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.