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Would You Be Miserable?

Dan Smith | Jun 8, 2026

"I'll consider it. Thanks!"

- Mark Gardner

Better Alternatives to Buying an Annuity

DavidHLancaster | Jun 10, 2026

"As to your point about the difficulty of building a TIPS ladder I would encourage the watching of the 2025 Boglehead's conference presentation titled TIPS Ladders with Kevin Esler. The free tool Mr. Esler has developed makes building a TIPS ladder less complex in my opinion. I like to keep my taxes simple so I only own TIPS is a traditional or a Roth IRA. I have bought my TIPS mostly at auction but have bought some TIPS on the secondary market to fill in my rolling 10 year TIPS ladder rungs. I would also note that the benefits from annuities are not indexed to inflation where buying individual TIPS, not TIPS funds, will return the real yield rate of the TIPS at purchase plus inflation if held to maturity. With annuities you may benefit from mortality credits from the members of the pool who die early but you suffer the expenses that are associated with annuities. Does the company issuing an annuity have the ability to fulfill their obligation to me under an annuity? Likely they do but I see TIPS as the most riskless asset I can purchase. I agree with you regarding using a financial ladder, TIPS or other fixed investments, runs will out of money when the ladder benefits ends. For me TIPS are just a large part of the fixed income portion of my overall asset allocation. I am a fan of the writings of financial writer David Enna and his website TIPSwatch and his statement about the purpose of TIPS when he wrote I want to state loudly that TIPS are for preserving wealth, not building wealth."

- William Perry

What Remains: Money and Me

Andrew Clements | Jun 10, 2026

"Andrew, what struck me most was the parallel between Jonathan and your father. Two men writing for entirely different reasons: one sharing his thoughts freely with the world, the other keeping them almost entirely to himself. Yet both left exactly the same footprint. It makes you wonder whether legacy through words is less about intention and more about authenticity. Write honestly, for whatever reason, and the words have a way of touching someone."

- Mark Crothers

The Ping

Mark Crothers | Jun 4, 2026

"SCao, if my post managed to make even one person smile, it was worth every second I spent writing it."

- Mark Crothers

Mourning the World

Jonathan Clements | Jun 5, 2026

"I lost my brother at 59 years old to Alzheimer’s and Lewy body dementias (he donated his brain to the memory disorders clicic at Mass General. He was non communicative for years before his death as well as unaware of his surroundings as well. At his passing I kept thinking is he in pain, does he hear us, and does he know what is happening? Six months later my father died at 85 of suspected Lewy body dementia and was non communicative for the last six or so months. Then my mother passed away at 85 six months after that after having dementia for more than a decade. She did not recognize any of the family for years. So for the passing of half of my family we could not support them, or know their thoughts as their lives were ending. It was horrible. Last year my mother in law passed away at 103 1/4 and was in complete control of her capacities until the day she passed away. She lived in senior housing until 102 when her husband went to a nursing home and she moved in with us. Other than by age she physically never would have qualified for nursing home care. The way the end of her life ended up going was a blessing for me. For the newer readers of HD you can read my thoughts on her under my David Lancaster profile (I had to create a new profile via Discus due to problems logging on to HD via X."

- DavidHLancaster

How to Use AI With Your Portfolio

W.D. Housley | Jun 9, 2026

"These were recently published articles."

- DavidHLancaster

Moving is Expensive!

DrLefty | May 29, 2026

"Congratulations on the move, Dr. Lefty. It is certainly a huge event and takes a lot of effort. Glad to hear you are settling in."

- SCao

Reflections on a Quiet Failure

Javier Escobar | Jun 7, 2026

"Yes, that's exactly what you said; my bad."

- Dan Smith

Peter Cancro from age 14 to 69 covered in oil and vinegar

R Quinn | May 31, 2026

"I like their turkey club. I’m going to try the cheesesteak though."

