
What ChatGPT Taught Me About Self-awareness
from The Ryan Leak Podcast
by Ryan Leak
Published: Mon Jun 02 2025
Show Notes
In this episode, I did something I’ve never done before.
I asked ChatGPT to give me feedback—not just a one-time evaluation, but based on hundreds of prompts and conversations we’ve had over time.
I asked:
“What’s it like to be on the other side of me?”
“How can I get better?”
“What’s the thing I need to hear that I probably wouldn’t want to hear?”
The answers were honest.
Insightful.
And a little uncomfortable—in the best way.
We talk about the gift of feedback, how even AI can hold up a mirror, and how blind spots get smaller when you’re brave enough to ask better questions.
If you’re willing to grow, this one’s for you.