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What I Retired To

"Thanks, Edwin. I think you’ve made an important point. We often hear that we need to “retire to something,” and for many people that’s true. But sometimes what we’re retiring to is simply the freedom to enjoy an unhurried morning, an extra cup of coffee or the luxury of letting the day unfold without a schedule. That’s a perfectly worthwhile destination too. And I agree, working for the wrong boss has probably nudged more than a few people into retirement a little earlier than planned!"
- Andrew Clements
Read more »

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

"CUSIP 91282CRE3 10 year TIPS issued 7/31/2026 appeared with both buy and sell options on today's, 8/1/26, Vanguard broker website after signing in where it was limited to sells yesterday for the secondary market. Of course TIPS on the secondary market need to be purchased or sold during the period the markets are open where purchases at the original and subsequent reopening auctions orders may be placed after the announcement of the auction is posted. A six month Tentative Auction Schedule of U.S. Treasury Securities is available at Treasury Direct."
- William Perry
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.
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 »

Taking a Loss?

"Same here. Got out just as they started going down years ago. Now have VG federal MM in my IRA rollover brokerage account. Paying 3.62% now."
- Boomerst3
Read more »

Today in Financial History

"Managing our assets since the 70s has never interested my better half. Therefore, reluctantly, I eased over 50% of our liquid assets to a financial management group that I've followed since the mid-90s. Completely trustworthy and very successful over the intervening years, they'll be able keep my wife's living style comfortable long after I've left this mortal coil."
- j deam
Read more »

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
Read more »

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

"Excellent article R Quinn. Always a good idea to think about inflation, the killer of all investments. For me the only way to beat it, is to invest in the S&P 500. Fortunately for me, that has worked out very well over the last 60 years, and I plan to keep it that way. The S&P has nicely beat inflation over those many years."
- William Dorner
Read more »

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

"Excellent question. I was downsized at age 48. A friend ask me to join his company which competed with my previous employer, the catch no salary, only commission. Decided to take the opportunity, and it worked out great. So went from 50 hours a week, to 30 hours, then at 65 more like 20, and then down to 5 hours a week. As you can see I really liked what I was doing selling inkjet ink and parts, and finally at 78 decided to fully retire. The nice part about it all, is I worked from home since 1994 and because of the internet could work from cruise ships or anywhere in the world. It was the best downsizing ever."
- William Dorner
Read more »

Subconscious Frugality

"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
Read more »

Fear of the Unknown…

"forgive me for not giving YOU any advice. I suspect you'll do fine. What I WILL DO is advise EVERYONE, EVERYONE, to put a HELOC on their home, assuming it has equity. If you hadn't saved and needed money that would be a good resource to tap. A HELOC doesn't cost you a penny unless you use it, and the payments are interest only. Principal often doesn't need to be paid back for 10-15 yrs, or if you sell. Don't wait till you're unemployed! Bank won't open a loan for someone with no income! PS notice I didn't say home equity LOAN..."
- B Petersen
Read more »

What I Retired To

"Thanks, Edwin. I think you’ve made an important point. We often hear that we need to “retire to something,” and for many people that’s true. But sometimes what we’re retiring to is simply the freedom to enjoy an unhurried morning, an extra cup of coffee or the luxury of letting the day unfold without a schedule. That’s a perfectly worthwhile destination too. And I agree, working for the wrong boss has probably nudged more than a few people into retirement a little earlier than planned!"
- Andrew Clements
Read more »

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

"CUSIP 91282CRE3 10 year TIPS issued 7/31/2026 appeared with both buy and sell options on today's, 8/1/26, Vanguard broker website after signing in where it was limited to sells yesterday for the secondary market. Of course TIPS on the secondary market need to be purchased or sold during the period the markets are open where purchases at the original and subsequent reopening auctions orders may be placed after the announcement of the auction is posted. A six month Tentative Auction Schedule of U.S. Treasury Securities is available at Treasury Direct."
- William Perry
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.
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 »

Taking a Loss?

"Same here. Got out just as they started going down years ago. Now have VG federal MM in my IRA rollover brokerage account. Paying 3.62% now."
- Boomerst3
Read more »

Today in Financial History

"Managing our assets since the 70s has never interested my better half. Therefore, reluctantly, I eased over 50% of our liquid assets to a financial management group that I've followed since the mid-90s. Completely trustworthy and very successful over the intervening years, they'll be able keep my wife's living style comfortable long after I've left this mortal coil."
- j deam
Read more »

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
Read more »

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

"Excellent article R Quinn. Always a good idea to think about inflation, the killer of all investments. For me the only way to beat it, is to invest in the S&P 500. Fortunately for me, that has worked out very well over the last 60 years, and I plan to keep it that way. The S&P has nicely beat inflation over those many years."
- William Dorner
Read more »

Free Newsletter

Get Educated

Manifesto

NO. 28: WE SHOULD nurture investment compounding—by buying stocks for the long run, minimizing costs and taxes, and avoiding risky investments where we could lose big.

think

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

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%.

