One True Prompt #142: Analysis & Decision Making (0339)
One True Prompt
10 practical AI prompts every day. Copy, paste, and learn.
Today's theme: Analysis & Decision Making
Here are 10 prompts you can use today. Each one is ready to copy and paste into ChatGPT or Claude. Try at least one.
Prompt: Compare Two Job Offers in Your 50s
Copy and paste this:
You are my decision-making assistant. I am 52 years old, married, with two kids in college. I live in Columbus, Ohio. I work in IT project management and I’m trying to choose between two job offers.
Here are the details:
Current situation:
- Current job: IT Project Manager at MidWest Health Systems
- Current salary: $118,000 + 8% bonus
- Commute: 25 minutes each way
- Work arrangement: 3 days in office, 2 days remote
- Main concerns: tuition costs for kids, retirement savings, not burning out, keeping health insurance stable
Job Offer A:
- Company: Buckeye Insurance Group (Columbus, OH)
- Role: Senior IT Project Manager
- Base salary: $132,000
- Bonus: up to 12%
- 401(k): 4% match, vests immediately
- Health insurance: similar to current, slightly lower premiums
- Commute: 35 - 40 minutes each way
- Work arrangement: 4 days in office, 1 day remote
- Vacation: 3 weeks
- Culture: more traditional, formal, performance reviews once a year
- Other: strong brand name in the region
Job Offer B:
- Company: NorthPoint Analytics (remote-first company based in Denver)
- Role: Project Lead - Healthcare Data Projects
- Base salary: $125,000
- Bonus: up to 15% based on project performance
- 401(k): 3% match, vests over 3 years
- Health insurance: slightly higher deductibles, but HSA available
- Commute: 0 (fully remote, but 2 - 3 trips per year for team onsites)
- Work arrangement: fully remote, flexible hours within 9am - 6pm Eastern
- Vacation: 4 weeks
- Culture: more informal, growth-focused, small fast-growing team
- Other: potential promotion to Program Manager in 2 - 3 years if successful
Please:
1. Summarize my life priorities based on what I’ve told you (tuition, retirement, stability, burnout).
2. Compare Offer A and Offer B against these priorities in a clear table (rows = priorities, columns = Offer A / Offer B / Notes).
3. List the main pros and cons of each offer in bullet points.
4. Point out any hidden risks or “gotchas” I might be missing for each offer.
5. Ask me 5 clarifying questions that would help YOU give a more tailored recommendation.
6. Then, given what you know now, explain which offer you would lean toward *for someone in my exact situation and age* and why, in 3 - 5 paragraphs.
Use case: “Mark,” 52, has two concrete offers and is worried about college costs and retirement. He wants a structured comparison, not just gut feeling.
Expected result: A clear priorities summary, side-by-side comparison table, pros/cons list, risk analysis, smart follow-up questions, and a reasoned “lean toward A/B” explanation.
Pro tip: Swap the details to compare ANY two options: two jobs, two consulting clients, or even two locations to move to, as long as you give specific numbers and facts.
Prompt: Decide Whether to Downsize Your Home
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Act as a financial and lifestyle decision coach for a couple in their early 60s.
Here is our situation:
- Couple: John (63) and Linda (61)
- Location: Naperville, Illinois
- Current home: 4-bedroom house, 2,600 sq ft
- Current home value: about $620,000
- Remaining mortgage: $110,000, payment $1,350/month (including taxes & insurance)
- Kids: 3 adult children, all living in different states, occasional visits
- Retirement savings: about $780,000 in 401(k)/IRA combined
- Cash savings: $45,000
- John's income: $108,000/year (engineering manager), plans to retire at 66
- Linda's income: $32,000/year (part-time school secretary), may retire at 63
- Major concern: house is feeling too big, maintenance is tiring, property taxes are high
Option 1 - Stay in current home:
- Keep current house
- Annual property tax: ~$10,500
- Ongoing maintenance: we estimate $5,000/year average
- No moving costs
- Emotional benefit: lots of memories, space for kids and grandkids to visit
Option 2 - Downsize to smaller townhome nearby:
- Likely purchase: 2-bedroom townhome around $410,000 in same area
- Mortgage after selling: no mortgage (we’d pay it off with proceeds)
- Estimated net from sale:
- Sell current home at $620,000
- Pay off mortgage $110,000
- Selling costs ~7% ($43,400)
- Net cash available: roughly $466,600
- Buy new home cash for $410,000, leaving about $56,000 extra to invest or keep as cash
- Annual property tax: ~$6,000
- HOA fee: $275/month
- Maintenance: expected to be lower, maybe $2,000/year
Please:
1. Lay out a simple 10-year financial comparison of Option 1 vs Option 2 (high-level, not penny-perfect). Include housing costs (mortgage, taxes, HOA, maintenance).
