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How Did You Find Paid Work After Retiring from Your Primary Career?

Jeffrey Chan | Jul 31, 2026

"I work part-time preparing lab materials at a local college. I love my little job -- a half-day or so each week, for two semesters a year, mostly on my own schedule. The work is intellectually interesting and provides for socialization and interaction with students. I also enjoy the feeling of responsibility the work provides. The position materialized soon after I retired, when a former colleague and friend related how he was doing lab prep as part of his teaching but was clearly overworked. I volunteered to help, provided the college would cover me legally. They did; I worked as a volunteer through that first semester and continued on in a paid position thereafter."

- Jo Bo

Inflation, prices, COLAs, retirement and the last 16 years

R Quinn | Jul 27, 2026

"I still maintain there will not be a cut and also that no changes to make the fix during this administration for several reasons I won’t go into here. However, that means there will only be 4-5 years for any changes to generate sufficient revenue by 2032-33 to keep full benefits being paid. To me that means some pretty dramatic revenue changes in a short time. There is talk now of changing the application of the COLA in the future for higher income beneficiaries, - like capping it at the average paid to those collecting SS, but that is only part of the puzzle. it seems to me that for higher income (yet to be defined) beneficiaries relying on SS COLAs in retirement will be problematic. "

- R Quinn

Taking a Loss?

Mark Crothers | Jul 28, 2026

"thank you"

- John Kaczka

$400,000 Mistake

ArticleBogdan Sheremeta | Aug 1, 2026

BOB MADE A very expensive tax mistake. Doctors told Bob that he only has a year to live… What did Bob do?

He decided to gift a house to his only son before passing away. The house is worth $2,000,000 that he bought back in 1970 for $50,000 in an expensive suburb of California.

The son decided to sell the house and paid about $430,000 in federal taxes.

$430,000 that could have been $0 instead…

How?

When you gift a property to someone, they receive a "carryover basis." It basically means the same price the original owner purchased it for.

The basis of that house was $50,000, so the son had to pay capital gains tax on the difference between the $2 million sale price and the basis, at rates reaching up to 23.8% on the top portion of the gain. But this is where a step-up in basis could come into play.

Assets such as a house or shares held in a brokerage account, when owned inside an estate rather than an irrevocable trust, receive a step-up in basis to their fair market value (FMV) at the time of the decedent's death, per IRC Section 1014. In our case, if Bob held that house in his own name, passed away, and his son received the house, he would've gotten a step-up in basis to the current value, or $2M.

At the time of the sale, if sold for $2M, he would pay $0 in federal taxes, though state tax might still apply. That's about $430,000 of "savings."

"But who cares, Bob is dead anyways?"

While true, many parents still want to make sure their children don't have to pay half a million in taxes. They want their children to enjoy the fruits of their hard labor.

Specifics

The step-up in basis can be a bit nuanced, depending on how the assets are held and titled.

First, the step-up in basis typically adjusts to the market value, unless an election is made to use the value six months after the date of death, subject to certain rules.

The step-up in basis also doesn't apply to assets held in an irrevocable trust , though we will cover some strategies for that later, or to assets held in qualified retirement accounts, such as IRAs and 401(k)s.

In a community property state (Arizona, California, Idaho, Louisiana, Nevada, New Mexico, Texas, Washington, and Wisconsin), the basis steps up whenever a spouse dies. You will typically need to complete a form to receive this step-up in a brokerage account.

For assets held in joint tenancy, the step-up applies only to the deceased partner's share. For example, Bob and Jenice have a house worth $300,000 with a $50,000 basis. After Bob passes away, Jenice will have a $175,000 basis in the house, calculated as ($300,000 minus $50,000) divided by two, plus $50,000.

There are also two additional things to keep in mind:

1. Living on the right assets

Bob, age 75, has two accounts: a traditional 401(k) worth $500,000 and a brokerage account worth $500,000. Bob's diagnosis isn't good.

From a tax-planning perspective, it might make a lot more sense to withdraw, say, $50,000 a year from the 401(k) to live on, $20,000 of which would be required minimum distributions (RMDs), and pass down the brokerage account to his beneficiaries.

