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.

BY THE 1990s, New York City had been in decline for decades. What brought about the city’s recovery? It was, in part, the broken windows theory.
Picture a vacant building with one window broken. Most people wouldn’t think much of it. But this one broken window sends a signal—and, soon enough, others get broken. How do you reverse this decline? It’s easy: You get rid of the broken windows, and make sure things stay that way.

WE ALL HATE LOSING—and life, alas, is full of it.
I’m not just talking about investment losses. There are the career successes we never had, the relationships that didn’t pan out and the purchases that fell short of our expectations. Almost all of us, I suspect, can recall countless situations that turned out less gloriously than we’d initially hoped.
Yet, even though my failures pain me, they don’t stop me from getting up each day and trying again.

I’M RELUCTANT TO ADMIT that HumbleDollar is run using smoke and mirrors. But if someone said that, I’d be hard-pressed to disagree.
I’ve long believed that the principles of sound money management are pretty timeless. What you should be doing with your money this year isn’t a whole lot different from what you should have been doing last year, and the year before that, and the year before that.
This notion is baked into how much of the site operates.

I can’t take credit for the headline here. Actually Jonathan wrote it for my section of My Money Journey.  I like it so much I use it on my blog too.
It articulates one word to me – responsibility, in this case financial and related matters.
We talk a lot about financial literacy and the lack thereof, but I don’t see even that as preventing basic prudent decisions about, saving, spending.
My grandson came home from high school yesterday and told his father the teacher in his financial management class told them to always spend on themselves first.

MY RETIREMENT IN July 2020 came at a stressful time. I was recovering from knee replacement surgery and we were in the midst of the pandemic. Luckily, I had physical therapy goals to meet, and I’d already purchased a huge supply of reading material. TV, music and my laptop were also there to distract me. In addition, my wife had retired eight months before, so we had each other for company.
As the pandemic stretched on,

WE MAKE CONSTANT tradeoffs as we allocate our time and money across our life’s many competing demands. What if we feel like all is not right in our world? We may be confronting the seven choices below—and favoring one option at the expense of the other, leaving us with what feels like an unbalanced life.
1. Between doing what we should and doing what we want. Here, I’m thinking about taking care of ourselves physically.

FORMER NEW YORK CITY Mayor Ed Koch used to frequently ask the city’s residents, “How am I doing?”
When I was younger, I’d ask myself that same question. I was always trying to keep up with others, whether it was socially, academically, athletically or financially. My big fear was that I wasn’t going to make it. I could never let down my guard, relax and take it easy. I was always having to compensate for whatever I was deficient in.