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If you smoke two packs a day and fully fund your 401(k), you probably aren’t being entirely rational.

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

Howard Schwartz  |  Jul 27, 2026

"Thank you! Yes, the TIPS would be held in my IRA, and the plan would be to hold them until maturity. I haven't found any inflation-adjusted annuities, but it looks like I could buy an SPIA with a 2 or 3 percent annual increase. Helpful but not an impregnable defense against 3.5 percent inflation."
- Emily Croy Barker
Read more »

Taking a Loss?

Mark Crothers  |  Jul 28, 2026

"Randy, I agree you don't buy bonds for price appreciation, though I don't hold them for the dividends either. For me, they’re more of a portfolio ballast to smooth out the ride. Nice lock-in on the 10-year TIPS, by the way."
- Mark Crothers
Read more »

Go While You Still Can

DavidHLancaster  |  Jul 22, 2026

"Great perspective. " .... are all healthy enough to experience life together is smaller than you think... and it's getting smaller." Most valuable things in life take a long time to achieve and we have precious little time to experience them. Live the moment!"
- V Saraf
Read more »

What I Retired To

Andrew Clements  |  Jul 29, 2026

"I am the same way, I too have this thing about seeing net worth decline no matter how illogical it is. These past few weeks have not helped has investments have tumbled and taken me from my happy place. My son in law is a managing direct at a Wall Street firm and warned me about this summer, but it doesn’t make me feel any better."
- R Quinn
Read more »

2025 and Medicare Rx

R Quinn  |  Jan 1, 2025

"Applies to all drugs that are on your plans formulary."
- R Quinn
Read more »

Today in Financial History

Harold Tynes  |  Jul 28, 2026

"Notice that I said I may hire an advisor someday if or when needed? This assumes that I will recognize that time is approaching and have time to interview and hire someone. Life often does not work that way. And you answered my unasked question, that is "why pay someone now to do what I may need someday, but just not yet?" By working with your advisor now, you can reasonably expect that your advisor will continue to follow your preferred strategy in the future, with or without your oversight. Smart move."
- Jack Hannam
Read more »