This is because the brokerage account likely has a lot of gains. Bob bought many stocks in his 30s and 40s that could be stepped up now. But a more in-depth analysis might be needed if Bob has a lot of income and is in a high marginal tax bracket.

2. Selling the right lots

Say Bob has a $500,000 brokerage account. Some of the stock purchases have a low basis, meaning a lot of capital gains, and some have a high basis, meaning fewer capital gains.

It's best to sell the high-basis stocks, which come with a lower capital gains tax, and pass down the low-basis stocks to the beneficiaries.

Planning matters. These mistakes can cost thousands of dollars in unnecessary taxes. As always, make sure to consult a licensed CPA or estate attorney with your unique circumstances.

Bogdan Sheremeta is a licensed CPA based in Illinois with experience at Deloitte and a Fortune 200 multinational.

Today in Financial History

Harold Tynes | Jul 28, 2026

"The 1971 view is obsolete. There is no need for a computer clerk."

- Cammer Michael

What I Retired To

Andrew Clements | Jul 29, 2026

"Thank you for sharing your story. It sounds as though you truly found your calling in medicine, and there’s no greater compliment than hearing from patients that you made a difference in their lives. I was struck by your comment that it wasn’t the work itself that led you to retire, but everything around it that changed. Sadly, I suspect many professionals have reached that same conclusion. It also sounds as though you’ve carried your love of learning into retirement through your reading, volunteering and staying engaged. I only wish there were an easier way for experienced physicians like you to continue helping others in a volunteer capacity. There is still so much wisdom to share."

