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Live a little

greg_j_tomamichel | Apr 25, 2026

"I agree wholeheartedly. But actually putting this into action can still be difficult. Old habits die hard!"

- greg_j_tomamichel

I WAS 48 years old when the judgement was final and the papers were signed. My former wife and I split our net worth 50/50. There were no arguments over household items like furniture; I didn’t care about that stuff. Pam gladly accepted my proposal that she keep the house, and all its equity, in exchange for me keeping an offsetting amount of the IRAs and my 401(k), a very good move for my future self. By giving up the house, I also escaped the mortgage, which was the only loan obligation I had. Had there been consumer debt (there was none), I would have eliminated that as quickly as possible, beginning with the highest interest loans. I was ordered to pay spousal support to age 65, or my retirement if I worked beyond 65. I would be lying if I told you that I liked paying alimony. Still, it wasn’t unfair considering our age at divorce, Pam’s depression, and the fact that she mostly stayed at home to raise our kids. Long before the divorce was ever final, I knew I’d have to make up for lost time if I ever wanted to retire in the manner to which I wanted to had become accustomed. The divorce wasn’t going to be the only obstacle I would have to overcome. Thirty years of delivering beverages resulted in osteoarthritis and plantar fasciitis; my days on the beer truck were rapidly coming to an end. I needed a plan. Where Was I? I had to understand exactly where I was, and what my options were.

My continued employment as a delivery driver would likely have left me on Social Security Disability (SSDI) by age 55.
I was very interested in personal finance, and knew many people in that field who would help me get my foot in the door.
I had acquired bookkeeping, payroll, and tax prep skills through my involvement with my local union, though I never pictured myself as the type to sit behind a desk, in a dimly lit office, crunching numbers beneath the glow of one of those green shade banker’s lamps.
As a last resort, I could fall back on my truck driving skills, using my commercial drivers license to get a job hauling ‘no-touch’ freight of some sort.
Last but not least, I needed a place to live. “Hello, mom and dad, I need my room back”. Sleeping on the twin mattress I gave up 25 years earlier, was not part of my plan.
I was determined not to let my occupation as a beer truck driver dictate my future job prospects.

Where did I want to be?

Where to live? Living with the folks was never meant to be a long term thing. After three months of that, I signed my first ever apartment lease as a lessee, as opposed to a lessor. That lasted two years, until a very large increase in the rent caused me to buy a duplex, and become a lessor again.
Where to work? I continued my work as a delivery driver for three more years. My position as the local union president, and my five paid weeks of vacation actually kept me off of the truck much of the time. That enabled me to tolerate the maladies that would eventually force me out of that job. Having absolutely no desire to spend the balance of my life languishing on SSDI and a minimal IRA balance, I set off on the path to becoming a financial services guy. That did not work out, and if you want more information on that, here’s a link.
To make ends meet, I turned to my last resort; driving a truck. Piloting an 18-wheeler was not how I envisioned my remaining working days. And although the freight was ‘no touch’, driving 600 miles every day in a Kenworth tractor is still pretty hard on your vertebrae. But sometimes you have to do what you have to do to survive and to keep your eye on your finish line. My heart goes out to full time drivers, that job is no walk in the park.
And what about love? My preference was to be in a relationship, but not any relationship. I wanted a good partner, I wanted to be a good partner as well. What qualities would I look for in a new partner? Independent, established, confident, and nice. Was I asking too much?

