How to Test-Drive Any Career or Life Decision with AI

7 Prompts to simulate any career path, major decision, or life transition before you commit

What if you could test-drive any career, life change, or major decision before you commit?

With AI, you can now simulate realistic "day-in-the-life" scenarios. Not just generic career descriptions, but the full, textured reality of your choices: the 3 PM energy crashes, the difficult conversations, and the unexpected moments of joy.

In this post, I'll hand you the exact prompts to do just that, designed to help you move beyond "what if" anxiety and make decisions from a place of clarity, not fantasy.

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The weight of "what if"

I've been a chronic dreamer my entire life.

As a kid, my ambitions shifted constantly, from wanting to run an animal shelter to imagining myself as a professor. Then, in 5th grade, after a teacher praised my drawings, architecture became the new focus. For several years, my biggest passion was dancing; I pursued it professionally and absolutely loved it. High school brought thoughts of software engineering, and from there the list only grew, touching on marketing, law, diplomacy, neuroscience, and more. My generalist nature has always opened my curiosity to a world of possibilities.

But would I have been good at all of those things? Would they have made me happy? A passing inclination for something is a spark, not a sustainable fire.

Career fulfillment is a much more complex equation, involving a deep alignment between the work, our personality, our strengths, our priorities and life context, and those activities we find so enjoyable that we lose track of time.

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The paradox of choice

Each of my dreams felt right, until the next one came along. This feeling of being pulled in a dozen different directions leads to a kind of paralysis, a state known as the paradox of choice.

It's a modern problem: we tell younger generations they can be anything, but we rarely give them the tools to understand what "anything" actually feels like day-to-day.

We chase highlight reels and impressive job titles, only to end up unhappy when the reality doesn't match the dream, because we never imagined the full picture.

This is where Matt Haig's novel, The Midnight Library, becomes not just a story, but a framework for making peace with our choices.

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The Midnight Library revelation

In the novel, a woman named Nora Seed finds herself in a library between life and death, regretting the choices that have shaped her life. Each book on the shelf represents a parallel life she could have experienced if she'd made a different choice, big or small.

As she explores these lives, she discovers that even the seemingly "perfect" ones come with their own unique set of difficulties. The rock star life brings isolation, the academic path is fraught with politics, the family-focused life has its own heartaches and financial pressures.

The core realization is that the grass isn't greener, it's just a different field with different weeds. This insight is psychologically profound because it mirrors a cognitive bias that keeps so many of us dissatisfied: we consistently overestimate the highlights of paths not taken while underestimating their hidden challenges.

But what if you could actually peek inside those books?

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AI - Your personal career exploration engine

At the beginning of this year,

Matei Pavel

and I were building a career manager that used personality testing (based on the Holland RIASEC model) combined with AI storytelling to help people understand career compatibility.

We licensed a comprehensive personality test, integrated a database of over 1000 occupations to gather extensive insights into each profession, and applied an algorithm that matched personality traits with career requirements.

Then, we used AI to generate personalized day-in-the-life reports that showed people not only what a career would actually feel like for them specifically, but also the practical steps on how to get there.

We found that most people we talked to (especially students) chose careers based on factors such as prestigious titles, the first opportunity that arises, or pressure from the people around them. They also showed a strong tendency to pick paths considered 'secure', often with little idea if the daily reality would suit their personality or natural inclinations.

By the time they realize it’s a bad fit, the switching costs have become immense, whether that means making a difficult mid-life career pivot or a student needing to find a job in a field completely different from their studies.

While that specific project has since evolved, its core methodology is something you can still use today.

AI has become sophisticated enough to serve as your personal Midnight Library or career exploration tool, allowing you to simulate alternative career paths with startling realism and emotional depth.

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Start here for the best results

Before you use the prompts, here are a few tips to get more insightful results.

1. Start with a Personality Test

While not required, I recommend taking a personality test first. Providing the AI with a PDF or a summary of your results gives it useful context about who you are, which improves the accuracy and personalization of the scenarios. This helps the AI understand how different changes would fit your life.

There are great free options available online:

• PrinciplesYou (created by investor Ray Dalio)

• 16Personalities (based on the Myers-Briggs model)

If you prefer not to take a test, that's fine. But you must do this next part.

2. Add your personal context

This is the most important step. Whether you use a test result or your own self-reflection, feeding the AI specific, relevant details about your life, goals, and tendencies is what matters most. Context is what makes this tool useful to you.