Widow Tax

ArticleJohn Urban  |  Jul 25, 2026

THE WIDOW TAX is sold to the wrong households. It gets pitched to affluent couples as the reason to convert to a Roth or buy life insurance. The pitch says that when one spouse dies, the survivor files single, lands in a higher bracket, and gets clobbered. I ran the numbers for three couples at three incomes, and at the comfortable end the widow tax often costs nothing, or even less than nothing. The real cost lands lower down, on households nobody is selling anything to. What follows uses 2026 federal figures to show what the widow tax actually does in dollars, not in scary percentage points. The pattern runs opposite to the marketing. The higher your income, the smaller the hit, and the lower you go, the more it bites. Three Things Move When the first spouse dies, three things change, and they get bundled under one frightening label. One Social Security check stops, and a pension may shrink or end. That is lost income, and it is usually the largest of the three. It is not a tax. Spending shifts as well. The survivor pays one Medicare premium instead of two, but the mortgage still comes out of the same account. The third change is the only one the tax code causes: narrower single brackets, a smaller standard deduction and lower thresholds for the Medicare surcharge. The widow tax is that third piece alone, and the three households below measure how big it really is. The Affluent Couple Both spouses are over 65. Their income is about $360,000: $80,000 from Social Security, $210,000 from a pension and required minimum distributions, plus $30,000 in qualified dividends and $40,000 in long-term gains. They sit in the 24% bracket, and both already pay the Medicare surcharge. One spouse dies. The survivor keeps the larger Social Security check and most of the other income, landing at roughly $308,000. As a couple, they paid about $53,900 in federal income tax and a Medicare surcharge of about $9,240. As a single filer, the survivor pays about $55,000 in federal tax and a surcharge of about $6,355. The effective rate rises from 15.7% to 18.7%, which is the headline people remember. But the federal tax barely moves, up only about $1,100, because the survivor has less income to tax. The Medicare surcharge actually falls about $2,900, because two enrollees in the couple's joint tier cost more than one survivor a tier above. Net it all out, and the survivor pays about $1,800 a year less than the couple did. The rate went up, and the dollars went down. At the high end, the widow tax measured in money hands back a small refund. This is why the Roth conversion pitch aimed at comfortable couples misfires. If converting to Roth would cut the survivor's future taxable income without cutting the couple's lifestyle, the converted money was surplus. Surplus is money the survivor never needed to replace. Edward McQuarrie, a finance professor emeritus at Santa Clara University, made a version of this argument in a 2023 paper. He found the dollar hit inconsequential for affluent couples, and located any real cost lower down, where the Social Security torpedo bites. Where It Actually Bites Drop down to a couple with $180,000 of income: $60,000 from Social Security and $120,000 from a pension and required minimum distributions, all ordinary income. Both are over 65. The couple files jointly at $180,000; the survivor files single at about $150,000. As a couple, they paid about $17,148 in federal tax and no Medicare surcharge. The survivor pays about $22,737 in federal tax and a new surcharge of about $2,885. The federal tax rises about $5,600, and a surprising chunk of that comes from the collapse of the new $6,000 senior deduction, which phases out against a lower income threshold for singles. Then the survivor crosses into a Medicare surcharge tier the couple never paid. The total cost of widowhood here is roughly $8,500 a year, set against a $30,000 income loss. This is the one band where both the dollars and the rate move the wrong way. Now take a couple with $90,000 of income: $38,500 from Social Security, about the national average for two retired spouses, plus $51,500 from a pension and distributions. The survivor keeps the larger Social Security check and the full pension, landing at $73,500. As a couple, they paid about $3,433 in federal tax, at an effective rate of 3.8%. The survivor pays about $5,278, at an effective rate of 7.2%. There's no Medicare surcharge at this income, and there never will be. But the survivor's effective rate nearly doubles, because more of the Social Security benefit becomes taxable, up to the 85% ceiling, when the single thresholds replace the joint ones. The added tax is about $1,845, and the lost income is $16,500. Real money for a household least able to absorb it. It doubles the effective rate, and it hurts.  Read the three together and the widow tax points the wrong way from the marketing. At $360,000 it costs less than nothing, roughly a $1,800 annual saving. At $180,000 it costs about $8,500. At $90,000 it costs about $1,850, but the effective rate doubles. The affluent couples being sold protection don't need it. The middle couples who feel the sting are not being sold anything, and they're the ones for whom a few thousand dollars a year actually constrains a life. The tax code has three different mechanisms, and which one finds you depends almost entirely on your income. At the top, the Medicare surcharge does the work, and it falls. In the middle, the surcharge appears from zero. At the bottom, the Social Security torpedo raises the taxability of the benefit from 75% to 85%. The mechanism changes with the income, and so does the household's ability to absorb the hit. Plan Ahead This is where the widow tax conversation usually stops, and where I think it should start. The moves most likely to leave a survivor better off are the ones you make years before, and they help whether or not the widow tax ever bites. Converting traditional IRA money to Roth over several years before retirement smooths your taxable income. It lowers the required minimum distributions that will later push a single filer into higher brackets. It can also keep a survivor under a Medicare surcharge tier the couple never worried about. Drawing accounts in a sensible order, spending down the right buckets first, reduces the future tax base that a single bracket structure will tax more steeply. Managing required distributions as they grow, rather than letting them balloon off a rising balance, limits the single bracket exposure that builds across a long widowhood. A more tax-efficient bequest helps the people who inherit what is left. None of that is widow rescue. It is good multi-year planning that happens to compound in the survivor's favor. The widow tax is one input to that planning, not the reason for it. The reason is that the year your spouse dies is the worst possible year to be making financial decisions, and the more of those decisions you have already made, the fewer you hand to someone who is grieving. You can do a rough version of this at your own kitchen table, and you should, ideally long before you need to. Estimate the survivor's income after the smaller Social Security check and any pension change, then estimate the survivor's spending from your actual budget, not a generic rule of thumb. Subtract. If reliable after-tax income still supports the life the survivor wants, with margin, the tax rate was never the thing to worry about. Then project the survivor's federal tax, the net investment income tax where it applies and the Medicare surcharge as a single filer, and compare it to the couple. Keep the tax separate from the lost income, so you can see what the tax code actually did. Sometimes, as the affluent couple shows, it does you a small favor. Only then does a planning move earn a look, and only if you can answer what it costs today, what it might save later, who benefits and what has to come true for it to work. The widow tax is real, but it isn't the catastrophe it's sold as. At higher incomes it's not a cost at all. Lower down it is a real cost, and the lower you go, the more it's worth measuring, because the households it constrains have the least margin to spare. The planning that matters most is the kind you do years ahead, smoothing income, holding down future distributions, managing the surcharge tiers and putting the estate in order. Do that, and you've done right by your survivor, for reasons that have little to do with fear and a great deal to do with care. You'll have done it in the years when you still had the time, and the clarity, to do it well. ________________________________________________________________________________ John Urban is the founder of RetireSmartIRA, a retirement tax-planning app. Earlier, he founded GT Nexus, a supply-chain software company acquired by Infor in 2015. He lives in Northern California with his wife, Kathy, and enjoys time with family, travel, reading, Bay Area sports, and the occasional deep dive into the fine print of the tax code.
Read more »