Truths

NO. 105: IN INEFFICIENT markets—such as those for microcap stocks and emerging market companies—skilled investors have a better shot at earning market-beating returns. But after investment costs, most investors will still lag behind the market averages and the shortfall will often be large, because the cost of active management is so high.

Financial life planner

Manifesto

NO. 28: WE SHOULD nurture investment compounding—by buying stocks for the long run, minimizing costs and taxes, and avoiding risky investments where we could lose big.

Spotlight: Retirement

Cash Balance Plan Explained

IMAGINE YOU ARE already doing all things possible to minimize your taxes:

You are maxing out your pre-tax 401k
You do tax loss harvesting
You did tax efficient placement
You are maximizing Roth IRA through Backdoor Roth

But what other strategies can you use to minimize taxes? You also might not want to start a business or buy real estate.
Another option that many people aren’t aware of is the cash balance plan (CBP).

Read more »

They’re Right, I’m Wrong, Sort Of

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,

Read more »

Tax Smart Retirement

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,

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.

Read more »

Funded Ratio vs Monte Carlo – Different Routes to Get to the Same Destination (or not)?

I find the “liability matching” concept as outlined in Dr. Wad Pfau’s “Funded Ratio”  helpful based on our household-specific inputs I provide.  This analysis, while based on different inputs than those of Monte Carlo simulation, has given me another way to project whether we expect to have adequate financial resources for the remainder of mine and my spouse’s life.
I have used Mike Piper’s simplified funded ratio example spreadsheet to “run the numbers” using the following inputs for each year of our expected life spans:

1) Select a conservative,

Read more »

401(k) participants want annuities – some form of guarantee – RDQ

I have expressed my opinion on the need for and desirability of a steady income stream in retirement, as guaranteed as possible. Next Friday my pension will be deposited in our bank account. On the second and forth Wednesday each month our Social Security will be deposited. All that has happened each month for the last seventeen years.
I don’t worry about withdrawal strategies, withdrawal percentages, guard rails, tip ladders or any similar strategy. The IRC tells me what I must withdraw from my IRA. 

Read more »

Spotlight: Wasserman

Taking Their Money

“UNCLE” PHAN, MY father’s closest friend and my godfather, committed suicide a few years ago. I regret not seeing him often enough when he was alive and not letting him know how much I appreciated his humor and generosity. I also regret not knowing his financial and emotional situation. Uncle Phan retired as a surgeon 20 years ago and took a lump sum distribution instead of a lifetime monthly pension. It should have been enough to last the rest of his life, but he became a victim of financial scams by close relatives and supposed friends. He also suffered depression and it all proved too much for him. At the time of this death, Uncle Phan was penniless and living alone in a small shack. Earlier this year, my father had a stroke that forced him to shutter his own medical practice. Working with my brothers, we went through his financial records, as we wound down the business. We discovered that he, too, was a victim of financial scams and exploitations that had been going on for years. He had been paying out large sums to current and former employees, each with a sob story of need, including his assistant to whom he had been a mentor. My father had always been a diligent saver and careful spending. Maybe that’s why we didn’t notice for so long. He was the one who taught his four children to favor saving over thoughtless spending. Yet, in his later years, here he was doling out large sums without thorough recordkeeping and, worse still, without regard to preserving the savings he and my mother needed for the rest of their lives. Luckily, my parents had a financial backup, in the form of a monthly pension my father continues to receive. My mother also has…
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Takes Skill

I WAS SELECTED IN 2015 for the “leadership pipeline program” at the major bank where I worked. It was a 10-month-long program for minority employees just below executive level. We were selected to learn all about corporate culture and what it took to advance to the next level. I felt honored to be among such talented and promising employees. Participants were from various departments from across the U.S.—technology, risk management, operations, compliance, human resources, retail banking, commercial lending and investments. The program opened with a one-week in-person training session at the bank’s corporate headquarters in Charlotte, North Carolina, followed by monthly meetings via video conferencing and online courses. Each participant was assigned a mentor from the executive level. The people I met in the program were diverse in terms of experience, education and age. We were all united, however, in wanting to learn the skills necessary to move up the corporate ladder. Rather than particular job skills, however, a major emphasis of the program was networking. “It’s not what you know but who you know.” Over and over, making the right connections was emphasized. The bank encouraged us to join multiple affinity groups (Asian, veteran, Latino, Native American, women, LGBT, African American and so on), to socialize and connect across divisions and departments, and to reach out to executives. In other words, we needed to promote ourselves if we wanted to move up to the next level. The emphasis on self-promotion as a career strategy never quite sat right with me. Partly, it’s because I’m an introvert. But mostly, I saw a problem with focusing so much on building a network. I always thought that the time and energy spent maintaining these relationships and joining the many affinity groups would, instead, be better spent learning new skills. And there’s a big…
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Brotherly Betrayal

