#taxes

Contribute to a traditional IRA, convert to Roth, done. That works cleanly only if your other traditional IRA balances are empty, and the balance that decides it is measured on December 31, not on the day you convert. Which means a rollover in November can retroactively tax a conversion you made in March.

Trip the wash sale rule in a taxable account and the loss is deferred, not lost: it moves into the cost basis of the replacement shares. Repurchase inside an IRA or HSA instead and there is no basis to move it to, so the deduction is gone permanently. Your broker will not flag it.

On the ex-dividend date the share price drops by roughly the dividend. The cash did not appear from nowhere, it moved out of the share and into your account, and in a taxable account it moved through a tax on the way. Which is also why dividend capture fails twice over.

Capital gains has two kinds of number. The brackets get re-indexed for inflation every year. Two others have not moved since 1978 and 2013, and because they never move, they capture more people every year without anyone voting on it.

RSUs are taxed as ordinary income the day they vest, but your employer withholds at a flat supplemental rate that has nothing to do with your actual bracket. That gap is why so many people in tech get an April bill they did not budget for. There is a second, worse error hiding on the 1099-B.

The whole Roth vs Traditional debate reduces to one question: is your tax rate higher now or in retirement? The math is symmetric. The decision is a bet on future tax rates. For most people under 40 who aren't high earners, Roth is the default that ages well.

A traditional 401(k) skips tax now and pays it in retirement. A Roth 401(k) pays tax now and skips it later. The whole decision is a bet on your future tax rate, and for a lot of people the answer is clearer than it looks.

Property tax is the most local form of taxation in the US, and the bill that finances most of public-school education, local police, fire, and roads. Here’s how to actually trace where the money lands.

Gross is what you earn. Net is what you keep. The space between those two numbers is where most personal finance mistakes live.