- Andrew Clements

Value of Waiting

ArticleDennis Friedman | Feb 7, 2026

I WAS THINKING ABOUT Jonathan the other day on my morning walk, which happens more often than you might think. It’s hard not to think about him when you have HumbleDollar coasters in your living room and a HumbleDollar shopping bag in your car that you use for groceries. My wife confiscated the HumbleDollar cup I had been using for my morning tea, and it now has a new home in our bathroom holding her toothbrush and toothpaste. There’s even an apron somewhere in the house that Jonathan once sent to all the writers. Ever since I started writing for HumbleDollar in 2017, Jonathan has influenced my retirement. I now own the Vanguard Total World Stock Index Fund (symbol: VT) in my investment portfolio because of his recommendation. He liked it for its “broad global diversification in one low-cost fund that covers virtually all publicly traded companies worldwide.” It struck me as a good way to simplify our holdings. I didn’t just borrow some of Jonathan’s investment ideas; I also borrowed some of his words he used when editing my articles. I began peppering my writing with words like fret, upshot, and folks. He once told me, “While your grammar is occasionally a bit dodgy, you have a great ear for language.” I was too embarrassed to ask him what he meant by a “great ear for language.” When I retired, I never imagined that writing for HumbleDollar would become such a big part of my retirement, and I’m grateful to Jonathan for that. I also didn’t think my retirement would be so fluid. I pictured something far more stable: remaining single, living in a one-bedroom condo, and fending for myself. My life now is different. I’m married and live in a three-bedroom home in another city. One of the biggest changes, however, has nothing to do with geography. It has to do with money—specifically, how financial decisions change when there are two people instead of one. I learned that lesson early in our marriage. We got married in August 2020. That December, I woke up one morning and saw blood in my urine. I went to an urologist who ran a series of tests, but it took about a month to determine the cause. During that time, I decided to consolidate our remaining investment holdings to make things easier for Rachel to manage in case something happened to me. Most of our money was already at Vanguard, except for a 401(k) from my former employer that was invested in a stable value fund. It still held a significant balance. Without much hesitation, I moved it into a bond fund at Vanguard. Not too long afterward, the bond market nosedived. The fund performed poorly—especially compared to the stable value fund the money had been in. The upshot: I panicked—and paid for it. It wasn’t a good time to make a financial decision while I was under stress. Some of the worst money moves happen when emotions are running high—selling stocks at the bottom of a bear market or rushing to act after an unexpected windfall. More often than not, it’s better to wait until you’re clearheaded before making a decision. At the time, I was also fretting about whether Rachel would qualify for my Social Security benefit, which is much larger than hers. You have to be married for at least nine months. I found myself counting off the days. Another financial decision became more complicated simply because we were now a couple: what to do with the three properties we owned—my condo, Rachel’s house, and the house I had inherited. Neither of us wanted to be landlords at this stage of our lives. We were excited about getting married and starting a new life together. I decided to sell my condo during the pandemic, which wasn’t easy. Rather than wait, I accepted an offer of $380,000—$43,000 below the asking price. Rachel decided to wait and rent out her house for two years. She didn’t get caught up in the excitement or rush into selling. As it turned out, that patience paid off. When the for-sale sign finally went up, I would stop by the house to water the yard and rake the falling leaves. One day, a real estate agent and his client were there looking at the property. They kept asking me whether the price listed on the brochure was correct. Rachel’s agent had intentionally priced the house at the lower end of the range in hopes of creating a bidding war. I told them they would have to talk to my wife and her agent because it wasn’t my house. The agent asked how long we had been married. When I told him two years, he nodded and said, “I get it. She wanted to wait until she was sure about the marriage before selling the house.” Rachel laughed when I told her what he said. She wasn’t waiting to see if the marriage would work. She waited because selling a house is a major financial decision, and she didn’t see any reason to rush it. Two years later, the timing turned out to be just right. The market had improved and the strategy worked exactly as planned. There were multiple offers, and the final sale price was well above what it would have been earlier. At the time my wife sold her house, Zillow’s estimated price of my condo was $484,000—$104,000 more than I received. I don’t really know why I was in such a rush to sell. Maybe it had something to do with the pandemic, my mother’s recent death, my sister and brother-in-law moving out of state, or the stress of renovating our new house. It was an emotional time for me, and I was probably searching for some stability in my life. What I’ve learned—both from Jonathan and from being married—is that good financial decisions usually come from patience, not urgency. When I feel anxious or pressured to act, I’m more likely to make a mistake. When I slow down, think things through, and listen—especially to my wife—the outcome is usually better. Managing money well isn’t about always making the right move. It’s about avoiding the wrong ones—and knowing when to wait. Dennis Friedman retired from Boeing Satellite Systems after a 30-year career in manufacturing. Born in Ohio, Dennis is a California transplant with a bachelor’s degree in history and an MBA. A self-described “humble investor,” he likes reading historical novels and about personal finance. Follow Dennis on X @DMFrie and check out his earlier articles.

Treasury Inflation Protected Securities (TIPS) are a Generational Bargain Right Now

Howard Schwartz | Jul 27, 2026

"Bill, thanks - great info as usual. Best, Rick"