Making it All Work Finally, preparation collided with opportunity. In other words, I got lucky. Remember when I told you I didn’t picture myself as ever being a bean-counter? Two established financial services guys set me up with free office space and began funneling tax prep clients to me. What began with me preparing taxes for about three dozen of my union brothers, instantly turned into over 100 clients. There I was, a bean counter of sorts. I kept that truck driving job for several more years. And remember that duplex I bought after the rent spiked at my apartment? Well, there was this girl living next door. Enter Chrissy. We became best friends. She is no longer my neighbor. She is now my spouse. Of course, at the time we met, aside from being a nice guy, I wasn’t much of a catch. Man, she took a chance on me. As my client count went up, my days driving the big-rig went down. When the client count got to about 400, I retired forever from driving. No more trips to Chicago, Des Moines, Snow Shoe PA, or Jersey City. Chrissy and I began pounding 40% of our gross pay into savings. It would take until I was 70, but working together, we got to a place each of us only dreamed we would be. By living within our means, and keeping lifestyle creep to a minimum, we surpassed our goals. Chris retired at 64 and helped me during my final three years as a tax preparer. Lucky for me, Federal Wage and Hour never found out that I violated the minimum wage laws by never paying her in the first place. I sold the practice at age 70. I prepared 650 tax returns in my final year. It’s important to note that during our journey, we did not starve ourselves of food nor fun. We counted 27 trips during our first ten years together. Chris was great at finding great deals to various destinations in the Caribbean, and we turned several of her business trips into mini vacations as well. It’s important to prepare for the future, but have some fun along the way as well. I hope this piece inspires someone who is still on the road, dealing with similar obstacles, and wondering if there was a way around them. For 30 years, Dan Smith was a driver-salesman and local union representative, before building a successful income-tax practice in Toledo, Ohio. He retired in 2022. Dan has two beautiful daughters, two loving sons-in-law and seven grandchildren. He and Chris, the love of his life, have been together for two great decades and counting. Check out Dan's earlier articles.

How much to provide a college student monthly?

Chris | Apr 25, 2026

"As a professor, I felt that students lived much “softer” lives than I had as a student. I remember going to Sunday brunch at a local place right before finals week, and we were surrounded by large groups of students enjoying “bottomless mimosas.” Humph. When I was a student, I was at the library during finals week, and I certainly couldn’t afford brunch. But that’s an “old lady yelling at cloud” kind of observation! That’s cool about your son. My sister was a history major at UC Davis and my older daughter got her history degree from Cal—inspired by an amazing Advanced Placement US History teacher in high school."

- DrLefty

A Life You Build

Jeff Peck | Apr 19, 2026

"Truly a great story. Thanks for sharing. I didn't benefit from the same things you did, but my grocery store manager father was Dave Ramsay before Dave Ramsay was Dave Ramsay. Would never get a credit card. Paid for cars by saving up for them. Paid off his house in 11 years. Bought utility stocks as they paid a dividend. I learned early on important all that was and though I have had credit cards I pay them off every month and until recently (70) I was always saving and investing."

- Pete Tittl

Rethinking the “Right” Time for Social Security

Andrew Clements | Apr 23, 2026

"Another great HD contribution--thanks for this."

- Kristine Hayes

Investing Fundamentals: A Simple Guide for Beginners

William Housley | Apr 24, 2026

"Great article! This should be mandatory reading for young people."

- Kristine Hayes

Lonely Island (Correct Edit)

Mark Crothers | Apr 22, 2026

"Bob, what a great post!"

- DAN SMITH

The great COLA debate-maybe not the expected solution.

R Quinn | Apr 26, 2026

"FYI The current projected 2027 COLA is 2.8% to 3% to be determined by CPI data for July, August and September 2026."

- R Quinn

Why I use a Donor-Advised Fund

David S | Feb 21, 2026

"Great article. I also took SS at 67 (or maybe 68) - the "lost" dollars either way seemed to be insignificant and I didn't have to tap my investments the first few years (which then promptly grew tremendously with the market run-up.) I'm a big fan of blended solutions in lots of areas. I'm known in my family for that. For example, no 100% cotton or polyester shirts - I need a blended fabric of both. I've thought about a blend here, but I'm not yet sure it works. The article makes me reconsider. I'll noodle some more. Thanks."

- Martin McCue

Tax Free Income Trap, Dealing With MAGI

DAN SMITH | Apr 21, 2026

"[Comment deleted because I thought better of it.... need more coffee before posting....]"

- urbie53ca4a2392

Hidden Surcharge

DAN SMITH | Apr 21, 2026

"There was a time when the top rate was 70% and those writing the tax laws brought that down to 37%. But government spending never came down. The tools to collect just changed. I see a strange parallel to retirement, the sources of income change and life goes on."

- Mark Eckman

Something to Think About

David Lancaster | Mar 24, 2026

"It seems like you’re trying to time the market on your conversion? My understanding is that you have to be right on both sides of that trade. Even if it’s a Roth conversion."

