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Spending

Is an 18% Service Charge a TIP?

James McGlynn CFA RICP® | Oct 13, 2026

"As to your last question. You mean like in most of the world?"

- David Lancaster

Careers

The Value Of Trust

Andrew Clements | Oct 14, 2026

"“keeping our promises, and taking pride in our work” seems to be sorely missing these days. I sound like an old codger. "

- David Lancaster

Behavior

"“It’s more than possible your engineer was happy with a situation where he paid high and regular premiums because the uncertainty of facing high out of pocket would be more taxing on him mentally.” This is why I chose a Plan G supplement. I would rather budget for the higher monthly cost than deal with unknown additional costs and hassle of copays and unknown out of pocket expenses I even believe Dick has a Plan G supplement, thus in the end he made the same decision, albeit a permanent one, such as the referenced employee."

- David Lancaster

Cars

Saved 85 Bucks

Dan Smith | Oct 13, 2026

"Good call on both! My buddy had a Saab turbo but lived up a two mile winding mountain road. The turbo would scream all the way up the mountain and then he’d pull into his driveway and shut the car off. Mechanic later told him that’s what led to premature death of his turbo. Should have led it idle for a bit after stopping to cool turbo."

- Mark Ukleja

From HumbleDollar Founder Jonathan Clements

Investing

My Investment Sin

I'LL CONCEDE IT'S HARD to justify—but I don’t believe it’s 100% unjustifiable. At issue: my strategy of overweighting stocks during big market declines. I…

Taxes

2026 Charitable Deductions

Rick Connor | Oct 12, 2026

"I agree. I'm a big fan and have learned so much from the Kitces site.The Kitces article covered the topic in its usual thorough fashion, with excellent examples and figures. I would note that, unlike HumbleDollar, Kitces' writers are finance professionals, and generally write for other professionals. But it is one of my go-to sites for information."

- Rick Connor

Life Events

Choosing a CCRC (Life PlanCommunity)

David Lancaster | Oct 14, 2026

"There are such people. I only know that because a friend of mine does it here in Cincinnati. Give it an internet or AI search to see if there's someone in your area. Good luck."

- Ben Rodriguez

Taxes

Time to QCD

R Quinn | Oct 12, 2026

"My dad was a long time, then emeritus board member of the Shriners Hospital in Montreal."