- Rick Connor

Social Security

ArticleAdam M. Grossman | Aug 1, 2026

AT FIRST GLANCE, Social Security appears straightforward. During our working years, we pay into it, and in retirement, it sends us a monthly check, guaranteed for life. Unfortunately, it isn’t always so simple. Below are five aspects of the system that are frequently misunderstood. Benefits estimates. Look at a Social Security statement, and an easy-to-read chart provides estimates of the benefits available at various ages. The heading above the chart reads, “Personalized Monthly Retirement Benefit Estimates Depending on the Age You Start.” That seems clear. But there’s a caveat that can make the chart misleading. Off to the side, there’s a further explanation that reads: “These personalized estimates are based on your earnings to date and assume you continue to earn [your most recently reported salary] per year until you start your benefits.” The numbers shown, in other words, are not guaranteed. Why would the statements be presented this way? It’s because the Social Security Administration can’t predict when any given person will stop working, so for simplicity of presentation, it assumes that someone will continue working and continue earning the same income each year into the future and will then retire and immediately claim benefits. For most people, this isn’t how it works out, but Social Security has no way to know what each person will choose. That’s why benefits statements shouldn’t be taken at face value. How can you forecast your actual benefit? Fortunately, Social Security’s website provides a calculator that allows custom calculations based on actual retirement expectations. Continuing to work. Some people worry that there would be a negative impact if they chose to continue working after claiming Social Security. This concern isn’t totally unfounded. It’s known as the Social Security earnings test, but there are some details to be aware of. First, the earnings test doesn’t apply after a worker reaches Full Retirement Age. And second, to the extent that benefits are reduced in the years before FRA, Social Security will add back those amounts to future checks. So working while on Social Security shouldn’t be viewed as so problematic. Maximum benefit. All things being equal, Social Security retirement benefits increase with each year that you wait, up until age 70. This is broadly understood. The problem, though, is that oftentimes people view it almost as a rule to wait until 70, but that isn’t always the best choice. For married couples, especially where one spouse has accumulated a larger benefit, there are two reasons why one spouse might claim earlier than 70. The first relates to what’s known as the spousal benefit. This is a feature that originated in the days when more families had just one working spouse, and it provides a benefit to spouses who haven’t worked the requisite 10 years to earn a benefit. In general, the spousal benefit is equal to half of the higher-earning spouse’s benefit at their Full Retirement Age (FRA), which is now age 67 for most people. The only requirement is that the lower-earning spouse can’t start benefits until the higher-earning spouse has started his or her own benefit. The spousal benefit is terrific, but a commonly misunderstood limitation is that—unlike a worker’s own benefit—it doesn’t continue to increase each year until age 70. It hits a maximum at the spouse’s FRA. For that reason, it’s important for a spouse to not delay beyond that point. Even when both spouses have accrued their own benefits, it often makes sense for the spouse with the smaller benefit to claim somewhat earlier than 70. To understand why, we need to look at it from the perspective of the higher earning spouse’s benefit. Because that benefit would also be available to the lower-earning spouse in the form of a survivor’s benefit (discussed further below), that larger benefit will be available to either spouse as long as either is living. The smaller benefit, on the other hand, has value only while both spouses are living. And while it’s unfortunate to say, that is statistically less likely. For that reason, I generally recommend that the lower-earning spouse claim at, or around, Full Retirement Age. When to claim. In most conversations about Social Security, people tend to talk about claiming decisions in round numbers—claiming at 67 or 68, for example. The reality, though, is that you can claim at any time between ages 62 and 70. You don’t need to wait for your birthday, and the benefit simply increases by a bit for each month that you wait. I find this helpful because it allows flexibility in how we think about claiming. Not sure whether to start at 67 or 68? You can easily split the difference. Survivor benefits. To understand how the survivor benefit works, imagine a married couple, Joe and Jane. Joe’s benefit is $5,000 per month, and Jane’s is $4,000. Now suppose that Joe passes away. At that point, Jane wouldn’t be able to claim the combined total of $9,000. However, she could claim a survivor’s benefit that would increase her monthly check from $4,000 to $5,000, matching what Joe was receiving. That’s the simplest case, but the survivor benefit decision is often more complicated because it also depends on the age of the survivor. Survivor benefits can be claimed as early as age 60, and that can be helpful in certain situations, but there’s also a penalty for claiming too early. Benefits can be reduced by nearly 30%. In other words, and importantly, Jane wouldn’t automatically be entitled to $5,000 just because that was what Joe was receiving. When would Jane be able to claim the full $5,000? For this determination, Social Security uses a yardstick known as the Full Retirement Age for Survivors. This isn’t exactly the same as the standard FRA, but it’s close. (Social Security provides a calculator to look it up.) What might this look like in practice? Suppose Jane were a year shy of the FRA for survivors at the time that Joe died. In this case, Jane would have a choice. She could claim her survivor’s benefit at that time, but her total check would come out to somewhat less than $5,000. Fortunately, Social Security doesn’t automatically turn on survivor benefits when a spouse dies, thus providing survivors more control. In Jane’s case, she might continue with her own benefit of $4,000 per month for one more year. Then, once she became eligible for 100% of the survivor’s benefit, she could claim the full $1,000 to reach $5,000. 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.

Spouses SS benefits don’t always equal half workers benefit.

R Quinn | Jul 31, 2026

"Got it!"

