AS WE HEAD INTO year-end, many are cheering the financial markets’ returns. The S&P 500 has gained nearly 25% and now sits just a hair below its all-time high. Bonds are also looking more attractive, with yields at 15-year highs.
As a result, many investors are feeling a whole lot better about their portfolio balances. That’s certainly one way to measure financial progress, and it’s an important one. But as you make plans for 2024,

INVESTING IS ABOUT finding a strategy that’ll allow us to meet our life’s goals—and which we can live with along the way. That brings me to a major portfolio change I made two years ago, and a series of changes I’m planning for the years ahead.
In late 2021, I split my portfolio in two. One part I’ll use to fund my retirement, while the other part I’ll leave to my two kids. This “bequest” portion consists of my three Roth accounts,

THESE WORDS STRIKE fear into the heart of any husband: “Honey, the [insert: A/C, heat, refrigerator, roof, foundation] doesn’t seem to be working.” But from 2017 to 2021, they were mere words to me, no different than, “Honey, let’s go out for coffee.”
For four glorious years, my wife and I traveled around the world and the country, unfettered and unburdened. If we ran into any equipment issues, they were immediately referred to the landlord for rectification.

MY DREAM WAS TO become a brilliant investor who knew when and what to buy and sell. I imagined myself doing the necessary research, which would allow me to make savvy decisions, which would then impress my wife and relatives, as they observed my uncanny ability to always know what to do and when to do it.
This never happened.
Instead, I took stock of who I was and how I’d consistently behaved. “Know thyself” was the advice of Ken Pangburn,

I’M A BELIEVER. SURE, I stray every now and then. But after a late start, I’ve now been a devotee of exchange-traded funds for many years—though some of the ETFs I own would be considered actively managed.
In his iconic A Random Walk Down Wall Street, Burton Malkiel strongly advocates long-term passive investing as the strategy of choice for individual investors. But he also confesses to having been “smitten with the gambling urge since birth.” Acknowledging that index fund investing can be “boring,” he takes pity on folks like me with “speculative temperaments,” who may need to indulge those instincts with some small portion of their portfolio.

I’M THE OWNER OF one-sixth of a house in Sarasota County, Florida. There was no cost to me to acquire it. I also don’t have to make payments for property taxes, maintenance, the mortgage or the homeowners’ association. And, no, I haven’t had a change of heart about investing in rental real estate and, no, the property isn’t part of some passive micro-investment syndication scheme.
Rather, my mother signed a life estate deed, also known as a quitclaim deed,

I RETIRED ALMOST TWO years ago, at age 56. My wife, who is nine years younger, decided to semi-retire so we could relocate from Rhode Island to Florida. We were able to afford early retirement in part because we’d lived below our means for many years, diligently saving while also paying off our mortgage and other debts.
Relocating to a state with a lower cost of living and lower taxes also helped. In addition,

HERE’S A RECIPE FOR disaster: a good internet connection, plenty of storage space, lots of time on your hands—and credit cards.
Impulsive shopping has a name, oniomania, and the above recipe makes it all too easy. If you have a credit card, research suggests you’ll spend significantly more than if you were paying with cash or a check. The availability of 24/7 online shopping makes it just that much worse.
Here are eight signs—besides the pile of packages outside our front door each day—that tells me impulsive spending has reached our house:
1.

THERE’S AN OLD SAYING: Good things come in threes. That’s certainly been true for one aspect of my life. I’ve lived in just three locations—and all of them have been featured in national “best places” lists.
My early years were in Moorestown, New Jersey, a quiet town with a population of some 20,000. It’s an affluent suburb of Philadelphia that defies stereotypes about New Jersey. In 2005, Money magazine identified Moorestown as the best place to live in the country.

I TRY NOT TO WORRY too much these days. Although I’m retired, it doesn’t mean my life is carefree. There’s always something I could worry about.
After all, as we age, we tend to have more health problems to fret about, and just as many money issues. We can also find ourselves alone for the first time in decades without our partner, the stabilizing force in our life.
My mother worried a lot after my father passed away.

THE HOLIDAYS ARE HERE. For me, the Christmas season brings back memories—along with anxiety and stress.

Let’s review the stress first. Where are we going to have Christmas dinner and who will come? Getting everyone together is virtually impossible.

Next come the decorations. It wouldn’t be so bad if they weren’t stacked this way and that in a storage locker. When we moved to a condo, we converted to an artificial tree. It looks real from two feet away,

WITH YEAR-END IN sight, it’s a good time for some investment housekeeping. What’s worth your attention? Last week, I discussed the importance of asset allocation. According to research, this is the most significant portfolio decision you can make. But while asset allocation is important, it isn’t the only decision. Within each of the major asset classes, there’s another set of considerations.
Bonds. Earlier this year, I conducted a survey on X, as Twitter is now known,

THE HOLIDAY SEASON used to be a time when we’d write and mail more checks than usual. Some were gifts to family, while others were year-end charitable donations. But with the rise in mail theft and check washing, we’ve been on a campaign to limit the number of checks we write, plus we’ve almost eliminated the mailing of checks. Here are eight things we’ve done to reduce our exposure to check fraud:

We opened a secondary no-fee checking account and opted out of the overdraft protection.

PROGRESS IN RECENT decades has been remarkable. We no longer do math using slide rules, talk on phones attached to walls, choose from just a handful of TV channels or drive clutching an unfolded map.
Less obvious—but arguably just as important—has been the progress in our financial thinking. Looking back over the post-World War II period, I see five key phases in our thinking about money, and those phases roughly parallel the needs and wants of the baby boomers,

A FEW DAYS AGO, I RAN the numbers on our likely 2023 taxes, and reached two conclusions: We have a small refund coming—and we should find a way to pay more taxes.
How can both be true? I project that our 2023 taxable income will be well below $190,750, which is the top of the 22% tax bracket for those married filing jointly. Getting taxed at 22% strikes me as a good deal, given the likelihood that we’ll be taxed at an even higher rate later in retirement.