Insurance can be a great defense against financial disaster. What happens when it’s contorted into an investment? It becomes the disaster.
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.
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.NO. 41: VERY FEW of us need life insurance for our entire life. That’s why term insurance makes sense and cash-value policies are usually a mistake—despite what insurance agents say.
CHECK YOUR Social Security statement to get an estimate of benefits and make sure your earnings record is correct. The easiest way to do this: Set up a “my Social Security” account, preferably adding two-factor authentication. This will also preempt scammers, who might otherwise try to set up an account in your name—and claim your benefits.
NO. 49: YOU CAN have stability of principal and stability of income but, in a liquid investment, you can't have both. Money-market funds and savings accounts offer stability of principal, but the rate paid can quickly rise and fall. Most bonds, by contrast, pay the same amount of interest each year until maturity, but they can fluctuate sharply in price.
ANCHORING. Imagine the S&P 500 is up 20% over the past year. You might balk at buying stocks, because you’re anchored on the market’s old level and feel you’re overpaying at current prices. Or imagine your neighbors sold their home two years ago for $300,000. You might be reluctant to accept less for your home, even if property prices have since fallen.
NO. 41: VERY FEW of us need life insurance for our entire life. That’s why term insurance makes sense and cash-value policies are usually a mistake—despite what insurance agents say.
FOR DECADES, RESEARCHERS have been looking at the link between money and happiness. The findings? In short, it’s a mixed bag.
To be sure, there are ways that money can boost happiness, and below are some ideas to consider. But there are also obstacles to contend with. We’ll look first at the obstacles before turning to the recommendations.
The most significant challenge is the fact that—to a great extent—our happiness level is hard-wired into us.
Dan’s post ‘Insomnia and the Back of an Envelope’ motivated me to review our expenses. Our top five categories are property taxes, home/car insurance, utilities, groceries, and healthcare premiums/deductibles.
Our home property taxes increased 23% from 2023 to 2025 while our home value increase 17%. The value of our ten-acre plot went down 1.6% from 2023 to 2024, but then increased 23.5% from 2024 to 2025 and property taxes increased by 30%.
Home insurance went up 46% from 2023 to 2025,
This is not criticism, it’s an inquiry.
Over the years I have read many times on HD about tracking expenses/spending. Some people pursue this in great detail, some seem to approach it like a hobby. There may be something motivating in knowing how every penny is spent.
As you may suspect, I don’t know in detail where or how we spend our money. As long as the big picture is in balance I am happy.
What I do know is the bank balance is $X at the end of the month,
MILESTONES MARK the growth of a child as she moves from infancy through school age. In similar fashion, we adults tend to measure our life’s progress with “firsts” or other significant events. Perhaps we remember the feeling of maturity that came with our first kiss or our first job. Milestones help us attach meaning to the course of a life that sometimes seems beyond our control.
Financial milestones often command special significance, like my first “real” job at age 15.
Suppose money were no object. If you could go anywhere in the world on your next trip, where would it be? If you could savor any experience, what would it be?
I was sitting on the deck of my holiday home, enjoying the morning sunshine and breakfast, when a deep rumble announced the arrival of an expensive, sporty car. It was my neighbour. He’s a very nice man in his 40s who always dresses impeccably, with two well-turned-out kids and an immaculate wife – to all intents and purposes, a family living the dream.
Contrast that with me: I drive a seven-year-old SUV with 70,000 miles on the clock,
One Piece Of Paper
Andrew Clements | Aug 5, 2026
Short term and long term Social Security planning
William Perry | Aug 4, 2026
How Did You Find Paid Work After Retiring from Your Primary Career?
Jeffrey Chan | Jul 31, 2026
When your 401(k) excludes target date funds
JM | Aug 1, 2026
Taking a Loss?
Mark Crothers | Jul 28, 2026
$400,000 Mistake
ArticleBogdan Sheremeta | Aug 1, 2026
BOB MADE A very expensive tax mistake. Doctors told Bob that he only has a year to live… What did Bob do?