- David Lancaster

Happiness

The Number Is Not The Answer

ArticleJohn Goodell | Oct 10, 2026

YEARS AGO, while practicing law, I was a frequent contributor to Humble Dollar. I loved Jonathan Clements’s vision for the site - a corner of the financial universe built on clarity, frugality, and the quiet dignity of living within one’s means. Then my life took a sharp pivot. I left legal practice to teach gifted-and-talented students and coach varsity athletics at a public magnet high school. Almost immediately, my submissions here dried up. I was consuming entire days guiding brilliant teenagers through complex history, breaking down match film, and grading papers long past sunset and on weekends. I wrote to Jonathan with genuine regret, apologizing for going dark on such a wonderful enterprise. His reply was quintessential Jonathan: he explained to me with characteristic, succinct warmth that his own adult child was a teacher, adding that he wasn’t sure there was a higher calling on Earth. He was right about the calling. But what nobody warns you about a calling is its capacity to consume you whole if you let it. The Cliff Edge This past year, the math simply broke. Between high-load AP teaching, head coaching, and the relentless calendar of high school athletics, I was regularly clocking 17- to 18-hour days during soccer season. My central nervous system finally redlined badly. Worse, I realized with a gut punch that I had missed nearly the entire senior year of my oldest son while running on that treadmill. This realization hit me at his graduation when I felt physically exhausted and unable to enjoy what should have been one of the proudest moments of my life. I was determined to make it up to him in whatever way I could (for example, we are visiting him today at college, and we go often to see him in San Antonio - a 90-minute drive from Austin). Moreover, I will not repeat this mistake and will enjoy the years I have left with my two high-school-aged daughters. With teenagers preparing to leave the nest and a close family member facing severe illness, I stepped away. I took a sabbatical. Maybe it will delay our retirement slightly, but as I will express further below, I am not sure I will ever really retire. The Void Financial planners love to reduce retirement to a single milestone: "The Number." The spreadsheets run 10,000 Monte Carlo simulations, the house is paid off, the withdrawal rates are dialed in, and the industry assures you: You have arrived. You are safe. At 45, I had not retired in the traditional sense, but I had stepped off the cliff of full-time professional identity because my body told me I needed to. And what I discovered in the sudden, unanticipated quiet is something many retirees spend years agonizing over without having the vocabulary to describe: The number is not the answer. When you abruptly remove the machinery of a demanding daily routine, you don't instantly find nirvana. You find a void. In a recent discussion on non-financial retirement readiness, former financial adviser Tyler Gardner framed this dilemma in his video on non-financial retirement needs around Self-Determination Theory, pioneered by psychologists Edward Deci and Richard Ryan. Deci and Ryan posited that human well-being rests on three basic psychological nutrients: competence, relatedness, and autonomy. For all its stress and bureaucratic friction, a demanding career supplies all three automatically. When you walk away from work, those three nutrients can vanish before your celebratory cake is even eaten. If you don't deliberately rebuild them, the fallout can be physiological. The Trap of "Mental Retirement" In aging literature, researchers study a sobering phenomenon bluntly termed "mental retirement" - the cognitive softening that occurs when a person ceases to be intellectually stretched. A decade-long study from Binghamton University examining China’s rural pension expansion revealed that early retirement significantly accelerated cognitive decline. Crucially, the researchers noted that the negative impact of reduced social and mental engagement outweighed the physical benefits of improved nutrition and sleep that the pension provided. Work forced us to solve problems under pressure. Sabbaticals and retirements do not. To counteract that loss, I had to create self-imposed challenges. During my grueling years in the classroom, exercise was the first thing pushed off the ledge. On leave, I reclaimed the time. I started chasing benchmarks for physical competence. Recently, I set out to regain a grueling standard: 10 continuous minutes on the Jacob’s Ladder. It was a benchmark an elite special operator had given me when I served as an Army JAG supporting special operations in Afghanistan in my late twenties. My first time back on the ladder? I barely completed one minute and staggered off it trembling and nauseous. But every week, I kept working at it - sometimes adding a few seconds and other times several minutes until I got to 10 minutes again this week. Crossing that threshold didn't merely burn calories; it restored a measurable gradient of physical competence and, with it, confidence. Whether it is conquering a brutal conditioning standard, learning a language, or mastering an instrument, we need something where we can objectively say: I am better at this today than I was last month. I will now find a new physical benchmark to pursue, while coming back occasionally to that masochistic Jacob's Ladder. The 40 Invisible People The second nutrient, relatedness, is where most folks get ambushed. When people contemplate retirement, they assume their social health depends on their spouse or a handful of close friends. But work provides something entirely different: a vast scaffolding of "weak ties." In a landmark 2014 study published in Social Psychological and Personality Science, researchers Gillian Sandstrom and Elizabeth Dunn found that daily subjective happiness and feelings of belonging rose noticeably on days when people had more peripheral interactions - even something as fleeting as a 20-second genuine exchange with a coffee barista. Broader public health research reinforces this with astonishing gravity. A massive meta-analysis led by Julianne Holt-Lunstad spanning over 300,000 individuals found that strong social integration increased survival likelihood by 50%. Remarkably, the mortality benefit was strongest for complex, varied social networks (the diverse web of people you bump into) rather than simple binary measures like living with someone. When I taught, I had hundreds of involuntary interactions before lunch: hallway greetings, banter with the front desk, coaching video sessions, cafeteria check-ins. On my sabbatical, I plunged into writing a historical thriller called The Blood Money Ledger set during the Vietnam War - a passion project rooted in my love of history and informed by my own military service. I was thrilled to find that the fiction flowed with unexpected ease. In fact, I am now leaning toward turning my main character, Tom Calder, into a series of books about morality, the law, and institutional rot. But writing is, by definition, solitary confinement. Left entirely unmanaged, isolation is insidious. To survive it, I had to engineer artificial friction:

