THIS IS THE STORY of how I thought I’d successfully timed the market—but didn’t.
I started investing in 2007, when the stock market peaked, which wasn’t great. But then came 2009 to 2019. Stocks enjoyed the longest and one of the strongest bull markets in history, averaging some 15% a year. Thanks to that great bull market, my wife and I found ourselves with more in our taxable mutual funds than we owed on our home mortgage.

IN THE ONGOING battle between those who believe that the stock market is in a bubble and those who don’t, you may have heard mention of something called CAPE, short for cyclically adjusted price-earnings ratio. Among market indicators, it has the strongest track record in predicting future market returns.
What does the CAPE ratio say about today’s market? It’s flashing red. According to CAPE, the U.S. stock market is more overpriced today than it has been at any time since the 2000 market peak.

ARE FINANCIAL MARKETS in a bubble? It’s a question I’ve never liked. I believe stocks and bonds are fairly valued most of the time, which means it’s extraordinarily difficult to beat the market averages and our best bet is to buy index funds.
But at the same time, during my adult life, there have been three key occasions when markets lost touch with reality: Japanese stocks and real estate in the late 1980s, technology stocks in the late 1990s and housing in the mid-2000s.

I RECEIVED A LETTER from the Social Security Administration telling me I need to apply for benefits immediately. I turn age 70 this year and there’s no advantage to delaying my benefits any longer.
How does reaching 70 feel? I know I get cold easily and don’t move as fast when I’m exercising. I’m also not as sharp mentally. But I’m actually looking forward to my 70s. It will be a decade more about living and with less thinking about money.

THERE’S SOMETHING very emotional about our homes—and how we think about their value. Take the conversation my wife and I had a couple of weeks ago.
“Did you see the house behind us went up for sale this week? They have it listed at 141% more than what we paid for our house.”
“Well, there’s no way their house is worth that much.”
“Oh really? I just talked to our neighbor—the one who’s a realtor—and he said they had five offers the first day it went up.

WANT TO RUFFLE SOME feathers? All you have to do is utter “FIRE movement” on social media or in a crowded room of financial advisors. FIRE—short for financial independence/retire early—has grown ever more controversial as rising stock prices have fattened the portfolios of super-savers and brought their early retirement dreams closer to reality.
I fit the mold of the super-saver. I’ve saved 90% or more of my after-tax income over the past few years.

OVER THE PAST TWO decades, investors have increasingly shunned actively managed mutual funds, instead embracing index mutual funds and exchange-traded index funds. This has led to a contrived debate over whether active or passive investing is better.
My contention: It’s wrong to position indexing as somehow the mirror opposite of active management. Why? Even if you eliminate active mutual fund managers and their fees from your portfolio, you still need to grapple with three crucial investment decisions—all of which involve the sort of judgment call active investors must make.

IF YOU’VE EVER RENTED a car, you’ll inevitability have heard the collision damage waiver (CDW) sales pitch. It sounds something like this: “I assume you want us to protect you bumper to bumper on the car, right?”
If you say, “yes, please,” then—for anywhere between $10 and $30 a day—the rental car will be covered for losses due to theft or damage, except for damage to certain portions of the car. Hint: Read the fine print.

AT LEAST ONCE A DAY, I find myself saying, “Another truism of financial planning is….” To be honest, I don’t know whether the 12 concepts below meet the strict definition of “truism,” but I’ve found them hugely helpful in navigating the world of personal finance:
1. There are always two answers to every question. There’s the mathematical answer and there’s the “how do you feel about it” answer. It’s okay—and, in fact,

AS A BANKER, I GOT a ringside seat from which to watch the many ways that people are separated from their hard-earned money. Some are illegal. Some are legal, but unethical. And many, while legal and ethical, would be unnecessary with a little more knowledge about managing money.
For me, the most disturbing experiences were when scammers extracted money from the naïve and innocent. I’ve seen the pain of customers who found out that their elderly mother had given her life savings to a manipulative TV preacher.

DURING MY SCHOOL days growing up in India, my exposure to English literature was confined to textbooks that reprinted essays and short stories, or portions thereof. One of them was a humorous piece by Stephen Leacock from his book Winnowed Wisdom.
The excerpt was titled “Old Proverbs Made New” and it seemed funny even to a middle-schooler with a limited grasp of the English language. It argued, with examples, that proverbs get outdated and need to be rewritten.

MY FIRST JOB AFTER college was at a global engineering firm. A roommate also worked there. It was a tedious office job, but my bosses thought I had potential and encouraged me to study engineering, which I didn’t.
Instead, I quit and went to graduate school to study linguistics, a field where I observed the most professors having the most fun. My last paycheck at the engineering firm included an extra sum. It was a refund for a retirement account that had failed to vest because I hadn’t stayed long enough.

WHEN WE MOVED to California from India in spring 2014, it was a culture shock—and not just because of the much higher standard of living. Financial life in the U.S. is very different. Here are just some of the surprises that my husband and I have encountered over the past seven years:
Health care. I remember walking into my first U.S. doctor’s appointment. I froze—unaware that I had to pay a $50 copay for each visit,

MY FATHER WAS A CAR salesman who, for many years, worked totally on commission, with no paid vacation. In 1953, when I was 10 years old, we went to Cape Cod for a week. A friend gave him a tip on a great place to stay. In his enthusiasm, my father booked for a week and paid in advance.
The place turned out to be worse than a Second World War army barracks. My mother refused to stay.

I KEPT THE LANDLINE number that my mother had when she was alive. I thought there might be friends I wasn’t aware of who would try to phone her. Indeed, I received calls from people like Helen who lives in Arizona, Cheryl in Colorado and Jan from Michigan. Eventually, however, the phone went silent, except for those annoying sales calls.
But I still kept the phone number. I just couldn’t give it up. It was costing me an extra $50 a month,