- R Quinn

Bucket Strategy

ArticleAdam M. Grossman | Jun 6, 2026

A WHILE BACK, I was speaking with a fellow who had recently retired. He shared this observation, only half-jokingly: “Working was easy,” he said. What he meant was that financial management during our working years is more straightforward than it is in retirement. We earn and save and hope that our savings grow. But when we get to retirement, it becomes more complicated to know exactly how to manage those savings. In the 1950s, a Ph.D. student named Harry Markowitz developed a framework to help investors answer this question. His approach, which is now known as modern portfolio theory, provided new insights on how to effectively diversify a portfolio. He later won a Nobel Prize for this work. But useful as it was, modern portfolio theory involved a lot of math and didn’t offer investors any practical help in managing their savings. Other academic theories have emerged over the years, but all of them involved similar levels of complexity. It was for that reason that in 1985, financial planner Harold Evensky developed an idea that’s now known as the “bucket strategy.” The idea is that investors—especially those in retirement—should segment their portfolios. To understand this idea, we can look at a simple example. Suppose Tom is a recent retiree and planning to withdraw 5% of his portfolio each year for the next several years. To protect against a potential stock market downturn, it would be reasonable for him to hold five years worth of withdrawals in some combination of cash and short-term bonds, since that corresponds, more or less, to the length of the worst stock market downturns we’ve seen in modern times. In Evensky’s model, cash and bonds would be the first bucket, and the math is straightforward: If Tom wants to withdraw 5% each year and wants to set aside enough for five years, then he’d hold 25% (that is, 5% x 5) in the first bucket. With that 25% allocated to bonds for stability, Tom could then feel free to allocate the remaining 75% to stocks. The benefit of this structure is that Tom would then have the flexibility to withdraw from either the stock or bond side of his portfolio depending on where the stock market stood in any given year. Most importantly, by putting a wall between his stocks and his bonds, Tom would be able to avoid selling stocks during market downturns. The bucket concept can be very useful, but it’s important to know that there isn’t just one bucket strategy. Since Evensky first introduced the idea 40 years ago, a handful of alternatives have evolved. Evensky’s original structure consisted of just two buckets. This makes it simple and easy to manage. A downside, though, is that bonds can still lose money, so neither of the two buckets could be considered truly safe. In 2022, in fact, total-bond market funds lost more than 10% of their value, and it took several years for investors to get back to even. Thus, one of the most popular ways to structure a bucket portfolio is to add a third bucket, for cash. To be sure, cash doesn’t offer much growth potential. But it would’ve been extremely helpful in a year like 2022, when both bonds and stocks lost money. While it provides more protection, the downside of a three-bucket approach is that it’s more complicated and somewhat harder to manage. Proponents, however, argue that it doesn’t require much more effort than traditional portfolio rebalancing and is well worth the effort. In his book, The Aspirational Investor, Ashvin Chhabra lays out another bucket alternative. Chhabra is less concerned with the distinction between bonds and cash. Instead, he advises investors to focus on the riskier side of their portfolios. He suggests that investors distinguish between standard, publicly-traded stock market investments and any alternative assets, such as private funds and real estate, that they might hold. Chhabra feels this segmentation is important because of the nature of alternative investments. They’re a little like lottery tickets: They can turn into home runs but can also go to zero. If you’re constructing a portfolio and like the idea of a bucket approach, which way should you go? Since each of these approaches has merit, you could combine them all, creating a four-bucket setup, consisting of cash, bonds, stocks and alternatives. That wouldn’t be unreasonable, but it would also ratchet up the complexity level. Here’s the approach I recommend: First, like Chhabra, I would draw a distinction between traditional assets and alternatives. Traditional, publicly-traded investments, including standard stock and bond mutual funds and ETFs, would go in your core portfolio. These are the assets around which you’d build your plan. Alternatives, if you own them, would go in their own separate bucket. In general, I don’t recommend these types of assets because their performance is more variable and more unpredictable, and because they tend to carry higher fees. But if you already own some alternatives, I’d separate them from your financial plan and view them only as a bonus if they deliver value. In other words, make sure that your financial plan will still work if you were to rely on only your core portfolio. Within the core, I’d have just two buckets: one for stocks and one for bonds. The result is that you would have just two buckets, plus alternatives, if you happen to own them. But what about cash, since, as we saw earlier, bonds aren’t guaranteed and can certainly lose money? In my view, a dedicated, separate cash bucket isn’t necessary. Instead, what I recommend is to be diligent in diversifying your bond holdings. I wouldn’t own a total-bond market fund. Instead, take a building block approach, holding some short-term and some intermediate-term bond funds. Short-term funds will shine when rates are rising because they’ll decline much less than total-market funds. Intermediate-term bonds, on the other hand, will shine when rates are dropping. You could also add some inflation-protected bonds to round out your holdings. At the end of the day, the best portfolio structure is the one that’s simple to manage while also protecting your savings from whatever surprises the market delivers. 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.

