FOR MUCH OF THE seventeenth and eighteenth centuries, European monarchs used a financial instrument known as a tontine to help finance their governments.  Tontines were first developed in the 1650s by an Italian government worker named Lorenzo Tonti and were similar to annuities: In exchange for a single, lump-sum purchase, tontines offered guaranteed payments for life. But tontines also offered some unique features. Unlike an annuity, where payments end with the death of the owner, tontine holders had the option of tying the payments to another person. A parent, for example, could name their son or daughter on a tontine, thus extending the payments over a much longer period. In the 1750s, however, a Swiss banker named Jacob Beaumont had a realization: While the owners of tontines typically named their children, a quirk in the rules permitted a tontine owner to name any individual. To Beaumont, this presented an opportunity: Why not name the youngest possible person, thus extending the stream of payments even further?  In his home town of Geneva, Beaumont identified ideal candidates for this role: young children who came from well-heeled backgrounds and were thus likely to have access to good healthcare. He then began loading up on tontines tied to the very long life expectancies of these children. The strategy worked exactly as expected and delivered Beaumont enormous profits. Other investors then piled in, mimicking Beaumont’s strategy, which, for a time, offered a virtually no-lose opportunity for profit. This went on until the French government, in frustration, discontinued its tontine program. When it comes to financial decisions, it’s the rare situation that’s as obvious as the one that Beaumont identified. Instead, most financial decisions entail some amount of uncertainty and are subject to judgment. Some choices, though, are closer than others to being obvious decisions. Here are six that I see frequently. 

1. Certain Social Security claiming decisions are without question. For example, if you’re married and plan to claim the spousal benefit, it’s important to know that this benefit hits a maximum at full retirement age (FRA), which is now age 67 for most people. Unlike workers’ own benefits, which can continue to increase all the way to age 70, spousal benefits are subject to a different rule, so there’s no benefit for anyone to wait beyond FRA.
2. You may be familiar with umbrella insurance. This provides additional liability coverage on top of auto and homeowner’s (or renter’s) insurance. Because it covers low-likelihood situations, such as someone slipping and falling on your front walk, umbrella coverage is extremely cost effective—sometimes as low as a few hundred dollars per year. I see it as an obvious benefit because the situations it covers, however unlikely, are also the ones that could be the most expensive. And because it would be the insurance company that would face exposure, insurers provide legal defense, at their expense, if there is ever a claim. How much coverage should you have? I generally recommend between $1 million and $5 million, but the key point is that almost any coverage is better than none. 
3. In choosing an asset allocation for your portfolio, I think it’s best to avoid rules of thumb, because everyone is different. At the same time, a recommendation that I see as universal is to avoid extremes. I wouldn’t get too close to 100% bonds because of the corrosive impact of inflation. And I don’t like getting too close to 100% stocks because of the volatility and risk of loss. That’s always been my view, but recent research can help investors narrow the range further. William Bengen, creator of the “4% rule,” published a book last year in which, for the first time, he looked at the question of portfolio longevity through the lens of asset allocation. What he found was that portfolios with stock allocations between 45% and 75% offered the highest sustainable withdrawal rates over multiple decades.

4. If you’ve recently retired, you may be considering a Roth conversion, whereby you’d move dollars from your pre-tax IRA to a Roth IRA. This is a popular strategy, but the catch is that a tax must be paid when a conversion is completed, and your tax bracket can increase as you convert more. Convert too much, and you can negate the benefit of a conversion. For that reason, it isn’t always obvious whether a conversion is advisable. There is one situation, though, where a conversion offers an almost obvious benefit: If your income, even with a conversion, would be in one of the two lowest tax brackets (10% or 12%), then it’s unlikely you’d ever find yourself in a lower bracket than that in the future. In that case, especially because of special deductions provided by the new tax rules, I’d view it as an almost obvious choice to proceed with a conversion up to the top of the 12% bracket.

5. Looking to make charitable gifts? Because the standard deduction is now so high, fewer taxpayers are able to itemize deductions, and that can limit the tax benefit of donations. But there’s still a way to gain a tax benefit: If you have appreciated stocks in a taxable account, you can donate them to a donor-advised fund. That would allow you to sidestep the capital gains tax that would otherwise be due if you sold those stocks. Many donor-advised funds have no minimums, making this an easy choice, in my view.
6. If you believe your estate will top the estate tax threshold (about $15 million per person at the federal level, but much lower in certain states), then I would be sure to use the annual exclusion (currently $19,000 per donor and per recipient) to make incremental gifts to your heirs. That's because this annual exclusion is in addition to the lifetime exclusion and doesn’t carry over from year to year.

Note that these gifts don't have to be made in cash if the recipients aren't yet in a position to receive them. As alternatives, you could make contributions to a 529 account or to a trust for their benefit, and these contributions would count toward the annual exclusion. 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.  

WHEN MY YOUNGER brother Jonathan died, I thought I knew who he was. After all, we had shared a childhood in England, years together at boarding school, family adventures in Bangladesh, and more than six decades as brothers. I knew the journalist the world admired, the devoted husband and father, and the man whose words quietly helped millions of readers live richer lives, not simply financially, but personally as well. I was wrong. Over the past several months, I've been searching for Jonathan's beginnings. I thought I was looking for old articles, forgotten photographs and the names of people who had influenced his career. Instead, something unexpected happened. Former classmates, editors, colleagues, friends and readers began sharing their own Jonathan. One remembered a trusted reporter who never misrepresented his intentions. Another remembered a laugh that never disappeared, even in the face of death. His children remembered a father whose greatest gift wasn't advice, but confidence. Piece by piece, they gave me back my brother. Not a different Jonathan. A fuller one. There was a Jonathan his readers and sources knew that I had never fully appreciated. He wasn't afraid to ask difficult questions, but he asked them honestly, respectfully and never with an agenda. Dina Isola, who dealt with Jonathan professionally for many years, remembered that his reputation for fairness and honesty meant people trusted him enough to agree to interviews even when the subject matter was difficult. Financial adviser Dan Danford remembered another quality. Jonathan held strong opinions, but he was never condescending or antagonistic toward those who saw things differently. Dan described him as open to genuine discussion, willing to listen as well as challenge. Bill Blase, a longtime media relations executive who worked with Jonathan, saw yet another side of that same integrity: how seriously Jonathan took his responsibility to readers. Bill remembered him as meticulous about every word, statistic and investment he described. Jonathan once explained why: "We're talking about real money here. So, the challenge is on getting it right, the first time. Not the second. This is not Monopoly." Jason Zweig, who became Jonathan's friend in 1987, distilled all of this into a sentence I'll never forget: "What you read is who he was." People trusted Jonathan because he was honest. They felt they knew him because he shared something of himself in every article he wrote. Jonathan wrote about personal finance, but his work was never just about money. It was about life, the choices we make and the experiences that ultimately matter most. Bill Bernstein captured that beautifully when he said Jonathan wrote about "things that were far beyond the beat of a normal finance writer." Perhaps Bill's most revealing observation was also his shortest: "This man knows my life." I suspect millions of readers felt exactly the same, not because Jonathan knew their individual circumstances, but because he understood something deeper about the hopes, fears and uncertainties we all share. As I continued listening, I realized there was still more of Jonathan to discover. Through his children, Hannah and Henry, I met perhaps the most important Jonathan of all. They didn't remember a celebrated journalist or one of the world's most respected financial writers. They remembered their dad. Hannah recalled telling Jonathan how strong he had been throughout his illness. His response surprised her: "You would be the same if you were in my situation." That simple reply revealed something profound. Jonathan seemed to see strength and confidence in other people long before they saw it in themselves. She also remembered her first day of kindergarten. Jonathan bent down and whispered, "We'll pay for the best college you can get into, so go work hard." It still makes me smile. It was vintage Jonathan: Encouraging, optimistic and quietly expressing his confidence in her future. Henry's memories were different. He remembered cups of tea, conversations and simply spending time together. They were ordinary moments that, taken together, painted the picture of an extraordinary father. Listening to both of them, I began to understand something I had never fully appreciated. Jonathan's greatest legacy isn't found only in the books he wrote or the articles he published. It lives on in the confidence he gave his children, the kindness they extend to others and the values they now carry forward. Elaine knew another side of Jonathan, the husband who could make her laugh from the moment she came downstairs in the morning until the last conversation before they fell asleep. She remembered that, despite the wonderful vacations and fine restaurants they enjoyed, Jonathan often said he was happiest during quiet Sundays at home, sharing coffee and croissants, watching the squirrels and birds in the garden, and simply knowing the other was there. Even his financial instincts followed them home and on vacation. Whenever Elaine contemplated a purchase, Jonathan would ask, “Do you really need that?” or, when traveling, “Do you have room in your suitcase for that?” Sometimes she listened and sometimes she didn’t. But even now, she says, his voice still guides her when she’s tempted to buy something. Most importantly, Elaine remembered Jonathan as a man of his word. When he said something, he meant it. He showed his love not through grand gestures, but through everyday acts of kindness and devotion. During his final year, as he quietly made sure Elaine and his children would be financially secure, she came to see those preparations for a future he knew he wouldn’t share as one of his greatest demonstrations of how much he loved them. Then there was Jonathan's humor. Cancer didn't take that from him. If anything, it sharpened it. Even as his world grew smaller, his laughter never did. Jason Zweig remembered that Jonathan "laughed at death the same way he had laughed at everything else, with that unquenchable cackle of his." Bill Bernstein saw the same remarkable spirit, recalling, "I never saw anyone who could laugh in the face of death the way he did." Jonathan himself joked that he "hadn't realized what a marvelous book marketing strategy a terminal diagnosis could be." Those stories weren't simply amusing. They revealed a man who refused to let illness decide who he would be. Like many readers, I assumed Jonathan started HumbleDollar as a retirement hobby, a way to stay connected to writing after leaving The Wall Street Journal. I couldn't have been more mistaken. HumbleDollar became another expression of the person he had always been. Jonathan devoted countless hours to writing, answering emails, interviewing readers, encouraging new writers and quietly building a community. Yet none of it ever seemed like an obligation. He genuinely enjoyed the conversations and the opportunity to help others. What struck me most wasn't the number of hours he worked, but how willingly he gave away his time. Whether responding to an email from a first-time reader or interviewing someone for an article, he made people feel they mattered. One reader told me Jonathan always replied with a handwritten thank you note after receiving a donation. Others remembered thoughtful emails, encouraging conversations and carefully edited articles that made them better writers. Individually, those acts seem small. Together, they tell us exactly who Jonathan was. The more I listened, the more I realized that Jonathan never forgot the people who had opened doors for him early in his career. Mrs. Dolezal helped him find his first reporting job. Leslie Leven patiently taught him the craft of journalism. Years later, Jonathan quietly became that person for countless others. I don't think he mentored people simply because he was generous. I think he did it because he remembered. In the weeks after Jonathan's death, I thought I was collecting stories. I wasn't. I was collecting pieces of a man. His readers showed me his integrity. His friends showed me his humanity. His children showed me his heart. His colleagues showed me his generosity. No one person held the whole picture. Not even me. But together they did. When Jonathan died, I thought I had lost the brother I knew. Instead, over the weeks that followed, I found myself discovering him all over again. The Jonathan I found wasn't different from the brother I had always loved. Through the memories of everyone whose life he had touched, I simply came to know him more completely.   After spending more than two decades building a successful landscaping business with his twin brother Nicholas, Andrew Clements retired in 2015 with a new appreciation for what matters most. Born in England, his essays draw on a life that has included growing up in England and Bangladesh, entrepreneurship, caregiving, family loss and travel. A regular HumbleDollar contributor, he enjoys tellingstories that remind readers life’s richest lessons often have little to do with money. Andrew is the older brother of HumbleDollar founder Jonathan Clements, whose life and legacy have inspired some of his most personal writing. He lives in Florida with his husband, Joey.

