Personal Finance Articles

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5238 Articles

Ian Cooper | May 31, 2026 at 8:25 AM EDT

The Quiet $32,000 Cost of Skipping the Medigap Open Enrollment Window at 65

Turning 65 comes with a quiet deadline most people never hear about until it has passed. The six-month window that…

Ian Cooper | May 31, 2026 at 8:20 AM EDT

How Corporate Executives With $7 Million 401(k)s Stay Under the Top Tax Bracket in Retirement

A retired executive sitting on $7 million across a traditional 401(k), a Roth 401(k), and a taxable brokerage has a…

Drew Wood | May 31, 2026 at 7:24 AM EDT

A 67-Year-Old Widow With $1.6 Million Discovers Her Late Husband’s IRA Will Cost Her Over $100,000 in Avoidable Tax Through Retirement

A reader writes in: her husband passed away last year at age 70, leaving behind a $740,000 traditional IRA. She…

Gerelyn Terzo | May 31, 2026 at 7:23 AM EDT

Why a Single Self-Employed 62-Year-Old Should Claim Social Security at FRA, Not 70

Picture a 62-year-old consultant who works alone, bills clients directly, and pulls in around $90,000 in net self-employment income most…

Carl Sullivan | May 31, 2026 at 6:52 AM EDT

A $600,000 Annuity Pays $3,700 a Month for Life. What About Your Spouse?

A 65-year-old retiree walks into a meeting with $600,000 in an IRA and walks out with a pitch. Hand it…

Michael Williams | May 31, 2026 at 6:30 AM EDT

How $500,000 in Life Insurance Can Earn $18,000 to $19,000 Annually While You Grieve and Decide

Two weeks after her 52-year-old husband died unexpectedly, a 54-year-old woman called Suze Orman’s podcast with the question hundreds of…

Michael Williams | May 31, 2026 at 6:20 AM EDT

Social Security Gets Taxed When Dividends Cross This Threshold. Most Retirees Miss It

When a Comfortable Dividend Stream Turns Into a Tax Surprise Picture a single retiree drawing $30,000 a year in Social…

Drew Wood | May 31, 2026 at 5:19 AM EDT

A 58-Year-Old Divorcée With $1.4 Million From a QDRO Discovers She Cannot Roll It Until She Resolves a 15-Year-Old Court Order

A 58-year-old woman who divorced in 2010 walks into retirement planning with what looks like a straightforward task. Her ex-husband’s…

David Beren | May 30, 2026 at 2:32 PM EDT

Locked Into a Lower Social Security Benefit? The 12-Month Fix You Need to Know

A reader recently described a situation that comes up more often than people realize. She lost her job at 62,…

David Beren | May 30, 2026 at 12:31 PM EDT

The Charitable Remainder Trust Strategy That Lets a 68-Year-Old Sell a $2.4 Million Concentrated Stock Position Without Triggering a $480,000 Tax Bill

A 68-year-old retired executive sits on $2.4 million of a single stock, likely shares from a long-ago IPO or decades…

Drew Wood | May 30, 2026 at 11:45 AM EDT

A 71-Year-Old Retired Federal Employee With $890,000 in a TSP Discovers His Pension Quietly Disqualified Him for the IRMAA Hold-Harmless Rule

A retired GS-13 with a solid FERS pension, a well-funded Thrift Savings Plan, and steady Social Security income would seem…

Michael Williams | May 30, 2026 at 11:30 AM EDT

The $2,076 Monthly Benefit Most Divorced Women Over 62 Never Claim From Social Security

Picture this: you are 65, divorced for years, and quietly worried that your Social Security check will not stretch far…

Maurie Backman | May 30, 2026 at 11:29 AM EDT

Retirees Are Furious That Their COLA Can’t Keep Up With Soaring Healthcare Costs

Social Security plays a big role in many people’s retirement. Without those benefits, a lot of seniors would not be…

David Beren | May 30, 2026 at 11:23 AM EDT

What Happens to a $4.2 Million Estate When the Older Spouse Dies First vs. Second, and Why the Order Determines a $700,000 Tax Gap

A 73-year-old husband and 70-year-old wife sitting on $4.2 million in retirement and brokerage assets generally assume the federal estate…

Drew Wood | May 30, 2026 at 11:21 AM EDT

Tax Aware Dividend Stacking: How a $750,000 Roth Portfolio Pays $42,000 Federally Tax Free

A 65 year old retiree sitting on $750,000 inside a Roth IRA can engineer roughly $42,000 of annual dividend income…

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Personal Finance Articles

All Personal Finance Articles

The Quiet $32,000 Cost of Skipping the Medigap Open Enrollment Window at 65

How Corporate Executives With $7 Million 401(k)s Stay Under the Top Tax Bracket in Retirement

A 67-Year-Old Widow With $1.6 Million Discovers Her Late Husband’s IRA Will Cost Her Over $100,000 in Avoidable Tax Through Retirement

Why a Single Self-Employed 62-Year-Old Should Claim Social Security at FRA, Not 70

A $600,000 Annuity Pays $3,700 a Month for Life. What About Your Spouse?