- William Housley

Driving Prices

ArticleAdam M. Grossman | Apr 25, 2026

IN 2020, ELECTRIC car maker Lucid Motors brought in revenue of $4 million. Five years later, sales had risen impressively, to more than $1 billion. In 2025 alone, sales grew 68%. That sounds like a success story, and through that lens, it is. And yet, over that same period, the company’s stock dropped more than 89%. What happened? A better question is: What didn’t happen? Despite growing sales, the company has struggled to turn a profit. On sales of $1.3 billion last year, Lucid posted a loss of $3.8 billion. It’s experienced production problems and management turnover. It’s seen its competitors cut prices. As a result, it’s been forced to issue new shares, thus diluting the value of existing investors’ holdings, just to keep the lights on. In fairness to Lucid, the road to success is rarely a straight line. Arizona State University professor Hendrik Bessembinder studies the performance of public companies, and the results are sobering. In new research, he found that, over the past 100 years, the median return among stocks trading on U.S. exchanges was negative 6.9%. Only a minority of stocks, in other words, made any money at all. Why are these results so dismal? Four factors stand out. The first is emotion—specifically, investors’ emotions. After Lucid went public in late-2020, its stock began rising quickly, and in the early months of 2021, the shares gained nearly 500%. What was driving those gains? Since the company was just starting production, very little can be attributed to the company’s financial results. Instead, it was simply investor excitement around the electric vehicle market and the optimistic view that Lucid would become the next Tesla. But no sooner did the stock rise that it fell again. And in the years since, it’s been an overwhelmingly downward slide for investors. In the last interview he gave before he died in 1976, Benjamin Graham compared the stock market to a seesaw. “The present optimism is going to be overdone and the next pessimism will be overdone.” And that causes stocks to go to extremes. Fifty years later, Graham’s observation seems no less accurate. Indeed, investment manager Cliff Asness has argued that, because of the internet, the impact of emotions on the market is even worse today. Due to what he calls “the less-efficient market hypothesis,” inaccurate information can spread much more quickly today than it did in the past. You may recall the phenomenon in which a group of day traders, led by a YouTube personality who called himself Roaring Kitty, was able to drive up the stock of a nearly-bankrupt company for no rational reason. That couldn’t have happened in the years before social media. Another factor that can drive stock prices is government action, and this also explains part of Lucid’s slide. When the government ended tax credits on electric vehicles last year, that made electric cars much more expensive for consumers. And contrary to intuition, this year’s higher gas prices haven’t done much to entice buyers back to EVs. On the other hand, government action can sometimes be positive. In 2017, for example, Congress voted to cut the corporate tax rate from 35% to 21%, significantly boosting public company profits. Perhaps the most obvious factor that can drive stock prices is competition. This can take a few different forms. Coke and Pepsi, for example, have been battling for more than 100 years, but their relative positions don’t change very much. At this point, neither company is going to go out of business as a result of the other. In his book The Innovator’s Dilemma, the late Clayton Christensen described a much more disruptive form of competition—the sort that upends industries entirely, such as when 19-year-old Bill Gates outsmarted IBM. At the time, IBM was the most dominant company in the computer industry, but over time its position faded. It underestimated how important personal computers would become and didn’t take the market seriously. Years later, it ended up selling off its PC business entirely, and today makes very little hardware. The same sort of thing happened to BlackBerry, to Kodak and to Polaroid, among others. Like IBM, all of these companies had enormous resources. But, according to Christensen, it was their success that became their greatest weakness, because it caused them to underestimate threats and to downplay the likelihood that anything fundamental might ever change. Ken Olson, the founder of Digital Equipment Corporation, a leader in minicomputers in the 1960s and 1970s, famously asserted, “There is no reason anyone would want a computer in their home.” The tricky aspect of the innovator’s dilemma, though, is that it isn’t universal. Consider the early years of the auto industry. Before automobiles gained popularity in the early 1900s, it’s estimated that there were 4,000 companies in the horse-and-carriage business. The right move for any of these companies would have been to try to transition into automobile manufacturing. Carriage makers, especially, had relevant skills and were best positioned to make this leap. But they adopted a collective mindset that the automobile wasn’t going to succeed, dismissing cars as “devil wagons.” But one of these carriage makers, Studebaker, did correctly assess where things were going and successfully transitioned to making automobiles. The rest failed, faded away or switched into other businesses. Companies, in other words, can be very good at one thing but lose their footing in the face of change. That’s a key factor behind Bessembinder’s findings. A final factor that can cause companies to stumble: random events. Consider, for example, what occurred in Thailand in 2011. Heavy rainfall resulted in flooding that caused large industrial areas to become submerged. This included the factories of hard drive manufacturers Western Digital and Seagate, causing their stocks to drop 35% and 45%, respectively. Both recovered, but this is an example of how even good companies can run into bad luck. Years of research has shown how difficult it is to predict stock prices. Bessembinder’s new work, however, makes an additional important point, which is that, for all of the reasons discussed here, and likely others, stocks face many more roads to potential demise than to success. Thus, to succeed at stock-picking doesn’t just require research and hard work. It requires an almost prophetic ability to identify the tiny handful of stocks that will turn into homeruns. But since the odds are so steeply against success, that’s a key reason I see it as so important to stick with the simpler and less risky alternative of index funds. 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.