- R Quinn

2025 and Medicare Rx

R Quinn | Jan 1, 2025

"You need to compare the total cost your pay for the combination of drug costs and premiums for the plan. Please go go Medicare.gov and click the drop down "Health and Drug Plans/Find Health and Drug Plans. This is the Medicare Plan Finder and may be the best thing the government has ever provided since it will provide the total costs for your specific mix of prescriptions under all available plans in your area. It even sorts the lowect cost plan on top. Humira is a biologic, so there is no generic, but there are interchangeable biosimilar drugs such as Cyltezo, Amjevita, Hadlima, Abrilada, and Simlandi that you might ask your provider about."

- Mark Eckman

Subconscious Frugality

Mark Crothers | Jul 31, 2026

"At 59, I’m still a spring chicken. I’m keeping everything crossed that I inherited my mum’s cast-iron stomach (that woman could eat nails and ask for dessert). My dad, however, treated antacid tablets like they were breath mints; he wouldn’t so much as pop to the shops without a pack rattling in his pocket."

- Mark Crothers

How Did You Find Paid Work After Retiring from Your Primary Career?

Jeffrey Chan | Jul 31, 2026

- Jo Bo

Inflation, prices, COLAs, retirement and the last 16 years

R Quinn | Jul 27, 2026

- R Quinn

Taking a Loss?

Mark Crothers | Jul 28, 2026

"thank you"

- John Kaczka

$400,000 Mistake

ArticleBogdan Sheremeta | Aug 1, 2026

BOB MADE A very expensive tax mistake. Doctors told Bob that he only has a year to live… What did Bob do?

He decided to gift a house to his only son before passing away. The house is worth $2,000,000 that he bought back in 1970 for $50,000 in an expensive suburb of California.

The son decided to sell the house and paid about $430,000 in federal taxes.

$430,000 that could have been $0 instead…

How?

When you gift a property to someone, they receive a "carryover basis." It basically means the same price the original owner purchased it for.

At the time of the sale, if sold for $2M, he would pay $0 in federal taxes, though state tax might still apply. That's about $430,000 of "savings."

"But who cares, Bob is dead anyways?"

While true, many parents still want to make sure their children don't have to pay half a million in taxes. They want their children to enjoy the fruits of their hard labor.

Specifics

The step-up in basis can be a bit nuanced, depending on how the assets are held and titled.

First, the step-up in basis typically adjusts to the market value, unless an election is made to use the value six months after the date of death, subject to certain rules.

There are also two additional things to keep in mind:

1. Living on the right assets

Bob, age 75, has two accounts: a traditional 401(k) worth $500,000 and a brokerage account worth $500,000. Bob's diagnosis isn't good.

2. Selling the right lots

Say Bob has a $500,000 brokerage account. Some of the stock purchases have a low basis, meaning a lot of capital gains, and some have a high basis, meaning fewer capital gains.

It's best to sell the high-basis stocks, which come with a lower capital gains tax, and pass down the low-basis stocks to the beneficiaries.

Planning matters. These mistakes can cost thousands of dollars in unnecessary taxes. As always, make sure to consult a licensed CPA or estate attorney with your unique circumstances.

Bogdan Sheremeta is a licensed CPA based in Illinois with experience at Deloitte and a Fortune 200 multinational.

Today in Financial History

Harold Tynes | Jul 28, 2026

"The 1971 view is obsolete. There is no need for a computer clerk."

- Cammer Michael

What I Retired To

Andrew Clements | Jul 29, 2026

- Andrew Clements

Value of Waiting

ArticleDennis Friedman | Feb 7, 2026

Treasury Inflation Protected Securities (TIPS) are a Generational Bargain Right Now

Howard Schwartz | Jul 27, 2026

"Bill, thanks - great info as usual. Best, Rick"

- Rick Connor

Social Security

ArticleAdam M. Grossman | Aug 1, 2026

Manifesto

Aug 2, 2026

NO. 21: A HIGH income makes it easier to grow wealthy. But no matter how much we earn, we’ll struggle to amass a healthy nest egg—unless we learn to spend less than we earn.

