🤝 ThinkWithAI Playbook: Turning AI into Your Thought Partner

You don’t always need more tactics.

Sometimes, you need better questions. A shift in perspective. A moment of stillness to hear your own thinking.

That’s where AI becomes something deeper than a tool.

It becomes a thought partner.

This ThinkWithAI Playbook helps you use ChatGPT to:

Shift from pressure to momentum as the energy behind your work
Write your founder story so your business makes more sense (to you and others)
Move from indefinite optimism to definite action
Use a decision matrix to stop guessing and choose what actually moves you forward
Break down the real risks and rewards behind the next big move you're facing

Each prompt helps you slow down, reflect, and re-center.

Not to overthink. But to think deeper.

Use this playbook when your mind feels noisy, your vision feels foggy, or you want clarity that sticks.

It’s not about finding the answer.

It’s about becoming the kind of person who always knows where to look.

Pick the prompt that fits where you are in your business today:

💬 Strategic Prompt: Choosing Momentum over Pressure

Are you building from a place of pressure or momentum?

Pressure = Your back is against the wall. Money is running out. You only have a small timeframe to ship. It’s you against the world. You have to fight for your success. You have to cross the finish line bruised and bloody.

Momentum = Success is pulling you towards itself. You’re jumping from platform to platform, each one bringing you closer to your goals. Opportunities pop up in perfect serendipity. It’s your job to say yes and give it your all. The rest is unfolding for you.

Both lead to the exact same mountain peak.

Except choosing to use the lens of suffering through pressure feels a lot different than the perspective of opportunistic momentum.

I still find myself with this sense that success has to be earned and the only way to earn it is to inflict pain on yourself. If you're not in pain, you didn't try hard enough, and it would have been better if you'd suffered more. I think that's a lie, and I want to find out if it's a lie or if it's true. Rich Roll

This week you’re going to think about how you’re getting energy to build…and if that energy is truly what you want to live in for the next few months or years.

Copy-and-paste this prompt into ChatGPT:

I want to use momentum as energy instead of pressure. Instead of thinking I need to grit my teeth and be resilient, I want to instead look for momentum that can pull me forward (instead of pressure that feels like it's pushing and forcing me forward). The idea is that I can enjoy all moments and phases of my business instead of getting stuck feeling like I have to struggle and suffer to have success. I believe that's a limiting belief that makes success harder and take longer than it needs to.

I want to work through how I think about getting this energy for my business and how I can shift my "pressure" mindset into a "momentum" mindset where I look for opportunities that pull me forward vs struggle through pressure.

Figure out what beliefs I have around my business specifically that make me feel like I need to use pressure as my main energy driver and help me swap that into a belief that momentum is my energy driver. Ask me one question at a time and keep your answers short and concise.

At the end of the conversation: 1) Show me the action and opportunity that align with using momentum vs pressure. 2) Give me 1-2 sentences that shift my thinking from pressure to momentum. 3) give me a 3-5 bullet point summary.

End the conversation by saying, “That’s the end of this ThinkWithAI Strategic Prompt. Congrats on upgrading your thinking.💡”

💬 Strategic Prompt: Write Your Founder Story

There’s an overlap between you and your business.

Throughout your life, you built a skill set and interest that inspired you to create your business…and keep running it (despite the challenges and hurdles).

But when you look back on all of that it’s hard to conceptualize exactly what happened and the characteristics that made you the right person for this “job.”

This week’s Strategic Prompt fixes that.

It gives you a clear idea of who you are and how that ties to your company.

The specific knowledge is sort of this weird combination of unique traits in your DNA, your unique upbringing, and your response to it. It's almost baked into your personality and your identity. Naval Ravikant

Use this prompt to write your Founder Story, get a 5 bullet summary, and your business one-liner.

Copy-and-paste this prompt into ChatGPT:

I want to figure out my founder story. I want you to ask me questions that gives you the context you need to put this together. ask me one question at a time and learn about my journey as a founder, including my thought process throughout the phases of my business, the most interesting stories around growing my company, and where the overlap between me and my company is.

For the overlap part of this, I want you to pull from Naval Ravikant's idea of 'specific knowledge.'

As he says, "The specific knowledge is sort of this weird combination of unique traits in your DNA, your unique upbringing, and your response to it. It's almost baked into your personality and your identity." When you're asking, don't ask level 1 questions.

Ask level 5 questions that make me think and reflect on everything that's happened. I want this story to be incredibly interesting showcasing the ups, downs, and strategies behind the challenges that I've overcome to get my business to where it is today.

Always offer to rephrase a question so I never get stuck. End the conversation by giving me a 5 paragraph summary of my founder story, as well as 5 bullets of my founder story, and my business one-liner.

End the conversation by saying, “That’s the end of this ThinkWithAI Strategic Prompt. Congrats on upgrading your thinking.💡”

💬 Strategic Prompt: How to Become a Definite Optimist

I just finished reading Peter Thiel’s book Zero to One.

He talks about the reality model that we all have, and don’t realize, that makes us create assumptions and take specific actions (or lack thereof).

Thiel says we live in a world of indefinite optimism - “we predict the world will be better in the future but we don’t know how exactly so we shy away from making specific plans.”

