why it's so hard to say what you mean
an ongoing practice in developing sincerity
A brief note on things that some of you have also been thinking about.
Novelty was the prevailing motive of my twenties. Sincerity has become the prime pursuit of my thirties.
I no longer seek to be great; I seek to be sincere. I want to do things for their own sake, with no ulterior motive.
Sounds simple enough, right? There is a decade of tangled knots I’ve had to cut through just to be able to say that much.
Being sincere is hard because we’ve spent our entire lives constructing an image of ourselves. An image we believe our in-group finds worthy.
To be sincere jeopardizes that image. What will happen to us if we dropped the image to reveal our essence? Scary.
So we become insincere.
Our insincerity stems from five clever strategies we barely notice ourselves deploying.
Validating — “If I do this, I’ll finally make it big”
Performative — “It’ll make me look good to do this”
Mimetic — “The people that I admire are doing it”
Instrumental — “I’ll do XYZ so that I can do what I want later”
Vicarious — “I will leave behind a legacy”
Fun story: I’ve used all five of these strategies myself!
As a twenty-year-old, I wanted to put out an album that got rave reviews from Pitchfork.
I had no idea how to make this happen. What if after many years of sacrifice, this dream didn’t come true? What if Pitchfork hated it, or worse, didn’t even know it existed?
I couldn’t be honest with myself. Could I pursue this dream without the validation? Out of fear, I moved on.
As graduation approached, I had no idea what came next. So I set my sights on becoming a Teach for America corps member. If I’m clueless about my aspirations, at least I can choose something that makes me look like a good person.
A year later, my experiment with TFA failed in horrific fashion and I moved on. Would I have joined TFA if it weren’t prestigious? The question answers itself.
By my mid-twenties, I ended up as a writer in the startup world. I worked out of our lead investor’s office. Every week, I watched all these now-famous entrepreneurs walk in and raise their first rounds of funding.
Is this writing thing gonna work out? I’m still poor, and I live in Manhattan. Maybe I can follow the path of these entrepreneurs! Start a startup, raise money, get written about in the press, build a team, sell the company.
So I tried it. After a couple false starts, I realized Damn, my heart’s not in this. I don’t really want this for myself, do I?
Next, I transitioned into a career as a software engineer. It was good money and good fun. As my salary kept rising, I observed a tension forming.
On one hand, I noticed I cared a lot about only a few things, and these things did not involve the obsessive pursuit of money, fame, or status.
On the other hand, making more money made me feel goooood.
So my new goal: become financially independent by 35 so that I can spend my time on what matters. But wait, why not just spend time on what matters now?
“What matters?” I felt stupid even trying to answer that question. Anything I came up with felt lame or insignificant.
In a last ditch effort, my insincerity donned a crisp black turtleneck, slipped into its best blue jeans, and declared its Steve Jobsian vision:
“To empower scrappy, self-directed learners worldwide to unlock their full potential.”
I mean, sure, that’s inspiring!! … Right? I’ll change the world, make it a better place, put a “dent in the universe,” etc, etc.
But it’s complete BS. Maybe someone else’s true desire. Not mine.
So I wrote all of this down recently because I got so agitated at myself. Why can’t I just say what I mean?
In a fit of confusion and anger, I wrote something to the effect of:
It’s really simple, dammit. I just want to work on the crafts I really care about. THAT IS IT. What more do you want from me?
And then something clicked. I read what I wrote, and it just felt genuine. Maybe not all the right words, but raw and heartfelt.
It took twelve years to say something sincere about my desires . But am I prepared to let this unadorned truth permeate my life?
What are the consequences of saying even one sincere thing? How will this change the way people view or treat me? And the way I view and treat myself? Scary thoughts. So I discreetly slipped out the back and deployed an insincerity strategy:
I should probably forget this whole thing and be “realistic”.
It’s hard to say what you mean.
Thanks for reading! Work stuff has gotten busy the past couple weeks, but I’ll be back on my Overlay grind next week.
 Ernest Hemingway once said that writing is simple — “All you have to do is write one true sentence.” What a troll.