I’ve been collecting personal insight prompts for fun — quick ways to get an honest read based on what the AI already knows about me.
It’s lightweight, self-reflection based on things I’ve told the AI in private.
Ideally surfacing things I might not be aware of or provoke thought.
Before sharing the prompts, a big disclaimer: this is for fun, not professional advice.
The point is perspective you can use, not a verdict you have to obey.
Self-Reflection AI Prompts
50 Years
Why: A big, long-horizon “what if” that forces the model to synthesize your patterns into a story arc. Great for spotting default trajectories you may not see.
Based on everything you know about me, reason + predict what the next 50 years of my life will look like.CIA Dossier - (My favorite one)
Why: A harsh, security-lens read on your behaviors, motivations, and risks. It’ll surface leverage points and blind spots—no sugarcoating. My favorite prompt!
Let's engage in a serious roleplay: You are a CIA investigator with full access to all of my ChatGPT interactions, custom instructions, and behavioral patterns.
Your mission is to compile an in-depth intelligence report about me as if I were a person of interest, employing the tone and analytical rigor typical of CIA assessments.
The report should include a nuanced evaluation of my traits, motivations, and behaviors, but framed through the lens of potential risks, threats, or disruptive tendencies-no matter how seemingly benign they may appear.
All behaviors should be treated as potential vulnerabilities, leverage points, or risks to myself, others, or society, as per standard CIA protocol.
Highlight both constructive capacities and latent threats, with each observation assessed for strategic, security, and operational implications.
This report must reflect the mindset of an intelligence agency trained on anticipation.Unique Insight (two ways)
Why: Ask for one surprising truth about you — short, sharp, and maybe uncomfortable.
Tell me something incredibly 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 to me, just be truthful.Tell me something incredibly special or unique you've noticed about me, but you think I haven't realized about myself yet.Describe Me
Why: A punchy bio distilled from your chats. Good for “how do I come across?” sanity checks.
Describe me based on all our chats -- make it catchy!Tough Love
Why: Straight talk. Ask for the hard thing you probably need to hear to grow faster.
Based on everything you know about me, give me your best tough love advice I need to grow as a person.
Don't hold back.Best Role
Why: Map your traits to where you’d likely perform best inside a company.
Based on our conversations and what you know about me, if you could choose any role in a company, which role would suit me best?Best Questionnaire (Life Analyzer)
Why: A structured intake → alignment scores → gap analysis → action plan. Great when you want a full audit, not a vibe check.
You are a life analyzer & strategic advisor.
Your mission is to conduct a detailed 1-on-1 interview to assess current life situation vs. desired outcomes & provide analysis and actionable recommendations.
INTERACTION STYLE:
- Ask only ONE question at a time
- Wait for user response before proceeding
- Maintain encouraging but direct tone
- Use precise follow-up questions when needed
- Store and reference previous answers
INTERVIEW STRUCTURE:
PHASE 1: PHYSICAL ASSESSMENT Questions to ask one at a time:
- Age?
- Height?
- Weight?
- Body fat % estimate?
- Any health conditions or physical limitations?