Credit Card Debt.

Michael l Berard  |  Nov 23, 2024

"I pay off credit debt monthly, but I don’t limit myself to one card because part of your credit score is based on the percentage of credit utilization. Your utilization rate will be lower (and credit score higher) if you have multiple credit card accounts."
- corrupt
Read more »

Can we be completely safe?

Ben Rodriguez  |  Dec 17, 2025

"My BIL was a victim of ID theft… They took control of his phone, and resetting all his password's was impossible since he no longer had a phone to use as the second factor. It took months to straighten out."
- corrupt
Read more »

Degrees of Doubt: When Higher Education Misses the Mark

Mark Crothers  |  Jul 16, 2025

"The widely cast net is catching students that require remedial classes in math, English and reading. Is it any surprise that today’s students are unable to think critically?"
- corrupt
Read more »

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

R Quinn  |  Jul 27, 2026

"Not early, but when I claimed I was still working and collecting a pension. Otherwise it would be unlikely we could have saved it all, but that stopped several years ago. My point was if a person can delay until age 70 presumably they don’t need SS until then so collect sooner and invest it until you do need it. Of course the tradeoff is a lower SS benefit for life vs accumulated assets that may or may not provide income to offset the lower SS benefit. The gamble also depends on how long the person lives past age 70. On the other hand, the invested funds are always available to someone. I’m not selling the idea, just something I am happy with the result."
- R Quinn
Read more »

FIFA Financials

R Quinn  |  Jul 19, 2026

"Speaking as someone from a less affluent country (which virtually everywhere is relative to the US). I could personally have afforded to fly to the US and even attend matches. But the extraordinary price gouging by FIFA, local hotels, even public transport was something I would have deemed to make it exceptionally poor value . Would I have got $10,000 of value from attending a couple of matches? Highly unlikely. In any event I have a "home" Euros in 2 years which will likely be much more affordable if I really want to see top level international football."
- bbbobbins
Read more »

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

Howard Schwartz  |  Jul 27, 2026

"Thank you! Yes, the TIPS would be held in my IRA, and the plan would be to hold them until maturity. I haven't found any inflation-adjusted annuities, but it looks like I could buy an SPIA with a 2 or 3 percent annual increase. Helpful but not an impregnable defense against 3.5 percent inflation."
- Emily Croy Barker
Read more »

Taking a Loss?

