MANAGING MONEY IS about managing risk. But which risks? We all have a different collection of financial worries, and that drives the investments we buy and the insurance we purchase.
Problem is, every choice we make comes with a tradeoff. If we seek to fend off one risk, we often open ourselves up to other dangers. Consider five such tradeoffs:
1. Dying young vs. living long. When should we claim Social Security?

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.

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.

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.

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,

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.

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.

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.