Eleven prompts, and a standard for judging what comes back. The first one values the part of your balance sheet that is not marketable, because if you have founder equity or a private stake, the number you feed every other calculation is probably wrong. The rest cover the gap, the allocation, the tax position, the drawdown, and the calendar. Every prompt carries an instruction block telling the AI to verify current limits, name its sources, and separate arithmetic from guesswork. Built on the same habits behind An Outsider’s Playbook. Free. No email required.
Whose words are whose
The prompts here are mine. The answers are not. Everything these prompts produce comes from whichever AI assistant you paste them into. It is not my analysis, not a recommendation, and not a plan I have reviewed. I have never seen it. Two people running the same prompt on the same day can get different answers, and both can be wrong.
That matters more here than with a stock. A bad answer about a ticker costs you one position. A bad answer about a withdrawal sequence compounds quietly for twenty years before anyone notices.
Turn on web search before you run these
Contribution limits, IRMAA thresholds, RMD ages and the standard deduction all move every year. Every prompt below ends with a clause telling the assistant to verify current rules. Without web search that clause does nothing — the model complies by confidently reciting whatever was true when its training ended, and the output reads exactly like a verified answer.
What a good answer looks like
It leads with the verdict. The conclusion is in the first two lines, not the last paragraph.
It dates and sources every rule. A contribution limit or bracket with no year attached is unusable.
It separates arithmetic from judgment. Compounding my numbers is calculation. Assuming a 6% return is a guess. A good answer labels which is which.
It refuses to invent my figures. If I did not give it my Social Security estimate, it asks rather than assuming one.
It names what needs a professional. QSBS eligibility, 83(b) status and state tax treatment turn on facts a model cannot verify.
Before you act on any of it
Pull your Social Security estimates from ssa.gov/myaccount rather than guessing them. Verify every limit against the IRS or the plan document. Treat the output as a structured starting point for a conversation with a CPA, an attorney, or a fiduciary adviser — never as a conclusion.
Version 1.0 · Prompts 02–11 adapted from a series by Hamidullah Khan, PhD. Prompt 01 is original.
Total invested: — Calculated from the five balances above.
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Run this first
Start here01Concentrated & Illiquid Positions
Value the illiquid part of my balance sheet for retirement planning. Do not treat these holdings as marketable securities. My positions: [paste your positions above]. For comparison my marketable portfolio is [total invested], I am [age], targeting retirement at [retirement age], wanting [yearly spending] a year. Give a downside, base and upside value per position rather than a point estimate, and state the discount you applied for illiquidity, minority position and stage risk. Show last-round notional and haircut value side by side, and tell me which positions I should carry at or near zero for planning purposes. Estimate the probability of each position reaching liquidity inside my horizon and the expected value that produces. Then show my retirement picture two ways, including these positions and excluding them entirely, and quantify the gap. Where my employment income and my equity sit in the same entity, model the joint failure case: the position goes to zero at the same time the income stops. Show what that does to my retirement date and to sustainable spending, and how many years of liquid assets would absorb it. Per instrument, identify what triggers tax and when: exercise versus sale, ordinary versus capital treatment, AMT exposure on ISOs, whether QSBS could apply and what would disqualify it, 83(b) status, and the cost of exercising early versus waiting. Flag any deadline already passed or approaching. Then evaluate the realistic paths to reducing concentration and the constraints blocking each, including restrictions my role creates that a passive holder would not face. Close with what my marketable portfolio must look like to be a real counterweight to this concentration.
Not from the source series. It runs first because it changes what portfolio number every prompt below should be using.
Diagnose
02Complete Retirement Plan
Act as a retirement-planning analyst. Using my age [age], location [state/country], income [income], savings [total invested], monthly contributions [monthly], employer match [employer match], retirement age [retirement age], desired spending [yearly spending], debts [debts], and expected benefits [benefits], create my retirement roadmap. Ask only essential missing questions. Show my savings target, projected balance, income gap, and required monthly contribution under conservative, moderate, and optimistic assumptions. Explain the calculations and give five prioritized actions. State which single input, if wrong, would most change the conclusion.
03Retirement Gap Calculator
Am I on track to retire at [retirement age]? I am [age], have [total invested] invested, contribute [monthly] monthly, expect [benefits] yearly from Social Security and pensions, and want [yearly spending] yearly in today's dollars. Model 4%, 6% and 8% returns, 2% to 3% inflation, fees of [fees], and longevity to age [age]. Show projected savings, income, shortfall, and the monthly contribution needed to close it. Label all assumptions. Show the gap as well if I delay retirement by two years and by five years.
