HOW WE SPEND DEPENDS on how we feel about money.
To be sure, we’re supposed to spend according to our financial situation and needs. But life experiences can so badly distort our attitude toward money that our financial decisions end up being ruled by fear and insecurity rather than questions of affordability. Such is the case with an acquaintance—let’s call her Satee—whose money habits are at odds with her financial standing.
Satee grew up in a typical Indian family of four.

I’VE PENNED MORE THAN 450 articles for HumbleDollar, so picking 10 favorites could have been a laborious task—if I’d bothered to look back through all the articles I’ve written.
But instead, I took an easier route, simply listing the articles that I could most easily recall. What made these articles memorable? Some were quite personal, while others broached ideas that I continue to grapple with to this day.

Really Useful Engine (Dec.

ABOUT HALF THE RENTALS that my wife and I own were foreclosures we bought around the time of the Great Recession. In fact, I closed on the first one on my wedding day—a fact my wife isn’t anxious to let me forget.

In 2000, a family had bought the house for $70,000. In 2006, JPMorgan Chase foreclosed on the house. In 2007, the bank unloaded the property for $93,000 to the Department of Housing and Urban Development (HUD),

I RECENTLY HAD a revelation about my adult children: When it comes to money, they’re a lot like me—and that’s both a good thing and a bad thing.

I had this revelation while dining with my 25-year-old son at a sports bar over the New Year’s holiday. The food was marginal—it was a sports bar, after all—but the plates came loaded with food. What’s more, the prices were quite reasonable, especially compared to those in Philadelphia and Washington,

MY FATHER RETIRED from a 35-year teaching career in 2002, when he was 56 years old. He hasn’t worked a day since. For years, his retirement was the primary model for my retirement aspirations—until I realized my path needed to diverge.
Like many dads, he worked a career he tolerated but probably didn’t love. It provided our family with a comfortable lifestyle in the suburbs of a low-cost-of-living city. Teaching enabled him to be ever-present during my youth,

I RECENTLY DISCUSSED Social Security with a friend. After trying to explain the program’s funding, I gave up when his reply was, “The facts are that the Social Security money was misappropriated and there’s no way it can be tracked after all these years. People die before they collect one Social Security check, and others get very few checks. You will never convince me otherwise.”

Yes, that’s the one thing we do agree on: I will indeed never change his mind.

RETIREMENT IS A HUGE decision, as readers of HumbleDollar well know. Retirement from a multi-generational business is even harder, because there isn’t really a day when you can say, “I’m retired.” Like the Hotel California, “You can check out any time you like, but you can never leave.”
I’m 65. That’s an age that carries a lot of social expectations. Age is not a continuum, but rather a series of milestones,

WHEN I RETIRED, I thought a successful retirement was primarily about money—about making sure I had enough income to fund daily expenses for 30 or more years. But now that I’m in my 70s, my investments don’t seem quite so important to me.
Indeed, other things in my life strike me as just as crucial as my investment portfolio’s size. Some say retirement is like a three-legged stool. No, not the traditional three-legged stool of personal savings,

WHEN I FOUND myself unexpectedly packaged off by the bank, I was initially very happy. I was planning to leave anyway because the stress was getting to me. When the bank gave me a severance check at age 59, I felt like I’d won the lottery.
Life was pretty good for a while, but then I was hit by a bad case of retirement shock. I lost my mojo, and had a constant feeling of being incredibly lost and vulnerable.

JEFF BEZOS ONCE asked Warren Buffett why everyone doesn’t just copy his example when investing. Buffett famously replied, “Because nobody wants to get rich slowly.”
The magic of saving diligently, coupled with decades of compounding inside tax-advantaged accounts, can ensure financial freedom. In fact, young married couples today have an outside chance of accumulating $10 million by the time they reach the new required minimum distribution age of 75.
To reach the $10 million jackpot,

WHAT A DIFFERENCE a rally makes. So far this year, the S&P 500 is up more than 6%. Not bad considering the doom and gloom from Wall Street forecasters at the end of 2022. Recall how strategists in early December were projecting large-cap U.S. stocks to finish 2023 in the red. Naturally, the market did the opposite of what most experts were thinking.
Stocks soared to jumpstart the new year. Many regions notched their best January in decades.

IN THE WANING DAYS of 2019, Congress passed the SECURE Act, a law that delivered a mixed bag of changes for retirement savers. Well, Congress has been busy again. At the tail end of 2022, a follow-up law—known as SECURE 2.0—was signed into law.
The good news: There’s a whole lot included in this new law. The bad news? There’s a whole lot included in this new law. SECURE 2.0 presents a number of new planning opportunities but,

HI RYAN, DON’T FREAK out because I’ve written an actual letter rather than an email. No big news here, no emergency, we’re fine. I just have something that’s been percolating and I want to share it with you.
Ry, it’s become clear learning about investing is not where you’re at right now. I’ve tried to think of what I might have done to turn you off. We know I was depressed and withdrawn for much of your childhood,

IF YOU KICK AROUND Wall Street for long enough, you’ll witness all kinds of investment fads—special purpose acquisition companies, cryptocurrencies, meme stocks, to name just a few. Each bubble differs, but the eventual comeuppance always feels brutally familiar.
But there aren’t just fads among investments. There are also fads among investment concepts. But while naïve investors tend to get caught up in investment bubbles, it’s the brainy types who fall in love with investment concepts,

FRANK CAPPIELLO and Carter Randall were longtime panelists on the television show Wall Street Week with Louis Rukeyser. Panelists typically worked at investment firms, with their affiliations displayed on the screen. At some point, Cappiello and Randall retired. On the screen, each was simply identified as an “independent investor.” At least one regular guest, John Templeton, also achieved this listing after retiring from running the Templeton Funds.
That “independent investor” label intrigued me then and does to this day.