humans

Aug 2, 2026

NO. 30: WE underestimate the power of compounding. Most folks grasp that invested money should grow over time, while carrying credit-card debt can trigger interest charges. But studies suggest we fail to appreciate just how much our money can grow if left to compound—and just how costly our debts can be if we fail to pay them off in short order.

think

Aug 1, 2026

GAMBLER’S FALLACY. When the dice hasn’t come up six for a while, we think a six is more likely. Similarly, if a money manager has previously beaten the averages or a Wall Street strategist has a history of predicting the market’s direction, we assume they’ll continue to make winning calls. But what if it's random, like the dice, and these folks were just lucky?

act

Aug 1, 2026

SET A FLOOR for financial pain. Suppose you have $400,000 saved. What’s the minimum amount below which you never want your portfolio to fall? Let’s say it’s $300,000, or $100,000 less. Divide that $100,000 by 0.35 and you get $286,000. That’s the maximum you should have in stocks. Why 0.35? In a bear market, the average loss is 35%.

Money Guide

Manifesto

Aug 2, 2026

NO. 21: A HIGH income makes it easier to grow wealthy. But no matter how much we earn, we’ll struggle to amass a healthy nest egg—unless we learn to spend less than we earn.

Spotlight: Retirement

You Might Be Ready to Retire…Who Would You Rather Be?

stelea99 | Jun 10, 2025

Dear HD readers: We had so much fun with the original version of this post, that I thought it might be fun to add a 3rd possible route to funding retirement at $138,000/yr. Of course, there is no reality in this, no real personal info, it is just a scenario. And, most important, any legal route that get you to your desired retirement income is the right one for you.

One of my friends is hitting 73 in August and we were discussing his need to do an RMD this year.

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 earn and save and hope that our savings grow. But when we get to retirement, it becomes more complicated to know exactly how to manage those savings.
In the 1950s,

Tax Smart Retirement

Adam M. Grossman | Mar 7, 2026

A POPULAR JOKE about retirement is that it can be hard work. That’s because financial planning is like a jigsaw puzzle, and retirement often means rearranging the pieces.
In the past, I’ve discussed two key pieces of that puzzle: how to determine a sustainable portfolio withdrawal rate and how to decide on an effective asset allocation. But there’s one more piece of the puzzle to contend with: taxes. Especially if you’re planning to retire on the earlier side,

They’re Right, I’m Wrong, Sort Of

Dan Smith | Feb 2, 2025

I was fed up with the people who claim we’d all be better off if an equivalent sum of money was deposited into private accounts instead of Social Security, so I set out to prove them wrong.
I deserve a slap on the back from my spreadsheet loving engineer friends. From my first year working in 1969 to retirement in 2022 I listed wages by year, SS payroll tax by year, and the growth after 54 years if invested in the S&P500,

Social Security vs. Private Investment Accounts – RCC runs some numbers.

Rick Connor | Feb 2, 2025

A recent post by Dan Smith took a crack at evaluating at the often heard statement that we would all be better off if the FICA taxes we paid into the Social Security (SS) trust fund were instead invested in individual accounts. The idea is that by investing our payroll taxes in something like an S&P 500 fund, we would be better off at retirement. This strategy has the benefit of long-term compounding, since many of many us will work upwards of 50 years.

Going too far with FIRE: The downside of being in the financial advice business – RDQ

R Quinn | May 30, 2025

I always thought the glowing stories of FIRE folks were a bit dodgy. Much of the time they aren’t even retired in the traditional sense. Sometimes they go too far sharing their acquired wisdom for cash.
I followed one blogger for several years. She shared her frugal ways, extreme in my view like buying her two-year olds shoes in a second hand thrift shop. She wrote a book, gained a lot of publicity, was featured in news articles and gave advice.

