Home - HumbleDollar

Saved 85 Bucks

Dan Smith | Oct 13, 2026

"Ditto for me ( except for dealerships). Greg, you sound like you ran/ run EXACTLY the kind of shop I would and do business with when I need something done that I don’t have time for or is over my head on equipment or knowledge. People like you are golden."

- Dunn Werking

Spending

Is an 18% Service Charge a TIP?

James McGlynn CFA RICP® | Oct 13, 2026

"I was thinking the same thing. We have a few family dinners next week, I will ask the server for details."

- Dan Smith

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

Careers

The Value Of Trust

Andrew Clements | Oct 14, 2026

"Dan, you picked up on something that really struck me as I was writing this. Who would have imagined that a pile of mulch nearly 34 years ago would lead to so many opportunities and lasting friendships? Nick and I always believed that when a customer called, their concern deserved our immediate attention. We took pride in treating their properties as our own, and that approach served us well. Looking back, though, it's those friendships that mean the most. Thanks, Dan, for such a thoughtful comment!"

- Andrew Clements

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

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

Taxes

2026 Charitable Deductions

Rick Connor | Oct 12, 2026

"I found the Kitces article described below to be a much better rendition of how the new deduction paradigm works, than any of the discussion here. The Kitces article includes tables and graphs that show it all."

- B Carr

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

Investing

Financial Lessons

ArticleAdam M. Grossman | Sep 26, 2026

WHAT'S THE MOST important idea in personal finance? It’s hard to single out just one, but over the years, I’ve found the following dozen ideas to be among the most useful.

Whether it’s on TV or online, there’s never any shortage of market prognosticators. Especially during a bull market, everyone seems to have an opinion on where things are headed. The reality, though, is that people can only guess about how the economy, the market or any individual investment will perform. Convincing as they might sound, no one has a crystal ball. That’s why, when it comes to investing, I suggest taking an evidence-based approach, one that relies as much as possible on data and research rather than on the simple stories, anecdotes and sayings that are so prevalent among market commentators.
What does the data tell us? Among the most significant research in recent years is the work of Hendrik Bessembinder. In looking at the historical returns of stocks, he found that just a tiny fraction—only 4%—have accounted for the vast majority of the market’s gains over and above what Treasury bills paid, and the median stock actually delivered a negative return. This is one of the key reasons I recommend index funds rather than picking individual stocks or investing in an actively-managed fund. Identifying that 4% is almost impossibly difficult. But if you invest in a broad-based index fund, you’ll have a high likelihood of owning the next Apple or Nvidia.
Be careful not to miss the forest for the trees. The most important driver of investment risk and return for most people, most of the time, is asset allocation. In other words, the dollars you have in stocks vs. in bonds or in cash will almost always be the most consequential decision. It’s easy to lose sight of that, though, because so much of the investment commentary from day to day focuses on details like small differences in fund expenses or small differences in bond yields. To be sure, details can be important, but only after considering the big picture.
Another challenge in investing is that certain rules of thumb gain so much popularity that they end up being seen as rules rather than just guidelines. For example, some say that the percentage of a portfolio allocated to bonds should be equal to an investor’s age. To me, that’s illogical. Consider Bill Gates. He’s 70 years old, but it stands to reason that he shouldn’t have the same asset allocation as any other 70-year-old. Rules of thumb are useful as points of reference, but we shouldn’t lose sight of the fact that everyone’s situation is different, and our investments should reflect that. More to the point, don’t worry if you’re doing something different from the next person.
Buy insurance, but only to protect against losses you couldn’t absorb on your own. What does this mean in practice? In many cases, it’s possible to significantly cut insurance premiums by increasing deductibles. For example, if you have a seven-figure net worth, you might consider raising the deductible on your homeowner’s insurance to $5,000 or $10,000 or even more. Similarly, you might re-evaluate your life insurance as your net worth grows. You’ll likely become “self-insured” at some point, and then you could reduce or drop that coverage.
Personal finance is quantitative, but we should never make decisions based only on the numbers. For example, a common question is how much cash to keep on hand. While we could work out an optimal number on a calculator, that shouldn’t be the final answer. You should also consider what would provide you with peace of mind. That is equally important.
Be wary of the psychological pitfall known as recency bias. This is the tendency to extrapolate from recent experience and to downplay the possibility that things might change. The most famous example? In the late-1920s, when the stock market was booming, Yale University economist Irving Fisher declared that the stock market had reached a “permanently high plateau.” Just nine days later, the market crashed, ultimately dropping 89% from its peak.
Avoid high fees. The research firm Morningstar once wrote, “If there’s anything in the whole world of mutual funds that you can take to the bank, it’s that expense ratios help you make better decisions. In every single time period and data point tested, low-cost funds beat high-cost funds.”
Keep things simple. Most importantly, I would be wary of investments that aren’t easily understood. Not only can this help keep investment costs down, but it also makes it much easier to monitor your financial picture. Legendary fund manager Peter Lynch said it best: “Never invest in any idea you can't illustrate with a crayon.”
Avoid “interesting” investments. So far this year, Wall Street has introduced more than 1,000 new exchange-traded funds (ETFs). How many of these are worth your attention? My guess is you could probably count them on one hand. More than 80% of these new funds are actively-managed, and more than 30% employ leverage. And there are more to come. Fund companies recently filed paperwork to create ETFs that will track the performance of major league sports teams. They won’t actually own shares in the teams; instead, they’re expected to rise and fall in response to each team’s wins and losses.
For years, I’ve argued that bitcoin isn’t a valid investment. Even though it’s gone way up since I first made that argument, I still feel the same way, and for the same reason: because it lacks intrinsic value. Unlike stocks or bonds, it doesn’t generate any dividends or interest. Bitcoin’s price is not anchored to anything measurable or tangible, and that’s why, in my opinion, its price is so volatile.
When it comes to investment risk, investors’ attention usually turns to the stock market. That makes sense, but as we’ve seen this year, bonds are not without risk. And unfortunately, the total-bond market index, which is often seen as the simplest, set-it-and-forget-it option, is one that carries quite a bit of risk. If you’re choosing bond investments, my recommendation is to pay attention to a metric known as duration. This tells you how sensitive a bond, or bond fund, will be to interest rate changes. In my view, investors should hold a sizable portion of their bond investments in a fund, or in individual bonds, with a duration of less than two years.

