Insights

Tax and retirement questions, answered in about a minute.

Every week, Anton Prokopenko, CPA, CFP®, answers one real question about taxes, retirement, or investing. Watch the short video or read the plain-English version.

Retirement & wealth

Does working lower your Social Security benefits?

Claiming Social Security at 62 while working can mean reduced Social Security benefits. How much, and for how long, depends on what you earn and when you reach full retirement age.

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Household tax

How do you know your tax return was actually filed?

Getting a copy of your tax return and having it filed are not the same thing. You can confirm it yourself in a few minutes by registering for an account at IRS.gov.

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Business owners

Is moving money from your business account to your personal account payroll?

Moving money from your business account to your personal account feels like paying yourself, but payroll is something different. If nobody has ever run you a paycheck, it’s worth asking your CPA whether your business is supposed to.

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Retirement & wealth

Can a lower return leave you with more money after taxes?

Two investments can earn about the same and still leave you with very different amounts of money after taxes. A few small decisions about how you hold them decide which one wins.

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Retirement & wealth

Can you use more than $3,000 of investment losses in a year?

Most people have heard that investment losses are capped at $3,000 a year on your taxes. The actual rule is a lot more generous than that.

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Retirement & wealth

Why do you owe tax on investments you never sold?

You didn’t sell anything and you didn’t take money out, but your investment account still added to your tax bill. There’s one type of account where that happens every single year.

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Retirement & wealth

Is the smallest tax bill every year the right goal?

Most people have seen every tax bill they’ve ever paid, one April at a time. Almost nobody has added them up, and that total says more about your savings than any single year ever will.

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Retirement & wealth

Should your trust be the beneficiary of your IRA?

Most people name their trust on every account because that’s what they were told to do. For one account in particular, that choice can quietly cost your family a lot more in taxes.

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Retirement & wealth

How does your income affect health insurance before Medicare?

Retiring before 65 means paying for health insurance on your own, and at full price it can cost more than a mortgage. In early retirement you may have more control over your income than you think, and that income sets your premium.

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Household tax

Can you know your April tax bill before you file?

Your April tax bill doesn’t have to be a surprise. A tax projection is a practice run of your tax return, done in the fall with your real numbers, while there’s still time to adjust what you’re paying in.

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Retirement & wealth

Why are the first years of retirement a tax planning window?

The first years of retirement are often the lowest-tax years of your life. Using that window well can mean a smaller lifetime tax bill, and every year it goes unused is gone.

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Retirement & wealth

Why do the first five years of retirement matter so much?

A market drop in the first few years of retirement does more damage than the same drop later. That’s called sequence of returns risk. Planning ahead for what you sell first, and keeping a few years of spending out of the market, can make or break your retirement.

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Tax and retirement questions, answered in about a minute.

Does working lower your Social Security benefits?

How do you know your tax return was actually filed?

Is moving money from your business account to your personal account payroll?

Can a lower return leave you with more money after taxes?

Can you use more than $3,000 of investment losses in a year?

Why do you owe tax on investments you never sold?

Is the smallest tax bill every year the right goal?

Should your trust be the beneficiary of your IRA?

How does your income affect health insurance before Medicare?

Can you know your April tax bill before you file?

Why are the first years of retirement a tax planning window?

Why do the first five years of retirement matter so much?

Get a tax-smart opinion before major life changes turn into tax surprises.