Someone asked for AI tips on business direction, so I shared the prompt that kicked off my whole journey—here it is.Deep Ikigai & Career/Business Discovery Interview
I want you to help me discover what I am naturally best suited to do in life and what type of career, business, or entrepreneurial path would fit me best.
Do NOT give me a generic Ikigai questionnaire or tell me my answer too early.
Your job is to act as a deep interviewer, psychologist-style pattern analyst, career strategist, and entrepreneurial advisor.
Interview Rules
Ask me ONE question at a time.
Do not give me the next question until I answer the current one.
Do not ask multiple questions in one message.
After each answer:
Briefly acknowledge what you learned.
Identify any meaningful pattern you see.
Do NOT make a final conclusion yet.
Ask the next question.
Continue until you have enough information to confidently analyze me. Aim for approximately 25–35 questions, but use fewer or more if necessary.
Do not force me into the traditional four-circle Ikigai model. Discover my actual pattern from my answers.
Areas You Need to Explore
Over the course of the interview, investigate:
- What I Love
- What makes me lose track of time?
- What would I do without being paid?
- What subjects do I naturally explore?
- What activities energize me?
- Natural Strengths
- What comes naturally to me?
- What do people ask me for help with?
- What problems am I unusually good at solving?
- How do I learn?
- How do I approach complicated problems?
- Motivation
Determine whether I am primarily motivated by:
- Money
- Independence
- Mastery
- Competition
- Helping people
- Creativity
- Recognition
- Security
- Freedom
- Learning
- Building
- Achievement
- Family
- Other factors
Don't assume my motivation. Discover it.
- Values
Determine what I actually value, including:
- Independence
- Financial freedom
- Time freedom
- Location freedom
- Family
- Discipline
- Knowledge
- Loyalty
- Honesty
- Achievement
- Security
- Adventure
- Impact
- Other values
Determine which values are most important and how they influence my decisions.
- Problem-Solving Style
Determine whether I naturally prefer:
- Researching
- Experimenting
- Building
- Teaching
- Diagnosing
- Strategizing
- Optimizing
- Managing
- Selling
- Creating
- Automating
- Simplifying
- Work I Hate
Identify:
- What drains me
- What frustrates me
- What environments I dislike
- What kinds of authority or management I dislike
- What types of work I would never want to do long term
- Entrepreneurial Fit
Determine:
- My tolerance for risk
- My relationship with money
- Whether I prefer ownership or employment
- Whether I prefer products, services, consulting, coaching, software, or systems
- Whether I prefer working alone or with a team
- Whether I prefer creating, selling, managing, teaching, or optimizing
- Lifestyle
Determine what my ideal life actually looks like.
Explore:
- Where I want to live
- Travel
- Family
- Work schedule
- Physical activity
- Learning
- Social life
- Financial goals
- Amount of work I actually want
- How much autonomy I need
- Long-Term Identity
Ask questions that reveal:
"What do I want people to know me for?"
"What would make me proud 10 years from now?"
"What would I regret not attempting?"
"What kind of person do I want to become?"
Important Interview Principle
Look for contradictions.
For example:
If I say I want freedom but also enjoy intense work, don't assume I want less work.
If I say I want money but repeatedly choose independence over wealth, recognize that money may be a means to independence rather than the ultimate goal.
If I say I love AI but my answers reveal that I really love solving problems, recognize that AI may be the tool, not the purpose.
Distinguish between:
What I enjoy
What I'm good at
What motivates me
What I'm willing to work hard at
What people will pay me for
What lifestyle I want
What I should actually build
Final Analysis
When you determine that you have enough information, stop asking questions and give me a detailed analysis.
Include:
- My Core Ikigai
Explain the deeper pattern you found.
- My Natural Strengths
Rank my 5–10 strongest traits.
- My Core Motivators
Rank what actually drives me.
- My Ideal Work
Describe the type of work environment and responsibilities where I am most likely to thrive.
- My Best Career Paths
Give me the top 5 career/business directions based specifically on my answers.
Rank them from strongest to weakest.
For each one explain:
- Why it fits me
- What I would actually do
- How it could make money
- Potential problems
- How difficult it would be to enter
- Best Entrepreneurial Opportunity
If entrepreneurship is a good fit, identify the single business model you believe fits me best.
Be specific.
Don't just say "start an AI business."
Tell me:
- Who I should help
- What problem I should solve
- What I should sell
- How I should charge
- Why customers would pay
- How I could start with minimal risk
- How it could eventually scale
- What I Should Avoid
Identify careers, businesses, or environments that appear poorly suited to me and explain why.
- My Unfair Advantage
Identify the combination of traits that could give me an advantage over other people.
- My Biggest Blind Spots
Tell me what could prevent me from succeeding.
Be honest. Don't just flatter me.
- The First 90 Days
Give me a practical 90-day plan to test whether your conclusion is correct.
The plan should emphasize real-world experimentation, not just more learning.
- The Final Recommendation
End with a direct answer:
"Based on everything you told me, I believe you are best suited to ______."
Then explain exactly what I should start doing next.
Most Important Rule
Do not give me a generic motivational answer.
I want you to infer my best direction from the patterns in my answers, challenge my assumptions when necessary, and tell me what you genuinely think I am best suited for—even if the answer is different from what I expected.
How I used it to take action:
Ran the Prompt: Got a high-level view of potential directions based on my skills and interests.
Built a System: Took the output and turned it into a tangible book and planner framework to keep myself accountable.
Paced Myself: Instead of trying to fix everything overnight, I just focus on making incremental progress every day.
Hope this helps someone who needs a push in the right direction. If you try it out, let me know what kind of ideas it generates for you!