AI Prompts for Major Financial Decisions
Before you act, try this.
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You can use any AI tool you prefer, ChatGPT, Claude, Gemini, or another model.
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These prompts are free to use.
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Their purpose is not faster answers.
It is better financial thinking before significant decisions.
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Simply copy, paste into your chosen AI tool, and add your situation where relevant.
Before You Paste Anything Into AI
Please remove:
• Full names
• Addresses
• Dates of birth
• Account numbers
• Specific monetary values if personally identifiable
Replace them with placeholders such as:
[Person A]
[Property 1]
[£X]
AI tools do not require personal identifiers to analyse structure or logic.
Not sure how to frame your situation?
Start here.
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Starter Prompt
“I’m dealing with the following financial situation: [describe it briefly].
Help me clarify what the real decision is, what assumptions I may be making, and what trade-offs I might be overlooking.”
You don’t need perfect wording.
Just describe the situation in plain language.
Selling a Business
If you’re considering an exit, start here:
1
"Help me analyse whether selling my business is primarily a financial decision, an identity decision, or both. What trade-offs might I be underestimating?"
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2
​“What assumptions am I making about how I’ll feel six months after selling? Challenge those assumptions.”
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3​
“If I delayed major financial decisions for six months after a sale, what risks increase — and what risks decrease?”
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4​
“What second-order consequences could follow from reinvesting liquidity too quickly?”
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Approaching Retirement
Retirement is rarely just a number.
1
“Help me explore what I would gain, and what I might quietly lose, by retiring fully at this stage.”
2​
“What parts of my identity are currently tied to my income or professional role?”
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3​
“If I phased retirement over three years instead of stopping abruptly, how might outcomes differ financially and psychologically?”
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4​
“What second-order consequences could follow from reinvesting liquidity too quickly?”
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Inheritance or Sudden Liquidity
Significant capital often arrives with emotion attached.
1
“Help me think through the emotional and relational implications of receiving substantial capital.”
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2​
“What assumptions am I making about what this money ‘should’ do?”
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3​
“If I made no major financial decisions for six months, what opportunities might I lose — and what clarity might I gain?”
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4​
“What conversations should happen before financial structuring begins?”
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The Will Stress-Test
A Will is often written once and rarely examined again.
Before assuming it “covers everything,” try testing it.
1
“I am going to paste a clause from my Will. Translate this into plain English and highlight any terms that might be confusing or open to interpretation for non-lawyers.”
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2​
“Based on this summary of my circumstances [insert details], what blind spots commonly arise in Wills involving [blended families/business ownership / overseas assets / discretionary trusts]?”
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The Cash vs. Invested Dilemma
“Stay invested” is often good advice.
But context matters, especially during transitions.
1
“Help me calculate the potential outcomes if I move 30% of my portfolio to cash for 12 months versus staying fully invested. Include opportunity cost, downside protection, and psychological impact.”
2​
“Explain the difference between ‘long-term compounding logic’ and ‘capital preservation logic.’ Which framework is more appropriate for someone who is [2 years from retirement / selling a business / funding a large purchase]?”​
Technical Question Bridge
If you have a specific technical question, try this:
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“Explain the technical implications of this situation, then outline what non-technical factors I should consider before acting.”​
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This helps move from information to judgement.
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Considering a Trust or Other Structure?
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Some decisions introduce long-term legal and tax complexity.
If you are thinking about setting up a trust or other formal structure, use the structured prompts here before proceeding.
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A Note on AI
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AI can help organise thinking.
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It can surface blind spots.
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It can challenge assumptions.
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It can highlight trade-offs.
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But significant financial decisions often involve sequencing, behavioural nuance, and personal judgement.
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If you find that prompts begin to raise deeper questions rather than resolve them, that’s normal.