Write like you talk

You’re a better writer than you let on


A handful of years ago I was volunteering for an organization here in Chicago where we helped high school kids prepare for their college applications. These kids were the first in their families, often underprivileged, to be applying to college.

One Saturday I met a student who wanted help editing his application essay. We went over to the computer lab and he pulled up a draft he’s been struggling with.

The essay was fine. It read grammatically well.

But it was terrible. It was dry and uninteresting. Artificial intelligence could have probably auto-generated it from a history of other applications.

I doubt any recruiter would remember him. How were we going to fix this?


Most of us trying to write to gain an audience, inspire people, market ourselves, etc. are all doing it wrong.

We stick with the education and rules we learned in high school and college: “Don’t end sentences with prepositions.” “Don’t start sentences with conjugations.” “Sentences have subjects and predicates.” We focus on the perfect paragraph and essay structure.

And if I asked most people to write an essay about their day. It’s likely going to come out a lot like my mentee’s. Stiff, formulaic, unoriginal.

But if we had an intimate conversation over coffee, the story about your day would be remarkably different. You wouldn’t worry about the word you used to start a sentence, or which of your sentences made up paragraphs. Instead, your struggles, achievements, and thoughts would hit my ears before you had a chance to think about: “Can I end a sentence with ‘at’?”

And because you weren’t worried about a hundred rules of grammar while you were talking to me, I’m that much closer to your internal voice.

The voice that makes you unique and interesting.


So my first step with the student above was just to ask who he was, what he does, and what he observes all day. And then I just typed what he said. A lot of it was run on sentences, and sentences without verbs. If he turned this draft into his high school English teacher, he’d have failed an assignment. So we edited it a bit to fit grammatical rules that someone reading a college essay might expect.

But what was on that computer screen was a story in his voice. A story of how just four years ago he came to the United States, poor, with a single parent, and could barely speak English.

Then over his high school career, not only did he become an amazing student, he became a man for others. He was tutoring kids in math and leading programs to help students who were in situations that he was in just a short time ago.

When he was done, I was sitting there, mouth open with goosebumps. Some jerk must have been cutting onions next to us.

His essay was original, dramatically compelling, and told an inspiring hero’s journey.

This kid was awesome. And an essay finally came to him because he stopped worrying about the correct way to write, and just wrote like he talked.


If you find yourself struggling to get who you are onto the page, record yourself talking on your phone and write out the transcript later if you need to. Just get your voice on the page first before you start worrying about a bunch of rules.

When you finally have YOU on the page, now go back and make your bits bend to the style you want them in. But be careful with spending too much time on the grammar and the rules. Go back and make sure it still flows like you’d actually say it. Read it out loud to yourself. You’ll know when you sound fake when you stutter a bit trying to read a sentence back.

Because we aren’t trying to get an A in an English class. Most of us aren’t journalists for the New York Times all trying to write in a similar and strict style.

We’re just trying to contribute to a real conversation. And we want to meet you.

P.S. You should follow me on YouTube: youtube.com/nathankontny where I share more about how we run our business, do product design, market ourselves, and just get through life.

And if you need a zero-learning-curve system to track leads and manage follow-ups you should try Highrise.