Mark Crothers  |  Jul 28, 2026

"Randy, I agree you don't buy bonds for price appreciation, though I don't hold them for the dividends either. For me, they’re more of a portfolio ballast to smooth out the ride. Nice lock-in on the 10-year TIPS, by the way."
- Mark Crothers
Read more »

Go While You Still Can

DavidHLancaster  |  Jul 22, 2026

"Great perspective. " .... are all healthy enough to experience life together is smaller than you think... and it's getting smaller." Most valuable things in life take a long time to achieve and we have precious little time to experience them. Live the moment!"
- V Saraf
Read more »

What I Retired To

Andrew Clements  |  Jul 29, 2026

"I am the same way, I too have this thing about seeing net worth decline no matter how illogical it is. These past few weeks have not helped has investments have tumbled and taken me from my happy place. My son in law is a managing direct at a Wall Street firm and warned me about this summer, but it doesn’t make me feel any better."
- R Quinn
Read more »

2025 and Medicare Rx

R Quinn  |  Jan 1, 2025

"Applies to all drugs that are on your plans formulary."
- R Quinn
Read more »

Today in Financial History

Harold Tynes  |  Jul 28, 2026

"Notice that I said I may hire an advisor someday if or when needed? This assumes that I will recognize that time is approaching and have time to interview and hire someone. Life often does not work that way. And you answered my unasked question, that is "why pay someone now to do what I may need someday, but just not yet?" By working with your advisor now, you can reasonably expect that your advisor will continue to follow your preferred strategy in the future, with or without your oversight. Smart move."
- Jack Hannam
Read more »