Time to share our financial info with children?

R Quinn | Jun 6, 2026

"I urge you to share, RDQ, with all four of your children. I suspect it will remove a huge, perhaps subconscious, load from your shoulders. My father began sharing his financial information with me, an only child, when I was in my 20s. Then, I hated it, as he reviewed his accounts and investment deliberations in great detail; I barely had the patience to listen. I also never counted on inheriting (the step family situation was fluid), and these talks did not alter my savings path. Over time, I grew to respect my father for sharing. I learned much, too. As his eventual executor, my understanding of his finances made my work that much easier. I already had a checklist. And the best part was that my father asked what I would do were I to inherit. We spoke of philanthropy and it pleased him to know that his money would be put to good use. He passed two decades ago, but I feel him with me to this day as I realize my giving plans."

- Jo Bo

A $1,000 Conversation With My Daughter

Mark Crothers | Jun 7, 2026

"Dan, my youngest daughter has never been great at listening to her old dad — so I figured I'd meet her where she lives. Sent it to her on WhatsApp. Funny how a phone screen carries more authority than I do. 😉"

- Mark Crothers

Would You Be Miserable?

Dan Smith | Jun 8, 2026

"I'll consider it. Thanks!"

- Mark Gardner

Better Alternatives to Buying an Annuity

DavidHLancaster | Jun 10, 2026

- William Perry

What Remains: Money and Me

Andrew Clements | Jun 10, 2026

- Mark Crothers

The Ping

Mark Crothers | Jun 4, 2026

"SCao, if my post managed to make even one person smile, it was worth every second I spent writing it."

- Mark Crothers

Mourning the World

Jonathan Clements | Jun 5, 2026

- DavidHLancaster

How to Use AI With Your Portfolio

W.D. Housley | Jun 9, 2026

"These were recently published articles."

- DavidHLancaster

Moving is Expensive!

DrLefty | May 29, 2026

"Congratulations on the move, Dr. Lefty. It is certainly a huge event and takes a lot of effort. Glad to hear you are settling in."

- SCao

Reflections on a Quiet Failure

Javier Escobar | Jun 7, 2026

"Yes, that's exactly what you said; my bad."

- Dan Smith

Peter Cancro from age 14 to 69 covered in oil and vinegar

R Quinn | May 31, 2026

"I like their turkey club. I’m going to try the cheesesteak though."

- R Quinn

Manifesto

Jun 10, 2026

NO. 50: WE SHOULD strive to raise financially responsible children. If our kids grow up to make foolish financial mistakes, we’ll likely ride to the rescue—and their problems will be ours.

act

Jun 10, 2026

GET A WILL. Less than half of U.S. adults have a will. Without one, many of your assets will be distributed according to state law, plus you won’t have a say in who becomes your children’s guardian. Some folks don’t bother with a will, because they have a living trust. But when you die, there’ll inevitably be assets outside the trust—and, for them, you need a will.

Truths

Jun 9, 2026

NO. 72: EXPECTED return and risk change over time. Historically, commodity futures have delivered great returns and been great diversifiers for stocks—but both qualities have waned, as investors rushed to take advantage. The same may be true for the high excess return from owning value stocks, smaller companies and stocks in general.

think

Jun 8, 2026

REBALANCING. For major market segments—emerging markets, high-quality bonds, small-cap stocks and so on—we should have target portfolio percentages. Every so often, we should bring our portfolio back into line with these targets, preferably making any sales in a tax-deferred account. Rebalancing controls risk—but it can also boost returns.

Money Guide

Manifesto

Jun 10, 2026

NO. 50: WE SHOULD strive to raise financially responsible children. If our kids grow up to make foolish financial mistakes, we’ll likely ride to the rescue—and their problems will be ours.