Adam M. Grossman is the founder of Mayport, a fixed-fee wealth management firm. Sign up for Adam's Daily Ideas email, follow him on X @AdamMGrossman and check out his earlier articles.

Cars

Saved 85 Bucks

Dan Smith | Oct 13, 2026

- Dunn Werking

Spending

Is an 18% Service Charge a TIP?

James McGlynn CFA RICP® | Oct 13, 2026

"I was thinking the same thing. We have a few family dinners next week, I will ask the server for details."

- Dan Smith

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

Careers

The Value Of Trust

Andrew Clements | Oct 14, 2026

- Andrew Clements

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

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.

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

Taxes

2026 Charitable Deductions

Rick Connor | Oct 12, 2026

- B Carr

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.

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.

humans

Oct 12, 2026

NO. 46: DIVERSIFICATION has been described as Wall Street’s only free lunch—but some folks take the notion too far. They’ll spread their money across multiple financial advisors, multiple funds that invest in the same market sector and far too many financial firms. The result can be high investment costs and an overly complicated financial life.

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: Advisors

Beyond fees, is using a financial advisor, advisable? If you do or don’t why?

R Quinn | Jul 10, 2025

There was a discussion recently on HD about the costs/benefit of a financial advisor. I have more questions. Who needs a financial advisor and why? I have looked up the pros and cons and certainly a case can be made for using an advisor, but…

Investing in Dimensional Funds

Jane | Feb 15, 2025

My husband and I are considering working with a firm that will develop a strategic financial masterplan that will include tax strategies, Roth IRA conversions, estate planning, charitable giving and gifting among other things . We are also talking with an advisor who invests in…

Less Funds More Gain

Sanjib Saha | Dec 11, 2021

READERS MAY RECALL Laura, my acquaintance who didn’t need life insurance but was sold a policy anyway. Alarmed by her ignorance, she vowed to manage her own money. As a first step, she parted ways with her financial advisor. The advisor had her invested in 35…

The Quiet Failure of Good Advice

Javier Escobar | May 29, 2026

A couple of year after retiring from a career in translation and the organization of international conferences, I enrolled in a graduate program for Financial Planners at Rice University and subsequently passed the CFP exam. I didn’t intend to go back to work, and I…

Does My Sister Need a Financial Advisor?

