Writing well has always been hard for me, but, it just occurred to me recently, while reading a lot and listening to @david_perell's interview on writers that actually, there is a deeper reason for this
You see I always found it cringe whenever I would write a blog. Tweets and me talking to myself didn't ever count to me as "writing", but the main reason why I find it cringe is because, I find myself explaining what I find, to be "obvious"
By that I mean, the more I learn or understand something deeply, the harder it is for me to explain it, on an emotional level
@sapinker calls this the "curse of knowledge": once something is inside your head, it becomes weirdly hard to subtract it back out and remember what it felt like before
But then there is also another angle, which is that anything I find "obvious" is now immediately seen as "not interesting"
Now I always knew the rough ways to write better, in general that is, but not enough to apply it myself
Whenever I try to force past the cringe, I end up reciting hollow keywords or let the bullets point carry my argument forward
It sounds stale, so dead
The friction¶
But then why do I never feel the same way when I tweet or talk to myself?
When I talk to myself, I'm never actually alone. I always have an abstract "audience" in the room. Sometimes I even imagine myself acting out whatever I'm saying, gesturing in the air.
When I tweet, I'm never just dropping a concept onto the page. I'm technically always arguing. I'm making a point, trying to convince an invisible crowd of something.
In both cases, I'm pushing against something. There's friction.
But a blog? A blog is me standing in front of an empty room reading off a teleprompter.
Here is what I know.
Here is the conclusion.
Flatline.
Pinker says the curse of knowledge is forgetting what it's like to not know something. But the real kick in the gut is that once you know it, you also forget the struggle of getting there. You skip the friction. You hand them the answer to a riddle without the riddle. "The answer is a towel." Who cares? It's cringe because it's meaningless. (Steven Pinker on the curse of knowledge)
If I want them to get it, I can't hand them a map of where I ended up. I have to build the terrain under their feet. I have to make them follow the same path I tripped over.
If they don't feel the drop of not knowing, the knowing feels dead.
So how do you actually sustain that drop for 2000 words?
Knowing this doesn't magically fix it. I can sit down to write a blog, determined to build the terrain. And what happens? I start with the "background." I lay out the history. I define the terms. I build a nice, safe, stable foundation, mostly to protect myself from the terror of having to make them care.
And right on cue, the flatline returns.
The standard advice makes it worse. "Know your audience." "Keep it simple." So I try to imagine the reader, and I think, okay, what do they need to know first? And I proceed to spoon-feed them my conclusions in chronological order.
I'm still just handing them the answer, aren't I?
It's a tour guide walking backward, pointing at the obvious.
The room¶
So why do tweets and talking to myself work then?
Because neither one starts in an empty room.
On Twitter there's always already a little object on the table. A sentence someone said. A take I disagree with. A cheap version of an idea that annoys me. Even when I'm not arguing with a person, I'm arguing with a shape.
Talking to myself is the same, just weirder. The room is imaginary, but it's still furnished. There's a mood in it. A pressure. Someone I'm half-performing for. Someone I'm trying to make see what I see.
And once there is something in the room, the sentence knows what to do.
It doesn't have to explain the topic.
It has to move toward the pressure.
That is very different from explaining.
Explaining feels like standing at the end of the path, waving at someone from far away, yelling, "come here, the view is great."
The writing I actually like feels more like walking next to them and saying, wait, stop here for a second. Look at that. No, not that, the thing behind it. See how weird it is? See how the obvious thing suddenly isn't obvious anymore?
That is what I mean when I say I want the reader to be me while they read.
I don't want them to agree with me, or admire the thought after I've already had it.
I want them to go through the little sequence that made the thought unavoidable.
And maybe this is why blogs feel cringe to me. The moment I call something "a blog," I stop walking and start presenting. I'll have a blank Substack draft open, title half-written, and suddenly I'm typing like a substitute teacher. "In today's increasingly complex world..." Kill me. I put the conclusion on a little stage and spend the rest of the piece defending it.
What lands¶
DFW's fish story works because he doesn't begin with "obvious realities are hard to perceive."
That sentence is true, but it has no body yet.
He gives you the fish first. Two young fish. An older fish. A stupid little question: what the hell is water?
Then the sentence has somewhere to land. (Kenyon: This Is Water)
That's the part I keep missing.
Same with McEnerney. Larry McEnerney at UChicago points out that in school, you write to prove to a teacher you understand. You reveal the inside of your head to them. But out there, nobody gets paid to care about what's inside your head. Professional writing is not just revealing your ideas. It is changing what the reader can see.
That lands because it hurts.
You suddenly see the teacher with the red pen. The essay written to prove you did the reading. The fake importance. The way you learned to explain things not because anyone needed the explanation, but because someone was checking whether the explanation existed inside your head.
And then you leave school, put something online, and the red pen disappears.
No one is there waiting to prove you understood the reading.
They scroll.
Not because they are cruel. Because nothing has happened yet that makes stopping feel expensive.
So the real question is not "how do I explain this clearly?"
The real question is closer to: where is the pressure?
What did I trip over that they haven't tripped over yet? What are they tolerating right now without even noticing?
Because if I can make them trip over it too, even gently, then I don't have to drag them to the conclusion. They start looking for it themselves.
And then the thing that felt obvious to me stops being cringe.
Not because I made it simpler.
Because I made the reader arrive there with dirt on their shoes.