13 synthetic households, 13 real questions. Open one and the planner arrives prefilled — edit anything, then run it yourself.
A Roth window in early retirement
Maya, 60, single, retired last year with $800k pre-tax, $50k Roth, and $150k in a brokerage account. Part-time work brings in $40k while her income is unusually low.
“What if I convert $50k a year to Roth for the next five years — and what does $80k a year look like instead?”
The projection shows — Side by side: which bracket each conversion size fills in each low-income year, the lifetime tax (present value) of each path versus doing nothing, and which years cross an IRMAA tier.
Try this scenario →What “fill the low bracket” actually costs
Devon, 38, single, earning $250k and planning to stop at 45 — leaving 28 low-bracket years before RMDs begin at 73, and a $600k brokerage account to live on in the meantime.
“A common rule of thumb is to convert enough to fill the 12% bracket in my low-income years. What does that do compared with a smaller conversion?”
The projection shows — First, that the rule of thumb is stated as a bracket but has to be paid as an amount — and $64,800 is the largest conversion that actually holds a 12% rate here, so a hand-picked $75,000 spends the year in the 22% bracket instead. Then, that filling the bracket properly still costs more: $558,455 of lifetime tax against $547,350 for converting nothing, while the smaller $35k schedule costs $494,418. Both schedules stay inside 12% the whole way and finish $482,000 apart in wealth after the tax still owed on it. What drives it is that conversion dollars also push Devon's own dividends and realized gains out of the 0% capital-gains bracket into 15%, so dollars that look like they cost 12% really cost about 27% — against RMD years taxed at 22%. Planners call this the long-term capital gains “bump zone”.
Try this scenario →Seeing the RMD years before they arrive
Raj and Priya, both 66, married, with $1.6M pre-tax between them, $40k/yr of Social Security, and $90k of annual spending.
“What do our tax brackets look like once required minimum distributions start stacking on Social Security — and how does converting $80k a year before then change the picture?”
The projection shows — The per-year bracket chart with and without the conversions: where RMDs push taxable income once they begin, how each path's IRMAA exposure differs, and the lifetime-tax comparison — all under assumptions they can edit.
Try this scenario →A two-year income gap
Dana, 55, single, earning $120k with $500k pre-tax and $200k in a brokerage account — and a layoff on the horizon.
“What if I'm out of work for two years starting next year? And what does converting $40k a year during that gap look like?”
The projection shows — Where the spending shortfall is covered from (which accounts are drawn down), how far the marginal bracket falls in the gap years, and what converting during those years does to lifetime tax versus riding the gap out.
Try this scenario →The leap to self-employment
Sam, 38, earning $150k, thinking about going full-time on a consulting practice they expect to net $60k in year one, growing 20% a year.
“If I quit next year and the business nets $60k growing 20%, how long do my savings carry the household — and what do my taxes look like?”
The projection shows — Whether and when a shortfall appears under those assumptions, the self-employment tax and QBI deduction each year, the quarterly estimated-tax set-aside the projected income implies, and how low the bracket sits in the lean years.
Try this scenario →Runway on a raise
Alex, 34, just closed $500k for their company. Revenue is $8k/month against $25k/month of spend, and they pay themselves $48k a year.
“When does the business run out of cash on this plan — and what does adding a $180k fully-loaded hire do to that date?”
The projection shows — Runway in months for each plan, the first year the household itself comes up short, the tax picture of the owner draw, and one-tap sensitivity on revenue growth, spend, and the hire. It also shows what the burn is worth later: the losses carry forward under §172 and never expire, so the years after the burn are taxed far more lightly than the raise alone would suggest — and a Roth conversion in a losing year is the cheapest one Alex will ever make.
Try this scenario →Buying a business on a seller note
Jesse, 40, single, left a $300k corporate job to buy a $900k-revenue business for $800k — 10% down, the seller carrying $720k at 8% over ten years. The business earns $350k before paying Jesse anything.
“If I pay myself $150k, does this beat the job I left — and what does the note cost me along the way?”
The projection shows — The tax on business profit lands whether or not the profit is drawn, so the two plans differ in what funds the household: the year the pre-tax accounts are exhausted, the first year the household comes up short, and the interest and principal split of the note in every year.
