Stock Market Live June 10, 2026: S&P 500 (SPY) Sinks on Fear of War

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Marc Guberti | May 23, 2026 at 9:07 AM EDT

The 401(k) Mega Backdoor Roth Strategy a Tech Worker Used to Build $750,000 of Roth Wealth in Six Years

A 30-year-old software engineer at Meta (NASDAQ:META | META Price Prediction), earning a $200,000 base plus refreshing stock grants, asked…

Ian Cooper | May 23, 2026 at 8:31 AM EDT

The $19,200 Medicare Surprise That Hits Retirees After One Roth Conversion in the Wrong Year

Picture a couple in their first year of retirement. Both are 64, both stopped working in January, and they finally…

Drew Wood | May 23, 2026 at 8:12 AM EDT

The Closed-End Fund Portfolio That Quietly Pays a 71-Year-Old $61,000 a Year on $850,000 and Trades at a Persistent Discount

A 71-year-old retiree holding $850,000 across a basket of closed-end funds is generating roughly $61,000 a year in distributions. That…

Austin Smith | May 23, 2026 at 8:00 AM EDT

Medicare Premium Jumps Hundreds a Month in 2026 From a 2024 Asset Sale You Forgot About

Picture a 67-year-old who sold a vacation home in 2024 for a $300,000 capital gain. The check cleared, and most…

Drew Wood | May 23, 2026 at 7:55 AM EDT

How $300,000 in JEPQ and JEPI Quietly Pays $24,000 a Year Without the MLP K-1 Headache

A 65-year-old single retiree with $300,000 split evenly between two JPMorgan covered-call ETFs can pull roughly $24,000 in annual distributions…

Danielle Liverance | May 23, 2026 at 6:40 AM EDT

I left law enforcement with a $60,000 state pension earning 4%. Should I roll it to a Roth TSP instead?

On the May 19, 2026 episode of The Clark Howard Podcast, Clay from Kentucky asked advisor Wes Moss whether to…

Drew Wood | May 23, 2026 at 5:33 AM EDT

Quitting at 59 and Bridging Eight Years to Social Security at 67? Here Is the $530,000 Income Portfolio I Would Build

For a 59-year-old hoping to leave work today, the math is unforgiving. A $530,000 brokerage account would need to generate…

Marc Guberti | May 22, 2026 at 9:47 PM EDT

The Triple Tax Free HSA Account High Earners Are Funding Before Maxing Their 401(k)

Picture a dual-income couple with combined wages well into the high six figures. They already max the 401(k). Their employer…

Marc Guberti | May 22, 2026 at 6:47 PM EDT

The Roth Conversion Strategy Affluent Investors Over 55 Are Using to Empty Their 401(k)s Before Required Distributions

The Bogleheads forum is full of posts that read the same way: a 56-year-old executive, $1.8 million in a traditional…

Michael Williams | May 22, 2026 at 3:30 PM EDT

How a Two-Year Tax Return Delay Costs Retirees $487 Extra Monthly on Medicare

Two retirees living next door can open their Medicare statements in January and see wildly different numbers. One owes $202.90…

Carl Sullivan | May 22, 2026 at 3:01 PM EDT

A Couple With $4 Million Discovers State’s Estate Tax Could Cost Heirs $280,000

With the federal estate and gift tax exemption sitting at $15 million per person, most families assume estate tax is…

Austin Smith | May 22, 2026 at 2:25 PM EDT

Widow’s Social Security Check Shrinks by $500 to $1,200 a Month After Spouse Dies. Here’s Why

A widow in her early seventies opens her bank statement a few months after her husband’s funeral and notices the…

Carl Sullivan | May 22, 2026 at 2:01 PM EDT

Has 50-Year-Old Couple With $1.1 Million Saved Enough?

A 50-year-old couple with $1.1 million in combined retirement savings is in pretty good shape, but have they saved enough?…

Marc Guberti | May 22, 2026 at 1:47 PM EDT

The In Plan Roth 401(k) Conversion That Saves a $400,000 Earner $58,000 in Future RMD Taxes

Picture a 55-year-old earning $400,000 with $1.5 million in a traditional 401(k). The plan’s summary plan description allows in-plan Roth…

Danielle Liverance | May 22, 2026 at 12:36 PM EDT

60-Year-Old’s Pension Dilemma: Financial Expert Explains Why the 7% Payout Rate Wins

Scott, age 60, called into Jill on Money with the kind of question that keeps soon-to-be retirees awake: “I can…

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Personal Finance Articles

All Personal Finance Articles

The 401(k) Mega Backdoor Roth Strategy a Tech Worker Used to Build $750,000 of Roth Wealth in Six Years

The $19,200 Medicare Surprise That Hits Retirees After One Roth Conversion in the Wrong Year

The Closed-End Fund Portfolio That Quietly Pays a 71-Year-Old $61,000 a Year on $850,000 and Trades at a Persistent Discount

Medicare Premium Jumps Hundreds a Month in 2026 From a 2024 Asset Sale You Forgot About

How $300,000 in JEPQ and JEPI Quietly Pays $24,000 a Year Without the MLP K-1 Headache

I left law enforcement with a $60,000 state pension earning 4%. Should I roll it to a Roth TSP instead?