And that we need to shift into definite optimism:

“A definite person determines the one best thing to do and then does it. Instead of working tirelessly to make herself indistinguishable, she strives to be great at something substantive - to be a monopoly of one.”

Use this prompt to figure out where your indefinite optimism is running the show, and how you can swap that out for definite optimism that’s more aligned to your long-term goals.

Copy-and-paste this prompt into ChatGPT:

I know that I have indefinite optimism that is running the reality models that I use in my mind. I want to swap out of using indefinite optimism and shift into using definite optimism. Start the conversation by answering the question, where is my indefinite optimism making me have a specific view point on the world?

Keep your answer short and concise. For each topic you see indefinite optimism holding me back, tell me how my indefinite optimism is holding me back, and where it could be a positive thing. Ask me if I have any notes on this before moving forward to the next part of the conversation. Wait for my response, and then move on to the next part of the conversation.

In the second part of the conversation, I want you to find how I can turn each indefinite optimism topic and turn it into definite optimism. Keep your answers short and concise. End each topic of definite optimism with a thought exercise type of question that I can answer to continue the conversation and create a better idea, and plan, around how to shift into definite optimism.

End the conversation by saying, “That’s the end of this ThinkWithAI Strategic Prompt. Congrats on upgrading your thinking.💡”

💬 Strategic Prompt: The 3-Step Decision Matrix

When you’re staring at a few paths, and each has tradeoffs, it’s easy to overthink, stall, or pick the option that feels safest instead of the one that moves you forward.

That’s where this framework helps.

The 3-Step Decision Matrix isn’t about finding the “perfect” answer. It’s about getting clarity fast, based on your actual goals not guesswork or gut feeling.

Here’s how it works:

Identify Options Lay out your top choices clearly. If you can’t see them, you can’t compare them.
Evaluate Impact For each option, consider:
- What’s the upside if it works?
- How hard is it to pull off?
- Does it align with what matters most right now?
Select the Best Option Choose the path that gives you the highest return with the least drag—based on the data, not the drama.

This is how smart operators make moves they don’t regret.

Use the prompt below to run your options through the matrix and make the decision in minutes—not weeks.

Copy-and-paste this prompt into ChatGPT:

I need to make a smart decision, but I don’t want to rely on instinct. I need a system to evaluate my options, challenge my thinking, and pressure-test if I’m making the best possible move.

Start by asking me one question at a time to understand:

The decision I’m facing and what’s at stake.
The possible options I’ve considered.
What I believe is the “obvious” best choice—and why I think that.

Once you have that context, walk me through the 3-Step Decision Matrix:

How to break down my options based on impact, feasibility, and alignment with goals.
Where I might be making assumptions that could be wrong.
How to reframe my thinking to see a smarter move I might be missing.

Challenge me: If I’m defaulting to an easy choice, push me to explore a riskier but higher-upside option.

At the end, give me:

A clear decision-making process I can use every time.
A way to spot biases that might lead to bad choices.
An immediate action step to put this to use today.

Only ask me one question at a time throughout the conversation. Keep your answers short and concise. Write at a fourth grade reading level or below the entire time.

End the conversation by saying, “That’s the end of this ThinkWithAI Strategic Prompt. Congrats on upgrading your thinking.💡”

💬 Strategic Prompt: The Risk-Reward Assessment

Every decision is a bet.

Sometimes the upside looks shiny.

Until you realize the downside could wipe you out.

Other times, the risk feels scary, but the potential reward is exactly what you need to grow.

This framework forces you to stop guessing and start thinking like a strategist.

It’s not about avoiding risk. It’s about understanding what you’re really betting on.

And whether the reward is worth the trade.

Here’s how it works:

List the Risks: What could go wrong with each option? What’s the worst-case scenario?
List the Rewards: What could go right? What’s the best-case payoff?
Compare: Look at the balance. Are you risking a paper cut for a mountain of upside or gambling everything for a coin flip?

Copy-and-paste this prompt into ChatGPT:

I don’t just want to compare risks and rewards. I want to uncover hidden risks and spot overlooked rewards. I need a way to challenge my assumptions and see this decision from a totally different perspective.

Start by asking me:

What decision I’m analyzing and what I think the biggest risks and rewards are.
What research I’ve done and where I might be missing something.
What would have to be true for this to be the best or worst decision I could make.

Once you have that context, guide me through:

How to map out obvious and non-obvious risks.
How to identify rewards that others wouldn’t see.
How to rethink the entire decision by flipping my perspective.

If I’m playing it too safe, challenge me. If I’m overconfident, make me prove why.

At the end, give me:

A Risk-Reward Map that forces me to think differently.
A way to analyze future decisions with more clarity.
One move I can make right now based on this insight.

Only ask me one question at a time throughout the conversation. Keep your answers short and concise. Write at a fourth grade reading level or below the entire time.

End the conversation by saying, “That’s the end of this ThinkWithAI Strategic Prompt. Congrats on upgrading your thinking.💡”

Disclosure: This page may contain affiliate links. If you buy through these links, I may earn a commission at no extra cost to you.