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Income taxes on retirees with Social Security

"And you are in a position to put your money where your mouth is and good for you no matter how you achieved that position. Nothing wrong with that. However, that is not the position for the great majority of Americans and never will be. The government dole is the use of our taxes. The government does not have money. For those in the lower two income quintiles, Social Security makes up over 80% of total family income.  For middle-income households, Social Security provides roughly 50% to 60% of overall income."
- R Quinn
Read more »

The Lottery of Birth

"Greg, thank you. I think that’s exactly it. Hard work and good decisions certainly matter, but they don’t happen in a vacuum. Where we’re born can determine the education, healthcare, security and opportunities available to us before we’ve made a single decision for ourselves. I’m increasingly aware that while I can take some credit for what I did with the opportunities I was given, I can’t take credit for having been given them in the first place"
- Andrew Clements
Read more »

Tax Complications – How SS Benefits interact with Other Income

"I think that caring for our older family members when they need our help often triggers us into planning and action so our children have as easy of time as possible when helping us. Let's hope that will not be soon."
- William Perry
Read more »

If Retirement  is Getting Close

"Good thoughts in your article Dan. My preference to make estimated payments is using IRS Direct Pay. No IRS personal account, no login, immediate online confirmation of the payment and amount is drafted from my bank account. Typically all the information you need to use IRS Direct Pay is found on your immediate prior year 1040 tax return assuming you have already filed the immediate prior year return (if not filed then you can typically use the year last filed). As for the amount of the current year estimated payments I like to use the prior year tax safe harbor amount which is 100% of your prior year tax (or 110% if your prior year adjusted gross income was $150K or more) paid in equal quarterly payments. If my needed current year tax payments are small I have just paid the entire year estimated taxes in the first quarter. If I am making quarterly safe harbor estimated tax payments I will project my current tax late in the current year and play the game of how close to zero tax will I owe when I file my return by adjusting the final quarterly payment but I usually do not pay less than the safe harbor amounts in a timely manner. As you know the 2026 third quarter ES payment is due 9/15/2026 is less than a month away. I would also note for those who insist in mailing estimated payments the postal service postmark dating has changed in 2026. The IRS "timely mailed, timely filed" mailbox rule itself has not changed under the law, but a U.S. Postal Service (USPS) rule update means machine postmarks now reflect when mail is first processed at a regional sorting facility rather than when it was deposited, risking delayed postmark dates for paper tax filings. Even before the USPS change if the IRS did not deposit your check by the due date you often have a argument you do not want with the IRS computer and if the check is lost then your certified mail return receipt only proves that you mailed something to the IRS, not necessarily a check. I try hard to not mail any checks, I just have seen to many things go wrong. I hope my thoughts help. Bill"
- William Perry
Read more »

What is the right percentage?

"Duly noted. Your 'inflation beware' advisement is duly noted.Thanks! Inflation muddles the mind. Using less than 4% of total portfolio value yields greater than 100% of former salary is another math point, but it's all inflated dollars."
- luigi767
Read more »

Preparing for SS at Age 70….. How Do I Transition to Monthly Part B Premium Deduction?

"Bill, I will be going through a similar process later this year when my wife and I begin our Social Security and Railroad Retirement. Railroad Retirement has its own version of Medicare which is similar to others except you pay the Railroad Retirement Board quarterly and the claims are processed by a private company in Augusta, Georgia. I am told my wife will have to convert to the Railroad Retirement version of Medicare. It will be interesting to see how things settle out between SS & RR."
- Harold Tynes
Read more »

TreasuryDirect changing login procedure to mandate ID.me later in 2026

"This is a welcome change for me. Last time I was able to get into my Treasury Direct account was April 2024. It's been locked since then. I had a whopping $54.70 in there last time I checked, so calling them (the only option) to fix my account access wasn't even worth the hassle."
- David Mulligan
Read more »

