I BECAME INVOLVED with employer health benefits in 1962. Back then, my job was to screen medical claims before sending them to the claims’ administrator for processing.

In the decades that followed, I designed, negotiated and managed health plans for a company with 15,000 employees and 4,000 retirees. My job was twofold: to make sure the health benefits were working correctly and to manage costs. The first goal was relatively easy. The second was nearly impossible.

DO YOU SEE THINGS clearly when it comes to money? Here’s a test to find out. Which of the following scenarios would you prefer?

A 5% raise, but the inflation rate is 10%.
A 3% salary cut, but the inflation rate is 0%.

If you chose the 5% pay raise, you’ve fallen victim to a “money illusion.” This term describes our tendency to view money in nominal terms instead of inflation-adjusted “real” terms.
In the first scenario,

ROUGHLY 20 YEARS AGO, I left the world of corporate finance. I saw some of the ugly, high-fee undiversified products many of my friends owned—and how those differed from the ultra-low cost, disciplined investing at the companies where I had been a financial officer. I wanted to change things.
But after two decades, I’d say I’ve struck out. Still, there are lessons to be learned from my failures, as well as some encouraging changes occurring within the financial industry.

BEFORE I BECAME a devotee of index funds, I began my investing journey in commodities, with a focus on commodity miners and producers. These firms extract a variety of goods from the earth, including precious metals like gold and silver, as well as energy-related commodities like oil, natural gas and uranium.
As a college student first studying the markets, I was drawn to the outsized returns that can occur in a commodity bull market.

I’VE USED QUICKEN since the DOS version, with my first entry made in August 1992. I’m trying to decide if I qualify as a power user. The fact is, there are so many Quicken features that I simply don’t use.
The product was first released in 1984 as a basic digital checkbook. It later moved to Windows and it’s now a subscription service. I love the ability to manage my checkbook, but over the years Quicken has added features aimed at managing my entire financial life.

HAVE YOU EVER MADE a plan and then had it go awry? Like the car breaking down on the highway when you’re driving to Christmas dinner, as happened to me several years ago.

Stuff happens. That’s why I can’t understand why many people preparing for retirement seem to have unwavering confidence in their planned budget—one that’s often generated using software or a spreadsheet.

Hiring a financial advisor may help. But for that advice to bolster your chances of success,

IT WAS 2010, I WAS age 52, I’d just divorced—and I found myself with neither a home nor a fulltime job.
As part of the divorce, we’d sold the house. Between the cash from that sale and some savings I’d amassed when I was single, I had a modest nest egg. I also had a teenage daughter who needed to stay in our current school district.
The rent on my lovely two-bedroom townhouse was devouring my savings.

EVERY MARKET DECLINE is different, but all of them can feel unnerving, even for the most steadfast of investors. Spooked by 2022’s financial market turmoil? There’s good news: Stock and bond values today look much more compelling than at the turn of the year.
Thanks to 2022’s 14% drop, the S&P 500 now trades below its five-year average price-to-earnings (P/E) ratio, based on expected profits. On top of that, corporate earnings rose impressively in this year’s first quarter.

IN A NOTE TO CLIENTS last week, Deutsche Bank analysts wrote that they expect a “major recession.” What should you make of ominous predictions like this?

First, don’t panic. Yes, Deutsche Bank is a big institution. But it’s worth noting that last week two equally prominent institutions also weighed in—with a different point of view. Goldman Sachs argued that a recession is “not inevitable.” UBS wrote that, “We do not expect a recession.” They can’t all be right.

IF PAST YEARS ARE any guide, about 40,000 shareholders will be in Omaha, Nebraska, today for Berkshire Hathaway’s 2022 annual meeting. I first went 35 years ago.
While working as a financial advisor in the mid-1980s, I began to read about the investment success of Warren Buffett and Charlie Munger. At the time, Berkshire’s stock sold for around $2,700 a share. Yesterday, it closed at $484,340.
I bought one share—and then booked a flight to Omaha for the 1987 stockholder’s meeting.

WHEN I GOT MY FIRST job in 1976, my employer didn’t offer a 401(k) for one simple reason—the plans didn’t exist. By 1985, a new employer did offer one, so I signed on.
Where had the 401(k) come from? Well, I met the man who put the K into the tax code, and he was beyond humble about it. In fact, he’d forgotten all about it.
Barber Conable Jr. graduated at age 19 from Cornell University to join the Marines Corps in World War II.

“ENOUGH” IS a powerful notion. Unfortunately, it’s largely absent from financial conversations.
The concept is rooted in deep self-awareness. It asks the question, how much do I really need to be happy? I believe we should ask this more often because, if we don’t, culture will fill in the blank—and the default answer will be “more.”
Enough has two dimensions. The first dimension is about spending. Too often, we succumb to the hedonic treadmill—the endless pursuit of the next thrilling purchase,

WITH THE MARKETS in a tizzy this year due to roaring inflation and the war in Ukraine, I’ve been kicking myself for not listening to my gut. At issue: an investment decision I made last fall.
When I left the corporate world in September, I took with me the 401(k) balance I’d built up over my five years with my former employer. I’d been aggressive with my investment choices in that 401(k), stashing half the account in Vanguard Small-Cap Growth Index Fund (symbol: VSGAX) and half in Vanguard Mid-Cap Index Fund (VIMAX).

RULES OF THUMB and conventional wisdom often serve us well. But we should make sure they’re truly applicable to our situation.
Like many parents, my wife and I prepared our first estate planning documents when our children were young. The estate planning lawyer suggested a so-called AB trust. If we’d taken his advice, when one of us passed away, half of our joint assets would have gone into an irrevocable trust. The surviving spouse would get the income from that trust,

WELL, I’M SIX MONTHS into my retirement from the corporate world. How are things going? Any regrets? Any big surprises?
No regrets, for sure. I knew that leaving the workplace at age 61 would be a tradeoff of freedom gained versus money forgone. But I had a second-act dream to pursue—becoming an author—and, for me, that tradeoff was worth going for. So far, it has been. I have my first book out and another in the works.