MY LIFE’S GOAL WAS to make money. I make no apologies for this. I’m not particularly gifted in this pursuit, but I did persevere.
I take satisfaction that I stuck to my goal despite all obstacles. There were many trips, falls, mistakes and failures along the way. I had to work hard and seek a new job each time my old employment ended. I set out to do something—and I did it.
That all changed when I retired.

THE WAVES AND WEATHER are always changing on the coast of Maine. Last summer, I paddled my canoe to a nearby island in the sun, and two hours later had to feel my way back through a fog that hid the mainland.
There are longer-term forces at play here, too. The black mussel beds I steered around as a child are all gone now. So is the sea grass that made a good hiding place for crabs.

I have been pondering for a week whether or not to post this out of concern it will be misinterpreted – I have experience with that. 
As Jonathan once told me,  “those who are financially prudent will most likely enjoy success, even if events don’t always go their way.” That’s it for me, mostly prudent and very patient. 
Is it always necessary to follow all the “rules,” to be precise with every financial decision you make,

I’m not much of a musicals guy, but I’ve always loved the song “Try to Remember” from The Fantasticks. Maybe it’s because as a kid growing up in Dallas, my parents took me to see a local production of the show. It ran 42 straight years off-Broadway, quite a record.
The first and best version of the song was by Jerry Orbach, who most folks know as the sarcastic cop Lenny from Law and Order.

BEFORE HE DIED LAST year at age 99, a friend asked Charlie Munger if he planned to leave his considerable wealth to his children. Wouldn’t it impact their work ethic, his friend asked?
“Of course, it will,” Munger replied. “But you still have to do it.”
“Why?” his friend asked.
“Because if you don’t give them the money, they’ll hate you.”
Few of us are billionaires. Still, I find Munger’s comment instructive. It illustrates a reality about personal finance: that the notion of a perfectly optimal answer to any financial question is just that—a notion.

Gosh, is it just me? Am I the only one who wishes that the pace of tech “Progress” would just slow down? I mean, I just updated to the latest IOS version, and I just read that there its another one coming soon and I have yet to use a single new feature from the last one. All these tech changes make it harder to deal with life including ones money. Do you have your ID.ME credentials set up yet?

I’VE BEEN HAVING DOUBTS about some of the financial decisions I’ve made. I don’t know if it has to do with age. They say you tend to lose confidence as you grow older. Life-altering events, such as the death of loved ones, health issues and retirement, can weigh heavily and sow doubt.
For instance, I’ve been thinking about whether I should have sold my condo in 2020, during the pandemic. If I’d kept it, it would be worth quite a bit today.

Every so often, we get an outbreak of generational warfare here on HumbleDollar, with the site’s generally older readership decrying the financial habits of younger generations, while proclaiming that things were so much better when they were growing up.
I find this rather silly. As I see it, people don’t fundamentally change from one generation to the next. Meanwhile, we’ve seen extraordinary progress in recent decades, but that’s also meant new challenges. Consider eight points.

THOMAS JEFFERSON once said that eternal vigilance is the price of liberty, and the philosopher Socrates opined that the unexamined life isn’t worth living.
Although they were talking about political freedom and personal philosophy, respectively, Jefferson and Socrates could well have been discussing personal finance. One of the best ways to engage in financial vigilance and self-examination is to keep a daily financial journal.
I’ve kept a personal journal since I was 14 years old,

As a psychotherapist well-traveled in the talking cure from both sides of the consultant’s couch, I am no stranger to anxiety. And as a former financial advisor, I am well-versed in how it affects financial choices and in particular the decision to select active or passive funds.
Let’s take your friend Dennis, whose attitude toward investing has been shaped by many different and often conflicting factors. Not a completely naïve investor, he listens to inspirational money-making podcasts and watches the market opening on CNBC while brushing his teeth.

A FEW YEARS AGO, I came across an announcement for a blueberry festival in Hammonton, New Jersey. My wife is always up for doing something different, so we made our way there one summer day.
It turned out to be a great way to spend the day and learn the history of New Jersey’s blueberry industry. The industry was founded by a woman looking to expand the crops on her family’s farm around the turn of the 20th century.

Even flying by the seat of one’s pants can work. As Nike says, Just do It!
I claim no expertise in investing, and rightly so. I read and listen about the basics like diversification, bonds vs stock and such, but not much more. 
To me the most important thing is to save and invest and keep doing it which I have done since I was eighteen – 63 years.  Probably more expertise would have meant larger fund balances,

WHO’S YOUR FINANCIAL hero? This should be someone whose qualities and character lend themselves to emulation in your own financial life.
Let’s set some ground rules here for picking a financial hero. First, your hero probably shouldn’t be the usual suspect: Warren Buffett. While Buffett is certainly a very successful investor, the investment game that he’s playing is very different from the one most of the rest of us are.
The same goes for folks like Elon Musk,

I WAS FORTUNATE to find enough time during my working years to pursue various hobbies and other personal interests. My part-time work arrangement allowed me to have four-day weekends. I’d hoped that, after retirement, I would have even more time to take on personal projects.
But surprisingly, I found myself with less free time. Not only was I failing to start new projects, such as writing software for the website of the nonprofit I cofounded,

MOTIVATIONAL SPEAKER Jim Rohn said, “You are the average of the five people you spend the most time with.” His contention: We should carefully pick the folks who surround us because, over time, we’ll become more like them.
Recent research offers some support for this idea. For instance, if we have a close friend who becomes obese, one study found we’re 57% more likely to become obese as well. If that’s so, we might also want to cozy up to skinny friends who count exercise as fun recreation.