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Subconscious Frugality

"I’m 72 and still have a cast iron stomach. I eat anything and everything, the hotter and spicier the better. I take after my mom who was like that into her 80’s. My wife is the complete opposite. She indulges my adventurous palate and can usually find something edible."
- Mike Wyant
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How Did You Find Paid Work After Retiring from Your Primary Career?

"I’ve done a lot of jobs since my official “retirement “ 15 years ago at age 57 due to a layoff. Fortunately I was fully vested in my union pension. Moved from California to Colorado, got my CDL and drove a gas truck for 6 years. Did a lot of very scenic (and sometimes scary) mountain driving. My wife tired of the cold winters, so we reretired, sold the house, bought a motorhome and started traveling. Found a company that paid us to travel doing gas line surveying across country. Did that for about 4 years and settled down near my oldest son to be near grandkids. To keep from being bored, I drove a school bus for 2 years. Now I only drive for overnight and longer field trips because they pay me for every hour I’m away from home. So it’s been a very gradual transition to fully retired."
- Mike Wyant
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Inflation, prices, COLAs, retirement and the last 16 years

"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
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$400,000 Mistake

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.  
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Today in Financial History

"The 1971 view is obsolete. There is no need for a computer clerk."
- Cammer Michael
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What I Retired To

"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
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Value of Waiting

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.
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Social Security

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.
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2025 and Medicare Rx

"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
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Subconscious Frugality

"I’m 72 and still have a cast iron stomach. I eat anything and everything, the hotter and spicier the better. I take after my mom who was like that into her 80’s. My wife is the complete opposite. She indulges my adventurous palate and can usually find something edible."
- Mike Wyant
Read more »

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

"I’ve done a lot of jobs since my official “retirement “ 15 years ago at age 57 due to a layoff. Fortunately I was fully vested in my union pension. Moved from California to Colorado, got my CDL and drove a gas truck for 6 years. Did a lot of very scenic (and sometimes scary) mountain driving. My wife tired of the cold winters, so we reretired, sold the house, bought a motorhome and started traveling. Found a company that paid us to travel doing gas line surveying across country. Did that for about 4 years and settled down near my oldest son to be near grandkids. To keep from being bored, I drove a school bus for 2 years. Now I only drive for overnight and longer field trips because they pay me for every hour I’m away from home. So it’s been a very gradual transition to fully retired."
- Mike Wyant
Read more »

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

"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
Read more »

$400,000 Mistake

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.  
Read more »

Today in Financial History

"The 1971 view is obsolete. There is no need for a computer clerk."
- Cammer Michael
Read more »

What I Retired To

"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
Read more »

Value of Waiting

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.
Read more »

Social Security

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.
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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.

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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.

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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?

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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%.

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Manifesto

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: Family

Navigating the Unknowns of Financial Decisions

WHEN IT COMES to financial decisions, there are, as I’ve argued before, two answers to every question: what the calculator says, and how you feel about it. There’s a fly in the ointment, though: Calculator answers might appear to be based in logic, but they’re still imperfect.
Why?
Ian Wilson, a former executive at General Electric, explained it this way: “No amount of sophistication is going to allay the fact that all knowledge is about the past,

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Easier for Rachel

PEOPLE WHO KNOW ME say I’m sentimental, and they’re right. I like visiting places like my elementary school, the house where I grew up and my first home away from home. They bring back fond memories.
As I’ve grown older, I’ve become more nostalgic, and it isn’t just me. I heard that the ashes of my childhood friend Brian were spread over our grade school grounds. He must have had a touch of nostalgia,

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When They’re 64

WHEN MY TWO CHILDREN were ages nine and five, I opened Vanguard Group variable annuities for them. No, variable annuities aren’t my favorite investment. Far from it. Indeed, I don’t think they’re anybody’s favorite investment vehicle, unless you happen to be an insurance agent angling for a big commission.
Still, tax-deferred annuities differ from other retirement accounts in one crucial way: You don’t need earned income to fund the account. That means it’s possible to open a tax-deferred annuity for a toddler,

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Allowance for Children: Yes or No?

