ACCORDING TO OXFORD Languages, the word invest means to “expend money with the expectation of achieving a profit.”
I like this definition better than some others because it includes the word “expectation,” which therefore should exclude casino gambling and sports betting. But what if you have an expectation of winning? Couldn’t casino gambling and sports betting both be considered investments? As Zach Galifianakis’s character said in The Hangover, “It’s not gambling if you know you’re going to win.”
How can one create this expectation?

THEY SAY THAT TAKING a cruise is a poor man’s idea of a rich man’s vacation. As an unsophisticated traveler, all I knew of cruises were the glowing reports I heard from others who had taken them—and the romanticized versions I saw in the movies.

 My aspirations were based on a movie I saw starring Doris Day, Romance on the High Seas. It’s about a glamorous, adventurous and romantic cruise with beautifully dressed people,

THIS IS MY FIRST article for HumbleDollar. I’m new to the site, but not new to writing for the public and, indeed, I’ve contributed regular columns to some small newspapers.
My life has had more twists and turns than going down a Kentucky country back road filled with hillbillies, of which I am one. Kentucky is either the poorest state in the country or next to it by any measure you want to look at.

PERHAPS YOU’VE SEEN charts like the one below, which comes from Dimensional Fund Advisors. The message: Investors who try to time the market in search of better returns often end up damaging their results. To many investors, this seems intuitive, because trading isn’t easy.
But to others, market timing appears to make a lot of sense. For instance, for years, Yale University professor Robert Shiller has been maintaining a measure of market valuation known as the cyclically adjusted price-earnings (CAPE) ratio.

I DON’T TRACK MY finances that closely and I don’t make big financial moves very often. Partly, it’s because I’m so busy with other things. But partly, it’s because I’ve come to see the virtue in benign neglect.
Still, this is shaping up to be a surprisingly busy year. I’ve taken a handful of financial steps—with three key goals in mind:
No. 1: Prepaying retirement. Like many others as they approach retirement,

NASSIM NICHOLAS TALEB has written a trilogy on the topic of chance: Fooled by Randomness, The Black Swan and Antifragile. I didn’t find these three books to be easy reading, plus Taleb has strong opinions, which may turn off some readers. Still, there’s a host of investment lessons to be culled from his works.
Taleb argues that randomness plays a powerful role in financial markets and,

MANY RETIREMENT savers fund tax-deferred accounts—with good reason: The money we contribute pre-tax to an IRA or 401(k) reduces our taxable income, plus that money grows tax-deferred until withdrawn.
But there are two lesser-known benefits that are worth keeping in mind. First, with IRAs and solo 401(k)s, you can contribute for last year right up until the tax-filing deadline in April of the following year. That means you can calculate your tax bill, make an IRA contribution that’s credited to last year—and voila—cut the tab you owe Uncle Sam.

MY FATHER-IN-LAW Carson was a stereotypical engineer—organized and precise. All four of his children know the motto “measure twice, cut once.” Carson applied these traits to his finances, which he managed on behalf of himself and Mary Jean, his wife. Mary Jean depended on this.
As they aged, Carson maintained his mental acuity, but he was the first of the two to deteriorate physically. Mary Jean was strong physically but slowly surrendered to Alzheimer’s.

I CAN’T TAKE IT ANY more: I need to rant about health care.

There’s absolutely no reason to continue the current health-care payment system, none, not one. Where’s the rationale for having private insurance, Obamacare, Medicare, Medicaid, TRICARE and the Children’s Health Insurance Program (CHIP)? Each was developed to deal with the same issue—paying for health care.

Some form of Medicare for all, or M4A as it’s sometimes known, is the only system that makes sense.

WE BEGAN IN 2019 to think seriously about what we wanted our retirement to look like. My husband had retired in 2018. I was aiming to leave my job in 2022. We were hoping to have a plan in place long before my final day of work.
Our first step was to decide where we wanted to live. We were both eager to escape the Pacific Northwest, so we zeroed in on a couple of potential destinations.

I GREW UP IN A SMALL three-bedroom home, the youngest of 14 children. I was always sharing a bed with one older brother or another. My father drove a garbage truck for the county and my mom washed dishes in the school cafeteria.
Money was hard to come by and, when it was in hand, it needed to be spent wisely. My parents engrained in me the importance of education, although neither had a high school diploma.

AS I SURF THROUGH my streaming channels, I wonder if I’m paying too much for too much.
Do you feel overwhelmed by the choices on Netflix and similar services? Are your personal watch lists constantly expanding because a channel keeps suggesting shows you might like? Even in retirement, who has that much time to spend? Before you know it, some shows on your list have disappeared—and you’re wondering whether you’re getting your money’s worth
I still believe streaming is a bargain compared with the outrageous cable bills I once received.

IN GRADE SCHOOL, when my mother asked me what I wanted to be when I grew up, I recall saying “entrepreneur.” I’m sure she would rather I’d said “doctor” or “lawyer.” But the thrill of building something new and providing something of value to others has always appealed to me.

My first entrepreneurial memory was selling Entenmann’s donuts and coffee to captive motorists waiting on long gas lines during the energy crisis of the 1970s.

IN THE NETHERLANDS in 1602, the Dutch East India Company conducted the world’s first initial public offering. Then, in 1610, the Netherlands saw the issuance of the first ever stock dividend. And in 1611, when the Amsterdam Exchange opened, the Netherlands became home to the world’s first stock market. Throughout the 1600s, the Netherlands continued to see further financial growth and innovation.
During that period, the Dutch economy was among the world’s largest. But its dominance faded over time,

I WAS AT WORK WHEN my daughter called. “Grandpa was taken to the hospital in an ambulance, and you need to meet Mom and Grandma there as soon as you can.”
I entered the hospital room 45 minutes later, and I saw my mom in tears standing next to my dad’s lifeless body. Dad’s hair and face were spotted with wood chips and dirt, and he was wearing a torn flannel shirt and old blue jeans.