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Humble 10% Win: The First Financial Benefit of Retirement

Mark Crothers  |  Aug 24, 2025

I’ve just encountered the first positive financial benefit of officially being retired from the workforce. My car insurance renewal notice appeared in my inbox, and being the person I am, I contacted the insurance company to inform them of my change in circumstances from employed to retired.
What’s particularly noteworthy for those of us just starting retirement is to remember to contact your insurer. Many people might just pay the renewal notice without thinking about updating their information.

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The Main Thing … and the scourge of complexity

greg_j_tomamichel  |  Aug 23, 2025

Like many HD readers, I really enjoy the writing of Morgan Housel. He recently wrote
“You should obsess over risks that do permanent damage and care little about risks that do temporary harm, but the opposite is more common.”
This tapped into a train of thought that I’ve been on recently – focussing on the important stuff. Or, as on old boss of mine use to say, “The main thing, is that the main thing, is the main thing”.

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The Most Cited Websites By AI Models

normr60189  |  Aug 19, 2025

When we ask a question of ChatGPT or Gemini or any other AI LLMs we may wonder about the source of the information contained in the answers.  I recently read an article about this.  LLMs rely on user-generated content and as we know, not all of these web based sources are accurate and so, neither will the answers be.
“According to an analysis by Semrush, LLMs like ChatGPT reference Reddit and Wikipedia the most for facts.  

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Data’s Double Edge: Why Spreadsheets are Both a Lifeline and a Possible Lie

Mark Crothers  |  Aug 11, 2025

Can you even begin to imagine the confusion and chaos that follows a major disaster, and the difficulty of communicating and coordinating a response? This is a situation where data management, especially with a simple but powerful tool like a spreadsheet, shows its magic.
One very well-known situation that comes to mind is the Space Shuttle Challenger disaster. Facing a complex amount of data, engineer Richard Feynman and his team had a hunch about the cause.

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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_j_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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Ever heard Down the Middle?

Ben Rodriguez  |  Jul 1, 2025

I’m betting that a large number of fellow HumbleDollarians have never heard of a podcast called Down the Middle (Down the Middle Archives | Creative Planning).  It is a pod hosted by our fearless founder Jonathan Clements and co-hosted by Peter Mallouk of Creative Planning. You can find it on Apple or anywhere podcasts are found.
It’s released only once a month at the beginning of the month. It’s one of the pods I most look forward to. 

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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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A new challenge for RDQ

bbbobbins  |  Jun 25, 2025

Not trying to post here with an intent of bullying etc not actually specifically wanting an individual response though I think it would be of value to him.  But given RDQ’s repeated themes of criticising outlets he comes across for missing some vital element of personal finances like tax or being fraud like FIRE sub 50 and maintaining that any spreadsheet or budget approach to life is unnecessary or too stressful, I truly think he would benefit from trying to learn how it might be done.

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Pension Funds are Sus: A Strange Little Post From A Grandparent

Mark Crothers  |  Jun 25, 2025

I have a new job, a chauffeur no less. This involves conveying my grandson to school. I don’t know how much education he receives, but on the journey, I’m certainly getting an education on the colourful language of Generation Alpha, for those not in the know that’s kids up to age fifteen.
While I freely admit this post has very little traditional financial content, I would contend it holds a vital message. So, without further ado,

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