Widow Tax

ArticleJohn Urban  |  Jul 25, 2026

THE WIDOW TAX is sold to the wrong households. It gets pitched to affluent couples as the reason to convert to a Roth or buy life insurance. The pitch says that when one spouse dies, the survivor files single, lands in a higher bracket, and gets clobbered. I ran the numbers for three couples at three incomes, and at the comfortable end the widow tax often costs nothing, or even less than nothing. The real cost lands lower down, on households nobody is selling anything to. What follows uses 2026 federal figures to show what the widow tax actually does in dollars, not in scary percentage points. The pattern runs opposite to the marketing. The higher your income, the smaller the hit, and the lower you go, the more it bites. Three Things Move When the first spouse dies, three things change, and they get bundled under one frightening label. One Social Security check stops, and a pension may shrink or end. That is lost income, and it is usually the largest of the three. It is not a tax. Spending shifts as well. The survivor pays one Medicare premium instead of two, but the mortgage still comes out of the same account. The third change is the only one the tax code causes: narrower single brackets, a smaller standard deduction and lower thresholds for the Medicare surcharge. The widow tax is that third piece alone, and the three households below measure how big it really is. The Affluent Couple Both spouses are over 65. Their income is about $360,000: $80,000 from Social Security, $210,000 from a pension and required minimum distributions, plus $30,000 in qualified dividends and $40,000 in long-term gains. They sit in the 24% bracket, and both already pay the Medicare surcharge. One spouse dies. The survivor keeps the larger Social Security check and most of the other income, landing at roughly $308,000. As a couple, they paid about $53,900 in federal income tax and a Medicare surcharge of about $9,240. As a single filer, the survivor pays about $55,000 in federal tax and a surcharge of about $6,355. The effective rate rises from 15.7% to 18.7%, which is the headline people remember. But the federal tax barely moves, up only about $1,100, because the survivor has less income to tax. The Medicare surcharge actually falls about $2,900, because two enrollees in the couple's joint tier cost more than one survivor a tier above. Net it all out, and the survivor pays about $1,800 a year less than the couple did. The rate went up, and the dollars went down. At the high end, the widow tax measured in money hands back a small refund. This is why the Roth conversion pitch aimed at comfortable couples misfires. If converting to Roth would cut the survivor's future taxable income without cutting the couple's lifestyle, the converted money was surplus. Surplus is money the survivor never needed to replace. Edward McQuarrie, a finance professor emeritus at Santa Clara University, made a version of this argument in a 2023 paper. He found the dollar hit inconsequential for affluent couples, and located any real cost lower down, where the Social Security torpedo bites. Where It Actually Bites Drop down to a couple with $180,000 of income: $60,000 from Social Security and $120,000 from a pension and required minimum distributions, all ordinary income. Both are over 65. The couple files jointly at $180,000; the survivor files single at about $150,000. As a couple, they paid about $17,148 in federal tax and no Medicare surcharge. The survivor pays about $22,737 in federal tax and a new surcharge of about $2,885. The federal tax rises about $5,600, and a surprising chunk of that comes from the collapse of the new $6,000 senior deduction, which phases out against a lower income threshold for singles. Then the survivor crosses into a Medicare surcharge tier the couple never paid. The total cost of widowhood here is roughly $8,500 a year, set against a $30,000 income loss. This is the one band where both the dollars and the rate move the wrong way. Now take a couple with $90,000 of income: $38,500 from Social Security, about the national average for two retired spouses, plus $51,500 from a pension and distributions. The survivor keeps the larger Social Security check and the full pension, landing at $73,500. As a couple, they paid about $3,433 in federal tax, at an effective rate of 3.8%. The survivor pays about $5,278, at an effective rate of 7.2%. There's no Medicare surcharge at this income, and there never will be. But the survivor's effective rate nearly doubles, because more of the Social Security benefit becomes taxable, up to the 85% ceiling, when the single thresholds replace the joint ones. The added tax is about $1,845, and the lost income is $16,500. Real money for a household least able to absorb it. It doubles the effective rate, and it hurts.  Read the three together and the widow tax points the wrong way from the marketing. At $360,000 it costs less than nothing, roughly a $1,800 annual saving. At $180,000 it costs about $8,500. At $90,000 it costs about $1,850, but the effective rate doubles. The affluent couples being sold protection don't need it. The middle couples who feel the sting are not being sold anything, and they're the ones for whom a few thousand dollars a year actually constrains a life. The tax code has three different mechanisms, and which one finds you depends almost entirely on your income. At the top, the Medicare surcharge does the work, and it falls. In the middle, the surcharge appears from zero. At the bottom, the Social Security torpedo raises the taxability of the benefit from 75% to 85%. The mechanism changes with the income, and so does the household's ability to absorb the hit. Plan Ahead This is where the widow tax conversation usually stops, and where I think it should start. The moves most likely to leave a survivor better off are the ones you make years before, and they help whether or not the widow tax ever bites. Converting traditional IRA money to Roth over several years before retirement smooths your taxable income. It lowers the required minimum distributions that will later push a single filer into higher brackets. It can also keep a survivor under a Medicare surcharge tier the couple never worried about. Drawing accounts in a sensible order, spending down the right buckets first, reduces the future tax base that a single bracket structure will tax more steeply. Managing required distributions as they grow, rather than letting them balloon off a rising balance, limits the single bracket exposure that builds across a long widowhood. A more tax-efficient bequest helps the people who inherit what is left. None of that is widow rescue. It is good multi-year planning that happens to compound in the survivor's favor. The widow tax is one input to that planning, not the reason for it. The reason is that the year your spouse dies is the worst possible year to be making financial decisions, and the more of those decisions you have already made, the fewer you hand to someone who is grieving. You can do a rough version of this at your own kitchen table, and you should, ideally long before you need to. Estimate the survivor's income after the smaller Social Security check and any pension change, then estimate the survivor's spending from your actual budget, not a generic rule of thumb. Subtract. If reliable after-tax income still supports the life the survivor wants, with margin, the tax rate was never the thing to worry about. Then project the survivor's federal tax, the net investment income tax where it applies and the Medicare surcharge as a single filer, and compare it to the couple. Keep the tax separate from the lost income, so you can see what the tax code actually did. Sometimes, as the affluent couple shows, it does you a small favor. Only then does a planning move earn a look, and only if you can answer what it costs today, what it might save later, who benefits and what has to come true for it to work. The widow tax is real, but it isn't the catastrophe it's sold as. At higher incomes it's not a cost at all. Lower down it is a real cost, and the lower you go, the more it's worth measuring, because the households it constrains have the least margin to spare. The planning that matters most is the kind you do years ahead, smoothing income, holding down future distributions, managing the surcharge tiers and putting the estate in order. Do that, and you've done right by your survivor, for reasons that have little to do with fear and a great deal to do with care. You'll have done it in the years when you still had the time, and the clarity, to do it well. ________________________________________________________________________________ John Urban is the founder of RetireSmartIRA, a retirement tax-planning app. Earlier, he founded GT Nexus, a supply-chain software company acquired by Infor in 2015. He lives in Northern California with his wife, Kathy, and enjoys time with family, travel, reading, Bay Area sports, and the occasional deep dive into the fine print of the tax code.
Read more »

Credit Card Debt.