I go to the gym at the exact same hour every day to see the familiar faces of regulars.
Once a week, a close friend and I meet at a local coffee shop; he reads while I hammer out words for the book. It’s quiet, parallel work, but the ambient presence makes the solitary act of writing sustainable.
I signed up for an evening furniture-making class to work with my hands alongside people I wouldn't otherwise meet - a skill I am going to start out terrible at and eventually become... less terrible at.
I took on a volunteer docent shift at the Austin History Center, trading archival stories with curious strangers.

None of these people are lifelong confidants - except my close friend who joins me for coffee. But together, they rebuild the 40 casual touchpoints work used to gift me for free. Anticipation Over Accumulation The final hazard is structural: time without seams. When we dream of retirement, we picture unstructured calendars and checking off items on an expansive bucket list. But behavioral psychology shows we often misunderstand how human satisfaction works. In a well-known 2010 study by Dutch researcher Jeroen Nawijn tracking over 1,500 adults, vacationers exhibited significantly higher happiness before their trips than non-vacationers. The post-trip happiness bump, however, was negligible and evaporated rapidly. Even though I haven't written for Humble Dollar much in the past several years, I have been a frequent lurker, and know that this is a topic we all understand well. The engine of joy is almost entirely anticipation, not completion. A bucket list should never be treated like a grocery list where the goal is an empty page. If you clear out your list with no new ambitions behind it, life goes flat. The real art is maintaining a continuous horizon of things you are eagerly anticipating: an upcoming course, a seasonal trip, an archival project, or a fresh manuscript draft. We are in the midst of using high school and college graduation presents as family adventures we take. For my son's graduation gift - he loves soccer - I took him and his soccer-obsessed sister to the World Cup. My other daughter, who is very much not soccer-obsessed, and my wife visited a spa together for significantly less money. Win-win. The Real Ledger The Monday morning after your final Friday, your spreadsheet will not ask how you are doing, provide an intellectual hill to climb, or hand you an unexpected laugh across a desk. The number is just the admission ticket that we too often obsess over. The actual show begins when you decide what will make your days count. John Goodell was a deputy director of policy and general counsel at the Texas Pension Review Board. Currently an Army Reservist, he previously served 14 years on active duty before leaving to become the general counsel at the Texas Veterans Commission. John has spent much of his career working with public sector employees on tax, investment, estate planning and retirement issues. His biggest passion is spending time with his wife and kids. Check out John's earlier articles.

Abuse

Jonathan’s Daily Musing, 10/13

Dan Smith | Oct 13, 2026

"Yes, Dan, I made it up, though I had a little help from the old fool and his money saying. Steal away. It’ll sound far better in your Yankee accent than my Irish brogue 😉"

- Mark Crothers

Update: Jonathan’s Getting Going on Saving Initative

Elaine M. Clements | Oct 12, 2026

"What great news Elaine. I think I see the fingerprints of President of the Board Christine Benz from Morningstar all over the recruitment of the University of Chicago. What a great partnership."

- David Lancaster

In Retirement

Momentarily Embarrassed by “Not Much”

Mark Crothers | Oct 9, 2026

"Jeff, I think the main takeaway is simple: stay active, stay social, and keep your mind sharp. Retirement shouldn’t mean retiring from life... although, we definitely deserve longer coffee breaks 😉"

- Mark Crothers

Spending

Is an 18% Service Charge a TIP?

James McGlynn CFA RICP® | Oct 13, 2026

"As to your last question. You mean like in most of the world?"

