“We lament the grocery-store coupon left at home, and yet we’ll raise our bid for a house by $10,000 without a second thought.”
This was one of Jonathan’s quips that appeared at the top of the blog a few months back. I immediately was reminded of a day spent with my pal Kenny and his wife in Las Vegas, sometime in the early 1990s. Ken and I were seated at a $5 blackjack table when his wife approached,

I suspect like me, most HD members are against paying large yearly fees to investment advisors. I have made all of our investment decisions and have done pretty well. I also do our taxes.
While I have no immediate plans to stop, because my wife has no interest in any of it, and is considerably younger, chances are she will be left alone at some point to figure out RMDs, SS, taxes, asset allocation etc.
I have looked at Vanguard,

I’m a diy 66year old new retiree. I’m also a proud follower of Jack B. I started out investing with the mentally of invest first the live off the rest. Borrowing from my 401k wasn’t an option and it bothered me to see others do it with no problem. My annual salary during my working year never exceeded $40k. But we never had to live off a budget. If the money wasn’t there, we didn’t buy it.

On August 13, 2025, my husband and I found my sister unresponsive in her home.
The moment was traumatic and terribly upsetting. My thoughts immediately turned
to my mother, how would I tell her she had lost her daughter while dealing with
her son’s terminal cancer diagnosis?
That was the personal side of loss. Days, weeks and months later came the
business side of dying.
My sister, Victoria, Tory to everyone who knew her, lived a full and colorful life.

This was my third season as an AARP volunteer tax aide…and my third post about my experiences. I volunteer two days a week from February 1 to tax day at two different senior centers which draw from different socioeconomic strata: one is definitely middle class; the other has many clients living on very little.
I began the season wondering how the Big Beautiful Bill would impact our clients. Since most are over 65, I expected the new $6000 senior deduction to have a big,

This month I am hosting a couple evacuated from the Iran/US war zone. They each (ages 40 and 29) have been saving money, but not systematically, and asked for some coaching on how to get their affairs organized.
We’ve had one session so far. Here is what we covered:
– Understanding that 15% of gross income should be saved for retirement.
– First, set up an emergency fund. (How much, why, where, have all been covered)
-Second,

This month I am hosting a couple evacuated from the Iran/US war zone. They each (ages 40 and 29) have been saving money, but not systematically, and asked for some coaching on how to get their affairs organized.
We’ve had one session so far. Here is what we covered:
– Understanding that 15% of gross income should be saved for retirement.
– First, set up an emergency fund. (How much, why, where, have all been covered)
-Second,

Those words are repeated in video after video on Facebook by seniors (possibly actors) complaining they can’t pay their bills because Social Security is inadequate and does not keep up with rising costs. “We worked our whole lives and paid into SS and this is what we get?” they ask.
What is disturbing to me are the thousands of “likes” the videos receive and the hundreds of agreeing comments posted every time.  In essence, 

BEFORE WE GET into it, a brief word. We lost Jonathan last year, and those of us who followed his work felt it more than we perhaps expected.  He had a saying that I always liked – that there are really only twenty stories in personal finance, and the financial industry spends most of its time telling them on repeat in slightly different hats. He was right, of course. He usually was.
It struck me that a fitting tribute might be to take his core principles and do something with them,

RECENTLY, The Wall Street Journal ran a story about a new type of investment known as a digital stock token. For now, they aren’t available in the U.S., but they’re coming soon, so it’s worth taking a closer look.
What are stock tokens? At the most basic level, they’re a technology designed to make stock market investing quicker and easier than it is today. With tokens, trading won’t be limited to traditional business hours.

In many personal finance circles, the conversation around aging inevitably turns to the “child as a safety net” strategy. We often assume the natural progression of life involves moving closer to our offspring, or perhaps moving them into our homes, so they can help navigate us through our final chapters.
But as I look around my age-restricted community, I see a much more diverse—and arguably more resilient—set of arrangements. While some neighbors do live with their adult children,

We have reached a point now we don’t need to use either free or paid tools or calculators for things like, figure when to claim social security, we have converted all our t-IRA accounts, so no RMD, nor NIIT, nor IRMAA. We have also done our estate planning and a letter of instruction, etc. We did very well with our budgeting with our spreadsheets.  All that is left to figure out annually are our annual retirement cash flow/income,

Three funerals in four weeks. A friend taken by bowel cancer. Another by a stroke. A third, most heartbreakingly of all, by his own hand. It’s got me thinking about life. The big questions no longer feel abstract; they feel like they’re sitting across the table, waiting.
So. Do you have any regrets about the choices you made in your younger years?
As the song goes, I have a few. Not spending more time with my daughters while they were growing up.

In his book “Die with Zero”, Bill Perkins lays out a framework for how to spend money to maximise your life. Ramit Sethi has his “money dials” to explain how to both enjoy money whilst still building a strong financial base.
But I reckon that the two wisest women in my life, specifically my wife and Mum, have it all worked out. And they didn’t have to write a book or start a podcast.
Mum was raised in a comfortable family home.

For context, I am 65, retired for seven years, married and have children and grandchildren. The lists below are based on my specific life details. I know items on your lists may be different, but I’d love to hear about them to learn from your experience.
Things I Am Doing Now As Compared To When I Was Younger

Learning to splurge a little more (as I am able)
Flying instead of driving
Using an Uber (versus park at the airport or ask someone for a ride)
Making larger financial gifts to loved ones (now instead of later)
Paying for meals at restaurants for our adult children and their families
Saving for the educational expense of grandchildren
Answering questions as the Identified go to person in my family for financial matters
Participating more at the local senior center I recently became a member.