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.

Business owners

Can IRS take back your heavy SUV tax deduction?

The heavy SUV tax deduction gets a lot of attention every December. What happens to it a few years later, when business use drops, gets a lot less.

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Retirement & wealth

Sold an investment? What part of it gets taxed?

Sold an investment for $80,000? You probably didn’t make $80,000. Here’s which part of the sale actually gets taxed, and why one date can change the bill.

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Business owners

When is a partnership or S corp tax return due?

Most people plan their year around one tax deadline. If you own part of a business with partners or an S corp, April 15 is not the only date that matters.

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Household tax

Why do you owe after going from W-2 to 1099?

Same work, same pay, and suddenly your tax return shows a balance due instead of a refund. What changed when your W-2 became a 1099?

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Retirement & wealth

Do your CPA and financial advisor talk to each other?

Most people have a CPA for taxes and an advisor for investments. Are those two ever talking to each other, and what can it cost you if they aren’t?

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Retirement & wealth

Can you do a backdoor Roth with a traditional IRA?

The backdoor Roth is supposed to be the clean way around the income limit. So why do some people end up with a tax bill from it?

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Business owners

Can you max out two 401(k)s with a side business?

A side business can open the door to a second 401(k). But does having two plans really mean you can save twice as much for retirement each year?

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Household tax

Can you deduct a parent's assisted living costs?

Assisted living can run thousands of dollars a month, and many families end up paying part of it for a parent. Does any of that show up on your tax return?

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Retirement & wealth

Should you give to charity from your IRA?

Most retirees give to charity by writing a check from savings. If you have an IRA and give every year, is there a better way to do it?

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Household tax

Does a Trump account save your family any tax?

Millions of kids now have a Trump account, and most parents aren’t sure what it does. Does it actually save your family any tax?

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Business owners

Should your new LLC be an S corp right away?

Making your LLC an S corp is one of the first tips new business owners hear. Is day one really the right time to make the switch, or should you wait?

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Retirement & wealth

Should your kids get the house now or inherit it?

Many parents plan to pass the house down to their kids someday. Whether they get it now or after you’re gone can change how much tax they owe when they sell.

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Household tax

Can you owe back your marketplace health insurance discount?

Marketplace health insurance discounts are based on a guess about this year’s income. What happens at tax time when the guess comes in low?

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Household tax

Do you owe tax on the profit when you sell your house?

Selling a home you’ve owned for years can leave a big profit. Do you owe tax on all of it? Here’s how the home sale exclusion works and where it stops.

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Retirement & wealth

Should you pay off your mortgage with IRA money all at once?

Paying off the mortgage with IRA money sounds like one simple decision. How you take the money out can change what it costs.

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Retirement & wealth

Do you have to withdraw from an inherited IRA every year?

You inherited an IRA, and someone told you that you have ten years. There’s a second rule that decides whether you can actually wait that long.

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Retirement & wealth

Retiring before 59½? Should you roll your 401(k) to an IRA?

Rolling your 401(k) into an IRA is the usual next step when you retire. If you’re retiring before 59½, there’s one rule to know before you sign the paperwork.

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Household tax

Can you deduct a home office as a W-2 employee?

Working from home means your office is in your house. Does that make it a tax deduction if you’re a W-2 employee? Here’s what the current rules say.

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Business owners

Does a new LLC mean a new tax return?

You just formed an LLC for your business. Does that mean a whole new tax return every year? The answer comes down to who owns it and how it’s taxed.

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Household tax

Can you get a second tax extension?

Your tax return is already on extension and the deadline is close. Can you get a second extension? Here’s what the IRS allows and what to do next.

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Retirement & wealth

Does working lower your Social Security benefits?

If you claim Social Security at 62 and keep working, some benefits can be held back. How much depends on your earnings 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 check it yourself in a few minutes with an account at IRS.gov.

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Business owners

Is a transfer from your business account payroll?

Moving money from your business account to your personal account feels like paying yourself. Here’s why it may not count as payroll, and when that matters.

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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 leave you with very different amounts after taxes. A few choices about how you hold them decide which 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, but your investment account still raised your tax bill. Here’s the one type of account where that happens every year.

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Retirement & wealth

Is the smallest tax bill every year the right goal?

Most people judge their taxes one April at a time. Adding up your lifetime tax bill says far more about your savings than any single year can.

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Retirement & wealth

Should your trust be the beneficiary of your IRA?

Many people name their trust as beneficiary on every account. For your IRA, that choice can quietly cost your family more in taxes. Here’s why.

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Retirement & wealth

How does income affect health insurance before Medicare?

Retiring before 65 means buying your own health insurance. Your income sets the premium, and in early retirement you may control more of it than you think.

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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 fall tax projection uses your real numbers while there’s still time to adjust what you pay 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 your lowest-tax years. Used well, that window can shrink your lifetime tax bill, and each unused year is gone.

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Retirement & wealth

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

A market drop early in retirement does more damage than the same drop later. Here’s what sequence of returns risk is and how to plan around it.

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Tax and retirement questions, answered in about a minute.

Can IRS take back your heavy SUV tax deduction?

Sold an investment? What part of it gets taxed?

When is a partnership or S corp tax return due?

Why do you owe after going from W-2 to 1099?

Do your CPA and financial advisor talk to each other?

Can you do a backdoor Roth with a traditional IRA?

Can you max out two 401(k)s with a side business?

Can you deduct a parent's assisted living costs?

Should you give to charity from your IRA?

Does a Trump account save your family any tax?

Should your new LLC be an S corp right away?

Should your kids get the house now or inherit it?

Can you owe back your marketplace health insurance discount?

Do you owe tax on the profit when you sell your house?

Should you pay off your mortgage with IRA money all at once?

Do you have to withdraw from an inherited IRA every year?

Retiring before 59½? Should you roll your 401(k) to an IRA?

Can you deduct a home office as a W-2 employee?

Does a new LLC mean a new tax return?

Can you get a second tax extension?

Does working lower your Social Security benefits?

How do you know your tax return was actually filed?

Is a transfer from your business 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 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?

Talk to Anton before your next big financial decision.