedictorian who went to an Ivy League school and was earning fat money being the hardest-working associate in my law firm.

It didn’t occur to me that the MOST creative, juicy, true and disruptive lives come when we reach for more peace and acceptance within ourselves. That some of the most centered people, deeply in touch with truth, have led some of the most world-changing movements.

That working until your soul is small and sad… that only earns you the right to more of the same work.


I wonder what kind of progress and technology and art and culture would have been created out of the pure, powerful, joyful curiosity of people, instead of out of a desperate need to prove themselves worthy?

  1. What I created out of striving to meet the expectations of others and earn all the external accolades… was another miserable corporate lawyer.

    <VERSUS>

  2. What I created out of exploring my own creativity and curiosity and speaking my ideas out into the world… was sweary calligraphy, teaching a craft to thousands of students, and inspiring thousands more to look at life in a different way. That was Crooked Calligraphy, and it was still fueled largely by my need for accomplishment and validation.

So what I’m wondering now is:

>>>What could I create out of a new energy of simply delighting myself… and seeing what comes of it?

With Delicious Curiosity,

Shinah