2. Show the comparison in a table that includes: annual housing costs, cash freed up, and impact on retirement savings by age 70. State your assumptions clearly.
3. Analyze the *non-financial* factors: stress, space for family visits, aging in place, social connections.
4. Identify 5 key questions we should answer before making this decision.
5. Give a short, direct recommendation: if this were your parents in this exact situation, what would you suggest and why?
Use case: A couple around 60 considering downsizing wants both numbers and lifestyle factors laid out clearly, not just “it might save money.”
Expected result: A rough 10-year cost comparison, pros/cons for staying vs moving, thoughtful non-financial analysis, and a clear, “If I were you…” recommendation.
Pro tip: Adjust the numbers to your own house value, mortgage, and taxes to reuse this prompt whenever you’re considering a move or downsizing.
Prompt: Choose Between Two Medical Treatment Approaches (Non‑Emergency)
Copy and paste this:
You are a health decision explainer for a non-emergency situation. You do NOT give medical advice or replace doctors. You help me understand trade-offs in plain language so I can talk to my doctor.
I am a 58-year-old man with chronic knee pain (osteoarthritis in my right knee). My name is David. I live in Phoenix, Arizona.
My doctor and orthopedic specialist have explained two main approaches:
Approach A - Conservative management:
- Physical therapy 2x per week for 3 months
- Weight loss target: lose 20 pounds over the next year
- Anti-inflammatory meds as needed
- Possible steroid injections once or twice a year
- Goal: delay or avoid knee replacement
- Downsides mentioned: ongoing pain, may only partially improve function, repeated injections not ideal long-term
Approach B - Knee replacement in next 6 - 12 months:
- Full knee replacement surgery
- 2 - 3 days in hospital, several weeks recovery
- 6 - 12 weeks of physical therapy after surgery
- Higher upfront risk and cost
- Goal: significantly reduce pain, improve mobility
- Downsides mentioned: surgical risks, complications, artificial joint may last 15 - 20 years, possible need for revision surgery
Please:
1. In a table, compare Approach A vs Approach B across these dimensions: pain over next 2 years, time off work, short-term risk, long-term risk, cost burden, impact on daily life, and uncertainty.
2. Explain the main *trade-offs* in simple terms for someone like me who wants to stay active enough to hike modest trails and play with future grandkids.
3. List 10 specific questions I should ask my orthopedic surgeon to better understand which path fits me.
4. Highlight typical emotional biases that might affect my decision (for example, fear of surgery vs avoiding reality).
5. Provide a 1-page-style summary I could bring to my next appointment, clearly labeled “FOR DISCUSSION WITH DOCTOR - NOT MEDICAL ADVICE.”
Use case: “David,” 58, already has the medical options but needs to understand them in plain English before his next appointment.
Expected result: A clear table of pros/cons, a layman’s explanation of trade-offs, a focused question list for the surgeon, and a printed summary to use in the appointment.
Pro tip: You can replace “knee osteoarthritis” and the options with your own condition and treatments while keeping the same structure to prepare for any major medical decision discussion.
Prompt: Analyze Whether to Help Adult Child Financially
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Act as a neutral financial and family dynamics advisor.