How $500,000 in Life Insurance Can Earn $18,000 to $19,000 Annually While You Grieve and Decide

Social Security Gets Taxed When Dividends Cross This Threshold. Most Retirees Miss It

A 58-Year-Old Divorcée With $1.4 Million From a QDRO Discovers She Cannot Roll It Until She Resolves a 15-Year-Old Court Order

Locked Into a Lower Social Security Benefit? The 12-Month Fix You Need to Know

The Charitable Remainder Trust Strategy That Lets a 68-Year-Old Sell a $2.4 Million Concentrated Stock Position Without Triggering a $480,000 Tax Bill

A 71-Year-Old Retired Federal Employee With $890,000 in a TSP Discovers His Pension Quietly Disqualified Him for the IRMAA Hold-Harmless Rule

The $2,076 Monthly Benefit Most Divorced Women Over 62 Never Claim From Social Security

Retirees Are Furious That Their COLA Can’t Keep Up With Soaring Healthcare Costs

What Happens to a $4.2 Million Estate When the Older Spouse Dies First vs. Second, and Why the Order Determines a $700,000 Tax Gap

Tax Aware Dividend Stacking: How a $750,000 Roth Portfolio Pays $42,000 Federally Tax Free

Dave Ramsey Is Baffled by a Debt-Free Couple Making $100,000 Who Can’t Save a Dollar: ‘I Just Can’t Fill Up All the $1,000 Holes’

The Analyst Who Loved Bank Stocks for 15 Years Just Flipped. Here’s What He’s Buying Instead

Union Electricians Risk Leaving Pension Money on the Table, Here’s the Fix

Dave Ramsey Is Baffled by a Debt-Free Couple Making $100,000 Who Can't Save a Dollar: 'I Just Can't Fill Up All the $1,000 Holes'

Union Electricians Risk Leaving Pension Money on the Table, Here's the Fix

Dave Ramsey Is Baffled by a Debt-Free Couple Making $100,000 Who Can’t Save a Dollar: ‘I Just Can’t Fill Up All the $1,000 Holes’

The Analyst Who Loved Bank Stocks for 15 Years Just Flipped. Here’s What He’s Buying Instead

Personal Finance Articles

All Personal Finance Articles

The Quiet $32,000 Cost of Skipping the Medigap Open Enrollment Window at 65

How Corporate Executives With $7 Million 401(k)s Stay Under the Top Tax Bracket in Retirement

A 67-Year-Old Widow With $1.6 Million Discovers Her Late Husband’s IRA Will Cost Her Over $100,000 in Avoidable Tax Through Retirement

Why a Single Self-Employed 62-Year-Old Should Claim Social Security at FRA, Not 70

A $600,000 Annuity Pays $3,700 a Month for Life. What About Your Spouse?

How $500,000 in Life Insurance Can Earn $18,000 to $19,000 Annually While You Grieve and Decide

Social Security Gets Taxed When Dividends Cross This Threshold. Most Retirees Miss It

A 58-Year-Old Divorcée With $1.4 Million From a QDRO Discovers She Cannot Roll It Until She Resolves a 15-Year-Old Court Order

Locked Into a Lower Social Security Benefit? The 12-Month Fix You Need to Know

The Charitable Remainder Trust Strategy That Lets a 68-Year-Old Sell a $2.4 Million Concentrated Stock Position Without Triggering a $480,000 Tax Bill

A 71-Year-Old Retired Federal Employee With $890,000 in a TSP Discovers His Pension Quietly Disqualified Him for the IRMAA Hold-Harmless Rule

The $2,076 Monthly Benefit Most Divorced Women Over 62 Never Claim From Social Security

Retirees Are Furious That Their COLA Can’t Keep Up With Soaring Healthcare Costs

What Happens to a $4.2 Million Estate When the Older Spouse Dies First vs. Second, and Why the Order Determines a $700,000 Tax Gap

Tax Aware Dividend Stacking: How a $750,000 Roth Portfolio Pays $42,000 Federally Tax Free

Dave Ramsey Is Baffled by a Debt-Free Couple Making $100,000 Who Can’t Save a Dollar: ‘I Just Can’t Fill Up All the $1,000 Holes’

The Analyst Who Loved Bank Stocks for 15 Years Just Flipped. Here’s What He’s Buying Instead

Union Electricians Risk Leaving Pension Money on the Table, Here’s the Fix

Featured Reads

Dave Ramsey Is Baffled by a Debt-Free Couple Making $100,000 Who Can't Save a Dollar: 'I Just Can't Fill Up All the $1,000 Holes'

Union Electricians Risk Leaving Pension Money on the Table, Here's the Fix