FIDDLER ON THE ROOF is the timeless tale of a poor Jewish dairy farmer in Russia during the early 20th century. What makes the musical timeless? It tells the story of a worker, husband, father and religious believer who’s trying to succeed in all these facets of his life.
One of the show’s most famous songs is, “If I Were a Rich Man.” As the title implies, the farmer dreams of a life of wealth and how wonderful that would be.

I SAW A GRAPH recently generated by some retirement-planning software. It showed the investor enjoying substantial portfolio growth over the course of his 30-year retirement. Forget running out of money. This particular software program says the guy’ll be a 90-year-old multimillionaire.

My curiosity piqued, I used the same software to run numbers for my finances. I ran optimistic and pessimistic assumptions. I entered my monthly expenses and my fixed income. I tried to run out of money,

APPLE COMPUTER WAS founded on April 1, 1976, by Steve Jobs and Steve Wozniak. What’s less well known is that originally there was a third co-founder, an engineer named Ronald Wayne. Wayne’s tenure at the company was short, though. Concerned by the risk—and by Jobs’s personality—Wayne sold his stake in the company after just 12 days.
In exchange for his 10% stake, Wayne received $2,300. Today, Apple is worth close to $3 trillion. Wayne’s decision to sell is sometimes cited as one of the worst missteps in financial history.

WHAT WILL BE YOUR legacy? It’s a question many of us ponder as we get older. My conclusion: It’s the wrong question to ask.
The fact is, the whole notion of a legacy is a tad delusional, and very likely a trick played on us by our genes, which want us to care deeply about future generations. The reality: Most of us will leave scant mark on the world and we won’t be remembered for very long after we’re gone.

I LED A RETIREMENT seminar some years ago at a large manufacturing company. During the question-and-answer session that followed my presentation, a 60-something welder told the group he’d never retire. I asked why. His response: All his friends who’d retired before him were already dead, and he didn’t want to follow in their footsteps.
What he said resonated with me—because I knew someone who suffered a similar fate. Gino was a client back in my banking days.

TODAY IS THE 50th anniversary of the most important day of my life. On Feb. 16, 1974, I met my wife. Choosing a life partner is arguably the most crucial decision we make. No other choice likely matters as much, including education, career, finances, where we live or even having children.
We’ve all heard the statistic that half of marriages end in divorce. In addition, marriage rates are declining, marriages are happening at later ages,

IT WOULD BE GREAT if my wife and I could stay indefinitely in the two-story colonial-style home where we raised our two children.
Right now, in our early 60s, taking care of the place doesn’t seem like a huge burden. The lawn is only a third of an acre and mowing it helps me stay in shape. Before I retired, we updated the kitchen and had a new roof installed. In the near term,

THERE USED TO BE a TV show called Lifestyles of the Rich and Famous. I assume it was created to make viewers envy rich people and want what they had. The memorable catchphrase of the host, repeated at the end of every episode, was “champagne wishes and caviar dreams.”
Envy is one of the seven deadly sins—for good reason. All it does is cause heartache and pain. When I was younger,

MONEY CONVERSATIONS are part of my daily life. I’ve written a personal finance blog for five years and recorded a related podcast for three years. I work full-time for a fiduciary financial planning firm. All of these activities expose me to folks seeking to improve their financial literacy.
I love talking money. But the more “money talks” I have, the more I see that people overlook the most fundamental principle of personal finance. What principle?

MY WIFE CONSTANTLY reminds me that I promised to get her a dog when we purchased our first home. Problem is, it turns out that I’m allergic to most animals with fur, so that promise fell through. Indeed, all too often, the only animal in the doghouse is me.
Many moons ago, as a cash-strapped student working toward my PhD thesis, I purchased plastic roses as a Valentine’s Day gift for my fiancée. The salesperson sold me on the fact that they’d never die and always retain that beautiful bright red color.

I’M IN NO HURRY TO retire—but I am making sure I’m prepared. I’m age 56, and I plan to work full-time until 70 and part-time until 75. I’m an English professor, and I enjoy teaching, service and scholarship. I also enjoy having three weeks off at Christmas and two months in the summer.
I received a fairly large inheritance, which has been growing over the years and which will allow me to do some special things in the years to come.

I’M NOT A SAVVY investor, nor do I pretend to be. Some people get paid to analyze and make predictions about stocks, often for people like me. How reliable are their opinions? I’m not so sure.

Take the newsfeed about my largest single stock holding, the utility Public Service Enterprise Group (symbol: PEG), that I got late last month from my Fidelity Investments account:

“Guggenheim Downgrades Public Service Enterprise Group to Neutral From Buy,

LAST YEAR WAS OUR first full year living solely off our portfolio, with no paycheck coming in.
How did it go? It was a vast improvement from 2022, when we not only retired, but also got hit with high inflation, tumbling bond prices and a sharp stock market decline. We were looking at sequence-of-return risk—that perfect storm of rising living costs and a shrinking portfolio that can derail those early in retirement—and I can recall feeling a bit panicked.

“YOU CAN PAY ME NOW—or you can pay me later.” Years ago, that was the catch phrase, spoken by an auto mechanic working on a broken-down car, in ads for FRAM oil filters. The pitch: If you spend a modest sum on routine car maintenance, you’ll avoid far bigger bills down the road.
The same philosophy applies to retirement savings. There’s a constant tradeoff between now and later.
Faced with life’s challenges, we need to strike a balance.

THE S&P 500 INDEX just hit a new all-time high, topping 5,000 for the first time. Is it now too high? For investors concerned about market risk, this is an important question. But it isn’t an easy one to answer.
For starters, there’s no single definition of “too high.” Consider the price-to-earnings (P/E) ratio, the most common measure of market valuation. By this metric, the market does indeed look pricey. The P/E of the S&P 500 stands just a hair below 20 based on expected 12-month earnings—far above its 40-year average of 15.6.