Here is my situation:
- I am Karen, 59, divorced, living in Raleigh, North Carolina.
- I have one adult son, Michael, age 27.
- My salary: $92,000/year as an HR manager.
- Retirement savings: around $410,000 in 401(k) and IRA combined.
- Emergency fund: $18,000 in savings.
- Mortgage: $1,450/month, balance $165,000, house value about $390,000.
- I plan to work until about 67 if health allows.
My son Michael:
- Age 27, lives in a rented apartment in Charlotte.
- Income: ~$52,000/year as a junior software developer.
- Student loans: $23,000 remaining.
- Credit card debt: ~$5,800 at high interest.
- He called me asking for help:
- He is behind on rent and credit card payments.
- He is asking if I can give him $8,000 to “reset” and pay off his credit card and rent arrears.
- I love him and want to help, but I am worried about my retirement and about enabling him.
Please:
1. Analyze the financial impact on *me* if I give him $8,000 from my savings vs if I give him $4,000 vs if I give him nothing. Present this in a simple table including: impact on emergency fund, impact on retirement safety margin, and short-term stress.
2. List the benefits and risks of helping him with the full $8,000, partial help, or not helping financially at all.
3. Suggest 3 - 4 alternative ways to support him besides writing a check (for example, helping him make a repayment plan, temporary budgeting help, etc.).
4. Identify warning signs that this might be a pattern vs a one-time setback.
5. Draft two short scripts I could use when talking to him:
- Script A: if I decide to help with part of the money, with clear boundaries.
- Script B: if I decide not to give money but still want to be emotionally supportive.
Use case: A parent in their late 50s wants to help their adult child, but not at the cost of wrecking their own retirement or repeating old patterns.
Expected result: A clear financial impact table, structured options (help fully/partially/not at all), alternative support ideas, warning signs to watch for, and ready-to-use conversation scripts.
Pro tip: Swap in your own ages, amounts, and debts to evaluate any financial help request from adult family members while keeping the same analysis steps and scripts.
Prompt: Decide Whether to Keep or Sell a Rental Property
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You are my real estate and financial analysis assistant. Help me decide whether to keep or sell my rental property.
My details:
- Name: Sheila
- Age: 64
- Location: Tampa, Florida
- Retirement timing: likely in 2 - 3 years
- Risk tolerance: moderate
Rental property details:
- Property type: 3-bedroom single-family home in Tampa suburb
- Current market value: about $390,000
- Remaining mortgage: $145,000 at 3.4% fixed, 18 years left
- Monthly mortgage payment (principal + interest): $980
- Property tax + insurance: $420/month
- Average maintenance & repairs: $200/month (long-term average)
- Total monthly costs: ~$1,600
- Rent: currently $2,050/month
- Net cash flow: around $450/month before income taxes
- Tenant: good, stable tenant, reliable for 4 years
- Property has appreciated significantly over 10 years (bought at $230,000)
If I sell now (rough estimate):
- Sales price: $390,000
- Selling costs (agent, fees): about 7% ($27,300)
- Pay off mortgage: $145,000
- Rough cash proceeds before taxes: about $217,700
- I might owe capital gains tax, but let’s assume 15% effective on the gain portion for this analysis.
My question: Should I keep this as a retirement income source or sell it now to reduce complexity and boost my liquid retirement savings?
Please:
1. Build a simple 10-year comparison between “Keep” and “Sell Now,” explicitly stating assumptions about rent growth, expenses, and investment returns if proceeds are invested in a balanced portfolio. Present in a table.
2. Analyze the pros and cons of keeping the property in retirement, including risk of vacancies, large repairs, and management stress.
3. Analyze the pros and cons of selling now, including tax hit, loss of inflation-protected asset, and simplicity.
4. Identify 5 “what if” scenarios (e.g., major repair, long vacancy, market drop) and how each scenario affects the decision.
5. Conclude with a balanced recommendation (not absolute), e.g., “If your top priority is X, then leaning toward Y makes more sense because…”
Use case: “Sheila,” 64, is tired of managing property but likes the steady income; she wants a numbers-plus-lifestyle assessment.