Live a little

greg_j_tomamichel | Apr 25, 2026

"I agree wholeheartedly. But actually putting this into action can still be difficult. Old habits die hard!"

- greg_j_tomamichel

Around the Obstacles

ArticleDan Smith | Apr 25, 2026

My continued employment as a delivery driver would likely have left me on Social Security Disability (SSDI) by age 55.
I was very interested in personal finance, and knew many people in that field who would help me get my foot in the door.
I had acquired bookkeeping, payroll, and tax prep skills through my involvement with my local union, though I never pictured myself as the type to sit behind a desk, in a dimly lit office, crunching numbers beneath the glow of one of those green shade banker’s lamps.
As a last resort, I could fall back on my truck driving skills, using my commercial drivers license to get a job hauling ‘no-touch’ freight of some sort.
Last but not least, I needed a place to live. “Hello, mom and dad, I need my room back”. Sleeping on the twin mattress I gave up 25 years earlier, was not part of my plan.
I was determined not to let my occupation as a beer truck driver dictate my future job prospects.

Where did I want to be?

Where to live? Living with the folks was never meant to be a long term thing. After three months of that, I signed my first ever apartment lease as a lessee, as opposed to a lessor. That lasted two years, until a very large increase in the rent caused me to buy a duplex, and become a lessor again.
Where to work? I continued my work as a delivery driver for three more years. My position as the local union president, and my five paid weeks of vacation actually kept me off of the truck much of the time. That enabled me to tolerate the maladies that would eventually force me out of that job. Having absolutely no desire to spend the balance of my life languishing on SSDI and a minimal IRA balance, I set off on the path to becoming a financial services guy. That did not work out, and if you want more information on that, here’s a link.
To make ends meet, I turned to my last resort; driving a truck. Piloting an 18-wheeler was not how I envisioned my remaining working days. And although the freight was ‘no touch’, driving 600 miles every day in a Kenworth tractor is still pretty hard on your vertebrae. But sometimes you have to do what you have to do to survive and to keep your eye on your finish line. My heart goes out to full time drivers, that job is no walk in the park.
And what about love? My preference was to be in a relationship, but not any relationship. I wanted a good partner, I wanted to be a good partner as well. What qualities would I look for in a new partner? Independent, established, confident, and nice. Was I asking too much?

How much to provide a college student monthly?

Chris | Apr 25, 2026

- DrLefty

A Life You Build

Jeff Peck | Apr 19, 2026

- Pete Tittl

Rethinking the “Right” Time for Social Security

Andrew Clements | Apr 23, 2026

"Another great HD contribution--thanks for this."

- Kristine Hayes

Investing Fundamentals: A Simple Guide for Beginners

William Housley | Apr 24, 2026

"Great article! This should be mandatory reading for young people."

- Kristine Hayes

Lonely Island (Correct Edit)

Mark Crothers | Apr 22, 2026

"Bob, what a great post!"

- DAN SMITH

The great COLA debate-maybe not the expected solution.

R Quinn | Apr 26, 2026

"FYI The current projected 2027 COLA is 2.8% to 3% to be determined by CPI data for July, August and September 2026."

