What would you do?
A recent 60-yr.-old retiree with a pension over $100K/yr. and rental income of ~$30K/yr. My expenses are ~$70K/yr. As you can see I have no need to withdraw any $ from my retirement accounts (~$1.09M in trad. IRA and $2.2K in Roth) or two brokerage accounts ($1.5M-a bunch of mutual funds (18) & $500K- Schwab Intelligent Portfolio-robo advisor; overall asset allocation of 85% stocks & 15% bonds.) Seriously considering doing Roth conversions before reaching RMD at 75.

I hear about this topic on YouTube retirement videos. It has also been a topic on HD from time to time. We all know about the process of preparing financially for retirement, but it seems that for many people facing a retirement lifestyle is equally challenging.
Honestly, I can’t relate. I never thought about what retirement living would be like. I had no expectations. Perhaps taking phased retirement for 18 months was a factor, but even when I decided on doing that it wasn’t with a plan to prepare for retirement,

IT’S TIME TO PAY IT forward.
That’s a phrase I often use when talking about helping the next generation. But my efforts have been mostly focused on my children and grandchildren. What about others in future generations, especially those from less affluent families?
Welcome to the Jonathan Clements Getting Going on Savings Initiative and the accompanying book, The Best of Jonathan Clements: Classic Columns on Money and Life.
The savings initiative aims to get young adults started in the financial markets with $1,000 contributions to Roth IRAs,

I usually go for my four-mile walk before sunrise. I like to get an early start to my day. I’ve gotten to know a few folks who I see on my way around the neighborhood. We exchange pleasantries as we pass each other.
But there’s one gentleman who is not so friendly. He looks like he’s in his early thirties—about forty years younger than me.
All the people I encounter walk on one side of the sidewalk,

Today’s WSJ has a Jason Zweig article about the the Jonathan Clements Initiative.
This will be paywalled. https://www.wsj.com/finance/investing/the-wsjs-jonathan-clements-wants-to-leave-a-living-legacy-19f1738d
Intrepid readers can also find a link or two about how to donate if you are not buying the excellent new book.

Many Humble Dollar readers, including myself, are on the older side – approaching retirement or already retired. Readership tends to be relatively affluent and educated. Our financial and social perspective may at times be influenced by a generational outlook. At the risk of overgeneralizing, here are some possible baby boomer versus Under 40 year old viewpoints:

Artificial Intelligence

Baby boomer: A new development with many unknowns and exciting possibilities. AI could play a dangerous role in future scams targeting them. 

On March 25, 2025, the President of the United States signed Executive Order #14249 titled Protecting America’s Bank Account Against Fraud, Waste, and Abuse, which was published in the Federal Register on March 28.
The fact sheet states that, effective September 30, 2025, the Federal government will cease issuing paper checks for all disbursements, including intragovernmental payments, benefits, vendor payments, and tax refunds.
The fact sheet also states payments made to the Federal government,

Love and heartbreak are human experiences.  Heartbreak is not restricted to the end of a relationship. It can be unrequited love, the death of a loved one, divorce, unmet expectations we have of another. Or other severe emotional conditions.
Harvard Medical School recently published an article about a phenomenon known as Broken Heart Syndrome. It is a real condition known as Stress Cardiomyopathy or Takotsubo syndrome, and can be deadly. But most people recover quickly without any long lasting effects.

On a recent family trip to the UK I learned something new about car rental insurance. During my many years of business travel, we were always told to turn down the collision damage waiver, or CDW, insurance offered by the rental company. Our personal credit card provides rental car insurance, but you must decline the CDW and reserve and pay with that card.
When we picked up our car hire just outside of Oxford we were pleased to see we’d been upgraded to a BMW 500 sedan. 

A few days ago Connie and I went to a unique NJ restaurant for a light dinner.
We each had a root beer, we shared a pastrami and turkey sandwich and one bowl of matzah ball soup. The bill was $108 before tip. Now you know why Harold’s NY Deli is unique. 
Have you concluded it is a upscale, white table cloth place or just a rip off? Now, the rest of the story. 
The sandwich is so large they give you six extra slices of bread to break it down.

https://obliviousinvestor.com/the-value-of-a-second-opinion/

I’m in the process of completing my retirement paperwork. For context, I’m retiring on the same day from two systems—the University of California (where I work now) and CalPERS (which administers the pension fund for the university system I previously worked for). My husband, who worked for a state agency, retired from CalPERS in 2016 and has been drawing his pension as well as using his retiree health benefits for both of us. We elected pensions with full survivor continuance for all three.

It’s been a topsy-turvy year in the financial markets. Has that prompted you to make any changes to your portfolio’s asset allocation? I’m thinking about four key dimensions:

Stocks vs. bonds vs. cash investments
U.S. stocks vs. foreign shares
Large-cap vs. small-cap stocks
Growth vs. value stocks

If you’ve tweaked your asset allocation, I’d love to know what changes you’ve made—and why.

While I was in Savannah last week, PBS was filming an episode of Antiques Roadshow, a show I’ve always enjoyed. On a lark, my girlfriend Patricia and I walked over and took a backstage tour with a woman who worked for Georgia Public Broadcasting. This is what we saw:
Hundreds of people who had won free tickets in an online lottery lined up at the entrance to the Georgia Railroad Museum. Most carried small items in tote bags.

Due to the COVID-19 pandemic and a spike in unemployment federal tax law was modified and the Employee Retention Credit (ERC) was born. The ERC was a refundable tax credit for certain eligible businesses and tax-exempt organizations that had employees and were affected during the COVID-19 pandemic. The business, tax community and the Internal Revenue Service continue to deal with compliance aftermath of the ERC.
On March 20, 2025 the IRS updated their frequently asked questions about the employee retention credit in the section headed “Income tax and the ERC”.