W.D. Housley | Nov 4, 2025

My sister called and asked if she should get a financial advisor. Her question made me pause, because I’ve wondered the same thing myself. How “right” do you have to be when you invest? How much better does an advisor need to be to make…

Costs Matter

David Lancaster | Nov 30, 2024

I’m sure many Humble Dollar readers have read various iterations of this innumerable times. I was just reading Adam Grossman’s (soon to be published on the HD website) weekly email where he quotes Warren Buffet as stating, “Performance comes, performance goes. Fees never falter.” John…

My 2023 Forecast

Greg Spears | Jan 8, 2023

AROUND THE TURN of the year, investment experts issue their forecasts for the next 12 months. Bloomberg says it has gathered more than 500 market predictions for 2023, with many forecasting a rough year for the financial markets. I’ve done my research as well, and I’m now prepared to offer my forecast: There’s an 80% chance that the S&P 500…

Fire the 4% Rule

Greg Spears | Jan 25, 2022

I DID ACHIEVE financial independence and retire early—if you count age 64 as early. My friend Jose, a true believer in FIRE, or financial independence-retire early, celebrated his retirement at 44. That took a steely nerve that I lacked, plus I had big college bills to pay before retiring. One big challenge of FIRE, of course, is that your savings…

Powerful Savings

Greg Spears | Sep 21, 2023

I BOUGHT AN EXPENSIVE new water heater last year for my house in Maine. The old heater had a ring of rust at the bottom, and I was spurred to act by an $800 rebate offered by the state of Maine, which was contingent on buying a heat pump water heater. The new water heater draws its heat from the…

Promises Broken

Greg Spears | Oct 5, 2021

VANGUARD GROUP is renowned for its rock-bottom investment costs, including announcing last week that it was lowering expenses on its target-date retirement funds. As a former Vanguard employee, I just learned how the company is, in part, paying for such cuts. Yesterday, Vanguard emailed retired “crew members” like me to say it was shutting down its retiree medical account program.…

Buffett’s Pension

Greg Spears | Jul 22, 2022

AS MY OLD NEWSPAPER company slid toward bankruptcy, it signed over the deeds to its newspaper buildings to the pension plan in an effort to meet its obligations. It was like burning the furniture to keep the house warm—and it worked about as well as you might expect. When the company finally filed for bankruptcy in 2020, it laid the blame…

New Year’s Tweaks

Greg Spears | Jan 1, 2022

LET’S NOT CALL THEM resolutions because that imposes a sense of obligation. Rather, think of these as adjustments that could give you—and maybe your kids—a smoother ride in 2022: Check the beneficiaries on your employer’s retirement plan, IRAs and life insurance policies. Sometimes money winds up with an ex-spouse or maybe a younger child gets left off the list. This…

Saved 85 Bucks

Is an 18% Service Charge a TIP?

Choosing a CCRC (Life PlanCommunity)

The Value Of Trust

My Investment Sin

Time to QCD

The Number Is Not The Answer

Jonathan’s Daily Musing, 10/13

2026 Charitable Deductions

Update: Jonathan’s Getting Going on Saving Initative

Momentarily Embarrassed by “Not Much”

Financial Lessons

Saved 85 Bucks

Is an 18% Service Charge a TIP?

Choosing a CCRC (Life PlanCommunity)

The Value Of Trust

My Investment Sin

Time to QCD

The Number Is Not The Answer

Jonathan’s Daily Musing, 10/13

2026 Charitable Deductions

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Manifesto

act

Truths

humans

Money Guide

Manifesto

Spotlight: Advisors

Beyond fees, is using a financial advisor, advisable? If you do or don’t why?

Investing in Dimensional Funds

Less Funds More Gain

The Quiet Failure of Good Advice

Does My Sister Need a Financial Advisor?

Costs Matter

Spotlight: Spears

My 2023 Forecast

Fire the 4% Rule

Powerful Savings

Promises Broken

Buffett’s Pension

New Year’s Tweaks