I WAS HAPPY to read in The Wall Street Journal that 401(k) plans are “minting a generation of moderate millionaires.” I spent the last two decades of my professional life promoting 401(k) plans to workers, so the news felt like validation.
Moderate millionaires were loosely defined as coupon-clippers with seven figures. Sound familiar? It should to many HD readers. At Fidelity, a record 654,000 investors had a million or more in the 401(k) in the third quarter of 2025.

WE LOST A brilliant mind and generous writer, Jonathan Clements, whose words guided thousands on life, finance, and happiness. Even as he faced the unimaginable, he continued sharing wisdom with clarity, humor, and humanity.
I wanted to take some time and dig into Jonathan’s earliest posts on HumbleDollar. Posts that even the most loyal readers may not have read. With that, I also summarized some main takeaways and learnings that can help us all better navigate our own complex lives.

I’M TRYING MY HAND at retirement. It isn’t going so well.
As a teenager and when I was in my early 20s, I would take to the couch and happily spend the day consuming a novel. Could I do that at age 62? It seems not.
At some point over the past four decades, I lost the ability to do things solely for my own enjoyment. It seems the endless demands of work, family and household chores have crushed my inner self-absorbed teenager.

TWO THINGS HEAVILY influenced my financial life. The first was my short stint after college as an internal revenue agent with the IRS. The second was getting married and having five children.
Result: I’ve spent most of my adult life as a tax-averse junky using retirement accounts to get my high, so much so that there’s a risk our retirement-account withdrawals will put us in a much higher tax bracket than when we made our contributions.

TED BENNA IS OFTEN called the “father of the 401(k).” In 1980, he implemented the first 401(k) plan based on his somewhat bold interpretation of the Revenue Act of 1978. He certainly couldn’t have envisioned the $11.4 trillion in “defined contribution” 401(k) and 403(b) accounts that we have today.
Individual retirement accounts also took off in the early 1980s, and traditional IRAs now hold an additional $11.3 trillion. Combined, that’s an impressive $23 trillion in tax-deferred retirement assets.

WITH THE ADVANTAGE of advanced age and flawless hindsight, I now believe the three most important contributors to retirement prosperity are a robust savings rate, an aggressive allocation to stocks and funding tax-free accounts, both Roth and health savings accounts (HSAs).
What about other financial factors, such as the investments we pick, whether we buy income annuities, when we claim Social Security and what Medicare choices we make? These matter on the margin, but I don’t think they’re as crucial to a successful retirement. 

RETIREES ENDLESSLY debate how best to draw down their retirement savings, and yet it all comes down to two simple rules: Don’t spend too much each year, and don’t sell stocks during down markets.
How do we put these two rules into action? Retirees can pick from a host of withdrawal strategies, including the five popular choices listed below. You’d likely fare just fine with any of the five strategies—but that doesn’t mean you shouldn’t pick carefully.

WE’VE BEEN TAKING stock of our nomadic life. We’re quite happy living as we are. But we’re also conscious that things could change at any time for multiple reasons, and we’re ready to shift gears if needed.
We aren’t exactly “living the dream”—because being nomadic was never our dream. We hadn’t even thought about it until a few months before we started our travels. We officially uprooted ourselves—meaning we sold our Houston home—after we’d been away from the place for most of the first year of my retirement.

FOUR 20-SOMETHINGS named Ben, Duncan, Jonnie and Dave came up with a great idea for a reality show in 2010. It involved a purple bus named Penelope, a cross-country road trip and a list of 100 things to do before you die. For every item they crossed off their list, they’d help a stranger achieve something on his or her own list. 
Some of their to-dos were ambitious, with a low probability of success: host Saturday Night Live,

THE TOUGH PART COMES last.
Saving for retirement is pretty straightforward: You sock away as much as you can, favor stock funds, diversify broadly, keep investment costs low and make the most of tax-advantaged retirement accounts. By contrast, paying for retirement can involve mind-boggling complexity—and a big reason is the tax code.
The good news: Once you quit the workforce, you have a fair amount of control over your annual tax bill, especially if you aren’t yet taking required minimum distributions (RMDs) from your traditional retirement accounts,

I MAY NOT BE THE best source of retirement advice. After all, I’ve called myself semi-retired for a decade and yet, faced with a grim medical diagnosis, I continue to work far too hard. Moreover, even if I opt to fully retire—which is doubtful—cancer will likely ensure my retirement will be all too brief.
On the other hand, I do run a website devoted to retirement issues, and that means I spend a lot of time reading and thinking about the topic.

MANY FOLKS CLAIM TO be ready for retirement, both financially and psychologically. But they’re often surprised to discover that the reality is different from what they expected.
I started planning well in advance of my 2023 retirement. I read dozens of books on the subject, and talked to many classmates and friends who’d already retired. Of all the books and videos that I reviewed, one talk on YouTube stood out: a TEDx Talk by Dr.

A RECENTLY RELEASED book titled How to Retire is a goldmine for those in or near retirement. For the book, Christine Benz—Morningstar’s director of personal finance and retirement planning—conducted interviews with 20 experts, covering every aspect of retirement.
The result is a valuable field guide for those tackling life after work. Below are seven insights I found particularly useful.
1. Social connections. When we think about retirement planning, most of us tend to think first about the numbers.

HUGE AMOUNTS OF TIME and money are spent planning for retirement. The focus is almost entirely financial—running the numbers, so to speak. How much do I need to save to retire by age 65? Can I retire with my current nest egg? What are the chances I’ll run out of money?
No doubt these are the sorts of questions that keep HumbleDollar readers up at night. And, yes, the numbers are important.

ONE SUMMER MORNING in 2023, my husband Warren and I had an ad hoc business meeting over bowls of cereal. He told me, “The pandemic really hurt my in-person speaker’s business. I’m not sure it’s ever going to come back.” Then I mentioned that my freelance-design income had also really slowed down, the result of a lack of marketing and enthusiasm on my part.
Neither of these was a newsflash. But that was the moment we realized this is what retirement looks like for a self-employed couple in their mid-60s.