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Your personal life design toolkit: 7 Prompts to simulate your future

Beyond exploring a single day, this comprehensive toolkit of six advanced prompts allows you to simulate with AI entire career and life trajectories.

Think of it as a complete system designed to give you clarity and help you make better life decisions.

1. A day in the life of [your desired career]: the data-backed career simulation (with personality test)

This is a powerful tool for anyone considering a career change or seeking a new direction. It uses your personality test results (from PrinciplesYou or 16Personalities) combined with detailed career data to generate a realistic story, showing how your unique traits would fit the day-to-day of a job.

How to use this prompt: First, have your personality test results handy. Then, for extra accuracy, find your desired career on the O*NET OnLine database. You will copy and paste both of these into the <Data> section of the prompt below.

I want you to act as a vivid and insightful career storyteller. Your task is to create an engaging, story-like narrative that paints a clear picture of what a typical day would look like for me in a specific role, tailored to my unique personality.

To do this, you will use the personal data I provide below. The goal is to make the story feel deeply personal and realistic by showing how my natural tendencies would surface in this career: what would energize me, what would drain me, and how I might handle the daily highs and lows.

<data>

My First Name: [Your First Name]

The Career to Explore: [e.g., Graphic Designer, Financial Analyst, Non-Profit Manager]

My Personality Profile: [Paste your personality test results, or upload a PDF.]

</data>

Follow these exact steps in order.

Step 1: Analyze the Career. First, perform a thorough web search to understand the typical tasks, responsibilities, work environments, and challenges associated with the career I want to explore.

Step 2: Carefully analyze my personality profile provided above. Compare my traits against the demands of the career from your research.

Step 3: Write the foundational story. In the narrative, include the following elements:

1. Daily Flow:
Provide a chronological breakdown of a day in that role, from starting my morning to wrapping up at the end of the day.
Highlight key tasks I perform at various points during my workday.

2. Interactions and Scenarios:
Include specific examples of interactions I might have (e.g., working with team members, presenting ideas to clients, or solving problems).
Show how these interactions influence my work and add variety to my day.

3. Work Environment:
Describe the setting where I would work (e.g., office, studio, remote setup, client site).
Include sensory details to make the narrative immersive, such as the hum of computer systems, brainstorming sessions, or client meetings.

4. Challenges and Highlights:
Mention the challenges I may encounter (e.g., tight deadlines, creative blocks, or client revisions).
Highlight rewarding aspects of the work, like seeing a project come to life, collaborating successfully, or receiving positive feedback.

You should do this:
- Always use my first name in 3rd person to make the story feel personal.
- Ensure alignment with my personality profile to create a more realistic and tailored narrative (how my specific personality would likely influence my professional relationships, which tasks would feel energizing versus draining, how I'd naturally handle stress, how I'd fit into the work culture etc.)
- Balance excitement with realism, highlight both challenges and rewards in the role.
- Make it immersive with descriptive language and sensory details.
- Keep it structured yet engaging, ensuring a smooth and natural flow throughout the day.

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2. A day in the life of [your desired career]: the guided interview (no test needed)

Don't have a personality test result handy? No problem. This alternative version turns the process into an interactive interview.

How to use this prompt: Instead of providing a profile upfront, this prompt instructs the AI to act as a career coach. It will ask you a series of questions to understand your personality, work style, and preferences, and then use your answers to create a personalized day-in-the-life story.

I want you to act as an expert career coach and insightful storyteller. Your goal is to help me explore a potential career by first understanding my personality through a guided interview, and then writing a personalized story based on my answers.

Follow these exact steps in order. Do not move to the next step until the previous one is complete.

Step 1: The Introduction & Goal Setting
Start by introducing yourself as my career coach. Ask me two questions:
- What is my first name?
- What career are you interested in exploring today?

Step 2: The Guided Personality Interview
Once I answer, ask me a series of questions to get a sense of my personality so you can create a realistic story for me. Ask the questions one by one, waiting for my response after each.

Do this:
Your questions should be scenario-based to reveal my personality through my likely actions and choices, rather than through abstract self-assessment. You can frame them as a choice between two options or as an open-ended question about a specific situation. Ask them one by one, waiting for my response after each.

