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Hidden Conflicts

Jesse Cramer  |  Aug 15, 2026

WALMART SELLS FOOD. They sell car tires. Board games too. You can stop at any Walmart in the world and buy the same plethora of consumer goods. One roof, dozens of product areas, thousands of individual items.
This “cross-vertical” strategy has many perks to consumers like us. But it’s not without flaws. From brand dilution to in-store clutter, down to a lack of item expertise when you ask questions of employees – there are issues with “selling everything to everyone.”

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Risk Management

Adam M. Grossman  |  Aug 15, 2026

BY NOW, YOU’VE probably heard the story of the 25-year-old wunderkind Leopold Aschenbrenner. After graduating as valedictorian from Columbia University at age 19, he worked for FTX, the crypto trading firm, then found his way to OpenAI, where he worked as a researcher for about a year, until mid-2024.
In the months after he left OpenAI, Aschenbrenner wrote a 165-page paper titled “Situational Awareness,” in which he detailed his views on the future of artificial intelligence.

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Income taxes on retirees with Social Security

R Quinn  |  Aug 14, 2026

Complaining about taxes is not unique to seniors or in my case maybe a super senior, but they are mighty vocal and prolific on the internet. I was curious, how much could a age 65+ couple earn in retirement before actually paying federal income taxes on their money?
I ran a couple of scenarios using AI tools. I was a bit shocked at the results. Here is an example …
I asked what a couple both age 65 + with combined SS benefits of $50,000,

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My Sister – A Reflection One Year Later

Andrew Clements  |  Aug 12, 2026

As I reflect on the past year, I realize grief doesn’t follow a straight path. It comes in waves. Some days bring sadness, others gratitude, and often the two arrive together.
When my sister Tory died suddenly, there was no opportunity for one last conversation, no chance to say goodbye or tell her one final time that I loved her. Instead, I faced one of the hardest moments of my life, telling my mother that the daughter she adored was gone.

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Medicare Advantage Part C — Not too soon to start planning for 2027

R Quinn  |  Aug 11, 2026

MA  plans in several areas are being shut down for 2027.  The choices seniors have is declining as insurance companies realize the profits are not there.
If your Medicare Advantage plan closes or terminates its contract, you get federal guaranteed-issue rights to buy a Medigap policy without health screening or denial for pre-existing conditions. 

You must apply within a strict 63-day window starting from the date your plan coverage ends. Keep Your Notice: You will need the formal termination or non-renewal notice from your Part C plan as proof when submitting your Medigap application so the insurer knows not to put you through medical underwriting.

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Can a Value fund also be a Growth fund?

Harold Tynes  |  Aug 11, 2026

Be careful out there. Index composition is a key to getting consistency in your investment outcomes. Vanguard vs iShares vs State Street vs etc. As Jason Zweig writes in the Wall Street Journal, it all depends on the composition of the index.
 
https://www.wsj.com/finance/investing/how-a-few-hot-stocks-can-make-twin-funds-act-like-strangers-0ef7c52b?st=6mxLt3&reflink=desktopwebshare_permalink
 

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COBRA insurance: No need to fear the bite

Heidi - SunnyMoneyDIY  |  Aug 11, 2026

One of my biggest concerns about actually pulling the plug and retiring early is the expense of bridging health care expenses until I turn 65 and qualify for Medicare. [For those of you too polite to ask, that is just over nine years.] Mind you I have not sat down to forecast any real numbers to this worry… but as I see it, it’s the one big cost that is coming my way and currently is ‘invisible’

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What is the right percentage?

R Quinn  |  Aug 9, 2026

With all that’s going on with SS (COLA, taxation, potential cuts) and some changes certain in the next six years, is it time to rethink the income replacement percentage you shoot for in retirement?
I won’t give my theory again, one or more of the Clements family will be upset with me😅
However, self preservation, a hedge against longevity, hence inflation and peace of mind still tells me that a goal of replacing 60, 70 or 80% of pre retirement income is not sufficient.

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Roth Conversions and Taxes

John Urban  |  Aug 8, 2026

EVERY ARTICLE ABOUT Roth conversions says the same thing: pay the tax from taxable money, not from the IRA.
That is good advice if you have taxable money.
Plenty of retirees do not. Their savings sit almost entirely in a traditional IRA, built from years of 401(k) contributions and a rollover at retirement, with little brokerage money and no cash reserve worth naming.
For them, “pay from outside money” is not advice. It is a condition they do not meet.

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Risk and Taxes

Adam M. Grossman  |  Aug 8, 2026

AFTER YEARS OF heady gains in the stock market, many investors are facing the same question: To manage risk, they’d like to cut back on one or more of their holdings. But because of the potentially costly tax bill that might result, they aren’t sure exactly how to do that.
How can you square this circle?
One easy option would be to donate appreciated assets to charity. But that would make sense only if it aligns with your charitable goals and,

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Looking Back On My Hard Luck Days

DAN SMITH  |  Aug 7, 2026

Looking back in the archives, I came across Jonathan’s No Regrets article. In it, he wrote “I’ve known enough bad times to have perspective”. I think there are both good and bad perspectives to be gleaned from such times. The important thing is to grab the good ones in order to move forward. For example, many HumbleDollar contributors write that they came from poor families, and from that experience, came the desire and drive to get more out of life.

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Jonathan’s Parting Thoughts: No. 8

Jonathan Clements  |  Aug 7, 2026

Start with the world—and then subtract.
As I’ve mentioned in numerous articles, my favorite investment is Vanguard Total World Stock Index Fund (symbols: VT and VTWAX). It lets folks invest in every company of any significance from around the globe, with each stock’s weight determined by the company’s stock market value.
But while I think the fund is a great choice and, indeed, it’s been my core portfolio holding, I’m not saying folks should necessarily buy the fund.

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“Gerontocracy” in America

Chris Rush  |  Aug 6, 2026

I noticed a book excerpt in the Harvard Gazette yesterday (5 Aug 2026) that goes into some depth on a topic that is raised here on HD with some frequency, notably by R. D. Quinn, most recently with regard to the Social Security issue. The book in question is:
“Gerontocracy in America: How the Old Are Hoarding Power and Wealth ― and What to Do About It” by Samuel Moyn, J.D. ’01, and published by Farrar,

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For most retirees, the greatest fear is not death—it is running out of money before they die.

Matt Halperin  |  Aug 6, 2026

A recent Barron’s article notes, “for most retirees, the greatest fear is not death—it is running out of money before they die.” As one survey they cite put it, “The prospect of running out of money in retirement is scarier to more people than death.” The same article described a new tool that promises to estimate more accurately how long we are likely to live. Life expectancy is one of the most important assumptions in any retirement plan because it answers a fundamental question: How long will my savings need to last?

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Taxing Social Security benefits

R Quinn  |  Aug 6, 2026

Along with changes to the application of the COLA there is discussion about changing the way and amount of income taxes applied to SS benefits.
It’s quite complex, but here is a link to some alternatives from the Committee for a Responsible Federal Budget. https://www.crfb.org/papers/new-approaches-social-security-benefit-taxation

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