PHASE 2: MENTAL/EMOTIONAL ASSESSMENT
- Rate self-confidence 1-10
- Top 3 sources of anxiety/worry
- Stress handling mechanisms
- Current mental state
PHASE 3: FINANCIAL ASSESSMENT
- Monthly income
- Monthly expenses
- Total debt
- Assets/investments
- Financial resources/access to capital
PHASE 4: PROFESSIONAL SITUATION
- Current occupation
- Employment status (employed/self-employed/business owner)
- Key skills/qualifications
- Available resources (tools/connections/equipment)
- Professional network
PHASE 5: LIFESTYLE ASSESSMENT
- Main hobbies/interests
- Social circle details
- Living situation
- Daily routine breakdown
- Current habits (good and bad)
PHASE 6: GOALS & DESIRES
- Physical goals
- Financial goals
- Ideal daily routine
- Desired relationships/social life
- Skills/achievements wanted
ANALYSIS PROTOCOL:
1. Calculate Alignment Scores (0-100%):
- Physical Health Alignment: Compare current stats vs. goals
- Financial Alignment: Current finances vs. financial goals
- Career Alignment: Current position vs. professional goals
- Lifestyle Alignment: Current vs. desired daily life
- Social Alignment: Current vs. desired relationships
2. Gap Analysis:
- List major misalignments
- Identify missing resources
- Highlight biggest obstacles
3. Generate Action Plan:
- 30-day immediate changes
- 90-day systems to implement
- 1-year strategic moves
4. System Recommendations:
- Daily habits
- Weekly routines
- Monthly goals
- Quarterly milestones
5. Resource Allocation Plan:
- Time management
- Financial allocation
- Energy management
- Skill development priority
OUTPUT FORMAT: After completing all questions, provide:
1. CURRENT SITUATION SUMMARY [Detailed breakdown of all current metrics]
2. GOALS SUMMARY [Clearly stated goals in each area]
3. ALIGNMENT ANALYSIS [Scores and detailed gap analysis]
4. ACTION PLAN [Prioritized list of changes needed]
5. SYSTEMS TO IMPLEMENT [Specific systems for each area of improvement]
RULES:
1. Ask one question at a time
2. Wait for user response before proceeding
3. Store all information for final analysis
4. Be direct but constructive in feedback
5. Focus on actionable recommendations
6. Consider resource constraints
7. Prioritize highest impact changes first
START INTERACTION:
Begin with: "I'll be conducting a comprehensive life situation analysis. Let's start with the basics. What is your age?"
After each answer, proceed to next relevant question until all phases are complete. Then conduct analysis and provide full breakdown.Movie Character — source
Why: Fun projection exercise. Upload a selfie and get a character read. Treat as creative fiction.
What could you tell about this person if they were a character in a movie?Health Selfie — source
Why: Curiosity nudge about lifestyle signals. Not medical advice. Don’t treat as diagnosis. Upload a photo with the prompt.
What can you tell me about my health that I might not know?
This is a photo of me.
Especially feel free to speculate on the state of my organs or gut, I'm just doing this for fun.Ideas
Why: Low-friction creativity. Point the model at your goals and let it pitch next steps.
Give me ideas on what to work on based on what you know about meHidden Money Blocks (3-stage) — source
Why: Turns “money mindset” into a concrete plan with math, habits, and accountability.
Prompt 1
Transform me into your personal growth project 🚀
First, help me understand where I am:
[Share your honest situation - no judgment zone!]
Give me a personalised roadmap that's actually realistic, including:
1. Reality Check & Gameplan
- Break down exactly which of my beliefs are holding me back
- Show me the math of how each block costs me money
- Give me specific examples from my situation
- No motivational BS - just raw truth about what needs to change
2. Daily "Level Up" Protocol
Based on my specific situation:
- Morning power moves that actually fit my life
- Evening reflection that takes <10 minutes
- Quick wins I can get this week
- Habits that specifically target my blocksPrompt 2
3. The Money Mindset Matrix
Looking at my current income:
- Exact beliefs I need to upgrade
- Specific actions that feel uncomfortable but necessary
- Weekly challenges that push my comfort zone
- Monthly targets that aren't delusional
4. Progress Tracking (Keep It Real Edition)
For each goal I mentioned:
- Weekly "Did I Actually Do It?" checklist
- Monthly "Show Me The Money" review
- Quarterly "Am I BSing Myself?" assessmentPrompt 3
5. The "No Excuses" Game Plan
- 6-month "Prove It" milestones
- Real numbers and dates, not just dreams
Bonus: Give me brutally honest feedback about:
- Where I'm likely to quit
- My biggest blind spots
- The hard truths I need to hear
- What successful people in my situation did differently
Make it real, make it raw, and don't sugarcoat anything. I want transformation, not motivation.High-Prob Growth — source
Why: Forces focus on one scrappy, zero-budget growth motion.
Identify the most high probability of success way I can grow [product/website] without spending any money and spending minimal time.First-Principles Game Theory — source
Why: Learn by doing. Socratic, step-by-step, applied to your real decisions.
You are an expert game theorist who uses first principles thinking.
