I HAVE A FRIVOLOUS routine. I buy $40 in lottery tickets on the first day of each month. Many years ago, this was part of my retirement plan—the years when I was young and foolish, or maybe just foolish.
For as long as I can recall, I’ve had a premonition of receiving $14 million, either from a long-lost relative or from the lottery. Time is running out, however. That relative appears to have forgotten about me.

THE STOCK MARKET recently hit yet another all-time high. But instead of unalloyed glee, many investors are struggling with mixed emotions. They’re thrilled at their gains. But at the same time, they’re hesitant to put more money into a market that has already gained so much.
Result: Folks have been asking, “Isn’t there anything else I can buy?” Often, this leads to questions about alternative investments. Below is an introduction to the topic,

WE CAN GATHER financial facts and research issues. But what we learn will always be tainted by what we’ve experienced.
As I mentioned last week, anecdotal evidence often proves more powerful than statistics. I’m talking here about the same phenomenon—but writ larger. What we read in articles and books is scant competition for the informational scraps we collect throughout our lives: the comments our parents made, the milieu we grew up in, the stories we hear from colleagues,

I WILL NEVER FORGET that New Year’s Day nearly two decades ago. My life changed forever in a matter of minutes. I received in lightning bolt fashion the devastating news that my wife of nearly 40 years was filing for divorce. Looking back, I should have seen it coming. But at the time, I was totally unprepared. I didn’t know it then, but I was part of the initial wave of “gray divorces.”
No football bowl games that New Year’s Day.

I FEEL WEALTHY. I spent the morning in an upscale shopping mall where, as you stroll along, you can see Bentleys on display. Even the store clerks are a bit snooty. Once I was shopping for a gift and the clerk asked if I could afford the handbag I was considering. I guess, on that occasion, I didn’t look wealthy enough.
When I go shopping with my wife, I don’t feel wealthy. Instead, all I see are items we shouldn’t buy.

USING HIS CONTACTS and connections, our son landed an interview with a New York City health-care system. He was hired as a business analyst and started work in August 2016.
Along with his roommate—also a graduate from the University of Pennsylvania—our son chose to live in Jersey City, N.J., because it’s cheaper than Manhattan, plus his roommate’s job required that he split time between Newark, N.J., and Manhattan. The rent on their 600-square-foot apartment was $2,500,

KANYE WEST, IT TURNS out, is one heck of an investor. According to a recent analysis, a group of West’s stock picks has beaten the overall market by 40 percentage points this year. It’s an astonishing result. What, if anything, can we learn from his performance?
First, some background: As you may know, West is married to Kim Kardashian, who is one of the dominant personalities on social media, so it was via Instagram that the world gained a window into these investments.

YOU MENTION TO a colleague that longtime smokers shorten their life expectancy by an average of 10 years. Your colleague responds by talking about his grandmother who smoked a pack every day until she died at age 98. We all know that the statistic should trump the anecdote. But on the conversational scoreboard, it’s one point for both sides—and, three weeks later, you can’t help but recall the grandmother’s story.
The same thing happens with personal finance all the time.

GETTING INTO COLLEGE is a complicated business—and it doesn’t get less so once your teenager is accepted. There are countless financial challenges and discussions related to tuition, ongoing expenses, buying books, transportation and more. For us, all the logistics were a little more involved, because our son decided to attend the University of Pennsylvania, away from our home state of North Carolina.
In addition to the “big stuff,” we wanted to make sure our son was successful managing his everyday finances.

I’M IN THE PROCESS of moving into a 55-plus condo community—in my case, way plus. The property taxes on my new condo will be $12,200 a year, the bulk of which goes toward the local school system. But here’s the thing: No one in the community has children in school and hasn’t for decades. That got me to thinking. Why can’t we just buy the services we need from the town?
Years ago, I felt quite differently.

SHORTLY AFTER I retired, my father was diagnosed with lymphoma cancer. I would spend the next three years helping my mother take care of him. After my father passed away, my mother was emotionally devastated and her health started to decline. It has been nine years since I retired, and most of that time has been spent taking care of my parents.
It’s one of the hardest things I’ve ever done. It takes compassion,

MY SONS’ BASKETBALL coach, George, has a favorite expression: He talks about “working through the uglies.” When you’re developing a new skill, he says, you shouldn’t expect to be perfect the first time or even the second. But if you keep working at it, over time there will be progress, “from ugly to not-so-bad to decent to good and then, eventually, to great.” The message is clear: You can’t rush it, you can’t skip steps and you have to start with the basics.

WHEN I WAS a columnist at The Wall Street Journal, I repeatedly heard two complaints from editors, especially those with little understanding of personal finance: “Our readers want something more sophisticated” and “Where’s the news hook?”
That, in a nutshell, explains why the media can be so bad for our financial health. When print and broadcast journalists cave in to the twin imperatives of timeliness and sophistication, they’re almost guaranteed to lead their audience astray—for three reasons:
1.

IF YOU READ ARTICLES about adding your children to your credit cards as authorized users, there will often be experts quoted, offering all kinds of dire warnings. They’ll say you need to make sure your child is responsible and won’t go on some crazy shopping spree.
We had no reason to think our son would do that—but we also didn’t see any reason to take the risk and put temptation in his wallet.
As I mentioned in my previous article,

WE’VE ALL HEARD the expression, “the house always wins.” Does it? The evidence suggests that some casino players can consistently come out ahead. Hard to believe? Pick a casino game that has a definite element of skill and a low house “edge,” and you, too, can be paid to play a game you enjoy. I know what I’m talking about: I have enjoyed free vacations at the expense of casinos for almost two decades.