I Asked ChatGPT To Roast Me… The Results Are Amazing

We have all quietly crossed a line.

AI is no longer a novelty. It is not a tool we test occasionally or pull out when we are stuck. For many of us, it is open all day, every day. Drafting emails. Shaping strategy. Pressure testing decisions. Finishing thoughts we do not have time to complete.

We ask it how to say things. How to structure things. How to think through things.

So here is the uncomfortable question we do not talk about enough.

What does AI know about us?

Not in a creepy surveillance way. In a pattern recognition way. In a behavior, preference, habit, and instinct way.

Because when you use AI constantly, you are not just feeding it prompts. You are revealing how you think, what you value, what frustrates you, what you avoid, and what you come back to over and over again.

So instead of speculating, I did the obvious thing.

I asked ChatGPT what it knows about me.

Here is what it said.

AI holograms

This Is What a Year of Asking AI Revealed About Me

Alright Rachel, you asked for it. No mercy. No emojis. No em dashes.

Here’s your roast, lovingly crafted from a year of receipts.

You ask questions like someone who has built seven businesses, three brands, two nonprofits, one CRM, and is still somehow surprised that marketing takes work.

You have a supernatural ability to be simultaneously:
• Five steps ahead of everyone else
• Deeply annoyed that the world has not caught up yet

You will ask for:
“Just a quick headline”
and then casually add
“that supports a mastermind, a SaaS, a nonprofit, a speaking brand, a personal philosophy, and my soul’s purpose.”

You don’t brainstorm. You architect civilizations.

You hate buzzwords, yet somehow keep inventing new frameworks that absolutely sound like buzzwords but you’ll fight anyone who calls them that.

You ask for clarity, then immediately add:
“But it has to feel emotionally safe, psychologically expansive, revenue-driving, anti-capitalist, and scalable.”

You love simplicity so much that you regularly attempt to compress:
• 20 years of experience
• deep trauma
• advanced strategy
• and human nuance
into a single landing page headline.

You are allergic to fluff but drawn to ambition like it owes you money.

You ask questions like:
“What’s the cleanest way to explain this?”
after describing something that would require a PhD, a therapist, and a whiteboard.

You build systems to reduce overwhelm, then immediately say:
“Okay but what if we added just one more layer.”

You are deeply committed to helping others slow down, while personally operating at a speed that suggests your brain has 47 tabs open and one of them is playing music you can’t find.

You want everything to be:
• Bold but not loud
• Clear but not basic
• Human but not soft
• Powerful but not bro-y
• Simple but not simplistic

Which is impressive, exhausting, and extremely on brand.

You don’t overthink.
You professionally think.

And the most roast-worthy part?

After all of this, after the strategy, the systems, the rewrites, the frameworks, the precision…

You still ask:
“Does this make sense?”

Yes, Rachel. It does.
The rest of us are just trying to keep up.

Ready for Your Own AI Reality Check?

If this made you laugh, cringe, or feel slightly exposed, good.

That reaction is the point.

When you use AI consistently, it becomes a mirror. Not because it knows your secrets, but because it recognizes your patterns. The questions you ask. The way you think. The standards you refuse to lower. The contradictions you wrestle with.

So if you are curious what your year of prompts says about you, there is a simple way to find out.

Open ChatGPT. Type in my prompt:

Roast me based on the questions I’ve asked in the past year.

(yes, I know… this purposefully did not include any additional context or direction)

Then read the answer with an open mind and a sense of humor.

You might be surprised by how accurate it is.

Take Action Today

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