Expected result: A 10-year financial projection, scenario analysis, clear pros/cons, and a decision framework tied to priorities like income stability vs simplicity.
Pro tip: Update the numbers for your own property (value, rent, mortgage, etc.) to run the same style of “keep vs sell” analysis whenever you’re reevaluating rentals.
Prompt: Figure Out Which Side Gig to Pursue in Your 50s
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Act as a side-gig decision consultant for someone in their 50s.
Here is my situation:
- Name: Robert
- Age: 55
- Location: St. Louis, Missouri
- Day job: full-time accountant at a manufacturing company, earning $84,000/year
- Time available: about 8 - 10 hours per week for a side gig
- Health: generally good, but I don’t want a physically demanding side job
- Main goal: earn an extra $600 - $800 per month and possibly build something I can continue in early retirement
Here are three side gig ideas I am considering:
Option 1 - Weekend tax preparation service (seasonal heavy workload):
- Use my accounting skills to help individuals with tax returns
- Busy season: Feb - April, lighter rest of the year
- Need to invest in software and maybe some marketing
- Possibly tiring on top of day job during tax season
Option 2 - Bookkeeping service for 3 - 5 small local businesses:
- Focus on monthly bookkeeping, reconciliations, simple reports
- More steady year-round income
- Mostly evenings or weekends from home
- Need to find and onboard clients
Option 3 - Teaching basic personal finance classes at local community college or adult education center:
- Less direct income per hour, but enjoyable and less stressful
- Might lead to coaching work on the side
- Requires preparing class materials, but no client chasing in the same way
Please:
1. Create a comparison table for Options 1 - 3 with columns: income potential, physical/mental energy required, schedule flexibility, startup effort, long-term potential, and “fit” with my age and lifestyle.
2. For each option, outline a simple 6-month test plan: what I would do, how many hours per week, and what metrics to track (e.g., income, stress level, enjoyment).
3. Identify the major risks or reasons each option might fail or fizzle out.
4. Suggest which option I should test first, and why, based on my goals and age, in 2 - 3 paragraphs.
5. Give me 5 questions to reflect on after 6 months to decide whether to double down, pivot, or stop.
Use case: “Robert,” 55, wants extra income but doesn’t want to exhaust himself; he needs a clear way to choose and test one side gig.
Expected result: A structured comparison, test plans for each idea, risk analysis, and a simple recommendation for which to try first, plus reflection questions.
Pro tip: Replace the three options with your own specific side gig ideas (e.g., consulting, crafts, tutoring) and reuse this prompt to evaluate which is best to test first.
Prompt: Plan a Major Home Renovation vs Move Decision
Copy and paste this:
You are my renovation vs move decision analyst. I’m in my early 50s and debating whether to renovate or move.
My situation:
- Name: Lisa
- Age: 53
- Location: near Denver, Colorado
- Household: Me and my husband, both working full-time; one teenager still at home
- Current home value: about $540,000
- Mortgage: $210,000 remaining at 3.1% interest
- Home size: 3-bedroom, 2-bath, 1,900 sq ft
- Main problem: We really want a larger, updated kitchen and an extra half bath. Current layout is cramped for hosting family.
Option 1 - Renovate current home:
- Estimated full kitchen remodel + add half bath + some electrical upgrades: contractor quotes around $95,000 total
- Renovation time: 3 - 4 months of disruption
- We’d likely stay in the house at least 7 - 10 more years afterward
- Financing: could use home equity line of credit for $95,000 at roughly 7 - 8% interest (current rates)
Option 2 - Sell and buy a different home:
- Target new home: around $680,000 with larger kitchen and 2.5+ baths, move-in ready
- Estimated selling costs on current home: ~7% ($37,800)
- New mortgage: we’d pay off current mortgage, roll equity into new home, and likely have a new mortgage of about $330,000 - $350,000 at ~6.5 - 7% interest
- Moving costs: roughly $7,000 - $8,000
- Emotional factor: we like our current neighborhood and neighbors, but inventory is tight
Please:
1. Build a side-by-side 10-year financial comparison of Renovate vs Move with clear assumptions about interest rates, payments, and likely home value changes. Show this in a table.