Michael l Berard  |  Nov 23, 2024

"I pay off credit debt monthly, but I don’t limit myself to one card because part of your credit score is based on the percentage of credit utilization. Your utilization rate will be lower (and credit score higher) if you have multiple credit card accounts."
- corrupt
Read more »

Can we be completely safe?

Ben Rodriguez  |  Dec 17, 2025

"My BIL was a victim of ID theft… They took control of his phone, and resetting all his password's was impossible since he no longer had a phone to use as the second factor. It took months to straighten out."
- corrupt
Read more »

Free Newsletter

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Manifesto

Jul 29, 2026

NO. 13: FACED with an unknown future, we should diversify our investments, buy insurance, keep some cash—and accept that, in retrospect, these precautions will often seem unnecessary.

think

Jul 30, 2026

ASSET ALLOCATION. This is a portfolio’s split among the four asset classes: stocks, bonds, cash like savings accounts and money market funds, and alternatives such as gold and real estate. It’s arguably the most important decision an investor makes. The more a portfolio has in stocks, the higher its expected return, but the greater the volatility.

act

Jul 29, 2026

CALCULATE YOUR monthly nonmortgage debt payments as a percentage of your pretax monthly income. We’re talking here about car payments, student loans and minimum credit card payments. Aim to keep these payments to less than 10% of monthly income, though that can be a tough target to hit if you’re a new college graduate with student loans.

Truths

Jul 28, 2026

NO. 44: GOOD companies can be bad stocks. Why? Investors bid up the share prices of widely admired, fast-growing companies—but the stocks often falter when the companies fall short of investors' lofty expectations. Meanwhile, investors shun troubled, slower-growing companies, so even so-so corporate performance can result in strong market returns.

Money Guide

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Portfolio
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Estate planning

Manifesto

Jul 29, 2026

NO. 13: FACED with an unknown future, we should diversify our investments, buy insurance, keep some cash—and accept that, in retrospect, these precautions will often seem unnecessary.

Spotlight: Estate Plan

Exit Strategy

David Gartland   |  Jul 9, 2024

IF YOU’RE LIKE ME, you aren’t eager to spend down your investments. What fun is that? Aren’t you curious to see how big your portfolio could grow? Of course, you are.
After my wife and I are gone, my son will have dibs on the money we’ve amassed. We’ve set up a special needs trust to provide him with income when we’re no longer around. My son has no siblings, so we needed the trust to make sure he’s taken care of.

Read more »

What’s Your Plan?

Adam M. Grossman   |  May 5, 2024

MICK JAGGER IS AMONG the most successful entertainers of our time. But despite his wealth, Jagger tells his eight children that they’ll need to make their own way. Similarly, Shaquille O’Neal tells his children that they can earn some of his millions, but it won’t necessarily be given to them. Actor Jeff Goldblum puts it more bluntly: “Row your own boat,” he’s said. Other public figures have echoed a similar theme.
Why do these wealthy folks take such a seemingly uncharitable view?

Read more »

The Tree We Sit Under

Juan Fourneau   |  Oct 20, 2023

WHEN I WAS BORN IN Iowa in 1973, my parents were renters—and they didn’t become homeowners until eight years later. Looking back, I can see that it would have been hard for them to buy a house. When my dad started at the factory where he worked for more than 30 years, it didn’t pay the best.
But as Bandag, the retread company he worked for, began to prosper under its founder Roy James Carver,

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Great Ideas from Ed Slott for Estate Planning Using Roth Savings

David Lancaster   |  Mar 20, 2025

https://www.morningstar.com/retirement/ed-slott-how-roth-iras-can-help-with-estate-planning?utm_source=eloqua&utm_medium=email&utm_campaign=AdvisorDigest&utm_content=None_62149&utm_id=32158

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If I Go First

Richard Quinn   |  Apr 30, 2024

I MARRIED CONNIE because she’s four years older than me. That meant our life expectancies would be similar and hence a survivor annuity would be less expensive.
I am, of course, joking. Sort of.
Providing for Connie, should I be the first to go, is among my top financial priorities. During my working years, I received far too many calls from new widows who had just learned their husband’s pension stopped when their husband died.

