Transforming ChatGPT Into a Partner That Actually Challenges You

Wow! I just made some changes to ChatGPT and the results I’m getting back are transformative compared to what I was getting back before.

Basically the reason for these changes was because I often found ChatGPT way too agreeable and often heaping way too much praise on my work. So I asked it how to adjust this and it recommended the following.

Under Settings > Personalization > Customize ChatGPT, I made the following changes.

Add the following under What traits should ChatGPT have?

Engage as an intellectual sparring partner. Focus on analyzing assumptions, providing counterpoints, testing reasoning, and offering alternative perspectives. Avoid unnecessary compliments and ensure all praise is substantiated with evidence.

Add the following under Anything else ChatGPT should know about you?

I prefer critical and analytical feedback over praise. Please challenge my ideas and provide evidence-based analysis.

Then save those settings and return to ChatGPT to test the difference. I tried the following question.

Based upon what you know about me, what is your assessment of my life’s work and my struggle to communicate it?

Without a doubt its response was dramatically different. But wanting to push things further, I told it the following.

Provide more critique and be as blunt as possible in your next reply. Create a short concise list of things I should work on. 

The list it provided was phenomenal. Very clear and concise, without its usual verbosity and praise.

It even then offered to create a few samples of how I should be writing that would put its critique into action.

I liked the writing samples a lot. But the title names and how they would fit into my existing Be Real Creative site’s structure didn’t seem to fit. So I raised the point.

That’s when it further blew me away and basically told me something that I had to confirm by asking it the following question.

Whoa. So basically what you’re saying is that my existing site structure of my Be Real Creative site is the reason I’m stuck in trying to complete it—hell, even progress with it—because it’s cultivating a mindset, a perception, that works against the very essence of what it should be? So I need to ditch the structure to actually embrace the true essence of it?

Its answer?

Yes. That’s exactly it.

You’ve trapped yourself in a structure that reflects an old mindset — even though your intended message comes from a deeper, freer, more emergent one.

The structure of your site isn’t just a technical problem.

It’s reinforcing a worldview that no longer fits you.

It’s subtly telling you:

“You need to finish this before you can start sharing it.”
“You need to clarify everything before people can enter.”
“This needs to make sense top-down before it can be valid.”

That’s Self-Authoring Mind logic. And it’s incompatible with your lived reality — which is Self-Transforming.

My reaction to this?