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Michael Williams | Jul 23, 2026 at 5:25 PM EDT

His 401(k) Held $400,000 of Company Stock. Rolling It Into an IRA Would Have Erased a Six-Figure Tax Break

Buried deep in the tax code sits a rule that could save a retiring employee with appreciated company stock a…

Michael Williams | Jul 23, 2026 at 5:16 PM EDT

The Real Cost of Retiring in Sun City, Arizona, on Social Security and a Small Pension

Sun City looks affordable on paper, but the homes hiding behind those low price tags carry a decades-old secret that…

Michael Williams | Jul 23, 2026 at 5:07 PM EDT

I’m 40 and my advisor wants me to switch from Roth to traditional 401(k). Dave Ramsey says it’s a million-dollar mistake

Her financial advisor pushed her to abandon the Roth 401(k) and take the traditional tax break instead, and it sounded…

Gerelyn Terzo | Jul 23, 2026 at 5:03 PM EDT

Kentucky Has 16 Million Barrels of Bourbon Aging. Here’s How a Retiree Can Actually Own One, and What a Sale Does to Social Security.

Owning a Kentucky bourbon barrel sounds like a bucket-list flex, but retirees who cash out a profitable barrel often discover…

Michael Williams | Jul 23, 2026 at 5:01 PM EDT

How Large Does Your Portfolio Need to Be to Generate $15,000 a Month?

Replacing a six-figure income with portfolio yield alone is a capital problem with a number most people underestimate, and the…

Gerelyn Terzo | Jul 23, 2026 at 3:02 PM EDT

The Helicopter Is the Fastest Way to the ER. The 20% Medicare Leaves Behind Is the Priciest Part of the Ride.

Medicare covers the helicopter, but a single rotor-wing evacuation can leave a retiree staring at a bill larger than a…

David Beren | Jul 23, 2026 at 12:38 PM EDT

Why Pulling From Your IRA Before Your Taxable Account Still Costs Retirees Five Figures, Even With No Penalty

Passing age 59½ clears the penalty hurdle on IRA withdrawals, but retirees who treat that milestone as a green light…

Marc Guberti | Jul 23, 2026 at 12:10 PM EDT

Roth Conversion Strategy Cuts $1.5 Million 401(k) Tax Bills in Half for Early Retirees

Most early retirees with large traditional 401(k)s follow the same instinct: leave it alone and let it grow until the…

David Beren | Jul 23, 2026 at 11:33 AM EDT

A $500,000 Annuity Pays About $3,100 a Month for Life. The 4% Rule Pays $1,667. Here’s the Catch

An annuity quote that looks nearly twice as generous as the classic retirement withdrawal rule sounds like a straightforward win,…

David Beren | Jul 23, 2026 at 11:19 AM EDT

Why the 4% Withdrawal Rule Breaks Down for Retirees Who Retire at 55

Retiring at 55 sounds like a triumph until you realize the most trusted rule in retirement planning was never built…

Gerelyn Terzo | Jul 23, 2026 at 10:04 AM EDT

IRMAA Isn’t Split Between Spouses: Cross the Line and You Both Pay Full Freight

A single dollar of extra income can quietly trigger thousands in surprise Medicare costs for both spouses, and the tax…

Gerelyn Terzo | Jul 23, 2026 at 10:03 AM EDT

Jamie Dimon Says the Economy Is “Resilient.” David Solomon Says It’s “Well Positioned.” A 72-Year-Old on Social Security Is Looking Through a Different Lens.

Jamie Dimon calls the economy resilient, corporate profits are surging, and yet millions of retirees feel their budgets shrinking every…

David Beren | Jul 23, 2026 at 9:05 AM EDT

One Wrong Rollover Move Can Make an Entire 401(k) Taxable in a Single Year. Here’s the 60-Day Rule.

A single procedural misstep during a 401(k) rollover can trigger a tax bill large enough to wipe out years of…

Gerelyn Terzo | Jul 23, 2026 at 8:02 AM EDT

Four Nights in a Hospital Bed Don’t Count If You Were Never ‘Admitted.’ The Nursing Home Bill Proves It.

A 78-year-old woman spent four nights in a hospital bed, received IV fluids, imaging, and specialist consults, then left with…

Carl Sullivan | Jul 23, 2026 at 7:33 AM EDT

Retired Electrician With $760,000 Discovers Pension Triggers Unwelcome IRMAA Surprise

One truck purchase and a bathroom renovation quietly pushed a retired electrician's Medicare bill well beyond what his neighbor pays…

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Personal Finance Articles

All Personal Finance Articles

His 401(k) Held $400,000 of Company Stock. Rolling It Into an IRA Would Have Erased a Six-Figure Tax Break

The Real Cost of Retiring in Sun City, Arizona, on Social Security and a Small Pension

I’m 40 and my advisor wants me to switch from Roth to traditional 401(k). Dave Ramsey says it’s a million-dollar mistake

Kentucky Has 16 Million Barrels of Bourbon Aging. Here’s How a Retiree Can Actually Own One, and What a Sale Does to Social Security.