He decided to gift a house to his only son before passing away. The house is worth $2,000,000 that he bought back in 1970 for $50,000 in an expensive suburb of California.
The son decided to sell the house and paid about $430,000 in federal taxes.
$430,000 that could have been $0 instead…
How?
When you gift a property to someone, they receive a "carryover basis." It basically means the same price the original owner purchased it for.
The basis of that house was $50,000, so the son had to pay capital gains tax on the difference between the $2 million sale price and the basis, at rates reaching up to 23.8% on the top portion of the gain. But this is where a step-up in basis could come into play.
Assets such as a house or shares held in a brokerage account, when owned inside an estate rather than an irrevocable trust, receive a step-up in basis to their fair market value (FMV) at the time of the decedent's death, per IRC Section 1014. In our case, if Bob held that house in his own name, passed away, and his son received the house, he would've gotten a step-up in basis to the current value, or $2M.
At the time of the sale, if sold for $2M, he would pay $0 in federal taxes, though state tax might still apply. That's about $430,000 of "savings."
"But who cares, Bob is dead anyways?"
While true, many parents still want to make sure their children don't have to pay half a million in taxes. They want their children to enjoy the fruits of their hard labor.
Specifics
The step-up in basis can be a bit nuanced, depending on how the assets are held and titled.
First, the step-up in basis typically adjusts to the market value, unless an election is made to use the value six months after the date of death, subject to certain rules.
The step-up in basis also doesn't apply to assets held in an irrevocable trust , though we will cover some strategies for that later, or to assets held in qualified retirement accounts, such as IRAs and 401(k)s.
In a community property state (Arizona, California, Idaho, Louisiana, Nevada, New Mexico, Texas, Washington, and Wisconsin), the basis steps up whenever a spouse dies. You will typically need to complete a form to receive this step-up in a brokerage account.
For assets held in joint tenancy, the step-up applies only to the deceased partner's share. For example, Bob and Jenice have a house worth $300,000 with a $50,000 basis. After Bob passes away, Jenice will have a $175,000 basis in the house, calculated as ($300,000 minus $50,000) divided by two, plus $50,000.
There are also two additional things to keep in mind:
1. Living on the right assets
Bob, age 75, has two accounts: a traditional 401(k) worth $500,000 and a brokerage account worth $500,000. Bob's diagnosis isn't good.
From a tax-planning perspective, it might make a lot more sense to withdraw, say, $50,000 a year from the 401(k) to live on, $20,000 of which would be required minimum distributions (RMDs), and pass down the brokerage account to his beneficiaries.
This is because the brokerage account likely has a lot of gains. Bob bought many stocks in his 30s and 40s that could be stepped up now. But a more in-depth analysis might be needed if Bob has a lot of income and is in a high marginal tax bracket.
2. Selling the right lots
Say Bob has a $500,000 brokerage account. Some of the stock purchases have a low basis, meaning a lot of capital gains, and some have a high basis, meaning fewer capital gains.
It's best to sell the high-basis stocks, which come with a lower capital gains tax, and pass down the low-basis stocks to the beneficiaries.
Planning matters. These mistakes can cost thousands of dollars in unnecessary taxes. As always, make sure to consult a licensed CPA or estate attorney with your unique circumstances.
Yet-Another Social Security Spreadsheet Analysis on what Age to Start taking Benefits
Big Green Monster | Aug 2, 2026
Beware the CFP Designation?
DavidHLancaster | Aug 3, 2026
Social Security
ArticleAdam M. Grossman | Aug 1, 2026
Before Someone Else Decides
Kathleen Rehl | Aug 2, 2026
Inflation, prices, COLAs, retirement and the last 16 years
R Quinn | Jul 27, 2026
Treasury Inflation Protected Securities (TIPS) are a Generational Bargain Right Now
Howard Schwartz | Jul 27, 2026