Ten Ways to Simplify

Adam M. Grossman  |  Jun 3, 2023

TODAY MARKS MY 300th weekly contribution to HumbleDollar. Over time, one key theme has emerged: While personal finance can be complicated, it doesn’t have to be. How can you simplify your financial life? Below are 10 ideas.
1. Tracking donations. In the old days, it wasn’t too difficult to track charitable gifts. You would simply refer back to your checkbook. But today, most people use debit and credit cards,

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When to Retire

Dennis Friedman  |  Jun 2, 2023

WHAT’S THE BEST DAY of the year to retire? Many people think it’s Dec. 31. But I used to think my ideal retirement date would be the day in February when the Cleveland Guardians played their first spring training baseball game. What better way to start my retirement than seeing my childhood baseball team in Arizona get ready for the upcoming season? When I wasn’t watching baseball, I could visit the Grand Canyon and Sedona.

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Cheapskates Win

William Ehart  |  Jun 2, 2023

NEW MORNINGSTAR research on bond funds echoes what the late Jack Bogle preached—and proved—for decades: Costs are the greatest predictor of fund performance, not stock or bond selection prowess. In investing, you get what you don’t pay for, said Bogle, Vanguard Group’s founder and creator of the first index mutual fund.

There’s a school of thought that claims it’s easier for active bond fund managers to beat their indexes than it is for their stock fund colleagues.

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The Journey Continues

Richard Connor  |  Jun 1, 2023

I WROTE MY ESSAY for My Money Journey 14 months ago. Since then, our family’s journey has continued apace—including rethinking where we live.
The highlight of the past 14 months was the addition of another grandchild. We now have four grandsons, ranging in age from five months to 10 years old. Last summer, our younger son and his wife purchased a home in Monmouth County, New Jersey, roughly an 80-minute drive north of us.

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May’s Hits

Jonathan Clements  |  Jun 1, 2023

WHAT ARTICLES AND blog posts caught the eye of readers last month? Here are the 10 most popular pieces published by HumbleDollar in May:

Did you end up with a surprisingly large tax bill? Next year, advises Rick Connor, see if you can trim that bill by making a belated contribution to an IRA or solo 401(k)—and perhaps even claim the saver’s tax credit.
U.S. stocks have outperformed foreign shares in 12 of the past 15 years—and yet there remains a strong case for diversifying internationally,

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Time to Decide

Scott Martin  |  May 31, 2023

I’LL BE TURNING 65 this year, so I’ve been researching my Medicare options. Even though I work in health care—and many of my patients are on Medicare—the task of choosing a plan is no less onerous for me.
I’ve read the information provided on and watched numerous YouTube videos from insurance brokers. These brokers tend to support two types of Medicare coverage. Retirees might opt for a bundle that includes Medicare Part A,

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Other People’s Money

Michael Flack  |  May 30, 2023

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?

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Not Quite Magic

Marjorie Kondrack  |  May 30, 2023

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,

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How I Got This Way

Ken Begley  |  May 29, 2023

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.

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Losing Value

Adam M. Grossman  |  May 28, 2023

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.

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Eyeing the Future

Jonathan Clements  |  May 27, 2023

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,

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Skill or Luck?

Philip Stein  |  May 26, 2023

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,

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A Late Save

Richard Connor  |  May 26, 2023

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.

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The Mary Jean List

Howard Rohleder  |  May 25, 2023

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.

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Medicare for All

Richard Quinn  |  May 25, 2023

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.

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