Money Scenarios

See what your money does over the next thirty years.

Type in your situation and a what-if. A Roth conversion, a year off, starting a business. You get the taxes, the brackets and the account balances for every year.

It also points out things you didn't ask about. For example, that converting this year will raise your Medicare premium two years from now, or that the capital loss you're carrying will never get used against the gain sitting next to it. These aren't things you forgot to fill in. They're things nobody would have worked out by hand.

Start a projectionProjections based on your assumptions. Not financial advice.

Findings

Things people didn't ask about

Three of the worked examples from further down the page. In each one, someone asked a question, got their answer, and also got told about a second problem they hadn't asked about. Every number here comes from an actual projection, and an automated test re-runs all of them on every build.

A $1,299 Medicare surcharge, caused two years earlier

“How much should I convert to Roth in these low-income years?”

Also found: The $80,000 converted in year 3 adds $1,299 in Medicare surcharges in year 5, two years after the conversion.

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Taxed on $104,904 of profit that never left the business

“If I pay myself $150k, does this beat the job I left?”

Also found: The business earned $254,904 but only paid out $150,000, so you're taxed on $104,904 you never received. The year's $71,758 tax bill pulls $44,758 out of your personal accounts to cover it.

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$863,000 of losses, usable only $3,000 a year

“I put $1.2M into that stock and $250k came back. What is a loss like that worth?”

Also found: The plan ends with $863,000 of capital losses still unused, while $2,457,333 of untaxed gain sits in the same brokerage account. Without a sale, the loss only offsets $3,000 of ordinary income a year.

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How it works

I

Describe your household

Ages, account balances, income, spending. The form explains why each answer matters (whether money is pre-tax or Roth changes almost everything), and if you skip a field it tells you what value it's using instead.

II

Ask a what-if question

“What if I convert $50k a year until I'm 73?” Your question is turned into a scenario you can read and edit, so you can fix anything it got wrong before anything is calculated.

III

Compare the results

Lifetime tax, which bracket you're in each year, when surcharges kick in, and how long the money lasts. Below that, anything else your numbers turned up. Change an assumption and everything recalculates.

The checks

What every projection is checked for

14 checks run on every projection. Each one looks for a spot where two of your own answers work against each other. A check only shows up if it applies to your numbers. None of them is generic advice for people in your situation.

Tax on business profit you never took out

A pass-through business is taxed on what it earned, not on what it paid you. If profit stays in the company, or the company spends it, the tax on it still shows up on your personal return.

Unused business losses next to a future tax bill

Business losses carry forward indefinitely and can offset any kind of income. A plan can end with losses still unused while a pre-tax account is waiting to be taxed on the way out.

A capital loss that never gets used

A capital loss can offset unlimited capital gains, but only $3,000 a year of ordinary income (a limit set in 1978). Without a sale to pair it with, the loss and the gain can sit in the same account for decades and never cancel out.

Selling founder stock before the five-year mark

The full QSBS exclusion needs five years of holding. Below that, you get a partial exclusion in steps. The same sale on either side of one date can be a very different amount of tax.

A higher Medicare premium two years after a conversion

Medicare sets each year's premium using your tax return from two years earlier, and the surcharge jumps in steps rather than sliding. So a Roth conversion this year raises your premium two years from now.

Losing the health insurance subsidy entirely

One dollar of income over the limit ends the premium tax credit completely. There's no taper. Most often it's a Roth conversion that pushes someone over.

A state clawing back its lower brackets

Some states add a supplemental tax at higher incomes that cancels the benefit of every lower bracket, so you end up paying the top rate on all of your income. You won't see this in a rate table.

A retirement contribution paid for with an early withdrawal

Maxing out a plan is what the rules allow, not necessarily what your income covers. A year that puts money into a plan while pulling money out of a pre-tax account early pays a 10% penalty on the withdrawal.

The surviving spouse taxed as a single filer

The year after a death, the survivor files single with the same accounts, the same required distributions and one Social Security check instead of two, but half the bracket width and half the standard deduction. Income goes down and the tax bill goes up.

A conversion that pushes your gains out of the 0% bracket

Long-term gains and qualified dividends sit on top of your ordinary income, so the 0% rate only applies to gains that fit below the threshold. A Roth conversion raises your ordinary income and pushes those gains up into the 15% bracket, even though you didn't sell anything.

A backdoor Roth that wasn't tax-free

The IRS treats all your traditional, SEP and SIMPLE IRAs as one account, so a conversion is taxed pro-rata across all of them. After-tax contributions only convert tax-free in proportion to your total IRA balance, including any old rollover.

Employer match left on the table

A match is only paid on what you actually contribute. If you defer less than the formula rewards, the difference isn't delayed or deferred. It's never paid at all, and nothing on your payslip shows what you missed.

Net worth you can't spend

Net worth includes your house, but you can't pay bills with it. A plan can show growing net worth every year and still hit a year where the accounts are empty and there's nothing left to spend.

A QSBS exclusion your state doesn't honor

The QSBS exclusion is federal law, and several states that founders actually live in don't follow it. The gain that was fully excluded on your federal return can be fully taxed on your state return.

Worked examples

25 made-up households with real questions. Open one and the planner is prefilled with their numbers. Edit anything you like and run it yourself. A dot marks the 17 examples where the projection found something the person hadn't asked about.

Read the full write-ups

Method

Where the numbers come from

The AI doesn't do the math

A language model reads your question and explains the results, but it never calculates anything. Every number on this site, including the findings above, comes from tax code we wrote ourselves and test to the cent against the IRS's own published examples.

You always know which assumptions are ours

Return rates, inflation and future tax law are all yours to change, and each one is labelled as our default until you do. The same goes for anything you leave blank. If you don't enter Social Security, the projection assumes you never claim it, and it tells you so, with a link to the field that fixes it.

This is not advice

A finding tells you what your numbers add up to and which input changes it. It doesn't rank your options or tell you what to do. This is a projection of the scenarios you describe, not financial or tax advice.

Pricing

What it costs

Free

$0

Everything you can work out for one household by hand, saved on this device.

  • · The household form, including what you haven't filled in yet
  • · Up to three hand-built scenarios, compared with doing nothing
  • · Every chart, the year-by-year table, and every assumption visible
  • · Findings from your numbers, and whether the money lasts
  • · Monte Carlo, sensitivity analysis, and how much you can convert under a threshold
  • · The full financing and exit calculator
Start free

Household

$149a year · or $15 a month

Save your plan, ask questions in plain English, and get every result explained.

  • + A saved plan link you can share with a spouse and open on any device
  • + Ask questions in plain English and get every run explained
  • + The best conversion schedule, plans that avoid the RMD spike, and a stress test
  • + How much you can spend at each confidence level

14-day free trial. Renews until you cancel. Refund available within 14 days of the first charge.

Business

$299a year · or $29 a month

Everything in Household, plus the business side: entity structure, owner pay, and the exit.

  • · Everything in Household
  • + Every business event: acquire, fund, borrow, operate, hire, draw, sell, change structure
  • + Which entity structure comes out ahead, with salary and timing tables
  • + Business decisions tested against your cash runway
  • + Carry an exit over into the household plan

14-day free trial. Renews until you cancel. Refund available within 14 days of the first charge.

One subscription covers one plan link. Share it with a spouse and open it on any device. Terms · Privacy