- David Lancaster

Careers

The Value Of Trust

Andrew Clements | Oct 14, 2026

"“keeping our promises, and taking pride in our work” seems to be sorely missing these days. I sound like an old codger. "

- David Lancaster

Behavior

Jonathan and me

R Quinn | Oct 14, 2026

- David Lancaster

Cars

Saved 85 Bucks

Dan Smith | Oct 13, 2026

- Mark Ukleja

From HumbleDollar Founder Jonathan Clements

Investing

My Investment Sin

I'LL CONCEDE IT'S HARD to justify—but I don’t believe it’s 100% unjustifiable. At issue: my strategy of overweighting stocks during big market declines. I…

Taxes

2026 Charitable Deductions

Rick Connor | Oct 12, 2026

- Rick Connor

Life Events

Choosing a CCRC (Life PlanCommunity)

David Lancaster | Oct 14, 2026

"There are such people. I only know that because a friend of mine does it here in Cincinnati. Give it an internet or AI search to see if there's someone in your area. Good luck."

- Ben Rodriguez

Taxes

Time to QCD

R Quinn | Oct 12, 2026

"My dad was a long time, then emeritus board member of the Shriners Hospital in Montreal."

- David Lancaster

Happiness

The Number Is Not The Answer

ArticleJohn Goodell | Oct 10, 2026

I go to the gym at the exact same hour every day to see the familiar faces of regulars.
Once a week, a close friend and I meet at a local coffee shop; he reads while I hammer out words for the book. It’s quiet, parallel work, but the ambient presence makes the solitary act of writing sustainable.
I signed up for an evening furniture-making class to work with my hands alongside people I wouldn't otherwise meet - a skill I am going to start out terrible at and eventually become... less terrible at.
I took on a volunteer docent shift at the Austin History Center, trading archival stories with curious strangers.

Manifesto

Oct 14, 2026

NO. 47: IF WE NEED a financial advisor, we should hire one who’s legally required to act as a fiduciary—meaning he or she should only make recommendations that are in our best interest.

think

Oct 15, 2026

WEIGHTING RETURNS. Typically, we see time-weighted returns, which reflect our gain over, say, 10 years, assuming we bought at the start of the period and didn't make further trades. A dollar-weighted return, by contrast, factors in when we bought and sold. If the market dipped during the 10 years and we invested more, that would boost our dollar-weighted return.

act

Oct 14, 2026

WHEN MAKING a purchase, ponder not just its virtues, but also the maintenance, repairs and other hassles involved—because those’ll eventually loom large. Take the country home. It may initially seem like a great escape. But soon enough, you’ll be just as focused on the drive back and forth, and on the chores you’ll have to do once you’re there.

Truths

Oct 13, 2026

NO. 70: WE INVEST now so we—or our heirs—can spend later. The goal of investing isn’t to get rich or beat the market. Instead, it’s about paying for the house down payment, kids’ college, retirement and other goals. Like a pension fund, we should identify our future financial obligations—and then figure out the surest way to meet those obligations.

Money Guide

Manifesto

Oct 14, 2026

NO. 47: IF WE NEED a financial advisor, we should hire one who’s legally required to act as a fiduciary—meaning he or she should only make recommendations that are in our best interest.

Spotlight: Retirement

Is saving really that hard? Nope, not for the great majority of Americans.

R Quinn | Apr 28, 2026

I posed this question to an AI program (because I don’t know how to use a spreadsheet). “If my income is $3,000 per month, I save 10%, I expect to earn 8% per year on invested money and my income will increase by 2.5% per…

Market Risks

Adam M. Grossman | Oct 10, 2026

YOU MAY BE familiar with a concept known as Pascal’s wager. Named for Blaise Pascal, a devout seventeenth-century French mathematician, it was a thought experiment in which he tried to weigh, in logical terms, the costs and benefits of believing in God. His conclusion: The…

Trump Accounts

Adam M. Grossman | Jul 11, 2026

INNOVATION IN THE world of retirement plans is decidedly slow moving. But as of July 4th, investors now have a new savings option known as a Trump account. In short, these are retirement accounts designed specifically for children. Trump accounts share some similarities with traditional…

