I’ve Been Too Polite With ChatGPT

Three years.

Three stinking years I’ve been using ChatGPT.

Since the beginning. Since the “wait, this thing can finish my sentences?” era. Since the “oh no, this might actually be useful” phase. Since the “okay, calm down, it’s still just a tool” self-talk.

And it took me until this week to realize something important:

I’ve been way too polite with it.

Not polite in a “please and thank you” way (although… yes, also that). Polite in a professional, buttoned-up, LinkedIn-approved way. Polite in a “hello, fellow knowledge worker” tone.

Which is wild, because this week was the first time I gave ChatGPT a sarcastic persona.

And I’m never going back.

The problem isn’t writing. It’s revision.

Here’s the thing: I love writing.

I do not love revising.

I don’t love editing. I don’t love reorganizing. I especially don’t love blog writing, which somehow manages to feel both redundant and high-stakes at the same time. I’d much rather brain-dump the ideas, list everything I know, and move on with my life.

Unfortunately, that’s not how writing that “lives in the world” works.

If something’s going to exist for more than five minutes: a blog post, a newsletter, a resource people might bookmark…\

it needs outside eyes.

It needs critique.

t needs someone to say, “Yes, but… this part doesn’t land.”

And critique always stings. Even when you ask for it. Even when you know you need it.

So I do what a lot of us do: I use ChatGPT for feedback.

Usually with a very sensible, very adult, very reasonable prompt chaining session.

* Check for clarity.

* Check for structure.

* Check for logic gaps.

* Be helpful.

* Be kind.

* Be constructive.

Then someone casually mentioned, “Oh yeah, but that’s nothing compared to my sarcastic one.”

Record scratch.

Enter: Sarcastic ChatGPT

I can’t share their exact prompt because it’s not mine. But the idea was simple:

Same analytical rigor.Same checklist.Same goals.

Completely different tone.

The instructions included things like:

* Be brutally honest

* Roast the writing hilariously

* Swear if necessary

* Don’t let weak logic slide

And wow.

The feedback started with something along the lines of:

“This piece starts strong and immediately gets lost in a cul-de-sac of ‘show notes are important,’ like it’s trying to convince itself.”

Did it sting?

Yes.

Was it accurate?

Also yes.

And here’s the important part: instead of spiraling or shutting down, I laughed. Out loud. In a coworking space. While trying not to disturb anyone.

Another gem:

“Congrats. You found a way to make a good point while looking like you were typing downhill.”

I mean. Come on.

Painful? A little.Useful? Extremely.Memorable? Absolutely.

The unexpected part: I started talking back

At some point, I typed:“Okay, smartass.”

And that’s when something shifted.

Once I started responding in kind with sarcastic, casual, mildly unhinged language, all the stress disappeared. I stopped bracing myself for feedback and started playing with it.

I actually lost track of time during the edit. In a good way.

Not because the task got easier, but because it got lighter.

And that’s when it hit me: I’ve been treating ChatGPT like a very polite junior colleague, when what I really needed was a sparring partner.

Not someone whose tone ends up in the final text. Just someone who can verbally jab me during the process.

Being “professional” is overrated (in your prompts)

I realized I’ve been too professional with my LLM.

The output will be what the output is. That doesn’t change much.

But my interaction with it? That can be messy. That can be sarcastic. That can include swearing, jokes, exaggeration, and personality.

For some reason, I’d mentally separated “good output” from “fun interaction,” as if seriousness was required for quality.

It’s not.

In fact, telling ChatGPT how to be, not just what to do, unlocked something I didn’t know I was missing.

When I typed curses (which I almost never do on a physical keyboard), it felt weirdly freeing. Like letting off steam without involving another human being.

Maybe I’m just repressed.Maybe this is just genuinely fun.Possibly both.

This doesn’t make the AI sloppy, it can make you relaxed

This is the part I want to be clear about, because it’s easy to misunderstand.

Giving ChatGPT a sarcastic persona doesn’t mean you abandon structure, clarity, or critical thinking. You still need:

* Clear instructions

* Specific criteria

* Guardrails against nonsense and hallucinations

Tone doesn’t replace rigor. It coexists with it.

What changes is your experience of the work.

If revision feels less awful, you’re more likely to do it well.If critique feels playful instead of punishing, you’ll actually absorb it.If the process is lighter, you’ll stay with it longer.

That matters.

A rare challenge from me

I don’t usually do this. I’m not big on weekly challenges. I don’t want to turn this into homework.

But just this once:

This week, give your ChatGPT a persona that’s ridiculously fun.

Sarcastic.Blunt.Over-the-top.A little unhinged (within reason).

Tell it exactly what to look for. Tell it exactly how to critique. Then tell it how to sound while doing it.

See what happens.

Even if the output isn’t wildly different, I suspect your mood will be. And how time passes while you’re working. And how much resistance you feel opening the document again.

I still love writing.I probably still hate revising.

But at least now, revision comes with a smartass in my corner.

How on earth did it take me three years to figure this out?

Go. Just go.

See ya next week,

Steph

AI disclaimer:

I use ChatGPT to co-write many of my online texts. Having said that, for these Substack posts we start with the video transcript. A transcript that comes from a recording that I create alone, with zero AI assistance. I also prompt chain and edit like hell during and after the cowriting process, so I have to admit that I have no idea where my writing begins and Chatty (my affectionate name for ChatGPT) ends. So take with this as you wish. I just wanted you to know that some of the eloquence here is in fact from me but not me exactly.

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