COBRA insurance: No need to fear the bite

"Heidi! Very timely post. Missus and me are in the same boat. We work for large companies with great health plans. We are 10 years out from qualifying for Medicare, but here we are contemplating early retirement. One of the things I have tossed around is this and it maybe something else you might keep in your tool box. We plan to retire at aged 57 and take COBRA because even with us paying full rates, it's gold standard health insurance and the full premiums would be comparable to a market place plan. At aged 57, we do get a small subsidy of about $4k per year towards health costs. Once COBRA at the current employer runs out, I might just take a role for 6-12 mos somewhere else, hop on their insurance, then do COBRA again for another 18 months. Then the missus can take a turn. This is hoping we can get hired, she's an RN, so that's in our favor. I could potentially take a job working retail at Home Depot or one of the chains and play the COBRA carousel. Just another path to consider. Of course it makes sense to compare ACA vs COBRA to see what make the most sense, but that's another option that most do not consider. Good luck and let us know how things go."
- Mike Xavier
Read more »

Medicare Advantage Part C — Not too soon to start planning for 2027

"MedigapSeminars is the site that I check to see what is the landscape each year. It helped me choose a plan with them when I retired and I have had to switch to another Medigap G plan last year based on their recommendation. Lots of information on the site to educate oneself."
- V Saraf
Read more »

Risk Management

BY NOW, YOU'VE probably heard the story of the 25-year-old wunderkind Leopold Aschenbrenner. After graduating as valedictorian from Columbia University at age 19, he worked for FTX, the crypto trading firm, then found his way to OpenAI, where he worked as a researcher for about a year, until mid-2024. In the months after he left OpenAI, Aschenbrenner wrote a 165-page paper titled “Situational Awareness,” in which he detailed his views on the future of artificial intelligence. The paper was full of dramatic pronouncements—“the exponential is in full swing now,” he wrote—and ended up being shared widely online. Capitalizing on that attention, Aschenbrenner established a hedge fund to make bets on the AI economy. He named the fund Situational Awareness, and at first, things went remarkably well. In its first two years, it grew to $45 billion in assets as he correctly identified some of the biggest beneficiaries of the AI build-out, including memory chip maker SK Hynix, fuel cell producer Bloom Energy and AI infrastructure provider CoreWeave. The fund also shorted traditional software company stocks, betting that AI would pressure their business models. And Aschenbrenner invested in some private companies, including Anthropic, the developer of Claude. For a while, these bets worked out extraordinarily well. In its first two years, the fund reportedly gained 1,000%. The rest of Wall Street began to follow him closely. In a June profile, The Wall Street Journal wrote that his fund’s regulatory filings “are studied like scripture.” But earlier this summer, both of the trends Aschenbrenner had been betting on reversed at the same time. Fears that AI infrastructure spending was becoming unsustainable led many of these stocks to fall 30% or more. And the traditional software stocks that Situational Awareness had been betting against—companies like Adobe and Salesforce.com—began to rebound, with some rising 20% or more.  