THE HOLIDAY SEASON is upon us. Our thoughts—or mine at least—turn to family, friends, wine, decorations, gifts, wine, food, fun and wine. But before I ring in the new year, I have a few financial questions I need to resolve.
Our 2022 income hasn’t been what I expected. I earn consulting income in two ways. I’m a part-time employee of a small engineering consulting firm. In this role, I’m an hourly employee with no benefits.

LIKE A SLOW-MOTION train wreck, we’ve spent recent decades inching toward a world where we have too few workers and too many retirees dependent upon their labor. Have we finally reached the tipping point?
Consider today’s confluence of economic events: a labor shortage, sharply higher inflation, massive government budget deficits, and depressed stock and bond prices. To be sure, all this can be explained by the pandemic and what followed—excessive government stimulus, supply chain issues,

I SPENT 40 YEARS practicing criminal law, and there was always a lot to read: police reports, lab reports, probation and pre-sentence reports, motions, orders and court opinions. These were required reading and there was little time left to read for pleasure.
One of the great joys of retirement is the freedom to read a lot—and whatever I choose.
Which, in this season of reflecting on the things we’re thankful for, brings me to one of mine: public libraries.

GOOGLE THE WORD “annuity” and you’ll receive 97 million and one results. Is there anything left to be said?
Yes, I think there is.
About 11 years ago, my 89-year-old mother asked me if she should invest more money in her Knights of Columbus annuity. Unbeknownst to me, she and my father had purchased it many years earlier. It earned a guaranteed 3.5% annual interest rate, which was better than every savings account or certificate of deposit available,

FOR THE PAST 20 YEARS, I’ve bought dividend-paying stocks and then reinvested my dividends. The big appeal: I increase my wealth with minimal effort.
Starting as a dividend investor used to be tricky, but it’s now much simpler. Many discount brokerage firms have no minimum to open an account and no longer charge stock commissions. You can also purchase shares through the dividend reinvestment plans offered by the transfer agents for many companies. These plans allow shareholders to reinvest their dividends and also purchase shares in amounts as little as $50 or $100.

I WISH I HAD HEARD the term “prehab” long ago. I think it would have prevented my current physical disability.
Many people delay surgery. Why not put off a potentially long recovery period—and a big medical bill? Often, this wait-and-see approach is harmless. But not always.
A little history might be useful. A couple of years after college, I joined my dad in his cash register business. Back in 1970, cash registers were massive and heavy—150 pounds or more.

DO YOU THINK differently about money today compared to a year ago?
Cast your mind back 12 months. Interest rates were near record lows, cryptocurrencies were surging and stocks were hitting new highs day after day. Checking your investment account balance was an instant dopamine hit. Ditto for homeowners, who could get a sense for their home’s skyrocketing value by perusing the local listings.
Last year was also a time when many Americans called it quits from the nine-to-five grind.

MY WIFE AND I JUST returned from our annual Thanksgiving vacation on North Carolina’s Outer Banks. This is a yearly outing for our immediate family, my wife’s four siblings and their families. This year we numbered 43, representing three generations of siblings, children, grandchildren, nieces and nephews, along with significant others.
I wrote an article about this family tradition three years ago. It started in 1995, and has been held 25 times since. We’ve only missed two years—one because of a family wedding in California and another due to COVID-19.

WHEN RESTRICTIONS ON travel eased this year, I visited Kolkata, India, where I grew up and my mother still lives. The airline ticket and other travel costs were almost 75% higher than my last visit four years ago.
This year, I’ve grown used to price shocks at every turn, from groceries to gas, so the steep ticket price didn’t shock me. What did surprise me was my feeling of affluence once I arrived.
Traveling to a low-cost country as a tourist doesn’t necessarily feel like a bargain because most items still have an international price tag.

MUTUAL FUNDS ARE about to send their shareholders some dubious holiday gifts—in the guise of capital gains distributions. These distributions usually occur mid-December and they represent a taxable event for investors who hold funds in a taxable account.
Even in a down year for stocks and bonds, a mutual fund may realize capital gains, which are then passed on to shareholders. These could come as a nasty surprise to investors already smarting from 2022’s steep losses.

YOU DON’T KNOW WHAT your future self will want. This is the tantalizing hypothesis of Hidden Brain podcast host Shankar Vedantam, who argues that we’re constantly becoming new people.
Vedantam offers the example of a hospice nurse who, having witnessed so much misery in her dying patients, made her husband promise never to extend her life if she became terminally ill. Yet, when her body was ravaged by ALS, often called Lou Gehrig’s disease,

I HAVE CHEERY investment news: Most Wall Street strategists are bearish on stocks. Last week, Bloomberg reported that 2023’s projected change in the S&P 500 by the best and brightest forecasters is negative. That hasn’t happened since at least 1999. Consider today’s bleak consensus to be a contrarian indicator. It could set the bar low enough for a decent 2023.
If you flip on financial TV or peruse investment magazines at this time of year,

PERSONAL FINANCE books don’t exactly rank as the most sought-after holiday gifts. Still, if there’s a money nerd in your life—or someone who aspires to be one—below are 10 personal finance book recommendations.
Why Does the Stock Market Go Up? by Brian Feroldi. This book seeks to answer 60 of the most commonly asked questions in personal finance. In so doing, it demystifies many of the concepts, terms and acronyms that we often ​hear but may not fully understand.

INVESTING CAN AND should be simple—and yet sometimes I make it so hard. Blame it on my ego and a faulty belief in my ability to pick winners among exchange-traded funds (ETFs) and, once in a while, individual stocks.

Problem is, I’ve had a few things go my way this year. Now that know-it-all feeling is rearing its ugly head again—“hey, I can pick stocks and sectors”—even though it’s hurt me badly in the past.

THE TWO-MINUTE CHECKUP is, I like to think, a unique financial tool: It aims to offer feedback across someone’s entire financial life based on no more than nine pieces of information. That’s an ambitious goal and—perhaps no surprise—some users have found the calculator wanting.
Meet Checkup 2.0.
Sanjib Saha, who writes for HumbleDollar when he isn’t busy writing software, and I went through all the comments that the calculator had received and made a host of changes.