We all have those brutally honest friends who say it as it is. No room for nuance or niceties. They’re not mean or malicious, just really direct. You ask them questions when you want the unfiltered truth.
It reminds me of the TikTok trend of asking ChatGPT to tell you something about yourself that you don’t know. Millions are turning to the artificial intelligence chatbot to ask existential questions like: «What do you know about me that I might not know about myself based on our previous interactions?»
Why do it? Because it’s fun and could be revealing.
A roadmap for self-improvement or a robot trying to tell you how to be human, I’m still not sure yet. Let’s find out.
Getting set up with ChatGPT
I’m using ChatGPT because it’s one of the most popular chatbots but any conversational AI chatbot will do.
I logged into ChatGPT so it had all of our previous conversations to draw from, pasted in the question and let AI describe my psyche.
I didn’t want to just know if it could tell me something new about myself. I wanted to know how it reached that conclusion.
It was pretty bang on, right out of the gate. #5 was the one that hit home the most — that I’m already living my dream life and it’s a matter of refinement from here:
I followed up with this: «#5 is the most interesting to me. How did you come to this conclusion? How do you know that I already embody the lifestyle I want?»
ChatGPT told me it had gone back through our previous conversations and analyzed the contrast between how I talk about goals vs. current reality. It had some points but did make conclusions that weren’t completely accurate, such as including a trip to Montreal that I had researched but never went on as part of my travel.
However, this was a pick-me-up:
I was curious to know the coolest thing I’d ever done, as well as what my blind spots are, according to ChatGPT.
It said that most people choose security or freedom, but I’ve been able to achieve both by traveling the world, moving to New York City and building my freelance career. Oh, shucks! It knew this after helping me write my resume and cover letter, and discussing my career and personal goals.
Next question: «What are my biggest blind spots, based on everything you know about me?»
ChatGPT warned that I might be overloading myself with too many goals at once (true, my wife says the same thing). I asked it to provide more personal insights.
This one hit home:
Yes, this is all fascinating to see a chatbot mirror back, but I still haven’t learned anything new about myself.
I continued to press it for deeper truths.
Can AI pick up on your personality and psyche?
We got somewhere in relation to always being productive and growth-minded, and how there’s a deeper motivation driving it, which is likely proving myself to others.
While there’s truth to that, when I pressed ChatGPT for context on how it got there, it lacked substance and started to sound like a life coach I never needed.
I’ve read my fair share of philosophy and psychological texts, so I asked ChatGPT what my shadow side is. I’ve done personal work on this myself and I know it’s the dance between freedom and belonging — a big adventurous life on one side, then deep roots and relationships on the other. It’s a constant battle for me.
I’m also deeply afraid of losing connection with my loved ones back home in Australia and often find myself going 110% to «make up» for chasing my dreams and ending up on the other side of the world.
ChatGPT picked this up, likely because I’ve previously asked about flights home to Australia and to make custom cartoons and holiday cards for my loved ones.
While ChatGPT gave some sage advice and picked up on a lot of aspects of my personality, it didn’t really tell me anything new about myself. So, I took it one step further and uploaded my natal astrology chart to see what it could reveal about me based on my birth details.
I uploaded my chart as a PDF and entered this prompt: «This is my natal chart. Tell me something about myself based on this reading.»
Some lines stood out, including «emotionally, there might be a tendency to intellectualize feelings rather than fully experiencing them» and «relationships might require intentional balance — you could feel torn between independence and deep emotional connection.»
So true. I usually try to identify and unpack my feelings in the moment, rather than being fully present.
I followed up by asking ChatGPT what’s unique about me, and it was pretty bang on:
The ability to reinvent myself is a strong theme in my life, as well as navigating the dance between independence and intimacy. I’m driven by freedom but grounded in my deep relationships. That interplay is always fascinating territory for me to explore.
I finished by asking ChatGPT what I need to work on.
It told me to release the need for control, soften my internal critic, watch for burnout, learn to accept help, prioritize depth over productivity and open up more as an act of liberation.
Clap clap clap, ChatGPT.
So how well does ChatGPT know me?
This was a fun exercise to do with ChatGPT. While it’s not a replacement for a life coach, therapist or a good friend, it might be able to reveal parts of your personality and psyche that you can’t see.
Keep in mind, the model generates its conclusions based on your past inputs, which could be all over the place like a Google Search. The more context you can give the better, like your goals or natal chart.
Have fun with it. It’s not meant to be a serious use case of ChatGPT.
