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7 Tax Mistakes People Make During Their First Year of Retirement

Retirement can eliminate the morning commute, the office birthday cake nobody wanted, and the annual performance review. Unfortunately, it doesn’t eliminate tax season. In fact, your first year without a regular paycheck can make your tax return surprisingly complicated.

The Free Financial Advisor · 19h ago

The ‘Make Money While You Sleep’ Trend Is Everywhere—But Which Side Hustles Really Work?

The dream of earning money while asleep has inspired a small internet industry of its own. Open social media, and someone will happily explain how to make money from digital products, rental properties, affiliate links, or an online store. Their videos often look suspiciously relaxing, with a laptop, an iced…

Clever Dude · 21h ago

Your 401(k) Looks Healthy — But Have You Calculated What Taxes Could Take?

A $750,000 401(k) balance looks like a serious retirement accomplishment. Unfortunately, your account statement doesn’t include a preview of your future tax bill. If you built that balance with traditional pretax contributions, the IRS still expects its share when you withdraw the money. Your retirement account shows how much you’ve…

The Free Financial Advisor · 22h ago

The 401(k) Mistake Workers Over 50 Could Make Under the New Roth Catch-Up Rules

A bigger retirement contribution can come with an unexpected side effect: a smaller paycheck today. Starting in 2026, certain workers over 50 must make their extra 401(k) catch-up contributions as Roth contributions, which means they generally pay income tax on that money now rather than later.

The Free Financial Advisor · Oct 28

Selling Your Home After Retirement? These 5 Tax Questions Could Save You From Surprises

Selling a longtime home can put a remarkable amount of money into your bank account, but the IRS may want to discuss the details. Retirement adds another wrinkle: a home sale can affect more than your tax return, depending on your income, Medicare coverage, and plans for the proceeds.

The Free Financial Advisor · Oct 27

The Documentation Gap Behind Missed R&D Tax Credits

The IRS has designated research credit claims as a Tier I audit issue, noting that claims are often filed using high-level estimates, invalid assumptions, lack of means between qualified research expenses and the business component without contemporaneous documentation to support the claim.

International Business Times · Oct 26

Grandparents Are Spending Thousands Helping Their Families — But Who’s Protecting Their Retirement?

A grandparent can help a grandchild buy a first car, cover a college bill, or afford a deposit on a home. The awkward part comes later, when that same grandparent needs new teeth, a major home repair, or enough money to cover another decade of retirement.

The Free Financial Advisor · Oct 25

The Inheritance Mistake That Could Leave Adult Children With an Unexpected Tax Bill

An inheritance can arrive with a peculiar surprise: the money itself may be tax-free, but what happens next could cost thousands. Adult children who inherit a parent’s house, investments, or retirement account can face very different tax rules, even when everything comes from the same estate.

The Free Financial Advisor · Oct 25

‘I Don’t Want You to Contribute to a Trump Account for a Child. Period’: Suze Orman Says Take the Free $1,000 and Your Employer’s $2,500, Then Stop.

Suze Orman says it doesn't make sense for most people to contribute to a Trump account.

Barchart · Oct 24

Do You Still Pay Federal Taxes on Social Security? What Retirees Should Know Before Filing in 2027

A bigger Social Security check does not necessarily mean more spending money. The IRS may want a piece of those benefits, even when retirement has replaced a regular paycheck. For retirees preparing their 2027 tax returns, one familiar rule still deserves attention: Social Security benefits can remain subject to federal…

The Free Financial Advisor · Oct 24