Those reversals alone would have been a problem, but it turned out that Situational Awareness had also been borrowing on margin to increase the size of its bets. According to estimates, it was leveraged up to 400%. That led lenders to begin closing in. It got even worse from there, when the fund’s high profile began to work against it. As it attempted to sell positions to reduce its debt, it got trapped. Because of the size of the orders it was placing, and their concentration among AI stocks, other traders were able to guess that Situational Awareness was the seller. That spooked investors, leading others to sell, thus compounding a downward spiral. In a letter to investors, Aschenbrenner compared it to a bank run. Over the course of the next few weeks, as the fund’s assets dropped from $45 billion to just $10 billion, Aschenbrenner found himself with few options. At the end of July, he announced that the fund had sold virtually its entire portfolio of publicly-traded stocks to the investment firm Citadel. Because the positions were so large and thus difficult to sell on the open market, Situational Awareness was forced to sell them at what was reportedly a significant discount. This story might not necessarily seem relevant for individual investors. But there are, I think, several conclusions to draw from this episode. First, and perhaps most important, it’s a reminder that risk management should always come first. After so many years of market gains, it would be easy to become complacent. But it’s precisely when the market is doing so well that investors should be diligent in considering rebalancing. This story also reminds us of the importance of diversification. To be sure, Situational Awareness made mistakes, but it also got one very important thing right: It was diversified. Though it had to conduct a fire sale of its publicly-traded holdings, it still holds a multi-billion-dollar stake in Anthropic. Without that, it might have faced total liquidation. The lesson: We should never go too far out on a limb with any investment idea. British economist John Maynard Keynes was famous for his observation that, “markets can remain irrational longer than you can remain solvent.” In other words, for an investment to be successful, it needs to be correct and correct over the right timeframe. In an ironic twist, in the few weeks since Situational Awareness offloaded its holdings at a discount, many have rebounded. If it had been able to hang on a little longer, the fund might have been able to avoid the situation it was forced into. The lesson: Liquidity is important. This is one of the many reasons I recommend that individual investors avoid private funds—because an asset really only has value if you can sell it when you want to, or need to. The Situational Awareness story also teaches us something about the narratives that surround the stock market. Because of the number of variables involved, it’s all too easy for market observers to paint virtually any picture they wish. And since no one has a crystal ball, no one can say that anyone else is necessarily wrong at any given time. Concerns about “circular” deals in the AI ecosystem have ebbed and flowed over the past few years, as have worries about the impact of AI on traditional software companies. The lesson: We should be careful to never worry too much about the news of the day because it’s often just that—today’s news, only to be replaced by a potentially different narrative tomorrow. There’s an easy comparison between the events at Situational Awareness and the failure in the 1990s of the hedge fund Long-Term Capital Management (LTCM). Both got off to a fast start, both involved leverage and both were run by extraordinarily impressive individuals. At LTCM, two of the founders had Nobel Prizes. But ultimately, IQ doesn’t guarantee success. Nothing does. And that, I think, is another key lesson for investors to draw. In managing our personal investments, we should always look for ways to maintain a balanced, center-lane approach.   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.
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Hidden Conflicts

