I BELIEVE MANAGING money should be kept as simple as possible. That’s usually the route to lower costs, fewer mistakes and greater financial peace of mind. But, alas, three crucial areas of our financial life defy simplicity: health insurance, taxes and paying for college.
This is hardly an original insight. Folks have complained for decades about the maddening complexity involved with all three. All are ripe for a total revamp, but there’s no sign that’ll happen any time soon.

I WAS FIRED OR LAID off 10 times during my career. Why did this happen so often? One reason: I made a decision that I’d never quit a job.
This position was formed during high school when I had a job parking cars at a local Chinese restaurant. I became friends with the guy who’d set up this deal with the restaurant’s owners. While the job was fun, I realized one night that the payment this guy received from the owners wasn’t being divided evenly among all the teenagers parking cars.

THERE’S A SAYING that “perception is reality,” meaning that what you believe is your reality, whether it’s true or not. Changing our perception isn’t easy. It takes effort, along with a willingness to discover and accept facts.
Many Americans’ perceptions are incorrect, leading them to make subpar financial decisions. Consider:

Social Security. Nobody stole the trust fund, it’s not going broke and, yes, it will be there for you.
Medicare. It’s not socialized medicine.

MY UPBRINGING WAS difficult. The alcoholism and rage among adult family members were often at their worst during the year-end holidays, and Thanksgiving could be particularly bad. What made this even worse was that I thought the popular images and ideas about Thanksgiving were accurate descriptions of other people’s good times.

One familiar depiction of Thanksgiving is Norman Rockwell’s iconic painting, “Freedom from Want.” The picture has come to represent the central moment of our Thanksgiving celebration: the roasted turkey arriving at the table as the prelude to eating ourselves into a tryptophan coma.

ZERO-WASTE LIVING. Kondo cleaning. FIRE, or financial independence-retire early. Whatever your feelings are about these three movements, frugality is at their core, with the focus on minimizing possessions and living simply.

To these, you might want to add another, “possum living,” which has been hailed as a manifesto for living cheaply. Possum Living is the title of a book written in 1978 by a free-thinking, resourceful young woman who went by the pen name Dolly Freed.

WHEN THOMAS EDISON was a child, he apparently set fire to a barn on the family’s property. After it burned to the ground, his parents were furious.
“Why would you do such a thing?” his father asked.
Young Edison replied, “I wanted to see what would happen.”
The story may be apocryphal, but I was reminded of it recently when I came across a study titled “Not Learning from Others.” A group of economists wanted to understand more about how people learn.

WE LEARN EARLY ON whether we’re stronger, faster or have better hand-eye coordination than other kids. We might initially harbor dreams that we’ll get better. But after a while, it’s hard to ignore the mounting evidence of our athletic mediocrity.
If only life were always so simple.
I’ve heard parents say, “You don’t have to tell your kids that they aren’t good at something, because the world will do it for you.” That’s true—except there’s an additional step involved: Your kids have to listen.

I LIVE IN CENTRAL New Jersey. Within walking distance of my house are some McMansions—huge homes clustered together in new developments. I look at them and think, “Who cleans these things?”
I live in a three-bedroom ranch-style house with an unfinished basement and a two-car garage. My garage is filled with two cars and my tools. The basement is filled with my wife’s stuff. We bought the house when my wife was pregnant. Thirty-three years later,

THERE ARE CERTAIN expressions I’ve heard during my lifetime which, for one reason or another, have stayed with me. In a previous article, I related how a coworker encouraged me to “keep on keeping on” when confronted with a challenge, and how Napoleon Hill’s expression “burning desire” struck me as a great way to describe a goal worth seeking.
Here’s another expression I’ve never forgotten: “The other side sucks.”
I’ve been a race car fan ever since my older brother introduced me to automobile racing in my youth.

ARE WE ANY GOOD at correctly analyzing simple financial situations involving probabilities? Kenyon, my brother and fellow HumbleDollar contributor, introduced me to a 2016 study that suggests that many of us are shockingly poor at doing so.
Sixty-one business students and young professionals at financial firms were presented with the following scenario: At a website, you’ll be given $25 and allowed to bet on a computer-generated coin flip. You may bet on either heads or tails.

“I ALWAYS MADE EVERY team I tried out for,” lamented a college freshman after failing to make the lacrosse team.
I tried to make him feel better. “I never made any teams,” I said.
His reply: “You’re used to failing. I’m not.”
That response took me by surprise. But I thought about it, and realized he was right. I had struggled all my life in academics, sports, socializing and with the opposite sex. I was getting used to others around me always being better.

MANY FOLKS—ESPECIALLY those still working—think retirement is “living the good life.” The truth is, unless you develop a solid plan for how to enjoy your newly available time, life after retirement can be filled with bouts of boredom, anxiety and even depression. My objective: Forewarn recent and soon-to-be retirees of the emotional dangers that lie ahead—and to suggest a road to a successful retirement.

Retirement isn’t a destination but a journey with three key stops.

“GOD, GRANT ME THE serenity to accept the things I cannot change, the courage to change the things I can, and the wisdom to know the difference.”
No matter what our religious beliefs, we’re constantly bombarded with reasons to invoke the serenity prayer. There are so many things we can’t control: what our bosses decide, what acquaintances say behind our back, how stocks and interest rates perform. This lack of control can be a source of endless anxiety,

WHETHER MONEY BUYS happiness is a matter of debate, but a recent incident reinforced my conviction that financial security does indeed help. The incident would’ve caused me considerable distress a few years ago, when I was earning more but was still dependent on my fulltime job’s paycheck. My newfound financial security, however, transformed the situation into a truly memorable experience.
My wife, Bonny, and I both enjoy attending Indian music and dance performances. We make it a point to see the live shows put on by local groups and,

HOW’S YOUR FRIENDSHIP account balance looking? I spent my life watching my bank account, and taking great pleasure as it grew and grew. I never cared much for what I could buy with the money, but I loved the feeling of security it offered.
Friendships, meanwhile, took a back seat. That was pretty much normal for my family, and maybe it’s more normal for most folks than we like to admit. We have a tight little circle that includes family,