Try this scenario →The structure the business is taxed under
Dani, 42, married, runs a profitable LLC throwing off $400k a year. Nobody ever elected anything else, so it is taxed as a sole proprietorship and self-employment tax applies to all of it.
“What would electing S-corp change — and if I incorporate to a C-corp before an exit, does it matter whether I do it now or in three years?”
The projection shows — The same $400k under three structures: self-employment tax on all of it, payroll tax on a stated salary only, or 21% to the company with a second tax on what it pays out. Then the conversion timing, where converting later means a shorter §1202 clock and appreciation that falls permanently outside the exclusion.
Try this scenario →The years before Medicare
Sam and Robin, 55 and 54, retire this year with $1.5M pre-tax and $400k in a brokerage account. They spend $60k and buy a marketplace health plan for $20k a year until Medicare at 65.
“How much can I convert to Roth in these low-income years without wrecking my health-insurance subsidy?”
The projection shows — That the conversion has two prices, not one. Alongside the bracket it fills, each size moves household income against the federal poverty level — and from 2026 there is a hard cliff at 400% where the entire premium tax credit disappears at once, not a slice of it. The year table shows the credit, the net premium, and the FPL multiple, flagged once a year crosses the line.
Try this scenario →Ninety days to decide on the options
Priya, 34, is leaving a startup with 50,000 vested incentive stock options at a $2 strike. The latest 409A puts the shares at $9, and she has 90 days to exercise or forfeit.
“What does exercising actually cost me — and would it be different if they were non-qualified?”
The projection shows — The $100,000 of cash for shares she cannot sell, and the $350,000 spread that appears nowhere on her regular return and lands on the alternative minimum tax instead. What the AMT takes comes back as a credit in later years, which the table counts down. The same spread as an NSO is ordinary income immediately and never touches the AMT at all.
Try this scenario →Thirty days on the 83(b)
Dev, 33, is incorporating and taking 2,000,000 founder shares at $0.001 on a four-year vest with a one-year cliff, in a company they expect to climb about 5x a year toward a Series A.
“Does filing the 83(b) actually matter — and what if the company doesn't take off?”
The projection shows — Both directions, because it is not the one-way door the folklore suggests. Filed, the whole grant is taxed once at a spread of nearly zero. Not filed, every vesting tranche is ordinary income at what the stock is worth that year — tax on paper gains that cannot be sold. But where the price stays flat, the election has bunched the same income into a single year and doing nothing wins.
Try this scenario →What the salary you pay yourself decides
Marta, 46, runs a consultancy netting $400k. She is thinking about electing S-corp status, taking a salary, and funding a solo 401(k).
“How much can I actually put away, and what does the salary I choose do to it?”
The projection shows — That the salary does three jobs at once and they do not point the same way: it is the base payroll tax applies to, the W-2 figure the §199A deduction is capped at half of, and the compensation the employer contribution is 25% of — so a quarter of every dollar cut comes out of the retirement room. The Structure panel prices each salary side by side and picks none: what counts as reasonable pay is a §162 question for her CPA.
Try this scenario →An exit, inside the rest of the plan
Priya, 41, married, takes a $180k salary from the C-corp she founded and holds stock with a $20k basis. An acquirer has put $12M of proceeds on the table; she has held the stock four years.
“What does selling actually leave me — and does it change when we could stop working?”
The projection shows — The sale taxed inside the year it happens: the §1202 exclusion at four years versus five, the capital-gains tax stacked on that year's own salary, and what the net does to net worth over the next thirty years. The Financing & exit page computes the proceeds from a cap table; this is what they do once they land.
Try this scenario →Reading an exit before signing
Jordan raised a $500k SAFE, is looking at a Series A term sheet, and wants to understand what a sale would actually pay out.
“If we take this round and later sell for $20M or $60M, what lands in my pocket after preferences and taxes?”
The projection shows — On the Financing & exit page: the stated rounds become a cap table, each sale price runs through the preference waterfall, and the founder's proceeds show long-term capital gains, NIIT, and the §1202 (QSBS) treatment — as consequence tables in the order the outcomes were stated. Any outcome can then be carried into the household planner, where the sale is taxed inside the year it happens and projected against everything else.
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