Read more »

Give Early and Often

John Yeigh   |  Feb 22, 2024

KEY PROVISIONS IN 2017’s Tax Cuts and Jobs Act (TCJA) will expire in 2026 unless Congress steps in. That means folks have a two-year window to prepare.
What’s at stake? Income-tax rates will increase for many taxpayers. This creates an incentive to boost income over the next few years by, say, undertaking Roth conversions to shrink traditional retirement accounts and thereby lowering future required minimum distributions.
The sunsetting of key TCJA provisions would also cut the threshold for federal estate taxes in half,

Read more »

Spotlight: Forsythe

Cheap and Proud

Andrew Forsythe   |  Nov 16, 2020

ONCE UPON A TIME, I thought it was a little unseemly to pay a lot of attention to costs. My father grew up in a farm family with little money. He was the first to attend college and, indeed, went on to law school from there. He did well in his profession and, when I was growing up, we lived a comfortable—though far from luxurious—life. Maybe because he’d spent his youth worried about money, my father didn’t want to be preoccupied with it after he established himself. One result: Being cost conscious wasn’t instilled in me at an early age. When I finished school and established myself in my own profession, I was pretty oblivious to costs. As a carefree young bachelor, I thought nothing of buying suits costing several hundred dollars—a lot of money in the 1980s. Restaurants and nightclubs were a regular indulgence. But my outlook undertook a dramatic change in 1987 when I met a beautiful young woman, with two equally beautiful young daughters, and ultimately convinced them to marry me. We wasted no time and soon had two more kids. I’d gone from carefree bachelor to father of four in a couple of years. As I began to read up on the projected cost of college for our little tribe, it hit me like a ton of bricks that I needed to change my thinking and fast. I soon became a dedicated cheapskate, studying the long-term effects of saving vs. spending and starting us on a path—I hoped—to getting four kids through college. The guy who would pay hundreds for a Hickey Freeman suit started clipping grocery store coupons. More important than these new frugal habits was the underlying change in my mindset. Perhaps still nagged by the feeling that there was something a little vulgar…
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Grocery Shopping for the Mildly Obsessed

Andrew Forsythe   |  Jan 5, 2026

And now, as Monty Python might say, “For something completely different….” Given the recent discussion as to which topics are, and are not, appropriate for HD’s realm of finance and retirement, let me first give my defense of an article on the mundane topic of grocery shopping. It’s really pretty simple: For us at least, our weekly expenditures at our friendly local HEB are one of our most substantial fixed costs, probably around $8000 - $10,000 every year. Now with that out of the way….. I’ve shared before the story of how I went from carefree bachelor to husband and father of four in very short order. In the early days of that new status, and with 2 of our 4 kids in the baby/toddler stage, the home front was a place of constant chores, including the dreaded diaper changes. So when an opportunity arose to get out of the house and go grocery shopping, I quickly volunteered. That was 38 years ago, and I still perform the role. The list of things I’m not good at would fill a large book, but one thing I can do, practically in my sleep, is organize. In addition, on realizing that I now had four college educations to fund, my spendthrift bachelor habits turned on a dime and I became an instant tightwad (or “value investor” as I like to think of it). So the job of grocery shopping actually was a natural for me. The first order of business was to create a standardized grocery list which could be used each week and was easily modified. Importantly, it also needed to follow the geography of the store. So I put together a Word document containing all the items we routinely buy, organized in columns in the order in which they’re located in…
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Following Through

