What’s the common attribute of everyday Americans who have amassed $1 million or more? They’re frugal—otherwise known as cheap.
From HumbleDollar Founder Jonathan Clements
NO. 77: TO BUY ourselves happiness, often the best strategy is to not buy anything at all. That can leave us with a plump bank account and the sense of financial security it offers.
NO. 100: THE BIGGEST “death tax” paid by your family will probably be the income taxes still owed on your retirement accounts. One possibility: Pay the tax to convert part of your traditional IRA to a tax-free Roth IRA, and then bequeath that account—an especially smart move if your heirs are likely to be in a higher income-tax bracket than you.
SHILLER P/E. Named after economist Robert Shiller, the Shiller price-earnings ratio—also known as the cyclically adjusted P/E ratio or CAPE—compares current stock prices to average inflation-adjusted earnings for the past 10 years. That smooths out cyclical fluctuations in corporate profits—a problem that can distort conventional P/E multiples.
LOOK FOR TAX savings—by reviewing your recent tax returns. Two danger signs: lots of interest income and realized capital gains, especially short-term capital gains. What to do? Avoid trading so much or, if necessary, confine it to a retirement account. Also use a retirement account to hold your taxable bonds and other tax-inefficient investments.
NO. 77: TO BUY ourselves happiness, often the best strategy is to not buy anything at all. That can leave us with a plump bank account and the sense of financial security it offers.
Regular HD readers know how old I am, but just for fun how about a trip down memory lane to a very different time.
When I was a child an ice cream cone was a dime, a slice of pizza was $0.15. There were no malls. Where there are malls today, there were dairy and cattle farms.
When I was really young our milk was delivered by horse and wagon kept cool by blocks of ice.
I have been getting more and more frustrated with many friends and relatives, I have tried, in vain , to share what I have learned from HumbleDollar, Ben Graham, William Bernstein , et.al..
I have decided that henceforth, whenever someone asks me what they should do with some cash, perhaps from the sale of a house in an estate sale, a small inheritance, or what investments to choose in a retirement plan, I now say, ”
I am certainly nearer the end of my life than the beginning. and I thought it wise to ask around, talking with everyday people, trying to get a good, accurate analysis of the overall economic outlook. Some may find this silly, after all, why not just heed the advice and wisdom of all of the experts, offering their views on market conditions, the direction of interest rates, both short and long term, etc. But, nothing ventured,
No, we don’t need to complete all 15 tasks by the end of this day. Still, we might knock them out by the end of the year. Meanwhile, I suspect that long before we’ve checked off the last of the list, we’ll experience less worry, better sleep–and hear fewer nagging reminders from our family.
1. Run an estimate of our 2026 taxes, while there might still be time to mull over, say, the size of a charitable donation or Roth conversion,
I’m not expecting readers to answer all eight of the thorny questions listed below. But I’d love to hear your thoughts on one or two.
What in your past or about your personality explains your investment risk tolerance?
What uses of money—giving it away, saving it, specific purchases—bring you the greatest joy?
Would you be okay financially if U.S. stocks had a 0% total return over the next 10 years?
If you’re still working, what would it take for you to leave the workforce with a sense of satisfaction?
At Thanksgiving, my son-in-law was asking me a number of financially related questions about retirement. He’s about 10 years away from retirement, but he knew I retired last year, so it was fresh in my mind. I created the following pre-retirement list for him to think about. Update: The list has been updated based on comments from the HD community.
HD Community: Are there any financially-related things you did to prepare for retirement that aren’t listed below?
In Retirement
The Security Money Can’t Buy
Dennis Friedman | Sep 25, 2026
In Retirement
Is your retirement plan counting on a Social Security COLA in the future?
R Quinn | Sep 24, 2026
Investing
What stock would you happily hold for the next 10 years?
Jonathan Clements | Aug 17, 2021
Investing
Target Maturity Bond Funds
DAN SMITH | Sep 18, 2026
From HumbleDollar Founder Jonathan Clements
Lists
Why HumbleDollar?
Health
My Name is Dan, and I’m a CPAP User
DAN SMITH | Sep 24, 2026
Taxes
Shouldn’t property taxes be a realistic part of retirement planning? Sorry, I think this is a major financial and social issue.
R Quinn | Sep 23, 2026
Spending
Anyone For S.K.I.ing?
Mark Crothers | Sep 22, 2026
Behavior
Time Is Priceless
Andrew Clements | Sep 23, 2026
Taxes
Does the new-for-2026 $1000/$2000 charitable deduction for non-itemizers reduce AGI?
Andrew Forsythe | Sep 22, 2026
Taxes
What I think about taxes- all kinds of taxes
R Quinn | Sep 21, 2026
Investing
Structuring Bonds
ArticleAdam M. Grossman | Sep 19, 2026