I WAS THINKING ABOUT Jonathan the other day on my morning walk, which happens more often than you might think. It’s hard not to think about him when you have HumbleDollar coasters in your living room and a HumbleDollar shopping bag in your car that you use for groceries. My wife confiscated the HumbleDollar cup I had been using for my morning tea, and it now has a new home in our bathroom holding her toothbrush and toothpaste.

WHAT’S THE BEST way to manage your investments?
A new book titled Your Perfect Portfolio helps answer this question. I spoke this week with the author, Cullen Roche.
Adam Grossman: The title is Your Perfect Portfolio with an emphasis on your. 
Cullen Roche: I was very intentional about saying “your perfect portfolio” because everyone’s different, everyone’s unique. So I wrote this book with the intent of studying lots of different strategies and styles.

I used to think that if people just knew the basics of personal finance, they would take action to better their lives.  Over the years, I’ve changed my stance.  I can now see that only people who come naturally to taking an interest will ever even seek the information.  This tracks with the ancient saying, “when the student is ready, the teacher will appear?”
Why is that so true?  In a way it’s a slight of hand. 

Last summer, I wrote about a frustrating dynamic in our household: I manage my portfolio with low-cost index funds, while my wife Suzie pays nearly 2% annually to a wealth manager. Several comments asked for an update on my campaign to win her over to a lower-cost approach that would benefit our combined future wealth.
My initial efforts got Suzie to open a Vanguard account, which we funded with cash in a money market fund. This let her get comfortable with the platform.

My wife was laid off the other day. After thirty years at one company. For the first time in her working life, forty years, she was told her services were no longer needed.
Even though we’re financially fine, and now that she may join me in retirement, I’m unsettled. I think it’s because we have both crossed the retirement line. We’re no longer actively working to make money. We’re now 100% earning money passively. We’re relying on all the acorns that we’ve saved,

A sensible recommendation is to invest 20% to 50% in foreign markets. That seems reasonable on the surface. But, which of the 3 sources of funds is best to invest in foreign markets? Broadly speaking, there are 3 big sources of funds: Tax-Free (Roth), Qualified (401k, IRA), or taxable brokerages.
My preliminary conclusion: Investing Tax-free and qualified funds in foreign markets would incur double-taxation. Taxable brokerage funds seem best.
USA has tax-treaty agreements with about 70 countries that avoid double-taxation.

Medicare Part D now limits the patient’s out of pocket costs to $2,100 a year (2026) adjusted each year.
There are conditions. Your Plan D is responsible for tracking your spending. 
Every time you fill a covered prescription:

The pharmacy submits the claim electronically to your Part D plan
The plan records: what the drug costs, what you paid, what the plan paid
Once you hit the limit, you pay $0 for covered drugs for the rest of the year.

I’m gifting a New York Times article on new legislation affecting Pharmacy Benefit Managers. There’s a lot of detail, but since the PBMs apparently opposed it, maybe it will help a little.
The medication I used to take for rheumatoid arthritis cost $2,000/month retail when it went on the market around 2012 (even though some of the research was funded by the government), but had risen to $6,500/month retail by the time I stopped taking it ten years later…

I retired at 58 years young. I feel there’s always been tension in the retirement world around when to actually pull the trigger. The common argument goes like this: your late fifties mark the peak earning decade of your career, so retiring early is basically sabotaging your future self. It’s a valid point, and the numbers usually back it up.
But here’s what I think: while the maths matters—and for some people makes early retirement impossible or genuinely foolish—for others,

We’re putting it off, we are planning to … when I turn 70. We will be doing that in a few years…
As I read HD I see many people mention plans they have for the future. For people retired, I have a suggestion. The future is now – Carpe diem
I don’t care what assumptions you put into your spreadsheet or what the SS actuarial table says, in retirement the old adage “Don’t put off until tomorrow what you can do today,”

Sharing this article (free link, I hope) because it does a great job explaining the ACA “subsidy cliff” — how a small change in income can suddenly make health insurance unaffordable. Hoping it helps people explain this to family or friends and sparks a real conversation about why subsidies matter and how the rules could be improved.
https://www.nytimes.com/2026/01/30/upshot/obamacare-subsidies-financial-cliff.html?unlocked_article_code=1.JVA.k0hc._GnYquc58qF6&smid=url-share
I’ve tried to explain the ACA and subsidies to a number of friends to limited success.  Between calculating MAGI,

Like most investors, I learned early about the elegance of the 60/40 portfolio.
Sixty percent stocks for growth. Forty percent bonds for stability.
I studied why it worked. Stocks historically delivered long-term returns, bonds reduced volatility, and periodic rebalancing enforced discipline.  60/40 has proved itself as a durable framework. It wasn’t exciting, but it was resilient.
I understood its importance. It shaped how I thought about diversification, risk, and balance—and it still does.
For many investors,

I’ve always been interested in retirement account alternative withdrawal strategies. Different strategies provide different outcomes. Some support higher initial spending rates, others leave larger amounts for a legacy. There is a middle ground with higher initial rate, and modest remaining amount.
RMD (Required Minimum Distribution) is an often discussed method of withdrawals from retirement accounts. There are others and Morningstar is publishing a series on nine different approaches. These range from simple to complex. “The best retirement withdrawal method depends on what’s most important to you.” The articles look at differing approaches with can support different withdrawal rates.

Vanguard just announced that they cut expense ratios of many funds:
“Vanguard has lowered expense ratios for 84 mutual fund and exchange-traded share classes across 53 funds, amounting to nearly $250 million in fee reductions in 2026. ”
Some popular ones:
VBIL 0-3 Month Treasury Bill ETF from 0.07% to 0.06%
VIG Dividend ETF from 0.05% to 0.04%
VUG Growth ETF from 0.04% to 0.03%
VV Large Cap from 0.04% to 0.03%
VB Small Cap from 0.05% to 0.03%
Full list

Prior to being on Medicare, I had a High Deductible insurance policy. I stayed on top of my claims, probably because I was using my hard earned dollars to pay for services. That was over seven years ago, now with Medicare I have become very lax about reviewing claims. What the heck, once I pay my deductible, Medicare and Plan G takes care of the rest; What, Me Worry?
My laxness is exacerbated by the fact that I live in a paperless world,