Ready-to-use retirement prompt

This prompt lets anyone run a retirement estimate. It's been run dozens of times, with fixes applied for things AI kept forgetting. It's built around one specific situation, so adjust it to fit yours and add whatever matters most.

To use it, replace the bracketed information with your own details.

The Prompt

I want a year-by-year retirement projection. Use current official figures from ssa.gov, medicare.gov, irs.gov, healthcare.gov, or my state exchange. If an official figure is unavailable, identify the assumption you used. Treat all balances as current today, so prorate the first year through December 31. Show everything in today's dollars. Household: I am [age]. Partner is [age or none]. Other household members: [number or none]. Filing status: [single / married filing jointly]. Location [city/state]. Target retirement age [age]. Partner stops working at [age]. Plan through age [85]. Income: my salary before taxes [$X/year], partner [$X/year], raises [3%]. Calculate our monthly take-home after taxes and listed contributions, show the calculation, and flag payroll deductions I did not provide. Other income: [none] or [$X/month, continues/stops in retirement]. Health insurance today: [through work, $X/month from my paycheck] or [I pay $X/month myself] or [none]. Contributions: my 401(k) [$X/year] plus employer [$X], Roth IRA [$X]. Partner's 401(k) [$X] plus employer [$X], Roth IRA [$X]. Remaining take-home after spending goes to [brokerage/is spent]. Living expenses: [$X/month] today, not counting debt payments or health insurance. In retirement [$X/month], also before healthcare. Car age [X]. Replace every [10] years for [$X]. Assets: [list every account and balance, you classify them]. Keep [$X] cash untouched. Debts: [balance, interest rate, monthly payment for each]. Stop each payment when the debt is paid off. Home: [own, worth $X, keep/sell at retirement]. Model assumptions: inflation [3%], investment return [4% above inflation], healthcare inflation [2% above general inflation]. Healthcare: before 65, use Marketplace premiums for my location and household, net of any premium tax credit. From 65, include Medicare Parts B and D plus a typical supplement for each person, including IRMAA when triggered. Identify the plans and prices selected. Social Security: I have worked [X] years and my partner [X]. Estimate benefits from our salaries under the current 35-year formula, including zero-earning years after retirement. We claim at [ages]. Apply current federal, state, and local taxation of benefits. Taxes and withdrawals: apply current federal, state, and applicable local tax rules, including capital-gains and early-withdrawal taxes. Withdraw in this order: [brokerage, pre-tax accounts, Roth]. Take RMDs when required under current law and reinvest any amount above that year's expenses and taxes into the taxable account. Output: the earliest age that works, including ages below my target; the year money runs out if I stop at my target; a year-by-year table; a table of every assumption marked as sourced, from my list, or your own pick, with what each pick is worth per year; every blank I left, flagged instead of quietly filled; and the one change that would most improve the result.

This was run in ChatGPT Work (Sol 5.6 High) and Claude Cowork (Opus 5 High); both handled it well. The results were then checked against ProjectionLab on identical inputs to confirm everything lined up.

What Usually Needs Fixing

1. Sources. Without them, premiums, tax brackets, and claiming rules come from the model's memory, which runs a few years stale.

2. The first year. Run this in September and AI still counts a full year of contributions. Compounded over twenty years, that's a five-figure error.

3. Healthcare. AI usually leaves it out, since employer-paid coverage today never shows up as spending. When it does add it, it skips the ACA credit, drops Part D, and grows the cost at general inflation instead of healthcare inflation.

4. Social Security. AI often skips it entirely. When it doesn't, it counts one benefit for two people and ignores the zero-earning years an early retirement adds. The prompt asks for it per person, based on years actually worked.

5. Withdrawals and RMDs. AI treats a 401(k) like plain cash, ignores account draw-down order, and once required distributions kick in, unspent money just vanishes from the math. The prompt sets the order, the taxes, and where any leftover goes.