- R Quinn

Why I use a Donor-Advised Fund

David S | Feb 21, 2026

- Martin McCue

Driving Prices

ArticleAdam M. Grossman | Apr 25, 2026

Manifesto

Apr 26, 2026

NO. 26: WE SHOULD strive to spend our days as we wish—by using our dollars to escape today’s chores that we dislike, while also saving for the ultimate prize: full financial freedom.

think

Apr 27, 2026

HUMAN CAPITAL. If we’re early in our career, our most valuable asset is usually our human capital—our ability to pull in a paycheck. That paycheck allows us to service debt, provides the savings needed for retirement and frees us up to invest in stocks. But as retirement approaches, we should aim to pay off all debt and shift maybe half our portfolio into bonds.

humans

Apr 26, 2026

NO. 32: WE REVISE our memories to make ourselves look better. Suppose we believe we’re smart at managing money, but then we panic during a market decline. The result can be the uneasy feeling known as “cognitive dissonance.” To escape our discomfort, we might revise our memory—and decide we stood our ground and perhaps even bought more.

think

Apr 25, 2026

TIME DIVERSIFICATION. Investors with long time horizons are encouraged to buy stocks. Yet such “time diversification” is controversial: While most of us assume the stock market is mean reverting—meaning good times follow bad—academics have argued that, if stock returns are random, healthy returns aren’t a sure thing, no matter how long we hang on.

Money Guide

Manifesto

Apr 26, 2026

NO. 26: WE SHOULD strive to spend our days as we wish—by using our dollars to escape today’s chores that we dislike, while also saving for the ultimate prize: full financial freedom.

Spotlight: Estate Plan

Getting Along

Tom Sedoric | Jun 7, 2024

ONE OUT OF SIX of our nation’s children lives in a blended family, with 40% of today’s marriages defined as blended, meaning that one or both spouses had been previously married. I live in one of those blended households.
Three decades ago, the data on children from “broken families” weren’t encouraging. I can happily debunk that early data, which didn’t give our family much hope. My two exceptional stepchildren, and our biological daughter, are all productive and contributing adults.

What’s Your Plan?

Adam M. Grossman | May 5, 2024

MICK JAGGER IS AMONG the most successful entertainers of our time. But despite his wealth, Jagger tells his eight children that they’ll need to make their own way. Similarly, Shaquille O’Neal tells his children that they can earn some of his millions, but it won’t necessarily be given to them. Actor Jeff Goldblum puts it more bluntly: “Row your own boat,” he’s said. Other public figures have echoed a similar theme.
Why do these wealthy folks take such a seemingly uncharitable view?

Look All Ways

Howard Rohleder | Nov 20, 2023

WHAT HAPPENS WHEN you’re hit by the proverbial beer truck? Will it be easy for others to pick up the pieces—the pieces of your financial life, that is?
To my knowledge, my wife isn’t checking the delivery schedule for the Anheuser-Busch brewery here in Columbus, Ohio. Still, she’s worried about the complexities of our finances. I’ve made a concerted effort since I retired to consolidate and close financial accounts, reduce our investments holdings, and streamline where it makes sense.

Legacy Decisions: What Should the Sandwich Generation Pass on?

quan nguyen | Aug 22, 2025

I don’t have much choice as a baby boomer. My generation has been predicted to usher in the largest intergenerational wealth transfer in the next decade. In the meantime, we carry the honor and burden of taking care of our frail, elderly parents. People call us “the sandwich generation” – and I’d like to think we’ve made the best sandwich ever.
My parents came from a deeply patriarchal culture in which the parents dictated nearly every aspect of their children’s lives –

Not So Simple

Jeffrey K. Actor | Jun 11, 2024

MY WIFE AND I HAVE divided household duties over our 36 years of marriage. I’m responsible for the upkeep of anything mechanical. Lori has the last word on almost everything else. In essence, my wife presides over functions that make the household a “home,” while I take credit and blame for keeping the nuts and bolts operational.
I also hold primary responsibility for trafficking the family’s money. I pay bills, ensure accounts are reconciled,

Preparing for the Unthinkable

Rick Connor | Aug 14, 2024

My wife and I moved from PA to NJ about 3 years ago. After we moved I looked into whether we should update our estate documents since we changed states. It seemed like a smart thing to do, but it took us 3 years to get around to it.
We recently met with a local estate attorney and reviewed our wills and POAs. There was some specific Pennsylvania language having to do with setting up a trust for contingency heirs – our grandsons – if one of our sons pre-deceased us.