Spotlight: In Retirement

Another interesting article on Social Security claiming

Rick Connor | Jul 5, 2025

A recent article by Michael Finke in Think Advisor discusses some anecdotal evidence he has been hearing about recent trends in SS claiming. Worry about a reduction in benefits apparently is leading some retirees to claim their benefits earlier than might be expected given their wealth. I have to admit that this year’s discussions around SS funding and administration have given me pause.
Two things about the article. It was published in a professional journal targeting financial advisors.

Let’s revisit an important retirement living topic. How’s it going? Great expectations

R Quinn | May 8, 2025

I hear about this topic on YouTube retirement videos. It has also been a topic on HD from time to time. We all know about the process of preparing financially for retirement, but it seems that for many people facing a retirement lifestyle is equally challenging.
Honestly, I can’t relate. I never thought about what retirement living would be like. I had no expectations. Perhaps taking phased retirement for 18 months was a factor, but even when I decided on doing that it wasn’t with a plan to prepare for retirement,

Changes in Social Security Claiming Age

Rick Connor | May 27, 2025

A recent paper published by Boston College’s Center for Retirement Research examined changes in the SS claiming age since 1985, and more recently during the Covid pandemic. The study shows that there has been a fairly dramatic decline in the percentage of those people claiming at 62 in the 20 years leading up to Covid, and that trend has remained steady since then. The study also shows that the average claiming age has increased by about 2 years.

2024 Update to the OASDI Beneficiaries by State and County

Rick Connor | Aug 25, 2025

Almost four years ago I wrote an article about the 2020 OASDI Beneficiaries by State and County report. The report is put out by the Social Security Administration (SSA), and provides a wealth of interesting statistics. Here is the link to the 2024 report where you can investigate detailed national and local data.
Here are some basic numbers for context. As of December 2020, the U.S. population was 329,484,123. Four year later it had grown 3.5%,

The Surprising Gift of Unhurried Time: My Retirement Revelation

Mark Crothers | Jun 20, 2025

This morning, while sipping coffee in my sunroom, a simple thought occurred – one of those rare insights, I don’t have them often! It struck me that since retiring, my morning brew has become more enjoyable. After mulling it over, I pinpointed the reason: time. More specifically, the luxury of extra time to truly savour and embrace the entire coffee experience.
This revelation isn’t confined to my coffee cup. It’s weaving its way into other aspects of my life too.

It’s The Little Things That Scare Me Now

Dennis Friedman | May 14, 2025

I’m going to be 74 next month, and I’m beginning to realize that the little things in life are starting to frighten me more. If I were younger, they probably never would have crossed my mind.
When I walk, I’m constantly scanning the ground for hazards. A raised sidewalk or uneven pavement could send me tumbling—and at my age, I’m not sure my bones would hold up to the fall.
Every night before I lie down,

Three Mistakes

Larry Sayler | Jul 14, 2022

DURING MY NEARLY 70 trips around the sun, I have made countless mistakes. Most have been minor, but three stand out. Two I have already made, and the third I’m about to make. Mistake No. 1: Go-Kart. When I was 12 years old, I bought a go-kart. It has a fiberglass body and was built to resemble the car driven to victory by legendary driver Jim Clark in the 1965 Indianapolis 500. It cost $300. I used the money I’d saved from my paper route. A friend and I would take it to an elementary school three blocks from our home and drive it for hours. More than 50 years later, I still have that go-kart. I assumed our kids would enjoy it. But we were living in Southern California at the time and there was no place they could take it out on their own. I was busy at work and our kids had their own interests. We never used it. Years went by. Grandchildren have now used it, but only a few times. I need to get rid of it. It’s taking up space and it isn’t getting used, and yet I’m emotionally attached to it. My children and grandchildren don’t want it. It would be hard to sell to a stranger for even a few hundred dollars. It wasn’t a mistake to purchase the go-kart. Rather, my mistake was not selling it when I got my driver’s license and largely lost interest in it. Mistake No. 2: Caboose. Until recently, we owned a full-size railroad caboose, parked on 40 feet of railroad track. Twenty years ago, my wife showed me an ad in the paper. “Look, someone has a caboose for sale,” she said. “Who would want a caboose?” My response: “Let me see that.” The caboose…

