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Insurance can be a great defense against financial disaster. What happens when it’s contorted into an investment? It becomes the disaster.

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When your 401(k) excludes target date funds

"First, we don’t know much about your plan (e.g. size, history, etc.) so it’s hard to directly answer your questions. It’s likely the people responsible for the plan are also company executives. However, if so, they are required to wear two hats, one as company executives, and one as fiduciaries to the 401k plan. As a plan participant, you actually have lots of rights, but you’ll have to decide how hard you want to push since it your employer, and you’ll have to trust the executives (who ultimately control your job) wear the right hat at the right time when dealing with you (i.e. no retaliation).   Under ERISA law, they are required to run the 401k plan for the exclusive benefit of plan participants, not for the benefit of the company. So you can make inquiries (make sure in writing) focusing on how and why the decisions were made to switch from Vanguard to Empower and the specific funds. In recent years, there have been numerous lawsuits over plan and investment expenses with many results favorable to participants. Your questions should focus on the plan’s fiduciary requirements under ERISA law as they are required to have a very structured and documented process how and why they make decisions resulting in the changes you dislike.  But, it is possible that your plan is a real outlier and still in compliance – that would be unfortunate because maybe your plan is just a dud, and you deserve better. Nonetheless, you probably still want to participate enough to get the employer match – you do have an employer matching contribution at least, right?"
- js
Read more »

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

"This from a quick search, Thank you for correcting me Sir! =========================================== Yes—Members of Congress are covered by Social Security for their work as members of Congress (they pay Social Security taxes and receive Social Security benefits based on their covered earnings). Their eligibility for Social Security is separate from their pension plan: they also participate in the Civil Service Retirement System (CSRS) or the Federal Employees’ Retirement System (FERS) for federal retirement, which is not Social Security."
- Donny Hrubes
Read more »

One Piece Of Paper

"Thanks, Rick. What a wonderful idea for an evening together. I can only imagine how fascinating it must have been to hear everyone’s “Coming to America” story. I also like the point you made about families who arrived generations ago. Over time it’s easy to forget the courage, uncertainty, and hope that brought our ancestors here in the first place. Whether those journeys happened two hundred years ago or within our own lifetime, they’re all part of the same American story. Thank you for sharing that experience. It fits beautifully with the theme of the article."
- Andrew Clements
Read more »

Short term and long term Social Security planning

"Hey Adam, What you wrote was exactly the point I was getting at. We have already made multiple financial sacrifices since we began our journey to retirement which depended a lot on what we were promised from Social Security. At this point I do not believe it would be fair to cut our benefits more, no matter our wealth. We were told when we began working what the deal was, then they changed it. It was early enough that we could make changes to our financial plans to accommodate the changes. But a this point we should get what we’re were told we were getting after contributing for decades. Those who were already, or close to retirement age were not subject to benefit cuts from the 1983 law, and neither should we. We have already made financial sacrifices to get us to this point in time. Enough is enough. If there are going to be further cuts in benefits and raises in taxation let younger people who have time to adapt their financial plans be the people to sacrifice to ensure their future beyond, just like we were asked to do in the past."
- DavidHLancaster
Read more »

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

"Thank you all for sharing your experiences and advice. I really appreciate the time you took to respond. One theme that stood out to me was how many opportunities came through relationships and simply staying engaged with the community, rather than through a traditional job search. That's given me a different perspective on what my next chapter might look like. I wish everyone continued health and happiness in retirement."
- Jeffrey Chan
Read more »

Taking a Loss?

"Rob - What you are describing is interesting. Would you describe how your ladder was originally structured in 2017?"
- S Sevcik
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 »

Yet-Another Social Security Spreadsheet Analysis on what Age to Start taking Benefits

"Thats a good point. We don't need it ourselves, but I am aware of others for whom it could be useful. As a retired physician, and unfortunately now as a consumer of healthcare myself, I second your opinion about Medicare and supplemental policy."
- Jack Hannam
Read more »

Beware the CFP Designation?