Quitting at 59 and Bridging Eight Years to Social Security at 67? Here Is the $530,000 Income Portfolio I Would Build

The Triple Tax Free HSA Account High Earners Are Funding Before Maxing Their 401(k)

The Roth Conversion Strategy Affluent Investors Over 55 Are Using to Empty Their 401(k)s Before Required Distributions

How a Two-Year Tax Return Delay Costs Retirees $487 Extra Monthly on Medicare

A Couple With $4 Million Discovers State’s Estate Tax Could Cost Heirs $280,000

Widow’s Social Security Check Shrinks by $500 to $1,200 a Month After Spouse Dies. Here’s Why

Has 50-Year-Old Couple With $1.1 Million Saved Enough?

The In Plan Roth 401(k) Conversion That Saves a $400,000 Earner $58,000 in Future RMD Taxes

60-Year-Old’s Pension Dilemma: Financial Expert Explains Why the 7% Payout Rate Wins

Stock Market Live June 10, 2026: S&P 500 (SPY) Sinks on Fear of War

Apple Might Haven Taken Aim at OpenAI with New Announcement. There’s Only One Problem.

Warren Buffett’s $400 Billion Is Going Nowhere for Now: Here’s Why Berkshire Hathaway Is My Top Pick for the Next 20 Years

Why One AI Giant Is Paying ~2.2X per GPU More Than What Anthropic Pays SpaceX

Retiring at the Coast Comes With a $9,800 Annual Insurance Shock

How a 401(k) Balance Over $1 Million Quietly Pushes 85 Percent of a Couple's Social Security Into the Taxable Zone

Apple Might Haven Taken Aim at OpenAI with New Announcement. There’s Only One Problem.

Warren Buffett’s $400 Billion Is Going Nowhere for Now: Here’s Why Berkshire Hathaway Is My Top Pick for the Next 20 Years

Personal Finance Articles

All Personal Finance Articles

The 401(k) Mega Backdoor Roth Strategy a Tech Worker Used to Build $750,000 of Roth Wealth in Six Years

The $19,200 Medicare Surprise That Hits Retirees After One Roth Conversion in the Wrong Year

The Closed-End Fund Portfolio That Quietly Pays a 71-Year-Old $61,000 a Year on $850,000 and Trades at a Persistent Discount

Medicare Premium Jumps Hundreds a Month in 2026 From a 2024 Asset Sale You Forgot About

How $300,000 in JEPQ and JEPI Quietly Pays $24,000 a Year Without the MLP K-1 Headache

I left law enforcement with a $60,000 state pension earning 4%. Should I roll it to a Roth TSP instead?

Quitting at 59 and Bridging Eight Years to Social Security at 67? Here Is the $530,000 Income Portfolio I Would Build

The Triple Tax Free HSA Account High Earners Are Funding Before Maxing Their 401(k)

The Roth Conversion Strategy Affluent Investors Over 55 Are Using to Empty Their 401(k)s Before Required Distributions

How a Two-Year Tax Return Delay Costs Retirees $487 Extra Monthly on Medicare

A Couple With $4 Million Discovers State’s Estate Tax Could Cost Heirs $280,000

Widow’s Social Security Check Shrinks by $500 to $1,200 a Month After Spouse Dies. Here’s Why

Has 50-Year-Old Couple With $1.1 Million Saved Enough?

The In Plan Roth 401(k) Conversion That Saves a $400,000 Earner $58,000 in Future RMD Taxes

60-Year-Old’s Pension Dilemma: Financial Expert Explains Why the 7% Payout Rate Wins

Stock Market Live June 10, 2026: S&P 500 (SPY) Sinks on Fear of War

Apple Might Haven Taken Aim at OpenAI with New Announcement. There’s Only One Problem.

Warren Buffett’s $400 Billion Is Going Nowhere for Now: Here’s Why Berkshire Hathaway Is My Top Pick for the Next 20 Years

Why One AI Giant Is Paying ~2.2X per GPU More Than What Anthropic Pays SpaceX

Featured Reads

Retiring at the Coast Comes With a $9,800 Annual Insurance Shock

How a 401(k) Balance Over $1 Million Quietly Pushes 85 Percent of a Couple's Social Security Into the Taxable Zone