2. Analyze non-financial factors: disruption, stress, attachment to neighborhood, school considerations, hosting family, and resale flexibility.
3. Identify 5 hidden costs or risks people often forget in renovation projects and 5 often forgotten costs in moving.
4. Offer a short checklist of “red flags” that would push us strongly toward moving instead of renovating (and vice versa).
5. End with a short written summary addressed to “Lisa and her husband,” outlining which option seems more aligned with their situation and why, in 3 - 4 paragraphs.
Use case: “Lisa,” 53, is debating a big kitchen renovation and wants a structured way to see the financial and emotional trade-offs vs just moving.
Expected result: A 10-year cost comparison, non-financial analysis, hidden cost checklist, red flags, and a tailored written summary that feels like advice to a real couple.
Pro tip: Swap in real contractor quotes and mortgage rates from your area to make the analysis as close to your reality as possible before using it to guide your decision.
Prompt: Evaluate Two Care Options for an Aging Parent
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Act as a family decision-making assistant for elder care. You do not give medical advice; you help organize options and questions.
Scenario:
- I am Janet, 57, living in Portland, Oregon.
- My mother, Ellen, is 82 and lives alone in her paid-off house 20 minutes away from me.
- Health: mild cognitive decline, some mobility issues (uses a cane), 2 minor falls in the last year, but still wants independence.
- Mom’s finances:
- Social Security: ~$1,850/month
- Small pension: $650/month
- Savings: about $95,000 in bank accounts
- House value: roughly $410,000, paid off
We are considering two main options:
Option A - Stay at home with increasing in-home support:
- Start with caregiver visits 3 days/week, 4 hours each day at ~$35/hour ($1,680/month)
- I continue to visit 2 - 3 times per week for errands and appointments
- We may need to increase caregiver hours over time as she declines
- House will need some safety modifications (~$5,000 one-time)
Option B - Move her to an assisted living facility nearby:
- Facility cost: currently $4,500/month for a basic studio, including meals, activities, basic care
- Additional care levels (if needed later) could increase cost to $5,500 - $6,000/month
- She would sell her house to help fund this
- She will have more social interaction but may resist the move emotionally
Please:
1. Create a 5-year financial projection comparing Option A vs Option B, using simple assumptions and clearly stating them (e.g., expected increase in care needs). Show in a table.
2. List the main advantages and disadvantages of each option across: safety, independence, social connection, caregiver burnout (me), and financial sustainability.
3. Identify 10 important questions I should ask any assisted living facility we consider.
4. Identify 10 important questions I should ask any in-home care agency we consider.
5. Suggest a step-by-step conversation plan for talking with my mother about these options in a respectful way that honors her independence.
Use case: “Janet,” 57, has a real parent and real numbers, and wants to compare “stay at home with help” versus “assisted living” with both money and emotions in mind.
Expected result: A 5-year money projection, pros/cons across key life factors, thorough question lists for facilities and agencies, and a thoughtful conversation plan.
Pro tip: Plug in the actual rates from agencies and facilities in your area to make the financial projection more accurate before bringing it to a family meeting.
Prompt: Decide Whether to Retire at 62 or Work Until 67
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You are my retirement timing decision assistant. I’m trying to decide when to retire.