"A CFA would be top-notch, but they generally don't work with individual clients."
- Ormode
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 »

Before Someone Else Decides

"Thanks for the suggestions! They’re exactly the kinds of things I love to do. Seems like my efforts yesterday put me on the path to some good outcomes. i meant this as a reply to David below, but learning about some different care options is also good."
- Marilyn Lavin
Read more »

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

"Howard, very good explanation about TIPs and the current “positive for investors “ auction. I did some research on Tipswatch.com (as suggested here by others) and found this very good article by David Enna explaining the benefits/ risks and workings of the current TIPS auction. I sent this to my FA who I have a call with this week to discuss if it might be appropriate for our portfolio. thanks again. https://tipswatch.com/2026/07/23/10-year-tips-auction-gets-real-yield-of-2-438-a-great-result-for-investors/"
- luvtoride44afe9eb1e
Read more »

When your 401(k) excludes target date funds

"First, we don’t know much about your plan (e.g. size, history, etc.) so it’s hard to directly answer your questions. It’s likely the people responsible for the plan are also company executives. However, if so, they are required to wear two hats, one as company executives, and one as fiduciaries to the 401k plan. As a plan participant, you actually have lots of rights, but you’ll have to decide how hard you want to push since it your employer, and you’ll have to trust the executives (who ultimately control your job) wear the right hat at the right time when dealing with you (i.e. no retaliation).   Under ERISA law, they are required to run the 401k plan for the exclusive benefit of plan participants, not for the benefit of the company. So you can make inquiries (make sure in writing) focusing on how and why the decisions were made to switch from Vanguard to Empower and the specific funds. In recent years, there have been numerous lawsuits over plan and investment expenses with many results favorable to participants. Your questions should focus on the plan’s fiduciary requirements under ERISA law as they are required to have a very structured and documented process how and why they make decisions resulting in the changes you dislike.  But, it is possible that your plan is a real outlier and still in compliance – that would be unfortunate because maybe your plan is just a dud, and you deserve better. Nonetheless, you probably still want to participate enough to get the employer match – you do have an employer matching contribution at least, right?"
- js
Read more »

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

"This from a quick search, Thank you for correcting me Sir! =========================================== Yes—Members of Congress are covered by Social Security for their work as members of Congress (they pay Social Security taxes and receive Social Security benefits based on their covered earnings). Their eligibility for Social Security is separate from their pension plan: they also participate in the Civil Service Retirement System (CSRS) or the Federal Employees’ Retirement System (FERS) for federal retirement, which is not Social Security."
- Donny Hrubes
Read more »

One Piece Of Paper

"Thanks, Rick. What a wonderful idea for an evening together. I can only imagine how fascinating it must have been to hear everyone’s “Coming to America” story. I also like the point you made about families who arrived generations ago. Over time it’s easy to forget the courage, uncertainty, and hope that brought our ancestors here in the first place. Whether those journeys happened two hundred years ago or within our own lifetime, they’re all part of the same American story. Thank you for sharing that experience. It fits beautifully with the theme of the article."
- Andrew Clements
Read more »

Short term and long term Social Security planning

"Hey Adam, What you wrote was exactly the point I was getting at. We have already made multiple financial sacrifices since we began our journey to retirement which depended a lot on what we were promised from Social Security. At this point I do not believe it would be fair to cut our benefits more, no matter our wealth. We were told when we began working what the deal was, then they changed it. It was early enough that we could make changes to our financial plans to accommodate the changes. But a this point we should get what we’re were told we were getting after contributing for decades. Those who were already, or close to retirement age were not subject to benefit cuts from the 1983 law, and neither should we. We have already made financial sacrifices to get us to this point in time. Enough is enough. If there are going to be further cuts in benefits and raises in taxation let younger people who have time to adapt their financial plans be the people to sacrifice to ensure their future beyond, just like we were asked to do in the past."
- DavidHLancaster
Read more »

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

"Thank you all for sharing your experiences and advice. I really appreciate the time you took to respond. One theme that stood out to me was how many opportunities came through relationships and simply staying engaged with the community, rather than through a traditional job search. That's given me a different perspective on what my next chapter might look like. I wish everyone continued health and happiness in retirement."
- Jeffrey Chan
Read more »

Taking a Loss?