How Large Does Your Portfolio Need to Be to Generate $15,000 a Month?

The Helicopter Is the Fastest Way to the ER. The 20% Medicare Leaves Behind Is the Priciest Part of the Ride.

Why Pulling From Your IRA Before Your Taxable Account Still Costs Retirees Five Figures, Even With No Penalty

Roth Conversion Strategy Cuts $1.5 Million 401(k) Tax Bills in Half for Early Retirees

A $500,000 Annuity Pays About $3,100 a Month for Life. The 4% Rule Pays $1,667. Here’s the Catch

Why the 4% Withdrawal Rule Breaks Down for Retirees Who Retire at 55

IRMAA Isn’t Split Between Spouses: Cross the Line and You Both Pay Full Freight

Jamie Dimon Says the Economy Is “Resilient.” David Solomon Says It’s “Well Positioned.” A 72-Year-Old on Social Security Is Looking Through a Different Lens.

One Wrong Rollover Move Can Make an Entire 401(k) Taxable in a Single Year. Here’s the 60-Day Rule.

Four Nights in a Hospital Bed Don’t Count If You Were Never ‘Admitted.’ The Nursing Home Bill Proves It.

Retired Electrician With $760,000 Discovers Pension Triggers Unwelcome IRMAA Surprise

Stock Market Live July 28, 2028: S&P 500 (SPY) Struggling to Stay Green

Live Nasdaq Composite: Semiconductor Sell-Off Drags Nasdaq Lower in Split Market

Goodbye, 4.7% COLA: Why the Latest Estimates for Social Security Recipients Just Changed

Congressman Who Oversees Military Contracts Bought $100,000 in SpaceX Stock. He’s Not the Only One.

3 Major Reasons for Investors to Buy AbbVie Stock Before July 31st

Goodbye, 4.7% COLA: Why the Latest Estimates for Social Security Recipients Just Changed

A Goldman Economist Says AI Will Take 15 Years to Show Up in the Economy. A 63-Year-Old Banking His Nest Egg on the AI Boom Should Listen.

Goodbye, 4.7% COLA: Why the Latest Estimates for Social Security Recipients Just Changed

Congressman Who Oversees Military Contracts Bought $100,000 in SpaceX Stock. He’s Not the Only One.

Personal Finance Articles

All Personal Finance Articles

His 401(k) Held $400,000 of Company Stock. Rolling It Into an IRA Would Have Erased a Six-Figure Tax Break

The Real Cost of Retiring in Sun City, Arizona, on Social Security and a Small Pension

I’m 40 and my advisor wants me to switch from Roth to traditional 401(k). Dave Ramsey says it’s a million-dollar mistake

Kentucky Has 16 Million Barrels of Bourbon Aging. Here’s How a Retiree Can Actually Own One, and What a Sale Does to Social Security.

How Large Does Your Portfolio Need to Be to Generate $15,000 a Month?

The Helicopter Is the Fastest Way to the ER. The 20% Medicare Leaves Behind Is the Priciest Part of the Ride.

Why Pulling From Your IRA Before Your Taxable Account Still Costs Retirees Five Figures, Even With No Penalty

Roth Conversion Strategy Cuts $1.5 Million 401(k) Tax Bills in Half for Early Retirees

A $500,000 Annuity Pays About $3,100 a Month for Life. The 4% Rule Pays $1,667. Here’s the Catch

Why the 4% Withdrawal Rule Breaks Down for Retirees Who Retire at 55

IRMAA Isn’t Split Between Spouses: Cross the Line and You Both Pay Full Freight

Jamie Dimon Says the Economy Is “Resilient.” David Solomon Says It’s “Well Positioned.” A 72-Year-Old on Social Security Is Looking Through a Different Lens.

One Wrong Rollover Move Can Make an Entire 401(k) Taxable in a Single Year. Here’s the 60-Day Rule.

Four Nights in a Hospital Bed Don’t Count If You Were Never ‘Admitted.’ The Nursing Home Bill Proves It.

Retired Electrician With $760,000 Discovers Pension Triggers Unwelcome IRMAA Surprise

Stock Market Live July 28, 2028: S&P 500 (SPY) Struggling to Stay Green

Live Nasdaq Composite: Semiconductor Sell-Off Drags Nasdaq Lower in Split Market

Goodbye, 4.7% COLA: Why the Latest Estimates for Social Security Recipients Just Changed

Congressman Who Oversees Military Contracts Bought $100,000 in SpaceX Stock. He’s Not the Only One.

3 Major Reasons for Investors to Buy AbbVie Stock Before July 31st

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Goodbye, 4.7% COLA: Why the Latest Estimates for Social Security Recipients Just Changed

A Goldman Economist Says AI Will Take 15 Years to Show Up in the Economy. A 63-Year-Old Banking His Nest Egg on the AI Boom Should Listen.