Jonathan Clements

WE LIKE TO ESCAPE the Northeast’s cold each winter, so we just spent 10 days in Sarasota, Florida. Like many others when they’re on vacation, we found our noses pressed against the windows of real-estate offices, perusing the listings and musing about whether we’d want to live there.
Fantasizing about the future is fun and free, but it can also be dangerous. It’s how folks end up buying timeshares and second homes during wonderfully relaxing vacations.

WHEN I FIRST LOOKED at the issue of portfolio withdrawals more than two decades ago, many financial experts suggested retirees follow a simple strategy: spend taxable account money first, traditional retirement accounts next and Roth accounts last. That way, you’d squeeze more years of tax-deferred growth out of your traditional retirement accounts, and even more out of your tax-free Roth.
If only things were so simple today.
Why have portfolio withdrawals become more complicated?

I GREATLY VALUE honesty. I think it’s important to be scrupulously honest with others and brutally honest with ourselves. That brings me to HumbleDollar’s annual report card.
After steady growth over the site’s first five years, our sixth year—2022—saw mixed success. Below are five key metrics that I track. These numbers, I believe, tell you not only about HumbleDollar, but also a little about the mood of Americans over the past 12 months.

MOST OF US ARE forever striving to be better versions of ourselves—usually with mixed success. Still, the changing of the calendar often prompts renewed efforts. But what should we focus on? Let me offer 10 words that I try to live by.
1. Pause. Throughout the day, we make snap decisions, and they usually work out just fine—except when it comes to spending and investment choices. Got an overwhelming urge to buy an expensive bauble or make a portfolio change?

I HAVE A CONUNDRUM: In 2023, I’ll have ample opportunities for tax-free growth—but probably not enough cash to take advantage.
It doesn’t get much better than tax-free, right? I remember the excitement when Roth IRAs came into being, thanks to 1997’s Taxpayer Relief Act. But today, the Roth is just the tip of the tax-free iceberg. Indeed, for 2023, I’m eyeing four tax-free accounts.
I want to fund a health savings account and my solo Roth 401(k),

READERS HAVE PERUSED almost 18 million HumbleDollar pages over the past six years. Many of those pageviews were garnered by the homepage, the latest articles page and the main money guide page. But what about the site’s articles? Below are the 30 best-read pieces since the site’s launch on Dec. 31, 2016.
If the list seems a little eclectic, there’s a good reason: Many of the articles that have enjoyed big traffic over the past six years have been those that got promoted by far larger sites.

WANT TO BE A PERSONAL finance columnist? I can’t claim expertise on many topics, but this is one where I draw on a lifetime of experience.
And it isn’t just as a writer. At HumbleDollar, I have a hand in editing every piece that appears, plus I get to see the numbers on which articles catch readers’ attention—and which get the cold shoulder.
To be sure, popularity isn’t necessarily the best way to gauge an article’s quality.

‘TIS THE SEASON WHEN many of us open our wallets and spend with reckless abandon. Along the way, we often end up buying a gift or two for that special person in our life—ourselves.
I don’t put too much stock in the accuracy of quick consumer surveys, but it seems the percentage of folks who self-gift might be 22% or 57% or even 77%. Whatever the right number is, I’m not inclined to be too judgmental,

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,

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.

FOUR DECADES OF falling inflation and declining interest rates have come to an abrupt halt—and that’s changed the calculus on a fistful of financial decisions.
Want to make smarter money choices in the months and years ahead? Here are seven new rules for financial success:
1. Carrying debt is less foolish—in some cases. Thanks to inflation, families can now repay the money they’ve borrowed with depreciated dollars. That won’t help you with credit card debt,

WHEN I PICK HEALTH insurance each year, my focus is twofold: What’s the monthly premium—and what’s the out-of-pocket maximum?
Sure, I want to stay with my primary care physician. But my doctor just announced that she’s leaving Philadelphia to return to her native Massachusetts, so that became a non-issue for 2023.
Meanwhile, I’ve long wanted a high-deductible health plan so I could fund a health savings account (HSA). But since 2014, when I started working for myself and had to buy individual coverage,

PESSIMISTS SEEM LIKE they’re clever and sophisticated, but—if you want to make money—take my advice: Invest like an optimist.
I’m not talking wild-eyed optimists who are over-enthused about meme stocks and nonfungible tokens. Instead, I’m talking about a fundamental belief that economic setbacks are temporary and the future will be better than the past. Struggling to stay cheery amid 2022’s rotten financial markets? Here are five reasons for optimism.
1. The news is terrible.

WHEN MARKETS PLUNGE, investors start questioning whether they have the right mix of stocks, bonds and cash. That’s no great surprise: Bear markets hammer home the investment risks we’re taking—and many folks discover their portfolio is too aggressive for their taste.
That’s a useful insight for the future. But it’s hardly one you want to act upon when, even after Thursday’s rally, the broad stock market remains down some 16% for the year-to-date and the bond market is off 14%.

COMPARISONS ARE the death knell of happiness—and they aren’t good for our wallets, either.
If we’re to get the most out of our time and money, we need to devote those two precious resources to things we consider meaningful. But how do we figure out whether something is indeed meaningful to us, and not a reflection of the influence of others?
For “meaningful,” dictionaries offer synonyms such as “important” and “significant.” What we’re talking about are things that have some special emotional resonance,