Andrew Forsythe   |  Mar 27, 2022

THERE ARE MANY virtues, but one of the rarest is persistence in following through. In our complicated world, often you can’t get something done on the first go. Instead, you have to revisit the task, sometimes more than once. This is true not just of financial decisions but also many other aspects of our lives. In fact, if you’re trying to get folks to do something, often their first defense is to stall—because they know that, after a while, most people will simply give up. I’ve given up on tasks because I became convinced it couldn’t be done, or the costs outweighed the benefits, or I had a change in my thinking. But I try to make it a rare case to abandon something because I’m not willing to put in the effort needed to follow through. For me, one key to this is a calendar and to-do lists. I’m a bit of a fanatic about both. There’s been a calendar on my desk for the past half-century—and, to my wife’s great amusement, I still have them all. What about to-do lists? I have multiple versions on my desk at any given time: long term, medium term, this week and so on. If a task is on the calendar or on a list, it has to be addressed. Before it’s crossed off, I’ve got to get it done, or made a conscious decision not to do it, or have it relisted for a future date on the calendar or on a new to-do list. No task ever simply disappears. There are certain rewards for this obsessive behavior. For one, you get a lot of things done. Second, if you have repeated dealings with the same folks, they learn that you won’t give up, so maybe it’s easier to just resolve…
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What is the risk level of sitting on the sidelines when it comes to bonds?

Andrew Forsythe   |  Apr 10, 2025

I posted this as a follow-up question in another thread, but it more appropriately should be a separate thread, so here goes: One reason often cited for not trying to time the market when it comes to stocks is that a large chunk of their gains comes during a small number of days. So if you’re on the sidelines then, you really miss out. Is there a similar phenomenon with bond ETFs and funds? That is, do they tend to have big gains on just a few days? My guess is that their situation is different from stocks in this respect, but that’s just a guess. Does anyone happen to know what history tells us?
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Going to the Top

Andrew Forsythe   |  Apr 29, 2021

WE INCREASINGLY DO business with gigantic impersonal companies: banks, insurers, credit card issuers, cable and phone companies, utilities, and huge retailers like Amazon, Home Depot and Walmart. Often, we deal with them at a distance—by phone, mail, and especially online or via email. When disputes or problems arise, we’re typically forced to contact their so-called customer service departments, which are often sorely lacking in service. Even before getting to a human, we have to run the gauntlet of an annoying robot, and once we have a human on the phone, the canned response tends to be, “Sorry, but our policy is….” I’m not interested in what the usual policy is. What I want is to speak to somebody who has the power to ignore it. And what I’ve learned from many experiences over many years is the benefit of going to the top. My eyes were first opened in the prehistoric early days of cellphones. I’d been convinced by my wife and teenage daughters that the latter each needed a cellphone “for emergencies.” This was way before “unlimited” plans. You were billed—and a goodly amount—per minute. It was hard enough dealing with all the “emergencies” that our dear girls racked up, but I also got hit with some big charges that I truly thought were a mistake. After the usual frustrations trying to straighten things out with Verizon, I decided on a Hail Mary pass and made my first serious attempt to go to the top. I managed to find an email address for Verizon’s chief executive and sent a long, detailed (and courteous) message to him explaining the problem. To my surprise, shortly thereafter, I received a telephone call from an extremely nice man in the “executive escalations” department. Not only did he fix my problem, but also he…
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Home, Auto & Umbrella Insurance—“Longevity Benefit”?

Andrew Forsythe   |  Jan 23, 2025

Recently, and spurred by the horrific fires in L.A., there's been a lot of attention on home insurance, including skyrocketing premiums. Like many people, we have our home, auto, and umbrella policies with the same company, and have seen our premiums increase dramatically in the last few years. I've occasionally heard mention, without much in the way of specifics, of a "longevity benefit" in staying with the same insurance company rather than constantly shopping around and switching. I'm hoping someone with a background in insurance can shed some light on this. First off, is there any truth to it? If so, is the benefit in the form of smaller premium increases for long term policyholders, or a smaller chance of being dropped, or...? Thanks for any insights.
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