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One Person’s Luxury, Another’s Necessity

Mark Crothers  |  Jul 21, 2026

My friend recently spent five days with us at our vacation home. At some point our conversation turned to his work situation. He’s an independent IT systems rollout contractor in his early sixties, based in London, with years of experience and a large network of industry contacts. The trouble right now is a prolonged downturn in the market, and contracts have been few and far between for the last fifteen months.
As a result, he’s been burning through his cash buffer faster than the occasional job can replenish it.

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FIFA Financials

R Quinn  |  Jul 19, 2026

Can any HD reader conceive of paying $5,000 and way more for a seat at a soccer match? Sorry, football.
That seems to go against any financial logic. 😎
I wonder if such spending is on the budget spreadsheet?

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Lessons on the Ground

Dennis Friedman  |  Jul 18, 2026

THE OTHER DAY, WHILE walking to my mailbox, I noticed a summer class schedule for a private gifted youth academy lying on the ground. I assumed it belonged to one of my neighbors, who has elementary-aged children.
Their interest in extra academics didn’t surprise me. Many families move to this area because of its excellent schools. Parents here clearly value education. On any given day, it’s common to hear children practicing the piano or violin as you walk through the neighborhood.

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K-shaped Economy

Adam M. Grossman  |  Jul 18, 2026

A TOPIC THAT’S been in the news recently is the so-called K-shaped economy. 
Imagine a chart plotting the relative standing over time of those with higher incomes and those with lower incomes. Owing to a strong stock market and rising home values, the shape of the chart for those with higher incomes would extend up and to the right and has been moving increasingly in that direction since Covid.
Folks with lower incomes, on the other hand,

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A Can of Worms

Dan Smith  |  Jul 17, 2026

I’m not making this up. I once overheard a conversation in a bar by a couple guys who were planning something nefarious. They were discussing what was essentially the same kind of risk/reward conversation we think about when making allocation decisions; the major difference was that they were weighing time in prison should they be caught. 
I don’t know how things worked out for the pair, but at least they were considering the can-of-worms they were about to open. 

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Danger, Junk Mail

Sonja Haggert  |  Jul 16, 2026

The nice lady in the card store told me I didn’t need to give her any information because it was on my coupon. I left the store wondering exactly what information that was.
According to Jose Lejin, a technical expert I contacted, I needn’t have worried. The barcode with my information told her the coupon belonged to me and might have been tied to a specific promotion. There is a privacy issue here in that the retailer may know the time and place I redeemed their offer.

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The Paradox of Wealth

Mark Crothers  |  Jul 15, 2026

I like to be humble, but I also like to be honest. I can’t deny that I ran a successful business for twenty-five years, that I own two homes, or that I had the resources to retire at fifty-seven. In short, I’ve been fortunate. It would be farcical of me to pretend money isn’t an important enabler in life, but it’s worth remembering that it isn’t the most important thing.
I’ve spent most of the last month at my vacation home,

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IRMAA & late filing of tax returns

Danbo  |  Jul 15, 2026

Have any HumbleDollar readers who are subject to IRMAA filed a tax return more than 2 years late? If so, I’d love to hear your experience.

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Will Your Death Double Your Spouse’s Tax Bill?

achnk53  |  Jul 15, 2026

I read this article from Kiplinger online about the four ways couples should prepare for the Widow’s Penalty.
https://www.kiplinger.com/taxes/tax-planning/how-to-prepare-for-the-widows-penalty
The article states that in an unfortunate twist of the tax system, losing a spouse may trigger a huge financial hit called the widow’s penalty.  The good news – you can plan for it.  It is a good read. Your thoughts and your plan.

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A discussion on health insurance, premiums, profits and such- a 50 year perspective most people don’t want to accept

R Quinn  |  Jul 15, 2026

The current standard Medicare Part B premium is $202.90 a month. That equals about 25% of the cost of Part B. The average American worker with employer coverage pays about 26% of premium for family coverage.
Remember, Medicare payroll taxes only fund Part A of Medicare. Part D and B are funded via premiums and general tax revenue. 
Combined, Connie and I pay $1,925.60 per month for Parts B and D and Plan G Medigap. That is over ten times my monthly employer payroll deduction the day before I retired. 

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Better Questions

Mark Gardner  |  Jul 12, 2026

I used AI as an editorial assistant to help organize and refine my thoughts; the underlying ideas and personal experiences remain my own.
For years, I maintained what I thought was a pretty good retirement spreadsheet. Like many retirees, it tracked my investments, estimated Social Security, projected taxes and summarized spending. Every year I’d update the numbers, glance through a handful of reports and file it away until the next review.
The spreadsheet faithfully answered every question I asked.

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About that inflation in retirement

R Quinn  |  Jul 11, 2026

No doubt you have heard or read the posts and comments, perhaps by friends about the Social Security COLA.
It’s not accurate, not fair, not enough, doesn’t keep up with our actual spending, use the CPI-E and all the rest.
One thing it does for sure is add to the Trusts growing shortfall.
Some people really need that annual boost, if for nothing else to help offset growing Medicare premiums. But others, including many in the HD community,

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Buying a car in retirement

Julie C  |  Jul 11, 2026

As I approach my 70th birthday I’ve decided it’s probably time to buy a new car even though my nearly 19 years old car runs well . Given my proclivity for keeping cars a long time, this is almost certainly going to be my last car.
My question is what are your thoughts on approaching this? I am not interested in leasing or buying used.  My sources of funds are a tax deferred account, a brokerage account and a money market account .

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So Maybe That’s What It’s All About

Mark Crothers  |  Jul 11, 2026

I was out for a walk along the coast when I stumbled upon a surreal sight: two luxury coaches wedged tight in a remote parking lot, and forty or so people clustered together, singing to a field of cows. To say I was taken aback would be an understatement.
I paused by a picnic bench to listen as they enthusiastically worked their way through a couple of tunes, until a voice called out that it was time to move on.

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Trump Accounts

Adam M. Grossman  |  Jul 11, 2026

INNOVATION IN THE world of retirement plans is decidedly slow moving. But as of July 4th, investors now have a new savings option known as a Trump account. In short, these are retirement accounts designed specifically for children.
Trump accounts share some similarities with traditional individual retirement accounts (IRAs), but there are also key differences. If you have children, grandchildren, nieces or nephews, this new option may be worth exploring.
Who is eligible for a Trump account?

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