WALMART SELLS FOOD. They sell car tires. Board games too. You can stop at any Walmart in the world and buy the same plethora of consumer goods. One roof, dozens of product areas, thousands of individual items. This "cross-vertical" strategy has many perks to consumers like us. But it's not without flaws. From brand dilution to in-store clutter, down to a lack of item expertise when you ask questions of employees - there are issues with "selling everything to everyone." The financial world is no different. Many national household names in financial services are "one name, many businesses." Retail banking, wealth management, investment research, custodial services, market making, investment banking, private market access. The list goes on. There is value in these institutions for consumers like us. Just as there is value to buying my snow tires and my peanut butter in the same Walmart store. But there's a core tension we must be aware of when financial services are a one-stop shop. The same connective tissue that creates value for customers also introduces deep conflicts of interest. Ready to Launch Let's examine SpaceX's recent initial public offering. Morgan Stanley served as a joint investment bank (with Goldman Sachs) and sole stabilization agent for the IPO. Morgan Stanley managed early trading, retail distribution, and - yes - earned massive underwriting fees (to the tune of ~$100M). As a consequence of Morgan Stanley's involvement, clients of Morgan Stanley and their subsidiary, eTrade, received special access to the IPO. For example, long-time Tesla shareholders who held TSLA in a Morgan Stanley or E*TRADE account for at least 10 years qualified for a supplemental allocation of SpaceX on top of standard offerings. Nice perk! In other scenarios, such cross-pollination might lead to lower-cost loans. It can lead to access to unique private investments. You can ask a question of your big bank and get a world-class expert to provide their niche answer. There's an upside here. Stuck on the Launch pad? But the same fuel that can propel you into the atmosphere can also blow up in your face. Deeper connections and internal conflicts are the same exact mechanism, just pointed in opposite directions. Let's step back to the late 1990s, when WorldCom was a darling of Wall Street. But much of WorldCom's meteoric rise was a result of perverse incentives at a large bank. Telecom analyst Jack Grubman of Salomon Smith Barney (owned by Citigroup) issued glowing ratings on WorldCom and other telecom stocks throughout the 90s. Those ratings flowed down to Salomon brokers on Main Street, who pushed WorldCom stock on everyday investors like you and me. SSB/Citigroup also acted as WorldCom's investment banker, earning huge fees as WorldCom acquired more and more small telecom firms. The same bank also provided wealth management services to WorldCom's CEO, Bernie Ebbers, frequently showering him with discounted shares of new IPOs. Give WorldCom a great review. Sell its stock to Main Street, pushing the price higher. Lend WorldCom more money to acquire smaller companies. Earn huge fees. Give the CEO backdoor access. Give them more great reviews. Sell more stock to Main Street...etc. The word you're looking for is: perverse. The rest is history. WorldCom collapsed amid $11 billion in accounting fraud. Grubman resigned, was banned from the securities industry, and paid fines. Ebbers was dragged in front of Congress and separately sentenced to 25 years in prison. Many individual investors were left holding the bag. The episode became a symbol of Wall Street's research/banking conflicts. Model Rockets, Too But the same conflicts happen on a smaller scale, too. Enter the "Smith" family. This is a true story. The Smiths have about $2.5M invested with a wealth management advisor at Bank A. I won't call out Bank A, but you know them. Their CEO is a borderline household name. You own them in any/all USA index fund. The Smiths' taxable account has about $200,000 in fixed-income assets (yielding around 4% interest). Also, the Smiths bought a small vacation home last year, splitting costs with family members. Their share was about $200,000. "How," the Smiths asked their advisor, "should we best pay for our share of the home? Where should we pull the $200,000 from?" Their Bank A advisor suggested they use a pledged asset line of credit. They are using their investments as collateral to borrow the $200,000 at an 8% interest rate. They still own the $200,000 in fixed income that earns 4%, while also borrowing $200,000 at 8%. They have locked in a negative arbitrage of $8000 per year. Bank A is still collecting their AUM fee on the $200,000 of invested assets - another $2000 per year. Did the Smiths receive advice in their best interest? Did their advisor/banker benefit from the path he steered them down? Did Bank A's diverse services work in the Smiths' favor? I doubt the Smiths' banker / advisor is a bad actor. But his incentives are conflicted. As the late, great Charlie Munger would remind us: Show me the incentives, I'll show you the outcome. It's Double-Edged The same size and clout that provides early access to the SpaceX IPO also leads to WorldCom's fraud and the bad advice given to the Smiths. The mega-financial firms are a double-edged sword. You don't get the good without risking the bad. Caveat emptor.   Jesse Cramer writes “The Best Interest” blog and creates the podcast, “Personal Finance for Long Term Investors.” After a decade as an aerospace engineer, Jesse switched careers and now helps families plan their retirements at an independent fiduciary firm. Jesse, his wife, and two daughters live outside Rochester, NY. His previous article was Happy Conclusion.
Read more »

