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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…

Austin Smith | May 30, 2026 at 11:00 AM EDT

The $200,000 Social Security Mistake Couples Make at 64 Without Realizing It

The Decision Sitting on the Kitchen Table You are both 64. One of you earned more over a long career,…

David Beren | May 30, 2026 at 10:27 AM EDT

The Cash Balance Plan a 58-Year-Old Solo Consultant Is Using to Shelter $312,000 a Year From Federal Tax

A 58-year-old strategy consultant working solo, with 2025 net Schedule C income of $480,000, has already filled the obvious retirement…

Carl Sullivan | May 30, 2026 at 10:27 AM EDT

73-Year-Old Widow With $2.1M Discovers Husband’s IRA Beneficiary Election Triggered a $96K Tax Bill

Margaret is 73. Her husband died in March, and six months later, her CPA delivered some bad news. A single…

Ian Cooper | May 30, 2026 at 10:21 AM EDT

Want $9,000 in Annual Passive Income? Invest $100,000 Into These 3 Monthly Paying Funds

A retiree with $100,000 in a brokerage account wants a predictable monthly check covering recurring bills. The target is $750…

Michael Williams | May 30, 2026 at 10:15 AM EDT

Social Security’s Windfall Elimination Provision is Gone. Here’s How to Claim What You’re Owed

A retired California schoolteacher watched her late husband’s Social Security survivor benefit get zeroed out the day she filed. A…

Drew Wood | May 30, 2026 at 9:46 AM EDT

A 64-Year-Old Single Restaurant Owner Selling for $1.2 Million Cash Discovers a 1031 Won’t Help Him But This Strategy Will

A 64-year-old restaurant owner has spent 25 years building an independent business and recently accepted a $1.2 million cash offer…

Austin Smith | May 30, 2026 at 9:30 AM EDT

The $450,000 Debt Trap That Costs Dentists $1 Million in Forgone Income

A dentist three years out of school carrying $450,000 in student loans is staring at a fork in the road.…

Drew Wood | May 30, 2026 at 9:18 AM EDT

The Two Bucket Income Portfolio That Pays $5,000 a Month Plus a Cash Reserve to Survive 2008 Style Drawdowns

Generating $5,000 per month in passive income works out to $60,000 annually, a level many retirees target to cover core…

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Personal Finance Articles

All Personal Finance Articles

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

The $200,000 Social Security Mistake Couples Make at 64 Without Realizing It

The Cash Balance Plan a 58-Year-Old Solo Consultant Is Using to Shelter $312,000 a Year From Federal Tax

73-Year-Old Widow With $2.1M Discovers Husband’s IRA Beneficiary Election Triggered a $96K Tax Bill

Want $9,000 in Annual Passive Income? Invest $100,000 Into These 3 Monthly Paying Funds

Social Security’s Windfall Elimination Provision is Gone. Here’s How to Claim What You’re Owed

A 64-Year-Old Single Restaurant Owner Selling for $1.2 Million Cash Discovers a 1031 Won’t Help Him But This Strategy Will

The $450,000 Debt Trap That Costs Dentists $1 Million in Forgone Income

The Two Bucket Income Portfolio That Pays $5,000 a Month Plus a Cash Reserve to Survive 2008 Style Drawdowns

Stock Market Live June 9, 2026: S&P 500 (SPY) Bouncing Back with Tech

Live Nasdaq Composite: AI Stocks Reclaim Lost Ground as Volatility Eases and Oil Pulls Back

Fintech M&A Watch: 3 Stocks That Could Be Next on the Block

Google Is Paying SpaceX Over $900 Million a Month for AI Compute

Shark Tank’s Kevin O’Leary: You Need “A Minimum of $1.5 Million By the Time You’re 65.”

Shark Tank's Kevin O'Leary: You Need "A Minimum of $1.5 Million By the Time You're 65."

Fidelity's 2026 Retirement Study Finds Men Are 18 Points More Confident Than Women About Retiring on Their Terms

Fintech M&A Watch: 3 Stocks That Could Be Next on the Block

Google Is Paying SpaceX Over $900 Million a Month for AI Compute

Personal Finance Articles

All Personal Finance Articles

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

The $200,000 Social Security Mistake Couples Make at 64 Without Realizing It

The Cash Balance Plan a 58-Year-Old Solo Consultant Is Using to Shelter $312,000 a Year From Federal Tax

73-Year-Old Widow With $2.1M Discovers Husband’s IRA Beneficiary Election Triggered a $96K Tax Bill

Want $9,000 in Annual Passive Income? Invest $100,000 Into These 3 Monthly Paying Funds

Social Security’s Windfall Elimination Provision is Gone. Here’s How to Claim What You’re Owed

A 64-Year-Old Single Restaurant Owner Selling for $1.2 Million Cash Discovers a 1031 Won’t Help Him But This Strategy Will

The $450,000 Debt Trap That Costs Dentists $1 Million in Forgone Income

The Two Bucket Income Portfolio That Pays $5,000 a Month Plus a Cash Reserve to Survive 2008 Style Drawdowns

Stock Market Live June 9, 2026: S&P 500 (SPY) Bouncing Back with Tech

Live Nasdaq Composite: AI Stocks Reclaim Lost Ground as Volatility Eases and Oil Pulls Back

Fintech M&A Watch: 3 Stocks That Could Be Next on the Block

Google Is Paying SpaceX Over $900 Million a Month for AI Compute

Shark Tank’s Kevin O’Leary: You Need “A Minimum of $1.5 Million By the Time You’re 65.”

Featured Reads

Shark Tank's Kevin O'Leary: You Need "A Minimum of $1.5 Million By the Time You're 65."

Fidelity's 2026 Retirement Study Finds Men Are 18 Points More Confident Than Women About Retiring on Their Terms