Punched in the Mouth

Dan Smith | Feb 13, 2026

I don’t have the right stuff to be an engineer, as the math involved boggles my mind. But that didn’t stop my infatuation with spreadsheets in the nascent days of computer ownership. That was around 1990, roughly the same time-frame as the implementation of my…

Bucket Strategy

Adam M. Grossman | Jun 6, 2026

A WHILE BACK, I was speaking with a fellow who had recently retired. He shared this observation, only half-jokingly: “Working was easy,” he said. What he meant was that financial management during our working years is more straightforward than it is in retirement. We…

Why Bonds Matter

Adam M. Grossman | Oct 3, 2026

RECENTLY, A READER—let’s call him Tom—posed this question: If stocks historically have delivered far better returns than bonds, then why should an investor own any bonds at all? Even with the stock market's unpredictable ups and downs, wouldn't you end up way ahead by…

No TIME Left For You

Michael Flack | Jun 6, 2025

On my way to better things (No time left for you) I found myself some wings (No time left for you) Distant roads are callin' me (No time left for you) - The Guess Who It had been a while since I had been mailed the opportunity to “get guaranteed income that you can’t outlive,” “preserve your capital,” and most…

Risk at Every Turn

Michael Flack | May 30, 2024

DEAR DAVID: LAST WEEK, you emailed me, “If you had $20,000, didn’t want to take risk and wanted the best return, how would you invest?” It’s a timeless issue, most likely first asked the day after money was invented. You may be wondering why, besides asking where your money is currently invested, which turns out to be Bank of America…

Good Enough Tech

Michael Flack | Nov 11, 2021

MY BROTHER-IN-LAW just told me about a technology issue that he’s been struggling with. He was trying to get an old scanner to connect with his Mac. The solution required him to upload some outdated software. When he finished explaining how he resolved the issue, I was happy he could scan again. I was even happier that I had a…

Beyond the Obvious

Michael Flack | May 12, 2023

I JUST FINISHED rereading a book every serious investor needs to reread: Moneyball: The Art of Winning an Unfair Game. It was written by Michael Lewis in 2003, but it’s still quite relevant to baseball—and to investing. It’s the story of the Oakland A’s general manager, Billy Beane, and his struggle to create a competitive baseball team on a…

13 Rental Car Rules

Michael Flack | Aug 20, 2021

IN SEPTEMBER 2017, my wife and I sold our home, car and almost all our earthly possessions. We spent the next four years driving across four continents. Along the way, I learned a great deal about renting a car that, in this rental-car-challenged world, could make your travels less costly and more reliable. 1. I use Expedia, Kayak and Hotwire to…

Other People’s Money

Michael Flack | May 30, 2023

ACCORDING TO OXFORD Languages, the word invest means to “expend money with the expectation of achieving a profit.” I like this definition better than some others because it includes the word “expectation,” which therefore should exclude casino gambling and sports betting. But what if you have an expectation of winning? Couldn’t casino gambling and sports betting both be considered investments?…

Is an 18% Service Charge a TIP?

The Value Of Trust

Jonathan and me

Saved 85 Bucks

My Investment Sin

2026 Charitable Deductions

Choosing a CCRC (Life PlanCommunity)

Time to QCD

The Number Is Not The Answer

Jonathan’s Daily Musing, 10/13

Update: Jonathan’s Getting Going on Saving Initative

Momentarily Embarrassed by “Not Much”

Is an 18% Service Charge a TIP?

The Value Of Trust

Jonathan and me

Saved 85 Bucks

My Investment Sin

2026 Charitable Deductions

Choosing a CCRC (Life PlanCommunity)

Time to QCD

The Number Is Not The Answer

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Manifesto

think

act

Truths

Money Guide

Manifesto

Spotlight: Retirement

Is saving really that hard? Nope, not for the great majority of Americans.

Market Risks

Trump Accounts

Punched in the Mouth

Bucket Strategy

Why Bonds Matter

Spotlight: Flack

No TIME Left For You

Risk at Every Turn

Good Enough Tech

Beyond the Obvious

13 Rental Car Rules

Other People’s Money