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A Broken Boy

Andrew Clements  |  Sep 30, 2026

I was 9 years old when my parents sent me to boarding school in England. I would spend the next seven years there, far from home, struggling academically, enduring the teasing of other boys and counting the days until I could leave. At the time, I couldn’t have imagined where my life would eventually take me. I only knew how that young boy felt: frightened, lonely and, in many ways, broken.
Nearly 50 years later, I tried to put those feelings into words in a poem I called A Broken Boy,

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Sourcing Taxes for Roth Conversions

Mark Ukleja  |  Sep 29, 2026

Hoping the HD community can provide some clarity on this issue.
We are in retirement, have some pension income, drawing the lesser social security benefit and deferring the larger till 70.  We are 4 years from the larger SS benefit and 9 ears from RMDS.
We have relatively large traditional IRAs as well as Roths which were funded during our working years,  however, we have minimal taxable investments.
We are starting to visualize the tax, IRMAA,

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Medicare Part D premium shock 2027

R Quinn  |  Sep 29, 2026

In 2027 my and Connie’s Part D premiums will increase from $72.30 to $130.00 per month and our individual deductible will increase from $615 to $700 per year (the maximum allowed). Those new premiums do not include IRMMA extra premiums.
That’s quite a jump in out-of- pocket costs, I’ll cope, but given these premiums have nothing to do with income, such increases will be a true burden for many retirees. More consequences in retirement virtually unable to plan for. 

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Will Congress Wait Until the Last Minute on Social Security?

Jeff Peck  |  Sep 27, 2026

I listened to an interview with a former Social Security deputy commissioner, and one point stuck with me: Social Security isn’t going to vanish, but Congress still needs to deal with its funding problem.
I’m getting close to retirement, so I’d like to know what to plan for. I can run the numbers with a smaller benefit. What I can’t do is guess which changes Congress might make—or whether they’ll wait until the trust fund is nearly depleted before making them.

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Keep an eye on Medigap policies

R Quinn  |  Sep 26, 2026

There are policy makers and think tanks who believe that Medigap coverage, especially Plan G (the most popular option) insulates retirees from out of pocket costs too much and as a result encourages them to use unnecessary health care, to not care what it costs.
I don’t know about you, but I have no desire to use any healthcare beyond what is absolutely necessary. In any case, discussions are underway to increase the out of pocket costs under Medicare with the idea of saving federal funds.

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Financial Lessons

Adam M. Grossman  |  Sep 26, 2026

WHAT’S THE MOST important idea in personal finance? It’s hard to single out just one, but over the years, I’ve found the following dozen ideas to be among the most useful.

Whether it’s on TV or online, there’s never any shortage of market prognosticators. Especially during a bull market, everyone seems to have an opinion on where things are headed. The reality, though, is that people can only guess about how the economy, the market or any individual investment will perform.

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Widow’s Penalty Redux

Richard Connor  |  Sep 26, 2026

A RECENT post by achnk53 about the impact of a spouse’s death on the survivor’s taxes piqued my interest.  The post referenced an interesting Kiplinger article about the “Widow’s Penalty”, or the negative tax implications on a surviving spouse after the death of a spouse. A surviving spouse can file Married Filing Jointly (MFJ) in the year of their spouse’s death. In the full year following the spouse’s death you must file Single. 

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The Art of Making Do

Mark Crothers  |  Sep 25, 2026

A few months ago, one of my daughters was home for a visit when she caught me red-handed, fishing a sock out of the kitchen trash bin. Cue the accusation: I was being “tight.” Some context first. Earlier that day, she’d been pairing up socks fresh out of the dryer when she found a hole in one of my sports socks and binned the pair without a second thought.
I should stress: I really don’t make a habit of rummaging through the rubbish.

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The Security Money Can’t Buy

Dennis Friedman  |  Sep 25, 2026

It was my mother’s birthday, so I placed some flowers on her grave. I learned a lot about growing old from taking care of her.
When I was planning for retirement, I was mostly concerned about having enough money and how I was going to stay busy. But after spending time with my mother, I realized there was something more important—or at least just as important.
It was companionship.
I learned from my mother that no matter how many people you have in your life,

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My Name is Dan, and I’m a CPAP User

DAN SMITH  |  Sep 24, 2026

If it hasn’t happened to you yet, there is a decent chance it soon will. The day when your spouse or partner says to you in the morning, “you hold your breath when you sleep”. Should that occur, there is a pretty good chance that you suffer from sleep apnea (SA). You would be in great company with these familiar folks; James Gandolfini, Regis Philbin, John Candy, Jerry Garcia, William Howard Taft, Reggie White, and Antonin Scalia to name a few.

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Is your retirement plan counting on a Social Security COLA in the future?

R Quinn  |  Sep 24, 2026

Projections for the 2027 COLA are around 3.5%, but that could be the last such increase.
As part the effort to fix SS solvency, the idea of a flat fixed dollar COLA has surfaced again. In short that would mean most retirees would receive less than under the current calculation. 
For example, the COLA adjustment would be based on a certain level of benefits, say the 20th percentile. That is currently about $1,200 to $1,300 per month. 

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Shouldn’t property taxes be a realistic part of retirement planning? Sorry, I think this is a major financial and social issue.

R Quinn  |  Sep 23, 2026

We bought a house in 1971 for $59,000. The property taxes were $2,700 a year. We lived there until 2018. We sold the house for a little over $500,000. In 2026 that property is assessed at $483,000 and the taxes are $15,000 a year. The average annual increase in property taxes is about 3.17%. 
Over the same period (1971 to 2026), the average annual U.S. inflation rate (measured by the Consumer Price Index, or CPI) was approximately 3.92% per year.

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Time Is Priceless

Andrew Clements  |  Sep 23, 2026

We spend much of our lives thinking about money: how to earn it, save it, invest it and, eventually, how to spend it. If we lose money, there’s always the possibility of earning it back. Time is different. Each of us is given an unknown amount, and before we know it, a day, an hour or even a moment has passed, time that can never be recovered. Perhaps that makes time the most valuable asset we’ll ever possess,

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Does the new-for-2026 $1000/$2000 charitable deduction for non-itemizers reduce AGI?

Andrew Forsythe  |  Sep 22, 2026

I’m hoping Bill Perry and/or one of our other tax experts can answer this.
For tax year 2026, non-itemizers can deduct charitable contributions of up to $1000 (single) or $2000 (married). What I’m trying to understand is whether this deduction is taken before figuring AGI (Adjusted Gross Income) or after. I just did a quick web search and got conflicting answers—even from apparently knowledgeable sources.
Why worry about it long before we’re doing our 2026 taxes?

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Anyone For S.K.I.ing?

Mark Crothers  |  Sep 22, 2026

I came across a term I’d not heard before in an article from my local newspaper. S.K.I.ing: the act of spending down your retirement portfolio and assets without regard for familiar inheritance. To my mind it’s basically blowing the budget on travel and other indulgent consumption. Apparently it’s a growing “thing” now.
The article in question came with glowing endorsements from practitioners and testimonials from the potentially inheritanceless children, telling their parents not to feel guilty and they never expected an inheritance anyway.

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