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Drew Wood | May 21, 2026 at 5:52 AM EDT

A $2.2 Million Dividend Portfolio That Quietly Pays $13,200 a Month Without a Single MLP Tax Headache

A 67-year-old couple filing jointly with $2.2 million in investable assets wants to generate $13,200 per month, or $158,400 annually,…

Jeremy Phillips | May 21, 2026 at 3:21 AM EDT

Roger Whitney to 60-Year-Old With $3.5M: ‘Continue to Save in Your Roth 401(k) and Use Your After-Tax Cash’

A 60-year-old caller named Sue wrote into the Retirement Answer Man podcast with a question that might sound mundane but…

Carl Sullivan | May 20, 2026 at 7:04 PM EDT

A Surviving Spouse With $1.4M Faces the Widow’s Penalty That Could Cost $42,000 a Year

The year your spouse dies, your tax bill barely changes. The year after that, the IRS treats you like a…

Marc Guberti | May 20, 2026 at 6:47 PM EDT

The 401(k) Bracket Smoothing Math: Why a 65 Year Old With $1.6 Million Should Convert Exactly $43,000 a Year Until 73

A 65 year old single retiree posted a familiar question on a Bogleheads thread last month: “I have $1.6 million…

David Beren | May 20, 2026 at 4:49 PM EDT

Northwestern Mutual’s 2025 Planning Study: Only 20% of Americans Now Expect to Receive an Inheritance, Down From 25% Last Year

Inheritance expectations are shrinking just as more Americans are quietly counting on them. According to Northwestern Mutual’s 2025 Planning &…

Carl Sullivan | May 20, 2026 at 3:00 PM EDT

What $7,000 a Month Really Looks Like in Retirement at Age 65

A 65-year-old who just stopped working with $7,000 in monthly gross income can feel comfortable or tight. It all depends…

Omor Ibne Ehsan | May 20, 2026 at 2:47 PM EDT

Social Security’s Judgment Day Is Rapidly Approaching, and President Donald Trump May Force the Fed’s Hand

It doesn’t matter if you’re 66 or 6 (you’re going places if you’re reading this at 6!), Social Security will…

Ian Cooper | May 20, 2026 at 2:42 PM EDT

Ted Turner Built CNN on Debt and Near-Bankruptcy. Here Is Why You Should Not Try to Copy Him

Ted Turner died at 87, and obituaries celebrate how he built his empire. He took an indebted billboard company into…

Carl Sullivan | May 20, 2026 at 12:59 PM EDT

What Retirement Really Looks Like at 65 With $1.6M and a $260,000 Mortgage Still on the Books

Many retirees have portfolios that look healthy on paper. But don’t forget about outstanding mortgages. Consider a couple turning 65…

Drew Wood | May 20, 2026 at 11:32 AM EDT

How Much Do You Really Need Invested to Replace a $40,000 Salary at 62 and Bridge the Five Years Until Social Security at 67?

A $40,000 annual income is often enough for a 62-year-old retiree living modestly while bridging the five years until full…

Drew Wood | May 20, 2026 at 10:22 AM EDT

Here Is the $850,000 Three-Bucket Income Portfolio I Would Build to Pay a 66-Year-Old Couple $4,612 a Month

A 66-year-old couple with $850,000 spread across three accounts wants to generate $4,612 per month in portfolio income. That equals…

Marc Guberti | May 20, 2026 at 9:46 AM EDT

How Engineering Executives Structure Their 401(k) to Pay Under 10 Percent Effective Tax in Retirement

A 62-year-old former engineering VP at a large public tech company logs into the brokerage one last time before handing…

Drew Wood | May 20, 2026 at 9:16 AM EDT

At 56 With $2.1 Million Saved and a Stressful CFO Job, the Math Tilts Hard Toward Quitting Now

A 56-year-old CFO making $385,000 in base salary plus a $200,000 annual bonus looks, from the outside, like someone in…

Drew Wood | May 20, 2026 at 8:42 AM EDT

A $475,000 Portfolio That Quietly Pays $2,800 a Month From Just Two Sectors Most Investors Ignore

A 64-year-old retiree with $475,000 who wants to generate $2,800 per month, or $33,600 annually, from dividends alone needs a…

Carl Sullivan | May 20, 2026 at 7:45 AM EDT

Retiring at 65 With $1.3 Million Means Navigating an $8,400 Annual Healthcare Gap Most Plans Miss

Healthcare is the line item that quietly breaks otherwise reasonable retirement plans. Pull $52,000 a year from a $1.3 million…

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Personal Finance Articles

All Personal Finance Articles

A $2.2 Million Dividend Portfolio That Quietly Pays $13,200 a Month Without a Single MLP Tax Headache

Roger Whitney to 60-Year-Old With $3.5M: ‘Continue to Save in Your Roth 401(k) and Use Your After-Tax Cash’