Income taxes on retirees with Social Security

"And you are in a position to put your money where your mouth is and good for you no matter how you achieved that position. Nothing wrong with that. However, that is not the position for the great majority of Americans and never will be. The government dole is the use of our taxes. The government does not have money. For those in the lower two income quintiles, Social Security makes up over 80% of total family income.  For middle-income households, Social Security provides roughly 50% to 60% of overall income."
- R Quinn
Read more »

The Lottery of Birth

"Greg, thank you. I think that’s exactly it. Hard work and good decisions certainly matter, but they don’t happen in a vacuum. Where we’re born can determine the education, healthcare, security and opportunities available to us before we’ve made a single decision for ourselves. I’m increasingly aware that while I can take some credit for what I did with the opportunities I was given, I can’t take credit for having been given them in the first place"
- Andrew Clements
Read more »

Tax Complications – How SS Benefits interact with Other Income

"I think that caring for our older family members when they need our help often triggers us into planning and action so our children have as easy of time as possible when helping us. Let's hope that will not be soon."
- William Perry
Read more »

If Retirement  is Getting Close

"Good thoughts in your article Dan. My preference to make estimated payments is using IRS Direct Pay. No IRS personal account, no login, immediate online confirmation of the payment and amount is drafted from my bank account. Typically all the information you need to use IRS Direct Pay is found on your immediate prior year 1040 tax return assuming you have already filed the immediate prior year return (if not filed then you can typically use the year last filed). As for the amount of the current year estimated payments I like to use the prior year tax safe harbor amount which is 100% of your prior year tax (or 110% if your prior year adjusted gross income was $150K or more) paid in equal quarterly payments. If my needed current year tax payments are small I have just paid the entire year estimated taxes in the first quarter. If I am making quarterly safe harbor estimated tax payments I will project my current tax late in the current year and play the game of how close to zero tax will I owe when I file my return by adjusting the final quarterly payment but I usually do not pay less than the safe harbor amounts in a timely manner. As you know the 2026 third quarter ES payment is due 9/15/2026 is less than a month away. I would also note for those who insist in mailing estimated payments the postal service postmark dating has changed in 2026. The IRS "timely mailed, timely filed" mailbox rule itself has not changed under the law, but a U.S. Postal Service (USPS) rule update means machine postmarks now reflect when mail is first processed at a regional sorting facility rather than when it was deposited, risking delayed postmark dates for paper tax filings. Even before the USPS change if the IRS did not deposit your check by the due date you often have a argument you do not want with the IRS computer and if the check is lost then your certified mail return receipt only proves that you mailed something to the IRS, not necessarily a check. I try hard to not mail any checks, I just have seen to many things go wrong. I hope my thoughts help. Bill"
- William Perry
Read more »

What is the right percentage?

"Duly noted. Your 'inflation beware' advisement is duly noted.Thanks! Inflation muddles the mind. Using less than 4% of total portfolio value yields greater than 100% of former salary is another math point, but it's all inflated dollars."
- luigi767
Read more »

Preparing for SS at Age 70….. How Do I Transition to Monthly Part B Premium Deduction?

"Bill, I will be going through a similar process later this year when my wife and I begin our Social Security and Railroad Retirement. Railroad Retirement has its own version of Medicare which is similar to others except you pay the Railroad Retirement Board quarterly and the claims are processed by a private company in Augusta, Georgia. I am told my wife will have to convert to the Railroad Retirement version of Medicare. It will be interesting to see how things settle out between SS & RR."
- Harold Tynes
Read more »

TreasuryDirect changing login procedure to mandate ID.me later in 2026

"This is a welcome change for me. Last time I was able to get into my Treasury Direct account was April 2024. It's been locked since then. I had a whopping $54.70 in there last time I checked, so calling them (the only option) to fix my account access wasn't even worth the hassle."
- David Mulligan
Read more »

COBRA insurance: No need to fear the bite

"Heidi! Very timely post. Missus and me are in the same boat. We work for large companies with great health plans. We are 10 years out from qualifying for Medicare, but here we are contemplating early retirement. One of the things I have tossed around is this and it maybe something else you might keep in your tool box. We plan to retire at aged 57 and take COBRA because even with us paying full rates, it's gold standard health insurance and the full premiums would be comparable to a market place plan. At aged 57, we do get a small subsidy of about $4k per year towards health costs. Once COBRA at the current employer runs out, I might just take a role for 6-12 mos somewhere else, hop on their insurance, then do COBRA again for another 18 months. Then the missus can take a turn. This is hoping we can get hired, she's an RN, so that's in our favor. I could potentially take a job working retail at Home Depot or one of the chains and play the COBRA carousel. Just another path to consider. Of course it makes sense to compare ACA vs COBRA to see what make the most sense, but that's another option that most do not consider. Good luck and let us know how things go."
- Mike Xavier
Read more »

Free Newsletter

Get Educated

Manifesto

NO. 14: WE SHOULD avoid impulse spending and investment decisions. Our instincts often lead us astray, but we can usually figure out the prudent choice—if we pause and ponder.

act

MAKE SURE SPENDING money is out of stocks. Calculate how much cash you’ll need from your portfolio over the next five years. That money should be out of stocks and invested in nothing more volatile than high-quality short-term bonds. You don’t want to be forced to sell shares at depressed prices—and that could happen if your time horizon is less than five years.

Truths

NO. 2: A DOLLAR not spent is worth more than a dollar earned. If you earn an additional $1, you’ll get dinged for payroll, federal and perhaps state income taxes, so you might wind up with 70 cents in your pocket. By contrast, if you cut $1 from your living costs, you’ll be $1 richer. The lesson: Focus less on earning more—and more on holding down costs.

think

OCCAM’S RAZOR. First proposed by Franciscan friar William of Ockham in the 14th century, Occam’s Razor holds that—if there are competing answers to a problem and all work equally well—the simplest solution is probably the best. Some have applied Occam’s Razor to finance and argued that folks should favor simpler financial products and less complicated portfolios.

Portfolio builder

Manifesto

NO. 14: WE SHOULD avoid impulse spending and investment decisions. Our instincts often lead us astray, but we can usually figure out the prudent choice—if we pause and ponder.

Spotlight: Houses

My House Divided

I’M A HOUSEHOLD of one—in theory. True, one adult child lives rent-free in our family home in California. Her first full-time job’s wages are too low for her to afford an apartment in our expensive urban area.
I’m also paying college expenses for another daughter living on campus 80 miles away. She’s working part-time and will graduate this coming spring semester. With a STEM (science, technology, engineering and math) degree, I hope she’ll find gainful full-time employment soon after.

Read more »

Should young people buy or rent?

My son is 30 something working in Silicon Valley paying outlandish rents and looking at expensive housing. Is it still a good option to purchase in this market? I was burned on real estate as a young adult and don’t want to advise him If it is not a good idea.

Read more »

Not My Thing

IN RICH DAD POOR DAD, author Robert Kiyosaki touts the virtues of owning real estate as a way to reach financial independence. He explains the difference between how his father handled money and invested in his education, versus his friend’s dad, who gained his wealth by investing in businesses.
There’s controversy over whether this is a true tale or just a literary device to explain how to invest in real estate.

Read more »

Who Will Care for Us?

At age 74, I like to think our retirement is pretty much set in stone. Most of the big health and financial decisions—Medicare, Social Security, Roth conversions—have already been made. But there’s one concern I’ve been thinking about a lot lately: how will Rachel and I get the help we need if we can no longer take care of ourselves?
Our family is spread out across the country, and we have no plans to move closer to them.

Read more »

Selling Your House and Reaping Tax Free Capital Gains May be in Jeopardy

The National Association of Realtors forecasts that by 2035, close to 70% of homeowners might have gains exceeding $250,000 and 38% of them will have more than $500,000.
Per AI
I just read an article in which it was reported that in comments to the press on Tuesday the President suggested he is considering eliminating capital gains taxes on the sale of homes.
The article reviews the rules to claim this benefit which is definitely in the near(er) future for Humble Dollar readers
If you have lived in it as your primary residence for at least 24 months (consecutively or not) in the previous five years before you sell it,

Read more »

Assisted Living: How Will You Choose?

There have been many discussions about assisted living and CCRC in HD. As I learn about how they staff and manage these facilities, there are many unanswered questions.
Currently, about 65% of elderly are cared for by their families at home. For 13% of those who aren’t living with family, the gap is partially filled by assisted living establishments. The median cost of care is $5,900/month, but ancillary services are extra. That can bring that cost over $15,000/month.

Read more »

Spotlight: Horiuchi

Rethinking My Mix

ASSET ALLOCATION is usually a set-it-and-forget-it exercise. At least, that’s how I’ve handled it until now. I decided on my appetite for risk, then set my stock-bond ratio accordingly. I tallied everything once or twice a year, and then rebalanced. I’d apply a portion of my winning positions to my less successful asset classes. Rebalancing this way forced me to buy low and sell high. Combined with dollar-cost averaging, it’s an investing approach that’s served me well for more than 20 years. Each year, I’d also consider how much I wanted to keep in cash investments. Now that I’m semi-retired, I’d been looking to reduce my stock exposure and add to cash. At least that was the plan, until now. The current “transitory” spike in inflation has forced me to me to rethink my entire approach. Here’s why: If the current inflationary bout should persist, my cash assets could lose nearly a quarter of their value over the next five years. This has me looking to trim my cash investments substantially, not add to them. Next, I’m concerned about what life will be like 20 years from now. The remaining baby boomers will swell the ranks of the over-80 crowd. They’ll be selling investments to pay for health care and many other senior-oriented necessities. The cost of these services has risen faster than consumer inflation for years. I don’t imagine that trend reversing now. The general investment selloff required to meet these expenses may depress returns for all of us. This creates a dilemma as I weigh my asset allocation. Higher inflation means low—or negative—real returns on cash and bonds. I may be required to own more stocks just to have a fighting chance against that loss of purchasing power. Of course, that would increase my investment risk during retirement—not…
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Thanks, Younger Self

SAVING FOR THE FUTURE entails a pinch in the present. Every so often, it makes sense to reconsider how much we save—and whether it’s time to take a break from saving. As a recent early retiree, I was pondering this, even before the latest stock market disruption. Unfortunately, none of us has a reliable crystal ball that tells us when to buy low or sell high. We also don’t have complete knowledge of our future self. Maybe future me will receive a windfall or die young, so I can get by with saving less. Or maybe I’ll develop a chronic condition and need more savings. We don’t know how lucky we will be on the way from youth to retirement—those years when we have the greatest opportunity to save. Savings aren’t “safe.” Risk is inevitable. Cash in an FDIC-protected bank account is guaranteed to keep its face value, but it’s also pretty much guaranteed to decline in real value each year due to inflation. Meanwhile, buying bad stock or bond market investments does little more than transfer your wealth to someone else. Recessions, market corrections and normal fluctuations can be difficult to stomach. And then we have occasional extraordinary events, like the economic and political disruptions caused by the coronavirus. Faced with all this uncertainty, I don’t try to divine the future. Instead, in setting aside a portion of my money for future me, I’m simply seeking to maintain purchasing power for a comfortable old age. With moderate luck and ongoing financial education, I might be able to eke out a percentage point or three above inflation, opening the road to a more prosperous retirement. I recently reviewed the Series EE and I savings bonds that I’ve purchased over the years. These ultra-conservative investments are rarely recommended. They’ve never been more…
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At the End

IT STARTED INNOCENTLY. A doctor’s visit. A blood test. Results. Admit to hospital for “a couple days of observation” that instead cascaded, over six days, into my husband’s death at age 71. His death certificate states “etiology unknown.” While doctors suspected prescribed medication, we will never know just what caused his liver to fail. Throughout, the situation had been confusing. Clarity regarding treatment options—and the likely outcome from procedures—was in short supply. He and I and doctors made medical decisions in the face of this uncertainty and without regard to costs. Crucially useful was my husband’s advance medical directive, completed a decade earlier when we updated our wills. I kept this at hand to reference as we made decisions. Language in directives is ambiguous and can be a poor fit to clinical decisions. Yet the directive was essential to working through differences of opinion among family members and to obtaining, in the final hours, a frank assessment from attending doctors and clinicians. Amid many roundtrips at all hours between home, hospital, airport and hotels, I lost my identification twice. Once, I was paying for parking at the hospital lot kiosk. I cancelled my credit and debit cards before getting my wallet back two days later, less the cash. “Nobody turns wallets in, ever,” said the hospital security guard as he handed it back. After that, I only carried keys, phone, my driver’s license and my backup credit card, and lost the license and credit card a couple of days later. It would be two months before I could replace my driver’s license with a new picture ID. In the interim, I carried my passport card and a printout listing my appointment with the DMV to replace my driver’s license. At the end, I was bedside with our three teenagers. Afterward, before…
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Twin Peeks

