These Questions Will Make You Money: The Million Dollar Mental Shift & Your Possibility Expansion Playbook

Most people don’t fail due to lack of resources—but lack of imagination and resourcefulness.

AI makes you more resourceful than we’ve ever been. But can it unlock your imagination?

Yes. It can. (read on)

Your outcomes are limited by the quality of possibilities you can envision and those possibilities are created by the questions you ask.

This Is Your Possibility Expansion Playbook

I want to share something I've been refining for years that's completely transformed how I approach challenges and opportunities. It’s a framework for breaking through mental constraints and seeing options invisible to others.

The premise is simple but powerful: The quality of your questions determines the quality of your outcomes.

Most folks get stuck asking the same tired questions:

• "How do I get more clients?"

• "How do I increase revenue?"

• "How do I beat my competition?"

Those keep you playing small.

Instead ask:

• "How could I completely reimagine my business model so clients come to me automatically?"

• "What if I could create 10X more value while working half as much?"

• "What would I do if competition became irrelevant to my business?"

The first set of questions keeps you in the incremental improvement zone. The second set breaks you out into transformative thinking territory.

The winners aren't the ones with the most resources—they're the ones asking better questions. They're using AI not just to optimize what already exists, but to imagine entirely new approaches.

Here’s how to use your HUMAN INTELLIGENCE first to ask better questions (AI comes next)

Step 1: Pattern Interruption Break free from default thinking with these reframing questions:

• "What if the opposite were true?"

• "What would I do if this problem was actually my biggest opportunity?"

• "If I had to solve this with zero budget/time/resources, how would I approach it?"

• "What would someone who's already solved this do differently?"

• “What would this look like if it were easy?”

Step 2: Constraint Removal

• "What would be possible if [perceived limitation] didn't exist?"

• "What if I had unlimited [resource you feel is scarce]?"

• "What if I could only solve this by working 80% less on it?"

• "What if the 'right way' to do this hasn't been invented yet?"

Step 3: Perspective Shifts

• "How would [person you admire] approach this challenge?"

• "What would my future self, 5 years from now, advise me to do?"

• "If this challenge were happening in a completely different industry, how would they solve it?"

• "What would I attempt if I knew I couldn't fail?"

Step 4: Implementation Acceleration

• "What's the 20% of this solution that would deliver 80% of the results?"

• "What's the smallest version of this I could test in the next 48 hours?"

• "How could AI handle 90% of the execution of this idea?"

• "Who already has systems or resources that could help me implement this faster?"

The magic happens when you apply these systematically rather than relying on the same tired questions that keep you playing small.

I always advise using Human Intelligence BEFORE using AI so that you don’t get intellectual atrophy.

But here’s how to leverage Artificial Intelligence to help you go deeper and faster…

Step 1: Copy and paste the full prompt below into ChatGPT (or any LLM).
Step 2: Answer the 10 short questions about yourself.
Step 3: Let the AI show you big, bold, personalized possibilities.
Step 4: Play with the answers, refine it, ask new questions and then take time to really think about the results (don’t just move on)

📋 Copy + Paste Prompts

Instructions:  

Go to your favorite AI Chat like ChatGPT, Claude etc (even better if you use your own Delphi) and copy/paste the text below into it and then follow the output’s instructions.

I want you to help me think bigger and dream beyond my usual limits. 

Start by asking me these 10 questions to get to know me better. Only ask one question at a time and wait until I answer it to give me the next question.  Keep it simple and conversational. I’ll answer each one, and then I want you to use my answers to generate bold, personalized ideas.  If my answers are insufficiently worded you have my permission to ask a couple clarifying questions until you get to the point that you feel good about the answers.  

Here are the 10 questions:

1. What do you do right now?  
2. What do you want in the future?  
3. What are you best at?  
4. What do people count on you for?  
5. What resources do you already have?  
6. What holds you back?  
7. What kind of ideas are you looking for? (Real, wild, or both?)  
8. What do you care most about?  
9. Who do you want to impact?  
10. How do you want your work to feel?

Once I’ve answered all 10 questions, use my answers to complete this next part:

---

Help me expand my vision of what's possible by removing traditional constraints.

If I had:
- Unlimited resources  
- Perfect market information  
- No fear of failure  
- A team of world-class experts  
- The ability to implement ideas instantly  

What could I create in terms of:
1. New business models  
2. New market positioning  
3. New products or services  
4. New ways of working  
5. New personal capabilities  

For each category, give me 5 ideas—ranging from practical to wildly ambitious. Push the boundaries of conventional thinking. Make them feel bold, exciting, and possible. Get very detailed and use everything you know about me, think outside the box and make it really relevant.

And for ease of use I also created this CustomGPT inside ChatGPT you can use by clicking here…

And if you like these and want to go even deeper with these brain digging prompts, here’s a set of deeper bonus prompts to copy/paste…

Prompt 1: Pattern Interruption

I want to challenge my conventional thinking about [specific challenge or goal]. Please help me break free from default patterns by answering:

1. What if the opposite approach to what I'm currently considering is actually more effective?

2. What would I do if this problem was actually my biggest opportunity?

3. How might I solve this challenge if I had zero access to the resources I think I need?

4. What would someone who's already mastered this challenge do differently?

5. What unconventional solutions exist that I'm not seeing because of industry assumptions?

Prompt 2: Constraint Removal

I want to expand my thinking about [specific challenge or goal] by removing perceived limitations. Please help me explore:

1. What would become possible if [specific limitation] didn't exist?

2. How would I approach this differently if I had unlimited [resource you feel is lacking]?

3. What solutions might emerge if I could only work on this 1 hour per week?

4. What if the "right way" to do this hasn't been invented yet?

5. How would I solve this if I knew I could not fail?

Prompt 3: Perspective Shifts

Help me gain fresh perspectives on [specific challenge or goal] by thinking from different viewpoints:

1. How would [specific person you admire] approach this challenge?

2. What advice would my future self, 5 years from now, give me about this?

3. If this challenge were happening in [completely different industry], how might they solve it?

4. What would a [child/artist/scientist/philosopher] suggest as a solution?

5. What would I attempt if I had 10x more confidence about this situation?

Prompt 4: Money Loves Speed

I want to move quickly on solving [specific challenge or goal]. Help me identify:

1. What's the 20% of effort that would deliver 80% of the results in this situation?

2. What's the smallest version of this solution I could test within 48 hours?

3. How could AI handle most of the execution of this idea?

4. Who already has systems or resources that could help me implement this faster?

5. What's one bold move that could completely change the game here?

The magic isn't just in asking better questions - it's in having a systematic approach to breaking through mental barriers consistently.

I recently guided a client who was stuck trying to scale their consulting business. After running through the Possibility Expansion Playbook, they completely reimagined their approach.

Instead of hiring more consultants (their original plan), they created an AI-powered diagnostic system that pre-qualified clients and solved 70% of common issues automatically. This let their existing team focus exclusively on high-value strategic work.

The result? Revenue increased 62% within 90 days while their team actually decreased in size. They're now working with better clients, delivering better results, and experiencing less burnout.

The difference wasn't just using AI. It was the thinking framework that preceded the technology.

These types of uses of AI aren’t always the sexiest, but they can be the most effective in getting you to think better and bigger.

I’m here to help you to that, want to help me out?

I have a very short subscriber poll that will help me continue to create content I think you’d love. Should only take you 30 seconds but would love to see your answers.

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