A Surviving Spouse With $1.4M Faces the Widow’s Penalty That Could Cost $42,000 a Year

The 401(k) Bracket Smoothing Math: Why a 65 Year Old With $1.6 Million Should Convert Exactly $43,000 a Year Until 73

Northwestern Mutual’s 2025 Planning Study: Only 20% of Americans Now Expect to Receive an Inheritance, Down From 25% Last Year

What $7,000 a Month Really Looks Like in Retirement at Age 65

Social Security’s Judgment Day Is Rapidly Approaching, and President Donald Trump May Force the Fed’s Hand

Ted Turner Built CNN on Debt and Near-Bankruptcy. Here Is Why You Should Not Try to Copy Him

What Retirement Really Looks Like at 65 With $1.6M and a $260,000 Mortgage Still on the Books

How Much Do You Really Need Invested to Replace a $40,000 Salary at 62 and Bridge the Five Years Until Social Security at 67?

Here Is the $850,000 Three-Bucket Income Portfolio I Would Build to Pay a 66-Year-Old Couple $4,612 a Month

How Engineering Executives Structure Their 401(k) to Pay Under 10 Percent Effective Tax in Retirement

At 56 With $2.1 Million Saved and a Stressful CFO Job, the Math Tilts Hard Toward Quitting Now

A $475,000 Portfolio That Quietly Pays $2,800 a Month From Just Two Sectors Most Investors Ignore

Retiring at 65 With $1.3 Million Means Navigating an $8,400 Annual Healthcare Gap Most Plans Miss

Live: Will Oracle Crush Q4 Earnings After the Market Closes Tonight?

Wall Street CIO: The AI Trade is “Technically Unsustainable.” Buy These Two Industries Instead.

Wall Street Strategist: SpaceX Will Force a Major Stock Market Repositioning. Buy These Stocks Instead.

3 Dividend Stocks Built for Retirement to Buy in June

Retired Couple With $1.9 Million Faces $4,800 IRMAA Surprise After Stock Sale

A $900,000 Nest Egg at 65 Only Translates to About $36,000 in Real Annual Spending After Taxes and Inflation

Wall Street CIO: The AI Trade is “Technically Unsustainable.” Buy These Two Industries Instead.

Wall Street Strategist: SpaceX Will Force a Major Stock Market Repositioning. Buy These Stocks Instead.

Personal Finance Articles

All Personal Finance Articles

A $2.2 Million Dividend Portfolio That Quietly Pays $13,200 a Month Without a Single MLP Tax Headache

Roger Whitney to 60-Year-Old With $3.5M: ‘Continue to Save in Your Roth 401(k) and Use Your After-Tax Cash’

A Surviving Spouse With $1.4M Faces the Widow’s Penalty That Could Cost $42,000 a Year

The 401(k) Bracket Smoothing Math: Why a 65 Year Old With $1.6 Million Should Convert Exactly $43,000 a Year Until 73

Northwestern Mutual’s 2025 Planning Study: Only 20% of Americans Now Expect to Receive an Inheritance, Down From 25% Last Year

What $7,000 a Month Really Looks Like in Retirement at Age 65

Social Security’s Judgment Day Is Rapidly Approaching, and President Donald Trump May Force the Fed’s Hand

Ted Turner Built CNN on Debt and Near-Bankruptcy. Here Is Why You Should Not Try to Copy Him

What Retirement Really Looks Like at 65 With $1.6M and a $260,000 Mortgage Still on the Books

How Much Do You Really Need Invested to Replace a $40,000 Salary at 62 and Bridge the Five Years Until Social Security at 67?

Here Is the $850,000 Three-Bucket Income Portfolio I Would Build to Pay a 66-Year-Old Couple $4,612 a Month

How Engineering Executives Structure Their 401(k) to Pay Under 10 Percent Effective Tax in Retirement

At 56 With $2.1 Million Saved and a Stressful CFO Job, the Math Tilts Hard Toward Quitting Now

A $475,000 Portfolio That Quietly Pays $2,800 a Month From Just Two Sectors Most Investors Ignore

Retiring at 65 With $1.3 Million Means Navigating an $8,400 Annual Healthcare Gap Most Plans Miss

Live: Will Oracle Crush Q4 Earnings After the Market Closes Tonight?

Wall Street CIO: The AI Trade is “Technically Unsustainable.” Buy These Two Industries Instead.

Wall Street Strategist: SpaceX Will Force a Major Stock Market Repositioning. Buy These Stocks Instead.

3 Dividend Stocks Built for Retirement to Buy in June

Featured Reads

Retired Couple With $1.9 Million Faces $4,800 IRMAA Surprise After Stock Sale

A $900,000 Nest Egg at 65 Only Translates to About $36,000 in Real Annual Spending After Taxes and Inflation