HOW DO SOME INVESTORS end up in places they don’t belong? Where do they turn for information and guidance? Who do they talk to before making important financial decisions?
What follows are the results of my unscientific research, which was conducted in some of the finest and most respected centers of advanced learning anywhere.
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FOR MY BIRTHDAY this year, my wife gave me a card that declares, “Not Dead Yet.” That might sound morbid, but I laughed. The reason: My wife had misinterpreted something I used to say to colleagues at my final job.
When they saw me at the coffee machine, they’d often ask, “How are you doing, Dave?”
Instead of saying “fine,” I used to say, “I’m still breathing. Count your blessings. Blessing No. 1: I’m still breathing.”
In many cases,

MOM AND DAD WERE products of the Great Depression. I feel like it affected every single day of their lives. Despite their difficult upbringing, they made good financial decisions that allowed them to live comfortably. Part of it was because Dad worked for the same company for almost 42 years. His pension paid him more than I earned in my first job as an engineer.
When Mom died in August 2004, she was almost 84.

JANE IS A SINGLE woman in her 80s, sharp and friendly. She’s a former state employee with a solid retirement income. Unfortunately, she’s suffered some health issues in the past few years that have forced her to make serious changes.
I became aware of her issues when she came into the local AARP TaxAide site where I volunteer. She was the last client of the day, and the other scheduled client had rescheduled, so she got our full attention.

I HATE BEING IN DEBT. It makes me feel anxious and uncertain, as though my finances are out of my control. If I don’t pay all my bills in full every month, I feel trapped, and I’m endlessly restless until I get free.
I understand that other people manage their finances quite differently, and are happy to pay their bills in installments. Not me.
Years ago, I made a small bet on a minor thing.

ONE OF THE POSITIVE outcomes of my unsuccessful life: I’ve had an incentive to study ways to be successful.
Among the self-improvement materials I’ve looked at, many have titles like “how to become…” or something similar. The good ones are easy to understand and make you feel it’s possible for you to achieve whatever they’re selling.
When the material is delivered in person, you get the advantage of a great presentation from a dynamic public speaker.

MICK JAGGER IS AMONG the most successful entertainers of our time. But despite his wealth, Jagger tells his eight children that they’ll need to make their own way. Similarly, Shaquille O’Neal tells his children that they can earn some of his millions, but it won’t necessarily be given to them. Actor Jeff Goldblum puts it more bluntly: “Row your own boat,” he’s said. Other public figures have echoed a similar theme.
Why do these wealthy folks take such a seemingly uncharitable view?

SUPPOSE YOU KNEW you’d live until at least age 90. How would that change your thinking about retirement?
It seems most of us focus less on the possibility of a long life and more on the risk of an early death. This grim view is buttressed by endless anecdotal evidence—celebrities who pass away in their 40s and 50s, terrible accidents that take multiple lives, old classmates and colleagues who die at tragically young ages.

I’VE ALWAYS BEEN a saver, and perhaps even pathologically frugal. Growing up, it pained me to spend money, even on food when I was hungry. Today, I have more than enough money, but I still resist paying full price for food.
Perhaps I’m just genetically frugal, or perhaps my feelings about money reflect my parents and my upbringing. My mom once shared that her aunt predicted that she’d make lots of money, but it would be like grains of rice and slip through her fingers. Meanwhile,

WHAT WILL BE YOUR legacy? This is something I’ve given a lot of thought to—right down to the funeral instructions.
Something I’ve learned through hard experience: One of the greatest gifts we can give to our families is a well-organized and well-communicated estate plan. They’ll appreciate it when the time comes.
Too many of us wait until an emergency to try to get our affairs in order. A severe illness or death is stressful enough.

I’M A SUCKER FOR those “10 best” lists. But are they accurate?
What if you had the best job in a poorly rated company? Would that be better than the worst job in a well-rated company? What if you move to a bad neighborhood in a well-rated city? Would that be better than an excellent neighborhood in a poorly rated community?
You get my point. Even among the worst, you can find some real gems.

I’M TYPICALLY FRUGAL and financially cautious. But this past January, I became reckless. No, it wasn’t love, at least not the ordinary kind. Rather, I saw a photograph and made an offer of $48,000 on a “park unit” located 1,000 miles from home.
Park unit, I learned, is a technical term for a variant of what I’d call a mobile home. My first task was to look up the term, so I’d know what I was offering to buy.

I MARRIED CONNIE because she’s four years older than me. That meant our life expectancies would be similar and hence a survivor annuity would be less expensive.
I am, of course, joking. Sort of.
Providing for Connie, should I be the first to go, is among my top financial priorities. During my working years, I received far too many calls from new widows who had just learned their husband’s pension stopped when their husband died.

DURING A RECENT VISIT to retired friends in Florida, I learned about YouTube TV, a streaming service from Google with more than 85 channels. I decided to try it when my wife and I returned home. I initially kept my TV trial private. I wasn’t ready to introduce the idea to my wife, who doesn’t like change and would rather just stick with cable TV.
I thought YouTube TV worked well. I still had to sort a few things out,

WHAT THE HELL WAS I doing all those years?

That’s the riddle that confounded me when I retired eight months ago. Much to my surprise, I didn’t find myself wandering in the desert of despair, missing my crowded email in-box. I was not bereft without staff meetings, diversity training, team-building exercises, cupcake Fridays. I felt not the slightest urge to lean in, stand up or spend any more time with management consultants.

I had a wonderful career as a financial journalist and public relations professional,