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The Paradox of Smart Money Decisions

Adam M. Grossman  |  Oct 25, 2025

SOME YEARS AGO, the scientist Edward Fredkin identified a quirk of human behavior.
When it comes to making decisions, Fredkin found, we tend to allocate our time inefficiently. Suppose, for example, you’re at the grocery store, looking for something basic like paper towels. In a big supermarket, there might be a dozen or more choices. The result: Because there are so many options, it can be hard to choose among them. In the absence of big differences,

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Best of Jonathan’s HumbleDollar Posts

Bogdan Sheremeta  |  Sep 27, 2025

WE LOST A brilliant mind and generous writer, Jonathan Clements, whose words guided thousands on life, finance, and happiness. Even as he faced the unimaginable, he continued sharing wisdom with clarity, humor, and humanity.
I wanted to take some time and dig into Jonathan’s earliest posts on HumbleDollar. Posts that even the most loyal readers may not have read. With that, I also summarized some main takeaways and learnings that can help us all better navigate our own complex lives.

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My favorite question.

Richard Hayman  |  Aug 6, 2025

It would be nice to hear more from HD readers who have been there and done that. And to answer the question, “Knowing what you know now, what would you have done differently?”

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Choosing Yes by Saying No

Mark Crothers  |  Aug 5, 2025

Are you definitely sure I can’t tempt you?” my friend asked for the last time as we finished our phone conversation. Once again, I replied in the negative before a few pleasant closing words and then hanging up.
Thinking back on our chat, I realized this was the fourth invitation to various activities I’ve turned down in the last few months. The invitations ranged from an opportunity to provide tax reporting services for an old friend at a decent billable rate to this most recent inquiry today to play doubles together in a badminton league come September.

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Putting Every Dollar to Work

Greg Tomamichel  |  Aug 1, 2025

Nearing the end of our recent catch-up with our financial adviser, the general discussion turned to how we ended up where we are now.  At 59 and 51 respectively, my wife Cindy and I are in a fortunate financial position. We never set out with aims of early retirement, or a target number that we wanted to reach. And despite that, we ended up in good shape.
It got me thinking about what we did right,

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Regular HD writers, readers and commentators are just not normal- in a good way

R Quinn  |  Jul 30, 2025

Over the several years I have been writing and commenting on HD it has been made clear that the HD community includes many sophisticated investors and planners. People who use budgets, track expenses, do their best to investigate and then make financial decisions based on information they develop. They use various type of software programs and, of course, their own spreadsheets. They analyze risk and investment expenses. They like details. They think about the future. And,

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A Personal Encounter with the Psychology of Money

Mark Crothers  |  Jul 28, 2025

I’ve been in a bit of a financial funk these last three months, and I’ve finally managed to overcome my heart and listen to my head. I’m really surprised how difficult I’ve found it, especially with my business and financial background. I mean, truly difficult.
It all started when I was setting up a 10-year fixed-term annuity before retirement. I had initially decided on a purchase amount and, to fund it, liquidated some of my developed world index tracker.

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Could you be (justifiably) a source of envy by others? Are you wealthy?

R Quinn  |  Jul 19, 2025

A great deal of wrath these days seems to target the wealthy although that generally means billionaires or close to it. However, being wealthy is very relative. I suspect many HD readers are looked upon as wealthy by their peers while perhaps not feeling so themselves. I admittedly fall in that trap.
Many comments on HD by those retired indicate to me being relatively wealthy or pretty close to it. 
So, look at the data as estimated as it may be,

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Here is my favorite word. What is your favorite word? Perhaps frugal, Roth, spreadsheet, planning, Monte Carlo, dividends? 

R Quinn  |  Jul 9, 2025

My favorite word is “aware.”
I believe that missed opportunities, stress, poor decisions of all types, just many of the things we complain about result from not being aware of what is happening around us. 
Being aware means having knowledge or perception of something. It involves noticing, recognizing, or being conscious of what’s happening either around you or within you.
In essence, being aware is about being connected to what is happening, both internally and externally,

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Beyond the Party: How Introverts Might Quietly Win at Retirement

Mark Crothers  |  Jun 30, 2025

I was reading an interesting article by Kristine Hayes, a contributor to Humble Dollar a few weeks ago. In it, she discussed her introverted nature. Since then, a thought’s been developing in my mind: Could an introvert have a distinct advantage when accumulating wealth for retirement and an above-average chance of enjoying a successful retirement?
I consider myself, for want of a better description, a “closet introvert.” While many people who know me genuinely think of me as the “life and soul of the party,”

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Eyes Forward

Adam M. Grossman  |  Jun 21, 2025

AT THE 2016 SUMMER Olympics in Rio de Janeiro, South Africa’s Chad Le Clos challenged Michael Phelps for the gold medal in the 200-meter butterfly. A famous image emerged from that event: Throughout the semifinal, Le Clos repeatedly looked over at Phelps as he struggled to keep up. Meanwhile, Phelps just kept looking forward. The result: Phelps ultimately won the gold, while Le Clos trailed in fourth place.
I believe there’s a parallel between what we saw in that race and what we see in the investment world.

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Do You Worry About Money Every Day?

R Quinn  |  Jun 6, 2025

An article in Employee Benefits News paints a dim picture of retirement. One that may reflect the real world beyond the HumbleDollar community.
Here again we are relying on a survey so who knows how accurate, but I bet worrying and anxiety over money in retirement is not uncommon. Can you imagine retiring with no clue about the viability of your finances?
It says retirees are struggling to make their savings stretch.
According to Schroder’s 2025 U.S.

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A Lesson in Accountability

DAN SMITH  |  May 29, 2025

I worked up quite an appetite at the gym late this morning. Luckily there is a great little diner just 2 doors down in the same strip. I’ve always enjoyed great food and friendly service at the Sunrise Skillet, but today was a little different, as service was a tad slow. Honestly I was preoccupied perusing my smart phone and barely aware of the time. Eventually my waitress, Britt, came to my booth, empty handed, telling me that she was paying for my lunch because she forgot to put in the order. 

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Creature of Habit

Fran Moore  |  May 15, 2025

Even though I’m retired now, I have certain routines to get me going every day. First, I make the coffee, then I peel an orange, and finally I curl up on my sofa with my coffee, orange and iPhone and read the latest posts that come into my inbox from Humble Dollar.
This week on two occasions, I didn’t receive my daily newsletter!  I finally went directly to the website and got caught up on all the recent posts that I may have missed.

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Quinn’s latest rant has serious consequences 

R Quinn  |  May 12, 2025

My favorite, beautiful word is “consequences,” and how it seems to be ignored.
We tend to forget that no matter what we do, there will be a result, a reaction. There will be consequences, some intended, others not.  We tend to address one problem but fail to think through possible consequences. 
The best examples are at the national level. Apply a surcharge such as IRMAA and people will attempt to keep income lower.  
Roth accounts were intended to increase retirement savings,

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