I DON’T THINK my parents ever had any sort of five-step plan to teach me about money. I was always parsimonious, so they weren’t very focused on how I spent. They did, however, teach me two powerful life lessons—which changed not just the way I thought about money, but who I am.
Everything has a cost. I attended private school from fourth to ninth grade, coasting by with B plusses and A minuses.

I RECENTLY RECEIVED an email from a friend asking, “What financial advice would you give to your younger self, now that you’re older?” I had to think for a while. But once I sat down to reply, I realized my attitudes about personal finance were already well-developed by the time I was in my 20s. I also realized my financial beliefs had been shaped, in part, by growing up in a family where money wasn’t exactly plentiful.

AS I THINK BACK over the past three decades, I have one overriding investment regret.
No, it has nothing to do with the investments I bought. For much of the past 30 years, I’ve owned a globally diversified portfolio, with 100% in stocks when I was younger and closer to 70% now that I’m in my mid-50s. Initially, I owned actively managed funds and a few individual stocks, but I substituted index funds as they became available,

I WAS STAYING on the outskirts of Mexico City, with no internet access. But I had my satellite radio and I was listening to CNBC. The reception wasn’t good, but the news was even worse. While bad financial news had been pouring in from every corner of the globe for months, it seemed matters had suddenly got much worse. It was September 2008.
The global financial crisis affected many companies, big and small, and the commercial landscaping company that my twin brother and I owned was no exception. 

HOUSING IS THE biggest expense for most American families, typically devouring a third of their budget. Are those dollars getting spent wisely? Here are 10 questions to ask yourself:

Should you buy? If you play around with the mortgage calculator at Bankrate.com, you can figure out how big a mortgage you could support with your monthly rent payments. That will give you a sense for whether homeownership is within reach. Even if it is,

I HAVE BOOKED eight one-way domestic flights this year, as well as multiple hotel nights—and I’ve done it all with the rewards points from my three Chase credit cards.
For those interested in earning rewards, you can’t go wrong with the dependable duo of Chase Sapphire Reserve and Chase Freedom Unlimited. Small business owners might also pick up Chase Ink Business Preferred.
The Chase Sapphire Reserve, the “premium” card of the trio, first made waves in August 2016 when it offered a 100,000-point signup bonus for those who spent $4,000 in the first three months.

WANT TO EARN THE derision of the so-called smart money? Here are 12 ways to get yourself labeled a financial rube:

Express optimism about the stock market.
Stick with capitalization-weighted total market index funds.
Pay off your mortgage early.
 “Arnott vs. Asness? Missed that one. Was it on pay per view?”
Shun alternative investments.
Buy and hold.
Have no opinion on the economy and market valuations.
Dollar-cost average.
Own a target-date retirement fund.
Never cite Ben Graham,

SAVING ENOUGH FOR retirement, and then turning those savings into a reliable stream of retirement income, together constitute our life’s great financial task. Want to make sure you’re on track? Here are 10 questions to ask:

Are you shortchanging your retirement by devoting too much of your income to other goals? For instance, can you truly afford private school for the kids? Do you really have the financial wherewithal to buy a second home?

SETTING OUT INTO the business world, I was age 27 with a negative net worth. Among life lessons, there are many strong contenders, but nothing introduced me to “adulting” like debt. For that, I had undergraduate and graduate school expenses to thank.
Having secured a good job out of business school, I started to rebuild my finances. My grad loans had a relatively high principal amount and an interest rate of 6.8%, so I prioritized that debt over my undergrad loans,

IT’S ANECDOTAL evidence, so take it with a grain of salt. Still, I’m once again hearing a dangerous argument—that you should always carry the largest mortgage possible, so you have extra money to stash in stocks.
During the roaring bull market of the late 1990s, and during the booming market for stocks and real estate in 2005 and 2006, readers regularly wrote to me, making the same argument. The strategy isn’t without logic—and it isn’t necessarily a sign that stocks are about to crash.

WHEN AN INVENTOR goes on record stating that his invention is “a monster” that he’d like to “blow up,” you know there’s a problem.
Such is the case with Ted Benna, who back in 1980 created the first 401(k) retirement plan. Since then, his invention has grown to become the dominant retirement vehicle for millions of Americans.
Why is Benna so negative on his creation? The problem, in a word: complexity. According to Benna,

SHORTLY BEFORE MY first child was born some two decades ago, I read a newspaper column urging parents to begin saving for college early in their children’s lives. Today, my son is not far from getting his bachelor’s degree in engineering, debt-free and (fingers crossed) with a bit in the bank for his master’s degree. My daughter starts college this fall and is on track for the same outcome.
I feel like we’ve been a real life middle-class experiment,

OVER THE 50 YEARS through year-end 2016, the per-share profits of the S&P 500 companies rose a cumulative 1,604%, equal to 5.8% a year, while inflation ran at 4.1%. If share prices had climbed in lockstep with corporate earnings, $1,000 invested at year-end 1966 would have been worth some $17,000 at year-end 2016. On top of that price appreciation, investors would also have collected dividends.
But in fact, over this 50-year stretch, investors fared far better.

FOR MORE THAN 20 years, I was a homeowner. Like most people, I had a love-hate relationship with the houses I owned. I loved building home equity in the two fixer-uppers I lived in. I loved knowing my mortgage payment would stay relatively constant from year to year. But I never enjoyed yardwork and I hated dealing with unexpected repairs, including replacing an aging sewer line in one house—to the tune of $10,000.
After I got divorced,

IT WAS APRIL 29, 2009. My 12-hour workday had already begun when, at about 4:30 a.m., I received the call from Jonathan, my younger brother. He never calls at that hour. In fact, we never phone without first texting each other to determine the best time to talk. I sensed bad news and sure enough it was. Our father had been killed 36 hours earlier while riding his bicycle. In the months that followed,