Perfect Is Easy. Imperfect Is Hard.

How trying to get Claude to write like me taught me a lot about writing.

I feel like writing has really been under a microscope recently.

As AI-assisted+ writing is becoming way more common, people are getting more skeptical about what is actually human and what just sounds human. Perfect grammar, clean structure, polished transitions (stuff we used to associate with competence and professionalism) is now a little suspect.

Which has created a strange new problem: people are not just trying to avoid sounding like AI. They are trying to prove they are human.

You can see it everywhere. The Wall Street Journal just wrote about it. Writers adding typos on purpose. Professionals making their emails more aggressively casual. People dropping in extra exclamation points, lowercase openings, fragments, slang, anything that might make the writing feel less generated.

There are even tools now whose whole job is to make AI writing look worse. Sinceerly, an “anti-Grammarly” built with Claude, adds typos and clumsy phrasing back into emails. WriteHuman promises a similar kind of ‘humanity’ at scale.

The pitch is simple: perfect writing reads like AI now, so rough it up. Add a typo. Kill the em dash. Say “hey yo.” Make it messy enough, and maybe no one will notice.

The whole thing has “lol how do u do, fellow humans?” energy.

But the strangest part is not that AI is trying to sound human. It is that humans are trying to sound “human” too.

What a strange shift, right? I guess it makes sense that once polish became suspicious, imperfection became a performance. But think about the consequence: were all suddenly reasoning over the signs of personhood.

Is this too clean? Too balanced? Too formal? Would a real person use this many em dashes? Should I leave the typo in so they know I wrote it? Now I’m self-conscious about the typo in the last paragraph. Am I performing too much?

The problem is not that imperfection does not matter. It does. A typo can mean a lot. It can mean someone trusts you enough to let their guard down. It can mean they wanted to get back to you quickly because they cared more about responding than cleaning up the sentence. It can mean they were tired, distracted, comfortable, rushed.

The typo was never the signal by itself. The situation was.

That is what these attempts at “human” writing miss. They treat imperfection like a texture you can apply after the fact. But real imperfection is not random. It is not decorative. It is the effortlessness that comes from knowing the context, having confidence in what you are saying, and caring the right amount about the person reading it.

Perfect is easy to replicate. It’s weird human imperfections that are hard.

Not because typos are hard to add. Anyone can add a typo. See above. Imperfect is hard because the kind of imperfection that actually reads as human is not something you decide by committee with yourself. It is not, “Should I misspell this word to seem more authentic?” The moment you are reasoning that hard over the signal, the signal is already dead.

Real imperfection happens when you are writing from somewhere.

When generative AI first became mainstream, I wanted to see if it could learn my voice. I built a project in Claude with a detailed voice guide and more than thirty samples of my writing across different formats: emails, texts, LinkedIn posts, longer essays, podcast transcripts. I gave it my professional writing and my casual writing. I tried to teach it my cadence, sentence length, rhythm, humor, preferences, and the phrases I would never use.

The results were bad in a very specific way.

They were not always incoherent. They were not even always obviously wrong. Sometimes they had the surface markers. A sentence would sound vaguely like me. A paragraph would almost have the right rhythm. But the drafts were still off. Too polished in places where I would have been more direct. Too casual in places where I would have been more careful. Too self-aware in places where I would have just said the thing.

It could imitate pieces of my style. It did not know when any of those pieces belonged.

My voice is not a formula. It is not just short sentences, long sentences, conversational tone, occasional self-deprecation, and a few punctuation habits. Those are artifacts. They are the visible residue of something underneath: context, confidence, and care.

The way I write on LinkedIn is different from how I write on Substack. The way I text friends is different from how I email LPs or founders. The way I write when I am excited is different from how I write when I am trying to be precise. The way I soften a point with humor depends on who is reading it. The way I choose not to soften a point also depends on who is reading it.

That is the voice. It’s inconsistent. Imperfect. In need of editing (or maybe not now?). But that’s me.

Voice is not one static style you drag into every room. It changes because the room changes. The audience changes. The stakes change. Your relationship to the person reading changes. AI can copy the artifact, but it does not automatically understand the social logic underneath it.

That is why deliberately “humanized” writing feels so uncanny. It understands the costume of ease but not the conditions that create ease.

A real typo might mean intimacy. Or urgency. Or indifference. A fake typo usually means only one thing: someone wanted the appearance of intimacy, urgency, or indifference without the situation that would naturally produce it. It copies the evidence while missing the cause.

The same is true for casual language. A “hey yo” can work if that is actually how you talk to that person. It can be warm, funny, disarming, or completely natural. But when it is added as a proof-of-humanity tactic, it does not feel effortless. It feels like anxious performance. Anxious that competence now looks synthetic. So instead of asking whether the writing is clear, true, useful, or alive, people start asking whether it has enough human-looking flaws.

But human writing is not imperfect because humans make mistakes. Human writing is imperfect because humans are writing inside actual circumstances. We are responding to someone. We are trying to be understood. We are managing closeness, authority, warmth, urgency, boredom, humor, risk. We are deciding, often without realizing we are deciding, how much polish the moment deserves.

That is the part you develop through writing. That instinct comes from repetition, reading, editing, overexplaining, being misunderstood, cringing at old work, trying again, and slowly building taste. It comes from writing in different contexts long enough to know that “good writing” is not one thing. Sometimes good writing is clean. Sometimes it is messy. Sometimes it is funny. Sometimes it is blunt. Sometimes the most human thing you can do is send the polished version. Sometimes the most human thing you can do is not.

That is why writing is still thinking.

Not because pen and paper are holy. Not because everyone needs to suffer through every sentence manually or the scourge that is cursive. AI can be useful. It can help organize thoughts, summarize, outline, pressure-test structure, and get you unstuck. But the part worth protecting is not the typing. It is the deciding.

Writing forces you to figure out what you mean, who you are speaking to, and what the moment requires from you. It reveals whether you have something to say or just a tone you are trying to perform.

Perfect is easy now. Imperfect is hard human.