I STARTED WRITING for HumbleDollar almost five years ago—and it’s become a big part of my retirement.

Some folks have likened me to Andy Rooney. It’s a comparison I’ve happily embraced. I try to offer pointed opinions leavened by a measure of humor. Here are my 10 favorite articles that I’ve written for the site.

Choosing Badly (April 24, 2018). This was my first piece for HumbleDollar. Employer-sponsored 401(k) plans are underutilized and misused.

IT’S HUMAN NATURE to be impressed by things that sound sophisticated or seem complex. In the world of personal finance, this certainly applies to the planning tool known as Monte Carlo analysis.
Its roots go back to the 1940s, when it was developed by Stanislaw Ulam, a physicist working on the Manhattan Project. Today, it’s a popular way to assess the strength of a proposed retirement plan. If you’ve seen presentations indicating that a financial plan has a particular probability of success,

I ADMIRE SUPER-SAVERS. I really do.
You know who I’m talking about: Ordinary people making ordinary salaries who are somehow able to sock away half or more of their disposable income and who accumulate enough to step away from the working world long before the rest of us.
We hear about these people all the time on podcasts. The couple who banked $1 million over the course of a decade by scrimping and saving.

HERE ARE MY TEN favorite articles that I’ve written over the three-plus years I’ve been a part of the HumbleDollar community. Although I write my share of technical and analytical articles, the ones I like the most have a human element.
As my wife will attest, I’m a bit of a softy, and care deeply about my family and friends. I like happy endings and want to see people succeed, especially the generations to come.

ONE WINTER DAY IN 2016, I jotted down a few comments about the financial markets and emailed them to a group of clients. I received a few responses—some of them positive—so I did the same thing the following week, and I’ve continued that practice every week since.
For better or worse, when it comes to investment markets, there’s always something new to discuss. But it can also be helpful to pause and revisit key investment principles from time to time.

IN SEPTEMBER 2014, The Wall Street Journal published a column entitled “The Simple Secret to Building Wealth.” An early paragraph began thus: “Wealth is born of great savings habits.”
As I read along, I found myself not only agreeing, but also wondering if the author had secretly consulted with my wife prior to penning the column. The similarities between his suggestions and our savings habits were striking.
I wrote an email to the author—who,

MY SIMPLE BUT successful financial life is the result of four lessons I learned through the school of hard knocks.
Lesson No. 1, learned as a child growing up on a farm: Chores are not optional and are never accompanied by cash bribes. Lesson No. 2, learned as a college student: Spend all your time studying, working jobs and sleeping, and you can earn a degree without taking out a loan. Lesson No. 3,

I BEGAN WRITING for HumbleDollar in early 2020. As a market junkie, but one who’s also deeply curious about personal finance, I was already a regular reader of the site.
Since then, I’ve contributed roughly 140 pieces. My articles and blog posts often focus on the financial markets and long-term investing, with a nod toward the financial independence movement. What do my 10 favorite posts have in common? They’re mostly focused on macro trends and my own financial journey.

I GRADUATED FROM college in 2007, shortly before the economy was brought to its knees by the Great Recession. I worked in asset management for Macerich (symbol: MAC), a publicly traded real estate investment trust. During the panic, the company’s share price plunged from $92 to $5.
There was fear in the markets. You might even say mass hysteria. Our executives were mostly miserable because their stock options were underwater. Waves of layoffs ensued.

LAST WEEK, I TALKED about Carveth Read, the English philosopher who’s famous for saying, “It is better to be vaguely right than exactly wrong.” This, in my view, is one of the most important ideas in personal finance.
My focus last week was on the “vaguely right” part of Read’s statement. But what about the second part—the importance of not being “exactly wrong”? Below are seven situations in which trying to be exactly right might,

I’M AN 81-YEAR-OLD retired radiologist. Early in my medical career, I realized my stock broker was managing my account for his benefit, not mine. I fired him and took charge of managing my own investments.
Today, I have four granddaughters who are starting to invest. Over the years, as I learned more about personal finance, I put together a 130-page financial notebook. My granddaughters probably don’t want to read my lengthy notes, so I decided to put together a one-page summary.

I GOT AN EMAIL last month that also went to half-a-dozen other HumbleDollar writers—those of us who have been the site’s most prolific contributors. It came from HumbleDollar’s editor. His request: Please come up with a list of your 10 favorite articles that you’ve written for the site.
I immediately knew what type of article I’d select—ones that weren’t just about personal finance, but rather were about more than money.

ONE OF THE MOST important ideas in personal finance comes not from a financial expert but from a 20th century English philosopher named Carveth Read. “It is better to be vaguely right,” he wrote, “than exactly wrong.”
Why is this idea important? It gets to the heart of why financial planning can be so tricky. For starters, few people—if any—can claim to be perfectly rational when it comes to money decisions. But more to the point,

RETIREMENT PLANNING videos and books can be frustrating because of the conflicting advice from so-called experts. Often, these experts are outside the mainstream. They retired in their 30s, or saved 50% of their income, or claim to be living so frugally in retirement that they need to replace just half of their old salary.

I prefer to think more about average Americans facing the reality and challenges of planning for retirement in the real world.

I’M NOT BIG ON MAKING New Year’s resolutions. Still, January is a good time to conduct some financial housekeeping. Below are 10 ideas to consider as the calendar turns over.
1. Portfolio cleanup. I sometimes feel like a broken record when I talk about the disadvantages of actively managed mutual funds. Among other issues, they tend to underperform and are tax-inefficient. But here’s the challenge: Even after factoring in 2022’s decline, the S&P 500 has risen more than 600% since 2009’s market bottom.