Making Waves

Larry Sayler | Mar 22, 2024

MY WIFE AND I recently returned from a 14-day cruise to the Caribbean with my 96-year-old mother. Since my dad passed away in 2009, my wife and I have gone on several cruises with my mom. We departed from and returned to Fort Lauderdale, visiting eight Caribbean islands: St. Kitts, Guadeloupe, St. Lucia, Barbados, Grenada, Trinidad, Martinique and Aruba. For my wife and me, the fare was $2,200 per person for a room with a balcony. This included travel insurance, taxes and port fees. To this, we had to add $15 per person per day for the mandatory gratuity. We still consider this a bargain for a room with a great view, fantastic meals and free on-board entertainment. Traditionally, single travelers have had to pay twice the per-person rate of a couple. Cruise lines would argue that, if a single person hadn’t taken the room, they’d place a couple there and collect two fares. But today, cruise lines are often more reasonable. My mother’s fare was $2,700 for a balcony room. She had a handicap accessible room, which was 50% larger than a standard room, with a spacious bathroom. My wife and I are early risers. My mother is not. We usually have coffee and pastries delivered to our room at 6:30. We sit on our balcony and watch the ocean roll by. When my mother gets up a few hours later, we head down to the dining room for breakfast. If there’s such a thing as a typical cruise ship, it’s 105 feet wide and 950 feet long. Why these measurements? This is the largest a ship can be and still pass through the original Panama Canal locks. These ships generally carry about 3,000 passengers and 1,500 crew members. New Panama Canal locks, opened in 2016, allow for bigger…

The Magic Number

Larry Sayler | Aug 25, 2022

WHEN SHOULD YOU start drawing Social Security? If folks want to maximize their lifetime benefit, I think the answer is fairly straightforward. Maximizing lifetime Social Security income isn’t always the goal, of course. Some people need Social Security to meet basic needs. These people usually claim benefits as soon as they reach age 62, the earliest possible age. Others view Social Security as longevity insurance. They want as much monthly income as possible in the event they or their spouse live a long time. These people typically wait until 70, the latest possible age, to start Social Security. But for many people, the goal is to maximize the amount they’re likely to receive during their lifetime. Financial nerds often toss around terms like “breakeven” or “cross-over.” More sophisticated analysts consider present values and appropriate discount rates. I like simple. Want to maximize lifetime income? I believe the decision rule is fairly simple. If I am likely to die early in retirement, I should start Social Security as soon as possible. If I know I am going to die at age 65 and I don’t have a spouse who will receive survivor benefits, I had better start Social Security at 62. It makes no sense to wait. On the other hand, if I am going to live a long time—perhaps to age 90 or even 100—I want the largest monthly check possible for all those years. I achieve that by waiting until 70 to start Social Security. If I have no reason to think I will either die early or live a very long life, it makes sense to start Social Security sometime between age 62 and 70. One might choose age 66, the midpoint between 62 and 70. Others might choose their Social Security full retirement age. For those born…

Motivated by Money

Larry Sayler | Nov 10, 2022

"WE BEHAVE BETTER when we know others are watching—so be sure to tell friends if you’re aiming to exercise more, lose weight or save more." I love the pithy sayings that appear each day at the top of HumbleDollar’s homepage. This statement appeared Oct. 19. A few years ago, when I was still working fulltime, some colleagues and I adopted this philosophy. Suppose one of us had a goal, such as losing five pounds by the end of the month. We could have simply told our coworkers the goal. But being type-A personalities, we took it to an extreme. We decided it was more effective if we backed our intentions with money. “If I don’t lose five pounds by the end of the month, I’ll give you $20.” None of us really wanted to take a colleague’s money, so we soon changed this to, “If I don’t reach my goal, I’ll give $20 to a charity of your choice.” This led to some interesting discussions. If we were of the same political party, had the same views on abortion or shared the same religion, the penalty for not meeting the goal was to give a contribution to an organization we both supported. That wasn’t much of a penalty. Someone pointed out it would be more motivating if the loser had to make a financial contribution to an organization with which he or she disagreed. If we were a staunch member of one political party and we lost our bet, we had to give $100 to the other major party. Now, that was motivating. Maybe we were exceedingly cheap, but the person always met his or her goal. I don’t recall anyone ever paying a penalty. Of course, we were on the honor system. The person making the contract simply self-reported…

