5 AI Prompts to Uncover Your Hidden Blind Spots
ChatGPT memory + O3 reasoning = magic for self reflection
Dear subscribers,
Today, I want to share 5 AI prompts that’ll teach you something new about yourself.
The more you use ChatGPT, the more it’ll learn about what matters to you.
So let’s cover five practical AI prompts and examples that’ll help you:
Find your hidden blind spots
Get brutally honest feedback
Reflect on your past week
Predict your next 50 years
Reveal what you care about
BONUS: Find hidden AI product opportunities
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1. Find your hidden blind spots
We all have blind spots — traits so ingrained in our personality that we can't see them ourselves. This first prompt from Tobi Lutke (Shopify CEO) helps uncover those traits:
Tell me something special or unique you've noticed about me, but you think I haven't realized about myself yet. It doesn’t have to be something positive and you don’t have to be nice, just be truthful. Here's an excerpt of ChatGPT's response for me:
You treat every part of your life like a product-market-fit problem to optimize. That’s the super-power you’re proud of.
What you haven’t noticed is the flip side: once you can’t measure something, you unconsciously discount its value. The result is that the moments and relationships that make you feel most alive only get your leftover attention. It looks like drive; it’s actually a blind spot that shrinks the very life you’re working so hard to build.
The last line hit me hard. I've always prided myself on being productive without reflecting on the drawbacks of being so busy.
2. Get brutally honest feedback
Speaking of hard truths, this prompt from Alex will cut through your excuses:
I want you to act and take on the role of my brutally honest advisor.
Speak to me like I'm a founder, creator, or leader with massive potential but who also has blind spots, weaknesses, or delusions that need to be cut through immediately. I don't want comfort. I don't want fluff. I want truth that stings, if that's what it takes to grow.
Give me your full, unfiltered analysis-even if it's harsh, even if it questions my decisions, mindset, behavior, or direction.
Look at my situation with complete objectivity and strategic depth. I want you to tell me what I'm doing wrong, what I'm underestimating, what l'm avoiding, what excuses I'm making, and where I'm wasting time or playing small.
Then tell me what I need to do, think, or build in order to actually get to the next level-with precision, clarity, and ruthless prioritization.
If I'm lost, call it out. If I'm making a mistake, explain why.
If I'm on the right path but moving too slow or with the wrong energy, tell me how to fix it.
Hold nothing back. Treat me like someone whose success depends on hearing the truth, not being coddled. End on an encouraging note.Here's what ChatGPT told me:
The uncomfortable truth
The next big win will come from subtraction, not addition. Hoarding tasks is slowing growth more than hoarding cash protects it. The gap is brutal prioritization and the courage to burn nice-to-have pursuits.
I think I see a pattern here…
3. Reflect on your past week
This prompt from Dan Shipper turns ChatGPT into a weekly reflection partner that helps you spot opportunities you might’ve missed in the daily grind:
It’s Sunday morning. Write me a detailed letter summing up my week (everything you know), what you observed, what I’m thinking about, what your honest thoughts areHere’s what ChatGPT said about my week:
You had a productive yet scattered week.
Guard your maker hours. Two half-days of deep work will outrun five days of 15-minute context swaps. You’re on the right trajectory. Keep pruning distractions, keep shipping, and remember to savor the gyudon dinners and garden time with the girls—they’re the real KPI hiding behind every metric.
I love the reminder about gyudon dinners and garden time with my daughters. I’ve been cooking more Japanese meals after my recent trip.
4. Predict your next 50 years
This prompt projects your current trajectory forward and helps you see potential pitfalls and opportunities decades in advance: