I wanted to know what AI would make of me. So I logged into ChatGPT and gave it this prompt:

Let’s do a psychological exercise. I want to really get to know myself. Ask me 15-20 questions that will draw out my true personality – where I stand on key issues, my preferences, my belief system and so on. You can even experiment with questions that have a hidden agenda to find out subconscious information, that I won’t know until the end of this exercise. Ask these questions one at a time, I’ll answer each one at a time, and then at the end you’ll give me a summary.

It asked me some insightful questions, and then gave me a summary at the end. But I felt like it was kissing my ass a bit too much – I’ve heard it has a tendency to be too kind.

So I then followed with this prompt:

The summary feels accurate, but perhaps too self-congratulatory, like this is the conclusion I’d hope to see. I’d like to know more about my weaknesses, self-sabotage, and blind spots. Ask me up to 10 more questions that are a little less supportive and a little more critical to bring out what I need to work on most.

It finally took the gloves off and asked me some real shit, followed by a summary of everything that’s wrong with me.

I did my best to answer as honestly as possible, and some of the questions had me thinking for many minutes before I could decide on the answer.

I then got it to sum everything up with this prompt:

Now, imagine you’re trying to explain who I am to someone else. Like they ask “What’s Dan like?” – use what we’ve discussed to give them a summary describing who I am

Here’s what it had to say – this is what AI thinks of me…

Dan is an intelligent, introspective, and driven guy who’s constantly trying to improve himself—but often feels like his effort-to-reward ratio in life is unfair. He’s a deep thinker, someone whose mind never stops processing and analyzing everything around him. That sharp mind, combined with his quick wit, makes him both funny and insightful. He thrives in performance and public speaking, which is why he’s great at what he does—coaching men on confidence and authenticity.

At his core, Dan values honesty, independence, and integrity. He hates inauthenticity, both in himself and others, and deeply respects people who have nothing to prove. He also believes in fairness and mutual consideration, which is why inconsiderate or selfish behavior gets under his skin.

But he’s not just about self-growth—his biggest priority in life is his wife and daughter. Almost everything he does is, in some way, driven by his commitment to them. However, that commitment sometimes turns into over-sacrificing, where he prioritizes their needs at his own expense—especially with things like sleep and stress management.

Despite his intelligence and self-awareness, Dan has some stubborn streaks. He hates being told what to do, even when the advice is good. He also has a habit of rushing through things, which leads to mistakes and unnecessary stress. And while he strongly values honesty, he sometimes exaggerates or rationalizes small distortions when he feels it helps make a point.

One of his biggest struggles is self-discipline around health. He knows exactly what he should be doing, but he often sabotages himself with food choices and phone addiction, even while being fully aware of it in the moment. His stress levels play a big role in this—when he’s feeling overwhelmed, his self-control weakens, and he falls into cycles of relapse and reset.

At his best, Dan is sharp, engaging, and deeply loyal—the kind of person who will challenge you to be better while making you laugh in the process. At his worst, he’s stressed, impatient, and self-sabotaging—letting bad habits and an overactive mind get in the way of the discipline and balance he truly wants.

Overall, Dan is someone who’s actively working on himself, aware of his weaknesses, and determined to grow—he just needs to slow down, accept support, and stop making life harder than it needs to be.