Exit Strategy

David Gartland | Jul 9, 2024

IF YOU’RE LIKE ME, you aren’t eager to spend down your investments. What fun is that? Aren’t you curious to see how big your portfolio could grow? Of course, you are. After my wife and I are gone, my son will have dibs on the money we’ve amassed. We’ve set up a special needs trust to provide him with income when we’re no longer around. My son has no siblings, so we needed the trust to make sure he’s taken care of. But until then, I view our portfolio as a beautiful garden that I need to nurture. I believe many investors are like me, and don’t really enjoy spending. Instead, they cultivate their wealth with an eye to passing it on to their heirs or their favorite causes. But what about those investors who don’t have anybody lined up to take over their money after they’re gone? We’ve had wealthy celebrities, like Prince and Aretha Franklin, who died without clear instructions for how their estate should be handled. I don’t understand such neglect. You’ve been caring for your portfolio with the goal of seeing how big it can get before you “kick the bucket.” That’s great. But you also have a responsibility to make sure your efforts don’t go to waste. You should have a plan in place for this thing you’ve enjoyed owning for so long. Some investors say, “Oh, I don’t care what happens after I’m gone.” That’s the wrong attitude. You owe it to your wealth to see that it’s put to good use after your death. Just find someone or some cause that you feel would benefit from all your hard work. Maybe your beneficiaries will fritter away your money. Maybe they’ll show respect for what you’ve done and keep your wealth growing. Maybe they’ll put…

Seeking Answers

David Gartland | Jan 22, 2024

I LEARNED OF MY brother’s death by Googling his name. I always wondered whether his family would let me know if he was ill or had died. After Google led me to his obituary, I had my answer. My brother and I were co-executors and co-beneficiaries of my mother’s estate. From the start, we couldn’t agree on how to settle her affairs. I wanted to sell everything and divide by two, but he wanted to hold off selling my mother’s house. Why? My mother passed away in 2007, when home prices were down sharply, and my brother thought we should wait for the real estate market to recover. But there was another reason my brother didn’t want to sell: He, his wife and one of his adult sons were living in the place. Thus began a difficult estate settlement. In 2021, the house was finally sold and the proceeds divided, but we still hadn’t finished settling the estate when my brother died the following year. The disagreement over the estate caused a rift between my brother and me. In the years before his death, the only information I received came from his lawyer and the mortgage company. Not being notified of my brother’s deteriorating health or his death didn’t surprise me, but it did bother me. I believe in divine intervention. I’ve recently felt spurred to seek out information about how my brother died. My parents both had heart conditions. I assumed my brother and I would suffer the same fate, but I wanted to know for sure. I guessed the location where my brother likely died, and requested a death certificate from two local townships. I lucked out, and one of the towns sent along his death certificate. It didn’t show a heart condition as my brother’s cause of…

Paid in Full

David Gartland | Jun 17, 2024

SPENDING ISN’T something I like to do. It doesn’t bring me lasting joy. I prefer just to buy what I need. For many folks, spending involves borrowing. If spending is your thing, incurring interest charges on credit card debt and car loans probably isn’t a big deal. But to me, borrowing to buy something means I’m overspending. If I can’t afford to pay cash, I shouldn’t buy it. Borrowing has been the downfall of many. Spending is a onetime event—unless you borrow to spend, in which case your spending has a long tail attached to it. I think people get used to borrowing. The interest charge is just the cost of doing business—in this case, the cost of buying something we can’t afford. When all goes well, the monthly interest charges just get attached to the monthly bills we have to pay. But if our income drops or we lose our job, those monthly expenses can become nightmares. For the worker who has always had a job and believes that the job will always be there, spending with borrowed money is comfortable and doable. You’ve always had a salary and you probably believe you’ll always have a salary, so why change? My experience has been different. As I’ve mentioned in earlier articles, I lost my job 10 times during my working life. While this was bad, it also made me good at finding a new job. I came to understand what I needed to do to make myself more attractive to the insurance companies that might employ me, such as earning my Chartered Property Casualty Underwriter designation. This involved taking 10 written exams, each three hours in duration, over a five-year period. The other, more important habit I learned was to save and not borrow. Losing a job with no…

