I RECENTLY CAME across an academic paper with an attention-grabbing title: “It has been very easy to beat the S&P 500.” Not just easy, but very easy. 
That got my attention because, in recent years, beating the S&P 500 has been anything but easy. In fact, it’s been maddeningly difficult. In eight of the past 10 years, domestic markets have outperformed international markets—by a wide margin. A dollar invested 10 years ago in the S&P 500 would be worth $4.37 today.

“FINANCIAL WRITERS always seem to assume everybody’s married.” That’s a complaint I’ve heard more than once—and it came to mind as I reviewed our 2018 tax return.
That tax return reflected the impact of 2017’s tax law, which—among other things—roughly doubled the size of the standard deduction, while capping the itemized deduction for state, local and property taxes at $10,000. One result: Many couples now get little or no tax benefit from either the mortgage interest they pay or the charitable contributions they make.

SITTING IN A COFFEE shop, I struck up conversation with a middle-aged woman. We were talking about winning the lottery and then, as if one thought naturally followed the other, we got onto the topic of retirement. She mentioned how difficult it was for her and her husband to pay the mortgage and the monthly bills.
“After saving for retirement?”  I interjected.
“We can’t save for retirement,” she responded. “Our plan is to get our mortgage paid off,

“YOU’RE FIRED” WAS made famous by Donald Trump as host of The Apprentice. Imagine my surprise when my broker delivered the same message to me two years ago.
In 2015, my job was transferred to Texas. I opted to become a long-distance commuter, while my family stayed in Maryland. Around that time, we moved homes, so our son could attend a better high school. In addition, I was helping to launch two huge long-term work projects.

AMONG THE 16 MILLION who served during the Second World War, many returned home, started families and pursued what would become an integral part of the American dream: homeownership. It’s during this time that the term “starter home” was coined.
My grandfather was one of those proud vets. He and my grandmother bought a place in South Dakota, where they started our family.
In 1950, the average new single-family home was 983 square feet.

I WAS SELECTED IN 2015 for the “leadership pipeline program” at the major bank where I worked. It was a 10-month-long program for minority employees just below executive level. We were selected to learn all about corporate culture and what it took to advance to the next level. I felt honored to be among such talented and promising employees.
Participants were from various departments from across the U.S.—technology, risk management, operations, compliance, human resources,

BABY BOOMERS ARE retiring every day and Generation X is right on their heels. With this, an increasingly large amount of wealth is making its way into IRAs and Roth IRAs, thanks to rollovers from employer retirement plans.
I’ve found that many folks don’t quite grasp the complexities of such accounts. On the surface, they seem pretty simple: You contribute to an IRA or Roth IRA, receive tax-deferred growth and then gradually withdraw the funds during retirement.

AS THE OLD SAYING goes, there are lies, damned lies and statistics. And then there’s investment performance, which may deserve a category all its own.
This topic came to mind recently when I saw a press release heralding the accomplishments of a retired nonprofit executive. Among the claims: that he had doubled the organization’s endowment. This struck me as impressive—until I considered it more critically. What did it mean that he had doubled the endowment?

YOU COULD ARGUE that U.S. stocks are reasonably priced, with the S&P 500 companies trading at 22 times their reported earnings for the past 12 months. That’s not much above the 50-year average of 19.3—and hardly outrageous, given today’s modest bond yields.
But you could also argue that U.S. shares are horribly overpriced. The S&P 500 stocks today offer a dividend yield of just 1.9%, versus a 50-year average of 2.9%. Shares also seem pricey compared to both the value of corporate assets and average company profits for the past 10 years.

I OFTEN TALK WITH estate planning attorneys—and they tell me that individuals typically complete an estate plan just twice in their lives: upon marriage and upon retirement.
On the one hand, this is good. Major life changes warrant a review of your estate plan and an update to key documents. On the other hand, this is not so good. Much like other areas of your financial life, your estate plan needs to be reviewed on a regular basis.

I’M A DEADBEAT. That’s what companies call people who pay off their credit cards in full every month and hence don’t incur interest. But I’m more than that. I’m a leverager. I leverage points and stars and credits everywhere I go.
Let me count the ways.
When I go to the gas station, I use my American Express card and my Exxon rewards card. I get credits from Exxon for buying the gas, which I apply to future gas purchases,

IN MARCH, I DROVE off the Tesla lot in a new Model 3 with Ben Franklin’s quote in my head: “So convenient a thing to be a reasonable creature, since it enables one to find or make a reason for everything one has a mind to do.”
Elon Musk had just announced availability of lower cost versions of the Model 3. After eight years of waiting for a Tesla that would cost less than my first home,

I WAS LISTENING recently to the Beatles’ song, “She’s Leaving Home,” and I wondered what I would tell a young person starting life on his or her own. If I had a few minutes before he or she walked out the door, here’s what I would try to say:
Relationships. Your personal relationships will matter most in your life. Choose your significant other and friends carefully. They will be your moral compass,

EVERY GENERATION faces its own unique financial challenges—and my generation has, so far, had a particularly rough time. Consider a 2018 report by the Federal Reserve Bank of St. Louis, which looked at the connection between birth year and financial well-being.
Some 48,000 families were divided into six groups based on their birth decade—from the 1930s to the 1980s. I was born in 1987 and hence belong to the 1980s cohort. The Great Recession affected all generations,

I RECENTLY HAD the opportunity to attend a panel discussion that included the prominent investment manager Seth Klarman.
Not familiar with Klarman? The simplistic version of his biography has him as a hedge fund billionaire. While that’s true, it doesn’t do him justice. Klarman is more like a cult hero, at least in the investment world. Some call him the “Oracle of Boston.”
Google his name, and you’ll see him described as “the next Warren Buffett.” Search YouTube,