Tools

When you have an extra dollar to save, where should it go first? This walks through the common order for putting savings to work: paying off high-interest debt, capturing the full employer match, an HSA, the main retirement accounts, backdoor and mega-backdoor Roth space, then a taxable account. At each step it explains the reasoning and shows the current contribution limits, so you can see how the order shifts for your own situation.

Your freedom number is the invested amount that would let work become a choice, and it keys off how much you spend, not how much you earn. This puts a figure on it from your annual spending, shows the Coast-FI milestone where your current savings could grow into that number on their own, and works out the spending a given portfolio can support, all under return assumptions you can change.

Your tax bracket is rarely the rate you actually pay on your next dollar. This stacks every layer that lands on a high earner's next dollar, including the federal bracket, the investment-income and Medicare surtaxes, state tax, the AMT interaction, and phaseout cliffs, and plots the real marginal rate across a range of income so the hidden spikes show up. You see what an extra dollar of income or a bonus really keeps.

A job offer's headline number is rarely what lands in your bank account. Enter the base salary, bonus, and RSU value of an offer and this shows what is actually spendable after federal tax, payroll, surtaxes, and state tax, with a line-by-line breakdown of what each layer takes. It also shows why the standard withholding on RSUs is not the real tax you owe.

Stacking more income on top of your year, such as a Roth conversion, can push you across a bracket edge or a surtax line where the next dollar suddenly costs more. Enter your projected income and this shows the room you have before each ceiling: the top of your current tax bracket, the next brackets up, the investment-income surtax line, and the Medicare surtax line. Each line comes with the rate you pay below it and the rate just above, so you can see what crossing it would cost.

Exercising incentive stock options has tax consequences that are hard to see until you run the math. Enter your grant details and a holding-period scenario, and this shows the Alternative Minimum Tax an exercise can generate even though the regular tax system charges nothing on the spread, plus how the eventual sale is taxed depending on how long you hold. It lays out the cost and timing tradeoffs as actual numbers across the scenarios.

Exercising incentive stock options can trigger a tax bill on a gain you have not actually cashed out. This estimates your exposure to the Alternative Minimum Tax: whether a given exercise pushes you into AMT, how much extra tax it adds this year, and where the AMT exemption phaseout quietly raises your rate. It shows the numbers so the cost of a large exercise is visible before you make it.

When RSUs vest, your employer usually withholds federal tax at a flat supplemental rate that sits below the true marginal rate a high earner actually pays, so you can owe far more at filing than was withheld, often tens of thousands of dollars on income you already received as shares. This estimates the size of that gap from a few inputs and shows where it comes from: federal, state, and Additional Medicare.

Founder and early-employee stock can qualify for the Section 1202 exclusion, which shields a large share of the gain from federal tax when you sell, but only if the stock clears a set of specific tests. This runs those tests one at a time on your facts, and for stock that qualifies, estimates how much gain the exclusion could shield and what tax is left on the rest. The date you acquired the stock decides which rules apply, so it shows both regimes side by side.

For a contribution made this year, this shows whether pre-tax (traditional) or Roth leaves you with more after-tax money at withdrawal, growing the same contribution at the same assumed return over the same horizon so the only thing moving the answer is your tax rate now versus your rate in retirement. Change the retirement-rate assumption and watch the two ending balances cross, so you can see why the rate comparison, not a rule of thumb, drives the choice.

An HSA that you fund, invest, and leave alone works more like a stealth retirement account than a way to cover copays. This grows your contributions forward to retirement and shows how much more the balance is worth than the same dollars in a taxable account, with the catch that the tax-free withdrawal holds only for qualified medical expenses.

If your 401(k) allows after-tax contributions and conversions, the mega backdoor Roth can let you put far more into a Roth than the usual limits suggest. Enter your own salary deferrals and your employer's contributions for the year, and this calculates the after-tax room you have left under the total 401(k) limit. It also explains why catch-up contributions do not eat into that room.

If you have an old pre-tax IRA balance sitting around, converting a fresh nondeductible contribution to a Roth can trigger tax on most of that conversion, because the IRS treats all your traditional, SEP, and SIMPLE IRAs as one pot. This shows how much of your planned conversion is taxable now and what changes if the pre-tax balance were out of the picture, so you can see the size of the trap and the size of the fix.

How your business is taxed changes how much you keep. Enter one year of profit and this runs it through three structures side by side, a sole proprietor or single-member LLC, an S-corp, and a C-corp, showing the total federal tax under each and the difference between them, so you can see the tradeoff each choice carries.

The Section 199A deduction for pass-through business income behaves in ways that surprise owners: the same business can get a clean 20% at one income level and nothing at a higher one, and service businesses are treated differently above the income thresholds. This estimates your deduction on your own numbers, shows what it saves at your tax rate, and explains why the thresholds and wage limit landed where they did.

Business owners can shelter far more for retirement than an employee can, and the plan you run decides how much. This shows the contribution capacity of a solo 401(k) and a SEP-IRA for your income and age, and explains how a cash-balance plan stacked on a 401(k) can shelter much more as you get older, so you can compare what each design admits.

Which account holds each investment decides how much of your return survives a lifetime of taxes. This ranks your holdings by how much tax they throw off in a taxable account, ranks your accounts by how well they shelter, and shows where the general rule would steer each asset, so you can see the reasoning behind putting the right pieces in the right places.

Selling an investment at a loss can lower this year's tax bill by offsetting gains first, then a capped slice of ordinary income, with the rest carried to future years. This walks a harvestable loss through that order and shows the tax saved at each step. It also makes the catch clear: harvesting mostly moves tax to later rather than erasing it, because the replacement holding carries a lower cost basis and a larger gain waits down the road.

Paying down the mortgage earns a guaranteed return equal to your loan rate, while investing the same money earns an uncertain one. This compares the two paths over a horizon you pick, finds the investment return where they break even, and keeps the certainty difference in view, since a guaranteed return and an expected one are not the same even when the numbers match.

Most people are nowhere near owing federal estate tax, but the ones who are want a clear number. Enter your total estate value, marital status, and any large lifetime gifts already made, and this tells you whether you are above the federal exemption, by how much, and the estimated tax on the amount over the line. It is a quick check on whether the estate-tax question applies to you, not an estate plan.

Superfunding lets you front-load several years of tax-free gifts into a 529 in one shot, and this shows the largest amount you and a spouse can put in for each child without touching your lifetime gift exemption. It also illustrates the head start that front-loading buys over contributing year by year, using a return assumption you can change.

Before a move, this puts your current state and a destination state side by side at your income and shows the annual difference in state income tax. It also surfaces the catch most calculators miss: deferred pay and equity that vests after you move can still be taxed by the state where you earned it, so a slice of tax follows you. The forward saving and the tax that follows are shown as separate figures, never combined into one inflated number.

Group disability coverage often leaves high earners underinsured once its monthly cap kicks in, and an employer-paid benefit is worth less after tax than it looks. This sizes the monthly income you would actually keep if you could not work, shows where your coverage erodes, and gives you the gap an individual policy would need to fill.