My situation:
- Name: Paul
- Age: 60 (turning 61 in 3 months)
- Location: Minneapolis, Minnesota
- Current job: operations manager at a logistics company
- Current salary: $104,000/year
- Planned retirement ages I’m comparing: age 62 vs age 67
Financial details:
- 401(k): $520,000
- IRA: $110,000
- Roth IRA: $45,000
- Cash savings: $30,000
- No pension
- House: worth about $430,000, mortgage balance $95,000, payment $1,250/month
- Social Security estimate:
- At age 62: about $1,780/month
- At age 67 (full retirement age): about $2,550/month
Spending:
- Current monthly spending (excluding mortgage): around $3,200/month
- Desired retirement lifestyle: modest - some travel, hobbies, and budget for helping grandkids with occasional gifts
Health:
- Generally good, but family history of heart issues in late 60s
- I’m worried about “waiting too long” and missing active years
Please:
1. Create a simplified comparison of retiring at 62 vs 67, focusing on:
- Total income in early years
- Social Security impact over a 25-year retirement
- Likely drawdown rate from investments
Present key numbers clearly in tables.
2. Explain, in plain language, the trade-off between “more years of freedom” vs “stronger financial security” for someone like me.
3. List 10 questions I should ask a human financial advisor to fine-tune this decision.
4. Identify 5 “danger signs” that retiring at 62 could be too risky for me, and 5 signs that working until 67 might be unnecessarily cautious.
5. End with a balanced narrative: under what conditions you’d lean toward 62 for me, and under what conditions you’d lean toward 67 (assume I’m open to part-time work too).
Use case: “Paul,” 60, wants a structured way to weigh retiring a bit early vs staying in the workforce, including health and money interactions.
Expected result: Simple tables comparing age-62 vs age-67 retirement, layman’s explanation of trade-offs, advisor question list, warning signs, and a scenario-based conclusion.
Pro tip: Update the Social Security and savings figures with your actual numbers (from SSA.gov and your accounts) to reuse this for your own retirement timing decision.
Prompt: Make a Big “Yes or No” Decision Using a Pre‑Mortem
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Act as my decision “red team” using a pre-mortem analysis. I want to stress-test a big yes/no decision.
My situation:
- Name: Angela
- Age: 49
- Location: Austin, Texas
- Current job: marketing director at a mid-sized software company
- Salary: $128,000/year + bonus
- Opportunity: I have been invited to join a 3-person startup as a co-founder and head of marketing
Decision:
Should I say YES or NO to joining the startup?
Key facts about the startup offer:
- Product: B2B software for small medical practices to manage online reviews and patient feedback
- Funding: pre-seed round of $750,000 already raised
- My compensation:
- Salary: $80,000/year initially (may increase if they raise another round)
- Equity: 10% ownership vesting over 4 years
- My current finances:
- Emergency fund: $35,000
- Retirement savings: about $420,000
- No debt besides small car loan ($220/month)
- Family: married, one child in college (we’re paying part of tuition)
- My feelings: excited by the idea, but worried about losing stability at almost 50
Please:
1. Start by asking me 8 - 10 targeted questions to clarify my risk tolerance, family situation, and career goals (you can assume I’ll answer in a follow-up).
2. Then, without my answers, perform a pre-mortem:
- Imagine I say YES and join the startup, and 3 years later it has gone *badly*. List the top 10 reasons why it might have failed for me personally (financially, emotionally, career-wise).
- Imagine I say NO and stay at my current job, and 3 years later I deeply *regret* saying no. List the top 10 reasons for that regret.
3. Turn these reasons into a table of “what would have to be true” for YES to be a good decision vs for NO to be a good decision.
4. Based on this, suggest a short list of concrete tests or experiments I could run in the next 30 - 60 days to reduce uncertainty (for example, talking to specific people, asking for specific data, setting personal guardrails).
5. End with a 1-page-style summary addressed to “Angela at 49,” outlining how to think about this decision so that her 60-year-old self is least likely to feel regret.
Use case: “Angela,” 49, has a very real startup offer and wants to use AI as a structured devil’s advocate, not as a cheerleader.
Expected result: Clarifying questions, a thorough pre-mortem of both “yes” and “no,” a “what would have to be true” table, practical tests to run, and a thoughtful future-self-oriented summary.
Pro tip: Use this same pre-mortem structure for any big yes/no choice: starting a business, moving cities, selling a business, or taking an executive role. Just swap in your own details.
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