I’m breaking up with my bank, my credit cards, and my mutual fund company.
My reasons were influenced by three things.

Many years back Roy and Pauline came to me for tax prep. Though not wealthy, they had about two dozen disparate investments in everything from amusement parks to oil wells. My first thought was that if Roy died first, Pauline was going to have a difficult time dealing with this veritable spaghetti bowl of K1s.

We need words of wisdom dealing with the stock markets.

This is not criticism, it’s an inquiry.
Over the years I have read many times on HD about tracking expenses/spending. Some people pursue this in great detail, some seem to approach it like a hobby. There may be something motivating in knowing how every penny is spent. 
As you may suspect, I don’t know in detail where or how we spend our money. As long as the big picture is in balance I am happy. 
What I do know is the bank balance is $X at the end of the month,

We sold our S&P 500 shares from one retirement account to roll them into another, perfectly timing the market peak. I’d love to boast it was our shrewd insight that nailed the sale, but honestly, it wasn’t. We were just moving money from our 401(k) to our Vanguard IRA. Picture a typical morning—coffee in hand, idly glancing over our account balances during our usual monthly check-in.
No brilliance needed—just sheer luck. Some label it dumb luck,

During his final months, my husband Jonathan worked tirelessly to complete his last book, Money and Me.  The book is now available for pre-order and will be released in May 2026.
What’s so special about this book?  This book features Jonathan’s best and most personal HumbleDollar articles.  The articles are curated in such a way to teach everyone about personal finance through Jonathan’s own money journey.  And sadly, his terminal cancer diagnosis is part of this journey about which he candidly writes.

The signs of this looming crisis are everywhere. Expensive home care, long term care and end of life care are going to be the biggest challenges facing baby boomers.
There are over 69 million baby boomers, 21% of the US population, holding 50% of wealth. Unfortunately, most are unprepared to face this crisis. I find that in my retirement community, most have not investigated options to provide for such care and have shown little interest. They say they will handle it if and when they need it.

Notice anything different? Today, the articles and “Second Look” sections disappeared from HumbleDollar’s homepage. What replaced them? You’ll find three new features.
First, at the top of the page, you’ll see a section called “Latest Posts” that includes nine Forum posts and articles. All new posts will appear here, along with other pieces—new and old—that are currently garnering comments.
Meanwhile, at the bottom of the homepage are two new “Spotlight” features. One section focuses on pieces devoted to one of 23 topics.

I just returned from a six-day silent retreat. What in the world could that have to do with retirement and financial life?  Maybe nothing or maybe a lot.  I’ve been going on silent retreats for more than 20 years, ever since I became a minister and they were part of my spiritual and professional development. These days in my semi-retired lifestyle they are still part of both.
One of my goals for the retreat was to write a draft article about moving to California for Humble Dollar.

Twenty years ago I would not have written this, but I have grown less naive.
Consider human nature…when thinking about paying for healthcare and generating retirement income
We have tried countless schemes to manage health care costs, and expand coverage.  Similarly we provide incentives to get people to save for their retirement. The evidence shows only modest progress, but nothing has really solved the basic problems. 
We humans are just short-term thinkers.
Over 20 million Americans still have no health insurance.

I’ve been doing a lot of reading on Roth conversions lately, and I’m seriously considering pulling the trigger on one this year. But before I make any moves, I wanted to get some feedback from those of you who have been through the process.
A little background: I’m in my mid-50s, still working, and in a relatively high tax bracket. I have a mix of retirement accounts – mostly in a traditional IRA and a 401(k).

I came across an interesting tax return the other day while volunteering at a local AARP TaxAide center. This is my 7th year doing free tax returns and I’m still learning. In this case, I didn’t prepare the return; I was the quality reviewer and did the outtake with the client. The client was a retired single woman in her mid-70s. Her income was modest and she didn’t have any fancy or complicated investments. What made her case interesting was her near obsession with making sure that she paid zero tax for the year,

Time for a pop quiz:

For those still working, what do you imagine your retirement will be like?
For those no longer employed, does your retirement match your earlier expectations?

This is not a political post, but the basis is a political action. Friday, Feb. 28, was the so-called Nationwide Economic Blackout. My wife and I decided to participate. For us, this wasn’t about specific retailers. We simply made no discretionary (or mandatory) purchases that day. It was not a difficult commitment.
Thinking about this over the weekend, I realized that the result of that day wasn’t anything special for us. There are many days that we spend absolutely nothing.

Last month I did my best to analyze investments to the market as an alternative to payroll taxes for Social Security. My conclusion was that the payroll taxes were worth it, though some readers respectfully disagreed.
But what if I could go back in time for a do-over. What if at age 16 I began to invest an amount into the market that was equal to and in addition to the payroll tax deducted from my pay?

THE U.S. STOCK MARKET has historically delivered similar returns under both Democrat and Republican administrations. For that reason, my view is that investors shouldn’t worry too much about who occupies the White House, and I tend to stay away from investment discussions that involve politics.
But sometimes, the news coming out of Washington dominates the headlines in a way that can’t be ignored. Such is the case today. Moreover, with the stock market faltering recently,