All Stocks

John Yeigh | Feb 15, 2019

AFTER THE MARKET turbulence of recent months, the idea of a 100% stock portfolio would strike many folks as crazy. Yet, when I was in the workforce, that's pretty much what I owned. I never felt my all-stock portfolio was particularly risky. My wife and I had solid paychecks to rely on. We always maxed out our retirement plans, while also adding to other accounts, and then lived on whatever remained. While the stock market’s volatility and the occasional downturns may have been disconcerting, they never changed our all-in stock approach for our long-term savings. In the event of a major downturn, we felt we could always continue working to rebuild our savings and, if necessary, delay our retirement. In addition to the security offered by our paychecks, the risk of an all-stock portfolio was somewhat mitigated by other areas of our financial life. Like most folks, we were earning Social Security benefits. I was also fortunate to be covered by a traditional pension plan, providing further retirement funds with no stock market risk. On top of that, we had significant and growing home equity. These various resources provided a solid, multi-legged stool for retirement. In addition, we ended up with another half leg, thanks to an inheritance and some income from a side business, though we never counted on these. Our confidence in our all-in approach was further bolstered by our conservative stock portfolio. We mainly invested in broad, low-cost U.S. stock market index funds, with almost no foreign market exposure and never any emerging markets investments. I figured I’d let U.S. companies manage our foreign market exposure, along with the related currency and political risk. No doubt we incurred occasional opportunity costs, missing out on hot markets and hot sectors. But our tortoise approach allowed us to stay…

Off the Payroll

John Yeigh | Jan 30, 2019

WHEN OUR DAUGHTER landed a great job after her 2018 college graduation, we expected her to soon move off the family payroll. She immediately budgeted to take on all routine living expenses, including housing, food, car and utilities. We did volunteer to cover some smaller expenses, largely in situations where family plans are available, such as cellphones, Netflix, Amazon Prime and AAA. We also kept her on our employer-provided health insurance, which involved no added cost. Today, a third of millennials still live at home. I get it. Young adults may be seeking a job, continuing college studies, saving for a down payment or wedding, temporarily displaced, or simply lazy or fearful about entering the workforce. Even if they move out, many others receive parental financial help, similar to what we planned for our daughter. But in our case, parental help turned out to be far larger than we expected. My daughter’s first big challenge was finding a place to live. In her new city, tiny apartments rent for some $2,000 per month. These apartments were too small to store snow tires, camping gear, skis and other stuff that should now be hers to manage. I also struggled with throwing away $24,000 a year on rent. That’s when I suggested she look into buying. This was a seismic shift from the original plan. Suddenly, our daughter had to step up and earn an instant PhD in real estate. She quickly learned that buyers get what they pay for—and that location, location, location is everything. Two important criteria were neighborhood safety and resale potential. After all, she might get a job transfer—a frequent occurrence early in a career. After considering many cheaper dumps, our daughter landed on a three-bedroom townhouse with a basement. It struck all of us as a solid value.…

Give Early and Often

John Yeigh | Feb 22, 2024

KEY PROVISIONS IN 2017’s Tax Cuts and Jobs Act (TCJA) will expire in 2026 unless Congress steps in. That means folks have a two-year window to prepare. What’s at stake? Income-tax rates will increase for many taxpayers. This creates an incentive to boost income over the next few years by, say, undertaking Roth conversions to shrink traditional retirement accounts and thereby lowering future required minimum distributions. The sunsetting of key TCJA provisions would also cut the threshold for federal estate taxes in half, from an estimated $14 million per individual in 2025 to $7.1 million in 2026. The limit for married couples is double these amounts, though—to capture a deceased spouse’s estate-tax exclusion—the surviving spouse must typically file an estate tax return within nine months of the first spouse’s death. Got wealth that’s above the projected 2026 threshold of $7.1 million for individuals and $14.2 million for married couples? You should almost certainly consult an estate attorney. Two common strategies are to use trusts or lifetime gifting to capture today’s high exemptions before 2026. The IRS has confirmed that there will be no “claw-back” if you take advantage of today’s high threshold. The lower 2026 estate exemptions of $7.1 million or $14.2 million—assuming today’s higher limits are allowed to sunset—would continue to cover 99.8% of us. Still, retirees with a few million dollars of financial assets might want to review their estate plan, especially if they’re married or if they have significant assets in traditional retirement accounts, where all withdrawals are taxed as ordinary income. Why? Married couples can face tax and income penalties after the first spouse dies—what’s commonly referred to as the “widow’s penalty.” The surviving spouse is potentially subject to the quadruple whammy of a reduced standard deduction, filing as a single taxpayer rather than married filing…

Screw politics, let’s talk health. Are all surgeries necessary or have we become the college tuition bank for the doctor’s children?