Lost in Translation

Larry Sayler | May 4, 2023

IN THE 1980s, I SPENT nearly 12 weeks in an Australian hospital. I learned that language is not always universal. I was a corporate auditor for General Electric, and the company had sent me to Australia for a three-month assignment. To Yankee ears, Australians have an accent. But at least we speak the same language. Or so I thought. Within a week of getting to Australia, I was diagnosed with subacute bacterial endocarditis (SBE), a serious bacterial infection of the blood. I was born with a slight heart defect which makes me more susceptible to SBE. Prior to about 1955, it was universally fatal. I don’t blame the Aussies for my infection. I’m pretty sure I contracted it before going to Australia. The general practitioner said I needed to go to a hospital and be hooked up to intravenous penicillin 24/7. I could go to a private hospital, which would be more like a U.S. hospital, or to a hospital for veterans. I asked which had the best equipment and doctors. He said the veterans’ hospital, so I went to Concord Repatriation General Hospital in Sydney. I had never been in the military. I have no idea why I was allowed to be treated at an Australian veterans’ hospital. Nurses are not nurses. There were no private or even semi-private rooms in the hospital. I was in a ward with 24 beds. Nurses would walk up and down between the rows. If we needed something, it was not unusual to call out for the nurse. I heard other patients call out “nurse” or “sister.” Thinking “sister” was somewhat derogatory, I always said “nurse.” One day, the head “nurse” confronted me. She asked why I called her a nurse; she was a sister. I learned that, in Australia, “nurse” refers to…

Get What’s Yours

Larry Sayler | Apr 14, 2022

AFTER THEY MARRY, some people discover their spouse has hidden debt. We had the opposite situation. Several years after we were married and while living in Illinois, my wife got a letter from the New York Secretary of State saying she may be the owner of an unclaimed savings account in the town where she was raised. This was before the internet. We had no idea how New York found her. Neither my wife nor her parents remembered the account. My wife filled out some paperwork and a few weeks later she received a check for a few hundred dollars. Apparently, it’s common for people to forget about things like bank accounts, retirement accounts and utility deposits. Because states don’t want financial institutions and other companies sitting on this money, with no incentive to track down the owner, they require that unclaimed assets be turned over to the state. As a result, states hold billions of dollars in unclaimed property. Today, thanks to the internet, searching for unclaimed assets is easy. Recently, I spent an evening checking for unclaimed assets in the six states in which my wife and I have lived. Using Google, I typed in the name of a state and “unclaimed property.” One of the first suggestions was always the official secretary of state site for unclaimed property. Most sites—though not all—had a “.gov” suffix, indicating it’s an official government website. Alternatively, you can locate official state sites by going to Unclaimed.org. The sites varied slightly, but usually I could simply type in a name and then hit “search.” I used only my surname. If you also enter a first name, you may not find assets where the first name is listed only as an initial. I never knew there were so many folks called Sayler. It…

Would You Be Miserable?

Better Alternatives to Buying an Annuity

What Remains: Money and Me

The Ping

Mourning the World

How to Use AI With Your Portfolio

Moving is Expensive!

Reflections on a Quiet Failure

Peter Cancro from age 14 to 69 covered in oil and vinegar

Bucket Strategy

Time to share our financial info with children?

A $1,000 Conversation With My Daughter

Would You Be Miserable?

Better Alternatives to Buying an Annuity

What Remains: Money and Me

The Ping

Mourning the World

How to Use AI With Your Portfolio

Moving is Expensive!

Reflections on a Quiet Failure

Peter Cancro from age 14 to 69 covered in oil and vinegar

Free Newsletter

Get Educated

Manifesto

act

Truths

think

Money Guide

Manifesto

Spotlight: In Retirement

Another interesting article on Social Security claiming

Let’s revisit an important retirement living topic. How’s it going? Great expectations

Changes in Social Security Claiming Age

2024 Update to the OASDI Beneficiaries by State and County

The Surprising Gift of Unhurried Time: My Retirement Revelation

It’s The Little Things That Scare Me Now

Spotlight: Sayler

Three Mistakes

Making Waves

The Magic Number

Motivated by Money

Lost in Translation

Get What’s Yours