I want to thank Jonathan Clements for his article on allowances for children many years ago while I was raising my children. After reading the article I decided to give my two children age 13 and 5 at the time a monthly allowance. For this allowance they had to buy their own clothing. My daughter at age 13 was initially appalled at having to buy her own clothes. We did agree that we would buy big clothing items such as a.

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Lessons for Life

WHEN HUMBLEDOLLAR’S editor was The Wall Street Journal’s longtime personal-finance columnist and his children were little, he often joked that he had a special incentive to see them succeed financially.
“It would be a tad embarrassing,” Jonathan wrote, if his children “grew up to be financial ne’er-do-wells.” For that reason, he used his own home as a laboratory of sorts, testing strategies to help set his children on the right financial path.

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Getting Roasted

“YOU WILL ROTH!”
“But Dad, I’m only 10.”
“Evan, it is never too early to start saving. Besides, this gives you 70-plus years of compounding.”
“Yes, Dad, but didn’t you tell me last week that I need a job and earned income to contribute to a Roth?”
“We can arrange to get you a paycheck. I’ll get a friend or neighbor to hire you. What would you like to do?”
“I like to play soccer.”
“Evan,

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Spotlight: Quinn

2025 and Medicare Rx

Remember, starting in 2025 the annual out of pocket cost for prescription drugs is capped at $2,000. Roughly 10 percent 0f those of us on Medicare will benefit … luckily. But it’s good to know there is a limit. My suggestion, build that $2,000 into your planning, just in case. Plan to set up your own Rx fund or if already retired start one now. I just like funds designated for a single purpose. Or, if you have a HSA,  that’s good too.
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Seeing It for Myself

THE TOPIC OF TRAVEL pops up occasionally on HumbleDollar, and I’ve even written about my own travels. The reasons for not traveling go from “can’t afford” to “no interest.” I can understand “can’t afford.” But the “no interest” is a mystery to me. The only budget we have in retirement is for travel. It’s funded with our Social Security checks. When I was in school decades ago, my favorite subject was history. That interest has never waned. Few days go by when I don’t watch a documentary on YouTube. Understanding history is vital. What happened in the past is how we arrived at our world today, both good and bad. I believe that, to understand the past, we must see it and feel it. That has driven me to view firsthand where things happened, to stand on the spot where a major event took place, and to absorb the atmosphere of the location and its people. You won’t find us traveling to lounge on a beach somewhere, but you might see me where the Battle of Little Big Horn was fought, looking out from the highest point. Several years ago in Sicily, we hired a driver to take us to the small village where my wife’s grandparents had lived. At the town hall, we obtained copies of their birth and marriage certificates, and visited the church where they were married. Even the town clerk was emotional when he gave the papers to my wife. In the center of the town square was a monument with scores of names engraved. I assumed it was a war memorial. But in speaking with an old man, I learned it was people killed by the Mafia. In Crimea, we walked the site of the Charge of the Light Brigade. My great, great grandfather fought…
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Should Social Security benefits be income tax free?

It would be nice, quite a windfall. However, we didn’t pay for our benefits. In the aggregate, beneficiaries pay for about 15% of all benefits received, hence maximum 85% of benefits being taxable. I checked my records a found that within six years of starting, I collected benefits (including spousal benefit) equal to all the taxes I and employers paid since 1959.  The law says the benefits are taxable income, but given the standard deduction, a lower income retiree may pay very little or no actual taxes on the benefits received.  The income taxes paid go to the Social Security and Medicare A trusts, not general revenue. Both trusts are underfunded and being depleted in a few years. How do the programs make up the lost tax revenue?  We have yet to hear of a plan to make either Social Security or Medicare sustainable. So, is it fair, prudent or necessary to make Social Security benefits income tax free? I have asked many people and overwhelmingly the answer is yes, benefits should be tax free - while they also demonstrated a total lack of information or understanding of the issue, with many still believing Congress stole the trust funds or they could have done better investing on their own without paying SS payroll taxes. Oh my. 😱
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Retirement Riddles