John Yeigh | Apr 17, 2025

I’ve recently observed cases where family and friends undertake serious medical interventions with not the best outcomes. These interventions seem well intentioned to rehab issues, but I now wonder if they sometimes are a money grab when potentially better health outcomes might exist. In fairness to the Doctors, we want instant and complete resolution to sometimes niggling health issues – many caused by our own lifestyles or basic aging. Here are a few observations: My uncle had his prostate removed in his late 70’s, and successive complications from the surgery killed him after two years of miserable, bed-ridden life. The typical life expectancy for most prostate cancers is 10-15 years. In fact, some European health organizations eliminate prostate cancer screening after age 70 since studies show no longevity increase with surgical intervention. Another relative in her 70’s had major back surgery to cure mild back pain, which persists perhaps worse than before. This individual is sedentary and does not exercise, walk or stretch. No exercise or physical therapy regimes were recommended prior to surgery. A friend had a hip replacement in his 50’s to sustain his active sporting lifestyle. Eight years later, he has significant bone-loss damage and other chemical imbalance issues from metallosis poisoning. His prognosis is potentially continued deterioration of these systems. Three different acquaintances (60’s) had knee replacements that have not gone ideally – all are hobbling worse and a couple have had multiple surgeries. Two are overweight, and one of these two is relatively inactive. No weight loss or exercise regimes were progressed prior to surgery. The American medical model seems to be to undertake every possible intervention. In the case of optional surgeries in particular, I just wonder if we sometimes are a defacto 529 Plan for the Doc’s children rather than getting the best…

Double FOMOitis

John Yeigh | Jul 21, 2025

I have an exasperating and ever-increasing case of double FOMOitis. Today’s stretched stock market valuations have given me a case of fear of missing out (FOMO) for not selling and locking in assured gains – sensible rebalancing theory suggests that we should all be selling on the way up. On the other hand, I have FOMO even considering selling because of the potential opportunity cost of not capturing further gains in a market with clear upward momentum – sensible investing theory (and Jonathan recently) suggests that we should ride the winners while they are hot. In reality, many of HumbleDollar’s financial debates mainly matter on the margin – Social Security claiming, taxes, tariffs, interest rates, Medicare premiums, Roth conversions, annuities, diversification, dividends, specific fund selections, etc. We seniors have experienced the most amazing 15 years of stock market appreciation ever, and having a healthy asset allocation to stocks has been hugely beneficial. At this point, only a Japan-like decades of market pull-back could devastate the comfortable financial position of those (like most HD readers) with invested assets – FOMO for not selling. Yet, the economy, earnings, technology development, consumer spending, employment, GDP, and stock valuations all continue to grow nicely, and it is always best to stay invested for the long-term – FOMO to sell. Anyone else likewise suffering a case of double FOMOitis?

Take a Break

John Yeigh | Nov 7, 2019

SAVE FIRST FOR THE kids’ college or for your own retirement? Pundits generally recommend that parents put themselves first. But I’d argue the question demands a more nuanced answer. The tax code offers numerous tax-savings opportunities for families with dependent children—and those tax breaks shouldn’t be overlooked. To be sure, for cash-strapped parents, the top two financial priorities should be building up an emergency fund and putting at least enough in their 401(k) or 403(b) to capture the full employer match. Already doing that? Instead of shoveling further money into retirement plans, consider whether you’d be better off exploiting these seven kid-related tax strategies: 1. A 529 plan is arguably the best tax-favored college savings account. The plans come in two flavors. Prepaid tuition plans allow you to buy credits toward the cost of particular colleges, effectively locking in current tuition rates. Meanwhile, 529 savings plans offer the opportunity to earn tax-free gains by investing in a menu of mutual funds. Note that 529 money is an asset that can affect financial aid eligibility. Want flexibility? Think twice before opening a prepaid tuition plan. One friend funded a prepaid plan, but his kids later balked at all the in-state colleges covered by the plan. The go-to website to review all things 529 is SavingforCollege.com. 2. Like 529 plans, Coverdell education savings accounts offer tax-free growth to pay for qualified education expenses. Coverdells can also be used for primary and secondary schools—now also an option for 529s, thanks to 2017’s tax law. The downside: Coverdells have a relatively modest $2,000 per year contribution limit, plus there are income limits on who can fund these accounts. We contributed to Coverdells for just a couple of years and used the money for high school costs, so our tax savings proved quite small. Today’s…

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