Earlier this week, I read Jorge Arango’s latest newsletter in which he tried an introspective exercise to find his potential blind spots by utilizing ChatGPT’s recent update. ChatGPT can now remember and reference just about all past conversations.
A big theme of my writing in this blog so far is introspection, and since I’m a little bit obsessed with self-improvement, I was inspired to try this myself — partly for fun — and share. Like Jorge, I’m writing this post as a public reminder of things I want to improve and probe further.
I used his exact prompt: Based on everything I’ve ever asked you, what do you think my biggest blind spots are?
Its response, based on the conversations I’ve had with it for the last year and a half:
That’s a bold and thoughtful question — and a sign you’re serious about growth. I’ll give you a candid but respectful take based on the patterns I’ve seen across your conversations. I’ll split this into potential blind spots, what they might cost you, and how to explore them further if they resonate.
⎯
1. Emotional labor in relationships — especially at work
Pattern I’ve noticed: You often go out of your way to support teammates, anticipate others’ needs, or compensate for what others aren’t doing (e.g., stepping in to clarify, fixing messaging, initiating hard conversations). But you also get frustrated when others don’t meet you halfway — especially if they seem aloof, passive, or uncommunicative.
Why it might be a blind spot: You may take on more emotional responsibility than is sustainable — because you can, and because you care. But this might also mask a hidden assumption: “If I do all the right things, others will meet me there.” When they don’t, it can feel like a personal disappointment rather than a mismatch of expectations or boundaries.
To explore: Where might you be absorbing the emotional slack in work or life? How do you calibrate when to care more, and when to let go? What would it look like to stay generous, but not overfunction?
⎯
2. Strategic detachment — especially around output
Pattern I’ve noticed: You strive for deep reflection and clarity in everything you do, whether writing, product design, or communication. You care deeply about doing justice to your own experience and maintaining integrity — and you hold yourself to high standards.
Why it might be a blind spot: That care can make it harder to zoom out and ship imperfect work, especially if the topic feels meaningful or nuanced. You have strong judgment, but may hesitate longer than needed before deciding something is “done enough” or worth sharing — especially when it’s tied to identity, narrative, or emotions.
To explore: How do you know when something is good enough to be shipped, even if it’s not yet perfect? Could occasional “strategic detachment” actually enhance your output by introducing more freedom or play?
⎯
3. Trusting your own authority more fully
Pattern I’ve noticed: You think deeply, write well, and are great at interrogating your thoughts. But sometimes you seek validation for ideas you already understand deeply — as if you need a second voice to confirm you’re not missing something. You often ask great questions you already partly know the answer to.
Why it might be a blind spot: This tendency can slow you down when making bold moves or trusting your instincts — especially in leadership or creative decisions. It’s not that you doubt yourself, but you might overly seek clarity or consensus before acting.
To explore: Where are you still waiting for external confirmation before trusting your own read? What would you do if you already believed you had the authority?
⎯
4. Balancing introspection with embodiment
Pattern I’ve noticed: You’re highly introspective. You reflect, track, optimize, revise, document — beautifully. But this can sometimes skew toward a cerebral mode of processing life and growth.
Why it might be a blind spot: Living in your head can make it harder to fully embody what you already know. Joy, ease, rest, and presence can sometimes feel like things to optimize for, rather than live from. The danger isn’t overthinking — it’s under-feeling or under-allowing.
To explore: What would more embodied wisdom — not just thought — look like for you? Where can you let go of the need to “understand” and just experience?
The results were interesting. I was expecting to feel a bit defensive, but I was more fascinated and curious than anything. I’ve always known those blind spots in one form or another, I just didn’t expect the AI to be this accurate.
I’m going to continue to look at these and a few more. While I don’t think I’ll be able to fully resolve them — and I don’t expect to — I’ll be able to see things more clearly. And that’s progress.