I SPEND SIGNIFICANT time reading the viewpoints of people who are planning for retirement or who are already retired. My frequent reaction: What are they thinking? When I review retirement planning discussions on Facebook and elsewhere, I often find the participants show little understanding of how to proceed or even what some basic terms mean. Here's a sampling of the confusion and uncertainty I come across: Should people aim to replace 70%, 80% or some other percentage of their preretirement income? And is that gross income or preretirement spending? Is it okay to retire with just enough money to pay the bills and get by? What is discretionary spending? Do you need to keep a detailed retirement budget? Does spending decline in retirement? Is inflation a big deal for retirees? Will seniors really spend $300,000 on health care in retirement? How big a risk is longevity? When should folks claim Social Security—at age 62, 70 or somewhere in between? Are the days of saving money over once you retire? Does the 4% rule still work? And how do you compute it? Maybe the confusion isn’t surprising. You can find financial experts who will answer these questions in entirely different ways. My bigger worry: I see too many people who either overestimate or underestimate their retirement needs, or whose view of the future is either too pessimistic or too optimistic. How’s that for a definitive statement? I try to be realistic about retirement—from my admittedly conservative financial point of view. My answers are opinions, though opinions based on decades of managing retiree benefits, conducting retirement planning programs and my own 12 years as a retiree. Still, they’re opinions nonetheless. With that caveat in mind, here are my answers to retirement’s thorniest questions: Replace what? My advice: Aim for 100% replacement of your…
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Quinn’s grand new way to plan for a secure retirement. It’s called the McDonalds strategy

Last year I earned $16.68 an hour - sort of. That’s more than the minimum wage in all but the District of Columbia and for California fast food workers who earn $20 and hour. Fast food workers are mostly part-time, I on the other hand are no time. That hourly rate is my dividends and interest converted to a equivalent full-time employment. 🤑 I suspect capital gains would boost that a bit- or maybe not this year. Given I don’t do a thing to earn that income, it is truly passive and a pretty neat system if you think about - and nearly everyone can do it-create passive income that is.  Have I stumbled on a new retirement planning concept? A new income replacement theory? What is a good passive hourly income rate relative to working hourly income rate? Can Monte (or even a spreadsheet) handle such a complex concept? 🤑 The only thing is, how do you, in advance, determine the passive income that will be generated from your aggregate investments? I guess if you dump cash in bonds, you know the interest to be paid. If you buy stocks for dividends you know that rate.  By George! There it is, and capital gains are icing on the cake - just like OT or a bonus.  😃 Oh wait, ✋we still need your income replacement needs, how much of your working hourly rate do you need in retirement? Please don’t ask me. However, at the next meeting with your financial advisor just say you want to earn 50% more per hour than a McDonalds employee in California. Or maybe 75% or 100%. $30.00 an hour gets you $62,400 a year. 😱 Careful, the minimum wage goes up most years. 
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Too Generous Yet Not

I JUST REVIEWED MY Social Security earnings record. It brings back memories. For instance, it shows I earned $105 in 1959 when I was age 16 and working after school in the city library for 75 cents an hour. I’ve paid Social Security taxes every year since, though in 2020 they were based on earnings of just $2,333 and I was counted as self-employed. That darn blogging money. Here’s something to put matters in perspective: Over 64 years, my employers and I have contributed $265,871 in payroll taxes. That’s a lot of money. But consider that, since I began collecting Social Security in 2008, it took just 9.4 years to get back that amount in benefits. If you consider my wife’s spousal benefit based on my earnings record, all the payroll tax payments were recouped in only 6.2 years. At age 65, life expectancy is 17.9 years for men and 20.5 years for women. That suggests that Social Security is a pretty good deal for other retirees as well. But it also highlights why the system’s finances are so precarious. To make matters worse, there are currently 2.8 workers for each Social Security beneficiary, down from 5.1 in 1960. By 2035, there will be just 2.3 workers for each beneficiary. That means less people forking over payroll taxes to cover the cost of Social Security for me and other retirees. Since my wife and I began receiving Social Security in 2008, our benefits have increased almost every year due to cost-of-living adjustments (COLAs). Medicare premium hikes have offset those increases somewhat and, indeed, my net annual benefit decreased during a couple of years. In 2021, there have been calls for higher annual COLAs and even a guaranteed 3% annual increase, regardless of inflation. No doubt many retirees could use the…
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