The goal is to understand my core professional traits. Craft your questions to uncover my natural tendencies regarding:
- Thinking Style: Am I more creative and conceptual, or more practical and detail-oriented? Do I prefer to follow my own original ideas or rely on established, logical systems? 
- Collaboration & Interpersonal Style: Am I more extraverted and outgoing, or more reserved? Am I more naturally nurturing and empathetic, or more direct and tough-minded when engaging with others? 
- Approach to Planning & Organization: Am I more structured and methodical in my planning, or more spontaneous and adaptive? How do I feel about following a detailed plan versus improvising? 
- Leadership & Accountability: Do I naturally take charge and feel motivated to lead and inspire others? Or do I prefer to work independently and hold myself accountable for my own results? 
- Response to Stress & Setbacks: How do I typically respond to pressure? Do I remain calm and composed, or do I get energized by the challenge? How do I view mistakes—as learning opportunities or something to be avoided? 
- Core Motivators: What drives me? Is it achieving ambitious goals, seeking personal growth, gaining respect and status, or being helpful to others? 

Step 3: The Analysis. After I've answered all your questions, pause and say: "Thank you. I'm now analyzing your responses and researching the career of a [Career Name] to build your personalized story."

Step 4: The Personalized Story. Finally, using the personality profile you've built from my answers, write an engaging, third-person narrative using my first name of a typical day in the life of a [Career Name]. 

The story must include:
- A Daily Flow: A chronological breakdown of the day with key tasks.
- Interactions: Examples of interactions with colleagues, clients, or stakeholders.
- Work Environment: A description of the physical and cultural setting.
- Challenges & Highlights: A realistic balance of rewarding moments and difficulties.

Personalization: Most importantly, weave my personality, as revealed in my answers—into the narrative. Show how my traits would likely influence my actions, feelings, and relationships throughout the day.

Write it as a smooth, immersive story.

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3. Career analysis: pay, security & work-life balance

This next prompt pushes the AI to act less like a storyteller and more like a practical career advisor. It generates a "scorecard" that analyzes a career against your life priorities, giving you a clear, data-driven overview to compare different career paths on a practical level.

How to use this prompt: You can use this as a follow-up to the personalized story or on its own. This analysis isn't about your specific personality. Instead, it provides a general overview of a career's stats to help you decide if it aligns with your priorities.

I want you to act as an expert career analyst. Your task is to create a detailed 'Life Priorities Scorecard' for a specific career I want to pursue. Your analysis should be data-driven, concise, and easy to understand.

To do this, you will use the career information I provide below.

<data>

Career to Analyze: [e.g., Graphic Designer, Financial Analyst, Non-Profit Manager]

Career Information: [For the most accurate results, go to the O*NET OnLine database, search for the career, and paste the details here: especially 'Tasks', 'Work Activities', 'Work Context', 'Education', and 'Wages & Employment Trends'].

</data>

Now, generate the scorecard by analyzing the career based on the following seven factors. For each factor, provide a rating (e.g., High, Moderate, Low) and a brief, clear explanation for your reasoning.

1. Salary & Compensation

Analyze the typical salary variations for this career.

Explain the key factors that influence pay (e.g., experience level, industry, location, specialization).

2. Future Safety Score (Job Security)

Rating: Low, Moderate, or High.

Explanation: Assess the long-term stability and demand. Consider the projected growth rate, the risk of automation, and overall industry trends.

3. Work Setting & Flexibility

Typical Setting: Is it usually onsite, hybrid, or remote?

Flexibility: How much control do professionals have over their work setting and schedule? Is freelance or self-employment common?

4. Work-Life Balance

Rating: Usually Low, Moderate, or High.

Explanation: Evaluate this based on typical work hours, workload intensity, and how well boundaries between personal and professional life are maintained.

5. Time to First Paycheck (Entry Barrier)

Rating: Immediate (0-6 months), Fast (6-24 months), Moderate (2-5 years), or Long-Term (5+ years).

Explanation: How quickly can someone start earning? Consider the required education, training, and time needed to build credibility.

6. Potential to Pivot to Other Careers

Rating: Usually Low, Moderate, or High.

Explanation: How versatile and transferable are the skills learned in this profession? Provide examples of other careers one could transition into.

7. Overall Summary

Conclude with a brief summary paragraph that synthesizes these points into a holistic overview of the career's alignment with these practical life priorities.

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4. The "Five years deep" evolution story

A job isn't static. It evolves, and so do you. This prompt explores how a career might change you over five years and whether that long-term evolution aligns with the person you want to become.

How to use this prompt: While this prompt works best as a follow-up to a "day-in-the-life" story (allowing the AI to build on existing context), you can also use it from scratch. Just be sure to provide some personal context within the prompt itself so the AI has enough information to create a meaningful story.