Allocate
04Best Use of My Next Dollar
Prioritize how I should allocate an extra [amount] monthly among emergency savings, debts, employer plan, Traditional and Roth IRA, HSA, mortgage, and taxable investing. My income is [income], emergency fund [emergency fund], debts [debts], employer match [employer match], tax status [filing status] in [state/country], and retirement goal [goal]. Create a step-by-step contribution waterfall explaining taxes, liquidity, risk and tradeoffs. Verify current limits with official sources.
05Three Portfolio Options
Create conservative, balanced and growth retirement portfolios for me. I am [age], retiring at [retirement age], have [risk] risk tolerance, and would [reaction] after a 30% decline. My current allocation is [allocation]. For each, give percentage ranges for U.S. stocks, international stocks, bonds and cash. Explain volatility, potential losses, diversification, fees, rebalancing, and which investor each suits. Use broad, low-cost fund categories, not hype or guaranteed returns. Tell me plainly if my stated risk tolerance and my stated reaction to a decline contradict each other.
Tax position
06Traditional vs. Roth
Compare Traditional, Roth and blended contributions for me. I am [age], income [income], filing status [filing status], state [state/country], current marginal bracket [bracket], expected retirement income [expected income], and my balances are pre-tax [pre-tax], Roth [Roth], taxable [taxable]. Compare today's tax savings, future taxes, flexibility, and three future-tax-rate scenarios. State which circumstances favor each choice, show the break-even future tax rate at which the choice flips, verify current rules, and list what a CPA should confirm.
07Roth Conversion Plan
Evaluate partial Roth conversions for my situation. I am [age], earn [income], file as [filing status] in [state/country], have [pre-tax] pre-tax and [Roth] Roth, can pay [cash] of conversion taxes from cash, and expect [benefits] from Social Security and pensions. Compare converting [amount] annually for [years] years against no conversion. Estimate taxes, future balances, required minimum distributions and Medicare premium effects. Identify the window of years when conversions look most favorable and the conditions that would make them a bad idea. Cite current official rules and flag items requiring a CPA.
Income design
08Social Security Timing
Compare claiming Social Security at 62, at full retirement age, and at 70. My estimates are [at 62], [at FRA] and [at 70] monthly, current age [age], marital status [marital status], spouse's estimate [spouse], planned work income [work income], expected longevity [age]. Calculate cumulative benefits and break-even ages. Explain taxes, inflation adjustments, survivor and spousal benefits, and working while claiming. Use SSA.gov rules and my actual estimates; do not invent missing figures.
Pull the three estimates from ssa.gov/myaccount before you run this. On guessed numbers the whole prompt is worthless, which is why the last line is there.
09Tax-Smart Withdrawals
Design a tax-smart withdrawal strategy using cash [cash], taxable investments [taxable], pre-tax accounts [pre-tax], Roth accounts [Roth], pension [pension], Social Security [benefits], annual spending [yearly spending], filing as [filing status] in [state/country]. Compare taxable-first, proportional, and bracket-managed withdrawals with possible Roth conversions. Show a five-year sample and explain taxes, Medicare premiums, required minimum distributions and portfolio longevity. Flag any year where an IRMAA threshold, a capital gains bracket or an RMD creates a cliff. Verify current rules and flag professional-review items.
Pressure-test
10Retirement Stress Test
Stress-test my plan using age [age], retirement age [retirement age], portfolio [total invested], contributions [monthly] monthly, spending [yearly spending], guaranteed income [benefits], allocation [allocation]. Test a 30% crash near retirement, low returns, 4% inflation, retiring five years early, living to 100, a [amount] emergency, and 20% higher spending. Rank the risks, estimate how each affects portfolio longevity, and recommend specific backup actions. Identify the single mitigation that protects against the most scenarios at once. Clearly distinguish calculations from estimates.
Execute
1112-Month Action Plan
Turn my finances into a 12-month retirement checklist. I am [age], have [total invested] saved, contribute [monthly] monthly, owe [debts], and want to retire at [retirement age] spending [yearly spending] yearly. My insurance and estate documents are [insurance and estate]. My three biggest concerns are [concerns]. Organize actions into this week, 30 days, months 2 to 3, 4 to 6, and 7 to 12. For each, show priority, purpose, effort, required documents, and whether I need a CPA, an attorney, or a fiduciary adviser. Keep the "this week" list to no more than five items.
Educational use only. This is not financial, tax, or legal advice, and nothing produced by these prompts is a recommendation to buy, sell, hold, convert, or withdraw anything. I am not a licensed financial adviser, a CPA, or an attorney. Retirement decisions depend on facts about your situation that neither this page nor any AI assistant can verify. Confirm everything with a qualified professional before you act.
Looking at a portfolio rather than a retirement date? The companion tool is The Outsider’s Stock Diligence Toolkit — eleven prompts for pulling a company or a fund apart.