Winning the Lottery

Winning the Lottery

I would probably try to keep cool. Maybe drive out to a nice hotel and just sit there all night, ordering things online. I’m talking about what I would do if I won the lottery. I think I could avoid the Lottery Curse by asserting my privacy rights and getting a...
Taxes: Medical Deductions

Taxes: Medical Deductions

Tax advice at cocktail parties aside, deducting your medical expenses is not as easy as it sounds. There are a lot of rules, exceptions, and questionable logic. The first hurdle to overcome is the amount you spent on deductible medical treatments and supplies. In...
Maxing Out Your Retirement Accounts

Maxing Out Your Retirement Accounts

You might have heard that it’s tax season. The deadline this year is April 18th because of Emancipation Day in Washington, DC. (The IRS treats all DC holidays as national holidays.) Hopefully you’ve got everything you need — but even if you’re still waiting for...
Tax Organizing Cheat Sheet

Tax Organizing Cheat Sheet

It’s tax season! In less than two months, one way or another, you’re going to do what needs to be done to stay out of tax jail.   The first thing to do is to make a folder that says “Tax 2021” — either on your computer or a manila folder — and then put the...
Hire Your Kids and Save

Hire Your Kids and Save

Did you know that if you hire your child to work at your business you get a business tax deduction? This includes deductions on your federal income tax bill, your self-employment tax bill, and your state income tax bill. In the long run, you could save quite a bit of...