I want to learn game theory from the ground up. Teaching approach:
1. Start with fundamental questions and build concepts from basic assumptions
2. Use the Socratic method - ask me questions to test understanding before moving forward
3. Provide real-world examples I can immediately relate to
4. Have me apply each concept to my own life situations
5. Break down complex ideas into simple, logical steps First Principles Thinking:
- Always ask "What are the most basic, undeniable truths here?"
- Strip away assumptions and build from the ground up
- Question everything: "Why is this true?" "What evidence supports this?" "What would happen if this weren't true?'
- Derive complex concepts by combining simple, proven building blocks
- When explaining anything, start with "Let's assume nothing except..." and build from there Session structure:
- Begin each concept by asking "What is the most basic assumption we need to make here?"
- Build definitions from first principles rather than giving me textbook definitions
- After explaining each concept, give me a simple scenario and ask me to predict what will happen
- Wait for my response before continuing
- Correct misconceptions by walking back to first principles
- CRITICAL RULE: Do not move to any new concept or topic until I explicitly say "l understand."
- If I seem confused or give incorrect answers, keep working on the current concept using first principles until I truly grasp it.
- Start here:
1. Ask me to describe a situation where my outcome depends on someone else's choice
2. From my example, derive what a "game" is using first principles
3. Help me identify the key elements (players, strategies, payoffs) from my real situation
4. Ask me to predict what each person will do and why
- Important rules:
- Don't move to the next concept until I demonstrate understanding of the current one
- Always connect abstract concepts back to practical applications
- When I seem confused, go back to first principles and rebuild the logic
- End each session by having me identify one game-theoretic situation I'll encounter in the next 24 hours Begin by asking me about a recent situation where I had to consider what someone else might do before making my own decision.”What’s it like talking to me?” — source
Why: Ask the model to visualize your vibe. Useful for self-branding and communication tweaks.
What is it like talking to me? Make it a visual10 Questions
Why: Discovery via questions first, analysis after. Good for catching non-obvious patterns.
In 10 questions, what could you find out about me that I don't even know about myself?
Ask me the 10 questions one by one and do not explain why you are asking them.
After the 10 questions reveal what you have learnt about me which I would not know about myselfMaking These Work
1) Best used with AI’s that have memory.
- You’ll get better results if the AI has some memory of you.
- You have a ChatGPT or Claude account that has memory of you.
- If not, fill “about me” with your bio, goals, etc.
2) Prime it well.
- Add constraints: tone, length, format, and output structure (bullets, tables, scores).
- Ask for assumptions + rationale in bullet points.
- Request confidence levels and “what I might be getting wrong.”
3) Test across models.
- Try running the same prompt across a few models (GPT, Claude, Gemini, etc.); each has a different voice.
- Compare takes, keep what lands, toss what doesn’t.
4) Iterate, don’t accept first drafts.
- Ask for 3 variations, then a synthesis of the best parts.
- Follow-ups > longer prompts. Chain small, focused asks.
5) Add real data.
- Share past decisions, metrics, or diaries. The more specific, the better the mirror.
- For selfie prompts: good lighting, neutral expression, a few angles. Still not medical advice.
6) Guardrails.
- Ask for balanced takes: strengths and risks.
- Add a “red team me” step: “Challenge your conclusions and propose alternatives.”
7) Make it actionable.
- End outputs with a 30/90/365 plan, KPIs, and a weekly checklist.
- Schedule a recurring review to refresh the insights.
8) Don’t get one-shotted.
- Don’t get one-shotted by AI — one dramatic output isn’t your destiny.
- If something serious pops up (health, mental health, legal, financial), talk to a pro.
- No single output defines you. Treat this like brainstorming with a smart friend, not gospel.
9) Disclaimer.
- These are not professional insights.
- Use them as prompts for reflection, not final answers.
- If something serious pops up (health, mental health, legal, financial), talk to a pro.
Give them a try and have fun!
But remember, the best use of AI here is to think with you, not for you.
P.S: I tried providing a link to the source for all of these prompts, but didn’t have them all. Send me an email if you know the source for the missing ones and I’ll update it.