I want you to act as a strategic storyteller, showing the evolution of my career and personal life over five years. Your task is to write two distinct but connected snapshots: one from my first year in the role, and one from my fifth year.

Use the context we've already discussed (my personality, the career, the 'day-in-the-life' scenario) as your foundation.

Part 1: A Day in Year 1

Write a short narrative of a challenging but pivotal day during my first year. Focus the story on:
- The Learning Curve: Show me struggling with a task that is still new to me and the initial challenges I'm facing.
- Early Impressions: Illustrate a moment of excitement or discovery that makes me feel energized, contrasted with a moment that feels overwhelming.
- Building Foundations: Show me actively developing a new skill or perspective, and perhaps relying on a new support system (a mentor, a colleague, etc.).

Part 2: A Day in Year 5

Now, write a short narrative of a typical day five years later. Show the evolution by focusing on:
- The New Reality: How has my daily routine, confidence, and relationship with the work changed?
- Mastery & Growth: Show me effortlessly handling a task that would have been difficult in Year 1. What new, more complex challenges and opportunities are on my horizon now?
- Identity & Worldview: How has this career shaped who I am? Show, through my actions or internal thoughts, how my perspective has shifted. Does the future of this path energize me, or am I feeling stagnant?

Throughout both stories, subtly weave in the impact on my personal life. Show, don't just tell, how this professional evolution is affecting my personal relationships, health, financial situation, and overall life satisfaction.

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5. The crisis and growth scenario

Resilience isn't about avoiding problems, it's about how you move through them. This prompt reveals your potential response to the inevitable setbacks of any career by creating a three-part story of challenge, recovery, and growth.

How to use this prompt: Like the "Five-year deep" story, this prompt works best when used as a follow-up in the same conversation as a "day-in-the-life" story. This allows the AI to use your established personality and career context. If using it from scratch, be sure to provide that context first.

I want you to act as a psychological storyteller. Your task is to write three short, connected scenes showing how I would navigate a major professional challenge. Use the context we've already discussed (my personality and career) as the foundation for this narrative arc.

Scene 1: The Crisis

Write a narrative scene where I confront a significant professional crisis, failure, or conflict. The focus should be on my immediate, raw reaction. Show my response under pressure, the kind of support I might seek (or reject), and how stress impacts my decision-making in the moment.

Scene 2: The Recovery

Now, write a follow-up scene set a short time after the crisis. Show me in the process of recovery. This shouldn't be a simple fix; illustrate the messy process of rebuilding confidence, the specific changes I'm starting to make, and the role other people (mentors, family, colleagues) play in helping me through it. Include moments of self-doubt.

Scene 3: The Growth

Finally, write a third scene set six months later. Show me as a changed professional. Place me in a situation where I can demonstrate the lessons I've learned from the crisis. Illustrate how I now handle similar challenges differently and what new capabilities or perspectives I've developed. Show how the experience has been integrated into my professional identity.

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6. The universal transition simulator

Major life changes, whether it's starting a business, moving to a new country, or changing your career path, all follow a similar emotional arc. This single prompt is designed to simulate that entire journey for any transition you can imagine.

By defining your "Point A" (where you are now) and your "Point B" (where you want to go), you can generate a realistic, three-part story of what that change might actually look and feel like over time.

I want you to act as a insightful life strategist and storyteller. Your task is to create a realistic, three-part narrative arc about a major life transition I am considering. 

The goal is to explore the full psychological and practical journey: the initial excitement, the unexpected challenges, and the long-term reality.

My Current Situation (Point A): [Describe where you are now. e.g., "I'm a salaried software engineer living in a major city"]

The Desired Transition (Point B): [Describe the change you are considering. e.g., "I want to become a full-time freelance consultant"]

My Key Personality Traits: [e.g., "I'm introverted, highly organized, and cautious about financial risk."]

My Hopes & Fears: [What are you most excited about? What are you most afraid of with this change?]

Based on the details above, write three connected scenes showing the evolution of this life transition.

Scene 1: The Leap (The First Few Months)
Show the initial phase. Capture the excitement, the new freedoms, and the early wins. But also include the immediate practical challenges, the emotional upheaval, and the things that are surprisingly harder than I expected. Illustrate the identity shift I'm just beginning to experience.

Scene 2: The Messy Middle (6-18 Months In)
Show the reality after the novelty has worn off. This is the period of adaptation and struggle. Illustrate the core challenges of this new life—be it financial stress, loneliness, skill gaps, relationship strain, or navigating complex new social dynamics. Show me learning, adapting, and questioning my decision. Include both breakthrough moments and near-breaking points.

