Make Sound Human Again

Using AI to sound smart is having the opposite effect

Last week I posted a software-dev project on Upwork and got back 15+ perfect pitches.

All of them communicated a clear technical solution to my problem. I booked calls with the top 5. It was hard to choose.

But when I spoke to them over Zoom, 3 of 5 straight up had no idea what the project was about. Like, literally no idea. When I summarized, they replied:

“Oh yeah, I can definitely build that. Let me write up an official proposal and send it over to you.”

🙄 “Ok, well, off the top of your head, how would you go about it?”

Silence. Maybe a little mumbling. A couple of wild guesses that were hilarious.

So they clearly just copy-and-pasted my Upwork post into ChatGPT and sent me the answer.

Annoyed that my time had been wasted, I went back and re-read the AI-written pitches that fooled me and compared them to the ones written by legit developers.

The impostors sounded overly clinical. Buzz-wordy. Skin-deep sophistication.¹ No personality.

The legit pitches had a unique temperament. One of them had awkward English. The other was a bit curt, bordering on annoyed. I liked that he was annoyed. It showed he didn’t want to waste time. He’s busy and wants to get to work.

I can relate to that feeling. Which made me feel connected to him. Which made me trust him. Which made me want to do business with him.

This phenomenon isn’t limited to freelancers on Upwork. It’s likely happening at your company right now.

Most of us have already experienced this even if we can’t prove it. Like reading an email that clearly wasn’t written by the person who sent it. Like when your Head of HR sends an all-hands meeting reminder and signs off with “Low-key obsessed with what this team is building…”

It’s like c’mon, Gladys! Zero chance you wrote that!

Why do I hate AI-written emails so much?

It’s because, although AI is an incredible tool for writing, it’s also a homogenizer. It sterilizes your words and strips them of your personality and sincerity when used the wrong way.

In a world of AI-written-slop, personality and sincerity are no longer fluffy ideals no one has time for. They have measurable value.

It’s precisely because AI gives everyone the ability to produce generic, MBA-level, corporate-polished writing that that style is no longer valuable.

What used to take years to master and was highly regarded as “elite” — namely, the talent of neutering your words of any trace of genuine personality to demonstrate cold, hard clarity — is now indistinguishable from what impostors can spit out with ChatGPT.²

I feel bad for the people who got good at corporate-speak only to have that skill inflated away overnight by LLMs mimicking their sought-after style.³

We spent centuries training humans to sound like robots. Now that robots are here, humans need to stop doing that.

So what then is the new gold standard for business writing? Or any writing that seeks to foster trust between writer and reader?

By my estimation, what makes a reader happy boils down to two equal parts:

50% | Content: The information you need or want (Insight)
50% | Connection: A felt sense of the writer’s idiosyncrasies (Authenticity)

Let’s apply this to my Upwork situation from Upbove.

The AI-written pitches had crystal-clear Content ✅ but failed to Connect. If everyone can pump out crystal clear technical content, the only way to differentiate is to nail the Content and the Connection ✅ part.

So next time you find yourself prompting “re-write email to boss, make sound smart,” consider the connection you’re losing, and consequently, trust, by muting your authentic self.

Instead, ask “what isn’t smart about this email to my boss? No rewrites, just feedback.”

This turns AI into what all your favorite authors had: A professional editor like Maxwell Perkins.⁴

Famous for helping some of the world’s greatest writers, Perkins never once did rewrites. Instead, he helped his writers identify problems in their prose and encouraged them to fix it in their own words.

In this way, he vastly improved his clients’ writing while preserving their unique voice and thus the connection with their readers.

You can and should use AI to improve your writing.

Just make it an editor instead of a rewriter so it doesn’t castrate your connection with your reader.

I wrote an AI feedback guide designed to do this efficiently so you can preserve your uniqueness and say what you need to say clearly: feedbackfreak.ai/guide

“We’re all imperfect... imperfections are what make each of us interesting.”

- Rick Rubin

P.S. Thanks to FF AI, Kimi K2, Gemini 3 Pro, Chris James, and most of all Delaney Zecha for your feedback.

1. A term I stole from Blake Stockton’s essay “Don’t Write like AI”

2. An analogy might be how a college degree used to be worth a lot, but now that everyone gets one, it doesn’t mean anything. What’s more, college costs a mountain of debt for little return so if you choose to get one now, it kinda almost means you’re dumb. It’s obviously more complex than that, but the point is to illustrate that things that used to be considered “elite” or desirable don’t always remain that way and sometimes even completely invert. Gemini suggested another analogy: highly processed white bread used to be a luxury item only the rich could afford because it cost more to process it, and the less refined whole grain bread was for the poor. Now it’s the opposite.

3. I also feel good that their genuine personalities can once more be liberated from the shackles of roboticism. Not in an idealistic way, but in a pragmatic way, where showing your quirks will become a necessity for building trust in an AI-dominated business world. Be yourself, create more shareholder value. Win-win.

4. Maxwell Perkins: influential editor of Ernest Hemingway, F. Scott Fitzgerald, and Thomas Wolfe