"Rob - What you are describing is interesting. Would you describe how your ladder was originally structured in 2017?"
- S Sevcik
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 »

Yet-Another Social Security Spreadsheet Analysis on what Age to Start taking Benefits

"Thats a good point. We don't need it ourselves, but I am aware of others for whom it could be useful. As a retired physician, and unfortunately now as a consumer of healthcare myself, I second your opinion about Medicare and supplemental policy."
- Jack Hannam
Read more »

Beware the CFP Designation?

"A CFA would be top-notch, but they generally don't work with individual clients."
- Ormode
Read more »

Free Newsletter

Get Educated

Manifesto

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.

act

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.

Truths

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.

think

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.

Homes

Manifesto

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.

Spotlight: Life Events

Close to Everything I Need

I DON’T HAVE MANY regrets in life. But there is one conversation with my mother that I wish I had never had. It was about moving her into an assisted living facility. She was in her 90s, and I thought it would be best for both of us.
My mother would receive better care, and I could take much-needed breaks. She could even keep her house and spend time there when I was with her.
It seemed like a middle-of-the-road approach to providing care.

Read more »

The Comeback

Despite my recent Ozempic nightmare and near suicide (see my article “My Ozempic Nightmare“) I’ve decided to go ahead with my Ironman Ottawa attempt this August at age 70.
I don’t want to live with the regret of not trying although physically I still have a long way to go. I lost a lot of muscle while on the drug and my energy levels are still low but I need to give it a shot as I consider it unfinished business.

Read more »

Extra Innings

More than 13 months ago, I was given 12 months to live.
I like to think I took my diagnosis in stride. I moved quickly to simplify my financial affairs, toss unwanted possessions, get new estate-planning documents and change HumbleDollar’s direction so the site could live on after my death.
I also focused on getting the most out of each day. Partly, that meant taking some special trips and spending more time with family.

Read more »

Tempus Fugit

I’m back in the Philadelphia suburbs today, heading to a funeral later this morning. My best friend’s Mother passed away at 91. She’s the last of my friend’s parents to go.  Of my in-laws, two mothers are still alive – one healthy and super-sharp, one quite infirm.  We attended a neighbor’s funeral last Friday at the Jersey Shore. She made it 85, and lived an active life almost to the end. An acquaintance recently died suddenly at 80.

Read more »

The Unsettling Relief of Saying Goodbye

It would have been my mum’s 91st birthday this week. She passed two years ago this June after the long goodbye from the thousand small cuts of dementia. Although I experienced grief and sadness, it truly was a relief to bid my mum the final farewell after the long marathon of loss over many years. I gave a final kiss to the echo of the woman before me as the heat of life left mum’s body.

Read more »

From Public Housing to Early Retirement: A Path Forged in Adversity

In my childhood, I grew up in public housing. From the age of 11, I attended what in the UK is the rough equivalent of a public high school. This was during a very volatile and violent phase of societal change in my country, set against a backdrop of illegal paramilitary organisations. They effectively “hoovered up” a high portion of my childhood friends, regurgitating them as dead bodies or incarcerated prisoners with no future. This was the reality of my childhood and formative years.

Read more »