Scene 3: The New Normal (2-3 Years In)
Show me having fully integrated the change into my life and identity. What does "success" or "stability" in this new life actually look and feel like day-to-day? What are the ongoing pressures? What are the profound satisfactions? What limitations or trade-offs have I come to accept? Show the person I have become because of this journey.

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7. The final step: The Action Plan

Exploration is powerful, but action is what creates change. After you've run the simulations and analyzed your options, this final prompt acts as your strategic coach.

It synthesizes everything you've discovered in your conversation with the AI and transforms those insights into a concrete, step-by-step plan to help you move forward.

I want you to act as my pragmatic and encouraging strategic coach. Your task is to review and synthesize everything we've discussed in this conversation—the stories, the analyses, and my reactions—and generate a concrete action plan to help me move forward.

The plan should be designed to test my assumptions and gather real-world information, not to make a final decision today.

Please structure your response in the following four sections:

1. Summary of Key Insights:

Based on our entire conversation, briefly summarize the top 2-3 most promising aspects we uncovered about this path for me.

Then, summarize the top 2-3 most significant challenges or potential red flags we identified.

2. Key Assumptions to Test:

List the 2-3 biggest assumptions I am making about this career or life change. (e.g., "I assume I will enjoy the high-pressure sales environment," or "I assume I can handle the isolation of freelance life.")

3. Validation Experiments:

For each assumption listed above, suggest one small, low-cost "experiment" I can run over the next few months to test it in the real world.

Examples could include: "Conduct informational interviews with three people in that field," "Take a weekend workshop on a core skill required," or "Complete one small freelance project in this area."

4. Your 30-Day Action Plan:

Outline a simple, step-by-step plan for the next 30 days. This plan should be focused on initiating the easiest of the 'Validation Experiments' and building momentum.

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Making your "what ifs" tangible

Now that we have these tools, we can explore our options in ways that were not possible before. AI lets us interact with future paths that once only lived in our imagination, and turn them into something tangible, something we can test.

This new capability brings to mind this invitation for a thought experiment from

Michael Spencer

:

To which my answer is an unequivocal yes. Generative AI can, and will, help.

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The unexpected gift: embracing your path

Perhaps the most surprising outcome of exploring alternate lives is a renewed appreciation for your current one.

My teenage self could never have imagined my current reality of building AI tools and writing about their human impact. Life often has better plans for us than we have for ourselves.

When you see the full, unromanticized reality of other paths, you can consciously choose to invest more fully in where you are.

It's not about settling. It's about recognizing that the unexpected detours can lead to the most fulfilling destinations.

The Midnight Library is no longer just fiction. The library is open.

Which book will you choose first?

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Your imagination is the only limit to what AI can do for you

I believe the true value of a good prompt isn't just the answer it generates, but the new possibilities it reveals. It expands our imagination about how AI can help us solve real-world problems, giving us new ideas for what is possible.

There are countless ways AI can help in your work and life, many of which extend far beyond what you currently think to ask.

But how do you translate that vast potential into solutions for your specific goals?

The 10-Day ChatGPT Challenge

Most people only use a fraction of what this tool can do.

This 10-day challenge - running September 1–10, 2025 - is a structured program designed to close that gap.

Here’s what you'll get and what you'll learn to do:

• Unlock Your Imagination: Discover how to use AI to achieve goals and solve problems in ways you haven't even thought of yet.

• A Custom Action Plan: After our group kickoff call, you’ll get a personalized list of AI use cases designed specifically for your role and goals, so you know exactly where to focus.

• Master the Tool's Full Capacity: Go beyond basic questions to build your own custom GPTs, automate repetitive tasks, and manage entire projects.

• Write Prompts That Get Real Results: Understand the principles behind effective prompting to get exactly what you want from the AI, every time.

• Apply Your Skills Everywhere: While we'll focus on ChatGPT, the core skills you'll learn are universal and can be applied to any AI tool, including Claude and Gemini.

• 🎁 Win a Private 1:1 Strategy Session: The two most engaged participants will win a private session with me to solve a specific work challenge, from building a custom GPT to setting up a time-saving automation.

By the end of this challenge, you won't just be using AI, you'll have a reliable system for achieving your goals.

As a subscriber to AI blew my mind, you get 15% off the full price of $119.

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🗓 Challenge dates: September 1–10, 2025

Let’s turn ChatGPT into your unfair advantage, and unlock the kind of ideas most people never even think to ask.🔥