IT'S BEEN AN UNUSUAL week in the bond market, and not necessarily in a good way. This has many investors questioning the value of bonds, which is understandable. Bonds are supposed to be the “safe” side of a portfolio, but they’ve struggled in recent years. Arguably, the drama we’re seeing in the bond market today began more than 50 years ago. To put today’s situation in perspective, I’ll briefly summarize that long history. Then we can look at what steps you might take to better protect your portfolio from here. Back in the 1970s, as you’re probably aware, inflation rose above 10%. Policymakers struggled for years to bring it under control, but in the early 1980s a Fed chair named Paul Volcker finally succeeded. He accomplished that by raising the Fed’s benchmark rate to nearly 20%. With this step, Volcker succeeded in calming inflation, and that allowed the Fed to begin lowering rates, a gradual process that continued for most of the following 40 years. Because bond prices move inversely to interest rates, that entire stretch was extremely beneficial for bonds. As rates fell, bonds rose. Between 1980 and 2020, intermediate-term U.S. government bonds returned 7% per year, on average. That multi-decade run helped seal the reputation of bonds as an easy and reliable way to offset the risk of stocks. But then the other shoe dropped. Due to pandemic-related government spending and tangled supply chains, inflation began rising around 2021. Well aware of what the economy experienced in the 1970s, the Fed responded by raising rates aggressively. For a time, that appeared to bring inflation under control, and the government had even started to lower rates again last year. But then the war with Iran started. That caused energy prices to jump higher, and that, worryingly, has caused inflation to start creeping back up again. In response, the Fed this week was forced to take action, raising rates in an effort to contain inflation before it gains steam. Interest rates on long-term bonds are now at 20-year highs. And because bond prices move inversely to interest rates, bonds are having another difficult year. Total-bond market funds like Vanguard’s BND are now negative year-to-date. Where the bond market goes from here is anyone’s guess, but this history is important, in my view, because bonds are unlikely to see another long, positive stretch like the one investors enjoyed a generation ago. Instead, I believe investors need to be more cautious.  What steps might you take? Since we don’t know whether rates will go higher or lower over any given timeframe, the approach I recommend is to own bonds in each of several categories. That way, you’ll benefit, in part, if rates go up, and you’ll benefit, in part, if rates go down. Here’s how I’d structure a bond portfolio today: For me, the most important thing is to own mostly short-term bonds. Specifically, you might allocate 60% of your bond portfolio to short-term Treasurys, using a fund like Vanguard’s VGSH. This fund should be among the most stable investments available because it’s backed by the U.S. government, which, for better or worse, has the ability to print money to meet its obligations. And its short duration means that, all things being equal, it will be less susceptible to rising interest rates if rates do continue to rise. As a point of reference, in 2022, when rates rose quickly, this fund lost less than 4% of its value. That’s in contrast to total-bond market funds, which lost an extremely unpleasant 13% that year. If you’re in a high tax bracket (over 30%), you could split your short-term holdings between Treasurys, which are taxable at the federal level, and municipal bonds, which are exempt from federal tax. You might consider a short-term municipal fund like Vanguard’s VTES or VWSUX. Next, I’d allocate 20% to intermediate-term bonds. While these will be more susceptible to losses when rates rise, they’ll also gain more when rates fall. Last year, for example, when rates fell, intermediate-term government bond funds like Vanguard’s VGIT gained more than 7%. So I see them as worth the additional risk. That said, if this risk concerns you, there’s a relatively easy alternative: For this part of your portfolio, you could purchase a ladder of individual bonds covering maturities between five and 10 years. While it requires additional effort to purchase individual bonds, what you’ll receive in return is greater certainty. At the moment that you purchase an individual bond, you’ll know the yield to maturity. Barring a default—which is unlikely with a government bond—that’s precisely the return you will earn. For the final 20% of a bond portfolio, I recommend inflation-protected Treasury bonds, known as TIPS. Here again, you could purchase individual bonds or a bond fund, and there’s a lot of debate on this topic. But according to research I find convincing, the best way to protect against inflation is with short-term TIPS. So to keep things simple, I would opt for a fund rather than a ladder of individual bonds, which would require frequent trading. One good fund in this category is Vanguard’s VTIP. At the end of the day, the most important thing, in my view, is to build a bond portfolio that’s diversified enough that you could reliably draw on it in years when stocks are down. And recognizing that even short-term bonds carry some amount of risk, it’s worth also holding a “floor” of cash, using a government money market fund, as an additional element in your portfolio. These won’t gain in value when interest rates fall, but they’re designed not to lose any value if rates rise. Put it all together, and I see this as an effective sleep-at-night structure no matter where things go next. 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.