I WROTE PREVIOUSLY about my parents being victims of financial abuse by one of my brothers. Recently, I returned to Bangkok, which gave me a chance to discuss this situation at length with the entire family, including my other brothers and my uncle. When the financial abuse of an elderly person is committed by a stranger, the rest of the family often has no chance to see warning signs. But 90% of abusers are family members or trusted individuals. In these cases, there are often warning signs, but the family may subconsciously not want to acknowledge the problem. In my brother’s case, my uncle said he’d noticed his free-spending lifestyle. He’d purchased new luxury cars for himself and his wife shortly after gaining control of half my elderly parents’ money through a guardianship. In many ways, however, this financial abuse was part of a pattern that could be seen going back to his youth. He was the only child, out of four, who’d continued to get substantial support from my parents throughout his life. While the rest of us have been supporting ourselves since we graduated from university, he continued to depend on our parents to make ends meet. It got to the point where he considered their financial assistance to be a normal part of his personal finances. It’s common for Thai families to have multiple generations living together. What’s uncommon is a son who doesn’t give part of his salary to his parents, or at minimum pay his own expenses, while living with them. My brother not only didn’t pay expenses while living with our parents well into his 40s, but also he lived there with his wife and two children. He relied on my parents to pay most of his family’s living expenses: cars, gas, food, mobile…
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Harder for Some

IS SUCCESS WITHIN reach for anybody willing to work hard? We like to think of the U.S. as a meritocracy with a one-to-one correlation between effort and achievement. It’s a notion that allows us to feel that we’re in control of our destiny and that we’ve fully earned the success we enjoy. But in truth, there are many factors that continue to tilt the playing field one way or another. Socioeconomic status, race and gender still sway the game. While the impact of such factors may have been reduced, comprehensive data show they remain important. Warren Buffett is clearly a winner at the success game, but even he says that not every person gets an even chance. Acknowledging persistent gender and race discrimination, he used the phrase "ovarian lottery" at a 1997 shareholder meeting. The ovarian lottery is “the most important event in which you’ll ever participate,” Buffett said. “It’s going to determine way more than what school you go to, how hard you work, all kinds of things.” He noted that he didn’t have to overcome barriers of race or gender. As Buffett admitted, “We won it by being White. You know, no tribute to us, it just happened that way.” [xyz-ihs snippet="Mobile-Subscribe"] Buffett’s comments from 24 years ago are still valid today. Consider three recent studies: A 2019 study by the Bill and Melinda Gates Foundation examined inequality and concluded that, no matter where you're born, “life will be harder if you are born a girl.” A large genome-based study of economic data bluntly challenges the idea of our system being a pure meritocracy, summed up by the headline, “It’s better to be born rich than gifted.” It found that the least-gifted children of high-income parents graduate from college at higher rates than the most-gifted children of low-income parents.…
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Reversing Course

THREE YEARS AGO, Jim and I decided to retire to Spain. We were attracted by the promise of excellent health care, warm weather, low cost of living and travel throughout Europe. From there, we’d also be able to fly with relative easy to both the U.S. and Asia, allowing us to maintain family connections. All of this gave us a great quality of life for almost three years. Then COVID-19 hit. Like everyone else, we had to say goodbye to many activities, events and travel. More important, we were cut off from family and friends. During the lockdown, we had more time to explore new things. But we also had time to reflect on the things we’d lost that had always been there, invisibly supporting us. We came to realize three aspects of life were essential. First, it’s important for us to feel connected to loved ones and to reach them quickly in case of emergency, even if we were separated by thousands of miles. With the pandemic raging, Jim and I realized that if both of us became seriously ill in Spain or if one of our sons had an emergency back in the U.S., it was impossible for them to get to Spain and almost impossible for us to arrange a quick trip back. The unavailability of quick travel “in the event” was disturbing. Second, living in a community with friends is crucial to our emotional well-being. It’s no surprise that the disruption strained mental health for everyone, causing increased stress and anxiety. Loneliness became more widespread. I’m fortunate to have a good companion like Jim. A few of the expats we knew felt such loneliness that they were willing to risk infection to meet others. Third, as an expat, it isn’t easy to form deep friendships—those relationships…
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My Top Career Advice

THERE’S TRADITIONAL career advice, such as clarify your goals, master essential skills, promote yourself, network and work smarter, not harder—whatever that means. While this general advice is great, it’s no sure-fire formula. There’s no guarantee that if you work hard and smart, you’ll get a promotion and a pay raise. Traditional career advice tends to assume that you, your boss and the company are all behaving logically, and that the system reflects that logic. What if they aren’t? Believe me, I’ve been there. I had to advocate for myself and, after some struggle, I succeeded. New job entrants, including my sons, their peers and some friends, have asked me for career advice. Looking back over my work life, here are my top three recommendations: 1. Know what kind of manager you really have. Your manager is the person who can make or break your career. I am not talking about a bad boss who creates an overtly unhealthy or even toxic work environment. If you’re working for one of those, leave as soon as possible. No, I’m referring to the sneakier kind of boss. They’re nice people. Everyone likes them. They talk in terms of the team and compliment you in their evaluations. Despite the pats on the back, however, they just never seem to promote you, no matter how hard you work or how good your work is. I had my fair share of managers like this. Several years ago, one of these nice managers gave me excellent reviews. I asked him for a promotion to senior analyst because, for more than a year, I’d taken on senior-level responsibility. He told me that I needed to continue doing senior-level work at my lower pay level to prove myself for “a few more years.” When I asked him if he…
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