CAN IT REALLY BE TWO years since I wrote about sending my twins off to college? One is a chemistry major, midway through her junior year. Meanwhile, for her twin sister, the artist, there have been big changes in her college trajectory. My initial criteria for college selections included published statistics on cost, likelihood of admission, timely graduation and low rates of loan default. I took this last stat as a reasonable proxy for post-college success. My daughter the chemistry major is on track to graduate after four years. This past semester was her first as an organic chemistry lab assistant. She’s applying for internships in her field. If that doesn’t work out, she’ll take any other job. Her sister, after three semesters in art school, came home without a degree. She’d become uncomfortable with the expense, not to mention the raw talent, Herculean effort and plain old good luck that would be essential to earning a living in the arts. She loved the big city and befriended amazing people. I’d paid tuition in full each semester, so she walked away debt-free. I’ve told her from the first to avoid the sunk cost fallacy—seeing something to completion only because she’d already invested considerable effort. Rather, I encouraged her to treat each semester as a new decision. She could continue at art school, look for work, switch to community college, become a volunteer or try something else. She returned home with “some college,” a category frequently found in job descriptions. A family friend suggested she volunteer at a school library. In our city, many elementary school libraries are open part of the day and staffed by volunteers. To take on this role at a public school required fingerprinting for a criminal background check and screening for tuberculosis. The principal explained the…
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My Lazy Investing

MY FIRST JOB AFTER college was at a global engineering firm. A roommate also worked there. It was a tedious office job, but my bosses thought I had potential and encouraged me to study engineering, which I didn’t. Instead, I quit and went to graduate school to study linguistics, a field where I observed the most professors having the most fun. My last paycheck at the engineering firm included an extra sum. It was a refund for a retirement account that had failed to vest because I hadn’t stayed long enough. This shocked me, since I hadn’t the foggiest sense that someday I would be old and need retirement funds. I didn’t know there was such a thing as a defined benefit plan. I spent the windfall, probably on rent and books, with nary a second thought. At my second job, I paid attention when bosses talked about the company’s 401(k) plan and insurance coverage. I worked there five years and, when I left, that money stayed in place. A lazy investor, I let it ride until I later rolled it over into my retirement account at my next employer. Throughout the remainder of my working life, I never cashed out that money. In fact, thereafter, I let all saved dollars ride, remembering that first little retirement check that got away. Some friends worked on picking better investments in an effort to boost their performance, but that sounded like extra effort with limited return for time invested. I just saved a little more, assuming my results were a little weaker. I’d ask others only general questions and tried to stay away from the worst investment mistakes, even when banner headlines managed to pierce my general disinterest in personal finance. During the dot-com boom, I met a couple of guys at…
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Goodbye Assets

MY TWINS ARE SENIORS in high school. That means, pandemic or no pandemic, we spent the fall applying to colleges. Here in California, the pandemic closed public schools in March and most did not reopen for in-person teaching with the start of the current academic year. That forced parents to stand in for college counselors. The preparations high school juniors usually engage in, such as visiting colleges and taking standardized tests, didn’t occur this past spring or summer. Student athletes spent the summer practicing in parks and driveways. Grades suffered under remote learning. For all these reasons, applying to college has been more difficult. And then there’s the price tag. Post-secondary education can be relatively inexpensive—or it can break the Bank of Mom and Dad. The federal government supplies some grants and many loans to limit the immediate financial damage, and colleges also dole out money from their own funds. Still, the student loan crisis is front page news. That’s one reason so many parents try to ensure their young adults don’t leave college with crushing debt. The federal government’s role begins with the Free Application for Federal Student Aid, or FAFSA, with “free” meaning it doesn’t cost you to ask. FAFSA calculates a family’s expected family contribution (EFC) based on the parents’ and student’s income and assets. On top of that, colleges use their own guidelines to distribute the grant money they control. For families earning below about $50,000, the EFC will likely be $0. After that, the amount rises sharply—and sometimes unfairly. For instance, middle-class single parents, along with older parents with a healthy amount of savings, may be shocked by how much they’re expected to pay toward college costs. There’s no way to sugarcoat it: Parents with decent incomes, or who’ve successfully set aside a chunk of…
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