Spotlight: Goodell

At Ease

I REMEMBER THE FIRST time we met. Josh—not his real name—and I went to rival high schools in the Washington, D.C., area. During our senior year, we competed in a track meet. Someone mentioned that we would be going to the same college in the fall, so I went over to introduce myself—a little awkwardly, as he had just annihilated me in a race. A few months later, knowing few people on campus, we were happy to discover that we’d both enrolled in the college’s Army Reserve Officers’ Training Corps (ROTC) program. Josh was garrulous, and he possessed that rare combination of incredible athletic and academic ability. When the U.S. Army decided what jobs we would have, they astutely assigned Josh to the artillery—with its loud guns and adventure, but also need for mathematical precision—while packing me off to law school. Josh’s career in the Army was cut short when he died in 2010, a result of complications stemming from a brain injury suffered during combat in Afghanistan. At the time of his death, Josh had just decided that his marriage was unsalvageable and headed toward divorce. Within days of that decision, he fell ill, slipped into a coma and eventually passed away. Josh died before he could change the beneficiary on his life insurance. Though it has been nearly a decade since his funeral, I still viscerally recall standing in Arlington Cemetery with a few of our ROTC classmates and watching Josh’s family sitting alongside his wife. His spouse would be receiving $400,000 in life insurance—the standard amount of coverage for those who serve in the military. I remember thinking about all the movies I had seen where the 21-gun salute rings out. Now, I was living that surreal nightmare here in our own hometown. Perhaps Josh might have found…
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Wrote and Grew Rich

IF YOU GOOGLE “best business books of all time,” you’ll find Napoleon Hill’s Think and Grow Rich at or near the top of the search results, ahead of works by luminaries such as Ben Graham and Jack Bogle. Truly helpful business analysis requires the reader to pay attention to evidence backed by boring data, a formula that’s hard to sell to the masses. Books like Think and Grow Rich or Jim Collins’s Good to Great offer the reader questionable assumptions built on anecdotal evidence, but these books satisfy our human preference for stories over data. Think and Grow Rich posits that if you persistently visualize becoming wealthy, the power of your subconscious mind will help make it so. Napoleon Hill claimed he wrote his 1937 book at the behest of Andrew Carnegie, who purportedly challenged Hill to interview wealthy folks with the goal of discovering a simple formula for success. This claim was made after Carnegie’s death, so it’s impossible to refute. Still, Carnegie’s biographer says that there’s no evidence the two ever met. Also, it turns out Napoleon Hill had serious grifter-like issues prior to writing his book. Thirty years before the publication of Think and Grow Rich, Hill cofounded a lumber company that would be subject to bankruptcy proceedings and allegations of mail fraud. Hill would then go on to found businesses in the automobile education and advertising industries, both of which failed. The former was effectively a multilevel marketing scheme, which collapsed, and the latter resulted in two warrants for Hill’s arrest. Grifters use aspects of the truth to gain the trust of the consumer. Think and Grow Rich uses the power of positive thinking, a valid concept that aids in everyday well-being, and repurposes it as a powerful tool to manifest better results in the form of lots…
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Don’t Be Deceived

AT FIRST GLANCE, personal finance might appear to have nothing in common with the world of personal fitness. I’d argue otherwise. Perhaps the clearest parallel is between the gains from diligent investing in low-cost index funds and the gains from proper diet and exercise. Both are hardly noticeable at first and, as a result, there’s a temptation to stray. But if we continue the process of saving and investing—or eating correctly and exercising—we can see tremendous gains over time. There is, however, another analogy—one I recently came across in an article discussing the rampant use of steroids in the fitness industry. The use of anabolic steroids among bodybuilders is widely known. But did you know that many famous fitness social media influencers, and even some of our favorite Hollywood stars, have likely bulked up using performance-enhancing drugs? The short-term gains are remarkable, though they mask significant longer-term health costs. Many fans don’t realize that these fitness gurus are effectively lying and cheating their way to profits. For average folks, the consequence is severe disappointment when they don’t enjoy results similar to those they emulate. As a 40-year-old who has worked out regularly since he was 16, I can attest that the first decade in the gym produced little result, and it was discouraging. If the Army didn’t force me to exercise continuously, I probably would have quit and never have realized some of my best fitness gains—many of which have only become obvious in my third decade working out. This same integrity issue afflicts the financial services industry. What we see online and on TV is rarely indicative of reality. The amount of investor assets that some CNBC pundit manages is akin to the number of followers a fitness guru attracts. Neither metric actually measures performance. No one should confuse…
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Wrecked by Tech

