How to Make Your Writing Impossible to Ignore

This is a comprehensive guide to the kind of writing that earns attention.

In school, we were taught to prove ourselves on the page.

Big words, long sentences; the kind of density that signals effort. A teacher sat at the front of the room, paid to read every word with a red pen in hand. She rewarded complexity and prose. We learned the lesson well.

Then we graduated, and the rules flipped. Our cover letters got buried in inboxes. Our meticulously crafted emails got skimmed and forgotten. Ideas we spent hours on got scrolled past in seconds. The writing that earned us praise in school just couldn’t hold people’s attention outside the classroom.

Jay Yang figured this out early. While still in high school, he pitched Noah Kagan with a 19-page deck and landed a job as his copywriter. Since then, he's spent years writing words that hold people’s attention and move them to act. His approach is radical, and it runs against everything we learned in school.

Essentially, Jay says, stop trying to sound smart. Instead, start making your reader feel smart.

In this clip, he explains why "real world writing" works the opposite way of everything you learned in a classroom:

The problem isn't what we're saying, but how hard we're making people work to understand it.

School rules don't apply here.

We tend to carry the writing habits we picked up in school without realizing it. We reach for the longer word, maybe something exotic we heard someone smart say. We let sentences run on because every anecdote feels important to making our point.

Why? Probably because, somewhere in the back of our minds, we still believe that complexity equals credibility.

Jay sees writing through a different lens.

"Nobody owes you their attention. I like to operate from the lens that everyone who reads my stuff is busy, distracted, and has a below fifth-grade reading level."

But it’s not as simple as assuming readers lack intelligence. Really, they don’t. What they lack is patience for the kind of writing that makes them work. The moment something feels hard to follow, they're gone.

"They cannot buy from you or be persuaded [by] you if they don't understand what you're trying to say."

Confusion doesn't make people try harder to understand. It just makes them leave.

Know someone whose writing could use Jay’s insight?
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Big words make you look less smart.

In 2006, Princeton psychologist Daniel Oppenheimer tested what happens when writers inflate their vocabulary to sound intelligent.

He polled 110 Stanford undergraduates. 86.4% admitted they had deliberately made their essays more complex to appear smarter.

But their plan backfired.

Oppenheimer took graduate school admission essays and swapped words for their longest thesaurus alternatives. Evaluators rated the complex versions lower for admission. He ran the same test on translations of Descartes. The simpler translation earned an author-intelligence rating of 6.5; the complex version, a 5.6.

All three of Oppenheimer’s experiments showed the same result: complex writing made readers judge the author as less intelligent, not more.

The mechanism at work here is processing fluency. When a sentence is hard to parse, readers don't blame the idea. They blame the writer. Difficulty registers as incompetence, and no one wants to put that on themselves.

Which means the students trying hardest to sound smart were undermining themselves. That schoolkid strategy most of us default to actively works against us.

The good news is, walking back from this habit doesn’t have to be complicated. Before you send your next email or cover letter, read it out loud. Swap any word you wouldn't say to someone face-to-face. If it wouldn't work out loud, it probably isn't working on the page either.

1) Nobody owes you their attention

In school, a teacher was paid to read your essays. Everyone else is busy, distracted, and one confusing sentence away from closing the tab, just like you.

2) Write for a fifth-grade reading level

People can handle complex prose, but they won't struggle through clumsy sentences to find out if the idea was worth it.

3) Read it out loud before you send it

If it sounds stiff when spoken, it reads stiff on the page. Relatable writing sounds like a real person talking.

4) Swap words you wouldn't say out loud

The thesaurus isn't making you sound smarter, and it’s probably making your readers trust you less. What word would you use right now, out loud?

5) Make the reader feel smart

The key to captivating your readers is to be so approachable that they credit themselves for catching on. Everyone likes to feel like they’re in on the thing, so let them.