Not My Thing

David Gartland | Jul 23, 2024

IN RICH DAD POOR DAD, author Robert Kiyosaki touts the virtues of owning real estate as a way to reach financial independence. He explains the difference between how his father handled money and invested in his education, versus his friend's dad, who gained his wealth by investing in businesses. There’s controversy over whether this is a true tale or just a literary device to explain how to invest in real estate. Either way, there’s a lot to learn from Kiyosaki’s book. One thing I learned: Real estate investing isn’t for everybody. That would include me. I’ve been aware of real estate’s appeal since Robert Allen’s 1984 book Nothing Down. I would see his late-night infomercials and think, “That’s what I need to do to reach my dream of personal wealth.” I attended free seminars on real estate investing. It all made sense, except for one thing: It didn’t excite me. At the time, I was renting a studio apartment in Brooklyn. I kept hearing about how all these people were making a killing in real estate. I wanted to be rich. But why would I buy a rental property when I was paying rent myself? Why wouldn’t I buy my own place first? I’ve owned two pieces of real estate in my life, a condo and my current single-family home. Kiyosaki talks about the joy he feels owning real estate. But I didn’t feel joy buying either home. I decided real estate investing wasn’t for me. That decision was confirmed by watching reality TV shows about real estate investing. One show stands out in my mind. It was based in South Carolina. The main character was a visionary with money. He could look at a house and see what needed to be done to make the house attractive to potential…

The Other Side Sucks

David Gartland | Nov 10, 2023

THERE ARE CERTAIN expressions I’ve heard during my lifetime which, for one reason or another, have stayed with me. In a previous article, I related how a coworker encouraged me to “keep on keeping on” when confronted with a challenge, and how Napoleon Hill’s expression “burning desire” struck me as a great way to describe a goal worth seeking. Here’s another expression I’ve never forgotten: “The other side sucks.” I’ve been a race car fan ever since my older brother introduced me to automobile racing in my youth. I especially enjoy Formula One racing. These international racing events gather the best of the best—mechanics, engineers, drivers and the sponsors who pay for it all. One of the Formula One race tracks I’ve visited is in Watkins Glen, New York. In the 1960s, Watkins Glen was the only race track that hosted a Formula One race in America. There were others in the years that followed but, at the time, Watkins Glen was the only one. The racing community that sponsored the event, along with the owners of the racing teams, were sophisticated. The same couldn’t be said of the fans at Watkins Glen, who weren’t necessarily from society’s upper crust. One area of the Watkins Glen track was known as “the bog.” It was a valley within the racing grounds that would become muddy following rain storms. This area became a gathering place for fans, who took great joy in directing late arrivals to this muddy area, especially after it was dark. Upon entering the bog, many cars would get stuck. Amid the resulting melee, cars would often be damaged. This led to Formula One’s sanctioning body to stop holding races at “the Glen.” On one particular night at the bog, two separate and distinct groups formed on each side…

My Retirement Prep

David Gartland | Nov 29, 2023

I DON’T KNOW THAT MY life has been all that different from that of others. Still, what’s happened to me has—I believe—been good preparation for retirement. Here are seven life lessons I learned on my journey from childhood through to my departure from the workforce just before my 70th birthday. Lesson No. 1: Doing it yourself can save big money. My older brother got me interested in cars. This was the late 1950s and 1960s, when drag racing and international road racing became popular in the U.S. Teenage boys back then were primarily interested in three things: girls, sports and cars. My brother was only interested in girls and cars. I was an eight-year-old trying to keep up with my older brother. I didn’t like girls, so cars were an easy choice. I helped my brother work on his cars. I learned they weren’t so intimidating and could be understood with a little effort, and that doing your own repairs could save a lot of money. The problem: I assumed my brother would help me like I helped him. But I didn’t have a girlfriend. My brother did, and the girlfriend didn’t like time away from her. Helping out a little brother wasn’t permitted, so when I did repairs, I had to do them all by myself. Lesson No. 2: Nothing lasts forever. When I was age 15, my father had a massive heart attack and died in the room next to where I was watching television. It was a shock that he was gone. The pain hits all at once. Then, over time, you come to accept it. I’ve since watched others suffer through long, drawn-out illnesses like cancer. Heart attacks, at least, are quick. At 15, I needed guidance to help me through my teenage years. I didn’t…

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