NOTHING IN INVESTING better exemplifies what the late Donald Rumsfeld called a known unknown than the concept of intrinsic value. The relationship between a company’s current share price and its actual value over its lifetime has always been tenuous—but perhaps never more so. Before the rise of modern technology, courtesy of Silicon Valley, intrinsic value was difficult to adjudge in a reliable way. Now, ascertaining intrinsic value has become nearly impossible—because "software is eating the world." Technology is engaged in the capitalist equivalent of the French Revolution, summarily beheading companies. (But hey, at least my BlackBerry makes an excellent paperweight.) Companies leverage software and artificial intelligence to disrupt legacy business models at a dizzying pace. They operate at massive losses while investors hope their stock prices will one day justify current valuations. Amid the ongoing disruption caused by competitors, it’s impossible to know whether a company’s growth has entered a terminal decline until several quarters or years have passed. This known unknown inevitably generates massive disparities between a company’s current stock price and the underlying business’s intrinsic value—during both the growth and decline phases of that business’s lifecycle. Technology has the potential to reduce inefficiencies and boost returns on invested capital. Those who pick the winners will continue to be richly rewarded. But if history is any guide, most investors won’t pick winners. That’s why using an index fund to capture the intrinsic value of all companies and industries strikes me as more appealing than ever. That way, you can be sure of capturing the returns of the business world’s successful revolutionaries, while avoiding the risk that you’ll bet too much on a future Robespierre.
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Making Good Time

PARKINSON’S LAW states that work expands to fill the time available for its completion. This law is a pervasive reality—and misguided practice—in much of the working world. But I recall first encountering it before I joined the ranks of the employed. During the summer before my senior year of college, I spent several weeks in Fort Lewis, Washington, for the ROTC training required for a commission in the Army. On the day when it was my turn to lead my peers, we had just returned from several days in the field. In military parlance, “the field” is shorthand for training outdoors, sleeping on the ground, and dealing with conditions meant to prepare you for war by being nearly as miserable. Consequently, everything was dirty, from our sleep-deprived bodies to our weapons. Before we could clean ourselves, we had to clean our weapons and turn them in to the arms room. The whole platoon worked for several hours cleaning the weapons, shoving pipe cleaners into every crevice of our M-16s to remove the grime. Here's a conundrum about weapons cleaning: You can never really get older weapons completely clean because a proper cleaning requires oil at the end to keep the weapons from rusting. Once applied, this oil generates a dirty-looking residue from the carbon that’s ossified on the weapon’s metal coils and springs. The smallest amount of carbon combined with oil makes it look like you never cleaned the weapon. Arms room sergeants who want to mess with trainees go directly to those coiled springs during an inspection of older training weapons. When we went to turn the platoon’s weapons in at lunchtime, the arms room sergeant discovered dirty-looking substances in the first two weapons he inspected. He sent us back to clean some more. This order provided me with…
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Black Beauty

AFTER 20 YEARS, the U.S. military has withdrawn from Afghanistan. The news brought back memories of the year I spent deployed there—and a crucial financial lesson I learned. Perhaps that lesson resonates even more today given the past year’s pandemic and the role deferred gratification has lately played in many of our lives. When you’re deployed to a combat zone, the government doesn’t tax your wages. Consequently, most soldiers can sock away a lot of money. From a financial point of view, being deployed is a lot like being stuck in your house during the pandemic—assuming you’re fortunate enough to remain employed. Your expenses drop precipitously, so you’re able to increase your savings rate sharply. For my wife and me, saving is an important part of our family ethos. Our savings rate typically approaches 50% of our income. But here’s the thing: During the year I was deployed, we saved nothing—and I have zero regrets. At that time, my wife was a medical student and first-year resident. While her income was negligible, we still had her rent and other bills to pay. With the remainder of my salary, I spent the entire year in Afghanistan saving for what most personal finance experts would consider one of the worst uses for money: buying a new car. That year was one of my life’s bleakest periods. Four months into my deployment, I committed to purchasing a car through a program offered to deployed servicemembers. I paid a large chunk of my salary each month until the vehicle was totally paid off at the end of the deployment. In return, I received a small discount on a car that I was allowed to customize. And it wasn’t just any new car. I bought a 2013 black Ford Mustang GT Premium California Special Edition.…
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