Flat-fee financial planner | Contributor to HumbleDollar | Check out The Investor’s Bookshelf for the latest personal finance books and ideas.

Boston, MA
Joined April 2016
Whether it’s on TV or online, there’s never any shortage of market prognosticators. Especially during a bull market, everyone seems to have an opinion on where things are headed. The reality, though, is that people can only guess about how the economy, the market or any individual investment will perform, because no one has a crystal ball. That’s why, when it comes to investing, I suggest taking an evidence-based approach, one that relies as much as possible on data and research and less on the simple stories, anecdotes and sayings that are so prevalent among market commentators. What does the data tell us? Among the most important findings, in my view, is the work of Hendrik Bessembinder. In looking at the historical returns of stocks, he’s found that just a tiny fraction of stocks over the years have accounted for the vast majority of the market’s overall returns. Just 4% of stocks have delivered returns better than Treasury bills, and the median stock delivered a negative return. This is one of the key reasons I recommend index funds rather than picking individual stocks or investing in a fund run by a stock-picker. Identifying the winners is just brutally difficult. Invest in a broad-based index fund, though, and you’re almost certain to own the next Apple or Nvidia.
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Adam M. Grossman retweeted
The market’s CAPE ratio is now higher than it was in 1929, just before the crash. And yet... @AdamMGrossman explains why every alarming stat has an equally convincing counter-story humbledollar.com/2026/10/bey…
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No distribution structure is perfect. An annual percentage with an override for specific needs provides flexibility if a child wants to buy a home or has other higher-than-normal expenses in a given year. The reality, though, is that this is the one that, in my opinion, provides the best balance.
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Investor Howard Marks advises investors to imagine a jar filled with a mix of balls of various different colors. No one can tell with the naked eye how many there are of each. By the same token, no economic indicator should be seen as conclusive, but taken together, they may provide a sense of where things stand.
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Why diversify internationally? These illustrations answer that question best.
Always funny to me to hear people say "International investing hasn't worked". What they really mean is "international investing hasn't worked for American investors during this cycle". It's worked splendidly for most investors in nearly all countries around the globe.... My favorite table on this concept is from Bridgewater (link broken) "This decade, the US has been the best performer so far, but it was one of the weaker performers in the previous decade following the dotcom bust; it was one of the best performers in the 1990s...but before that you have to look back to the 1920s to find a decade in which US equity performance was better than middling." mebfaber.com/2020/01/10/the-…
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Survivor benefits can be claimed as early as age 60, and that can be helpful in certain situations, but there’s also a penalty for claiming too early. Benefits can be reduced by nearly 30%. Social Security doesn’t automatically turn on survivor benefits when a spouse dies, so it wouldn’t automatically reduce the survivor benefit. Instead, she would have a choice.
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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. IQ doesn’t guarantee success. Nothing does. In managing our personal investments, we should always look for ways to maintain a balanced, center-lane approach.
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There is one clear route to inoculating part of your portfolio against tax increases, and that’s to look for ways to build up dollars in a Roth account: If you’re in your working years, you could contribute to a Roth IRA or a Roth 401(k). If you’re retired or happen to have a low-income year, consider a Roth conversion.
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If you’re in your 60s and considering when to claim Social Security, that decision offers a powerful lever. Because Social Security benefits increase with inflation and also increase with each year you delay claiming, it’s maybe the most effective way to build additional inflation protection into your plan. Photo by Alexander Grey on Unsplash.
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Secure the login to your bank account by setting up two-factor authentication. If your bank supports it, switch to a passkey. This is a newer technology that represents a significant advance over traditional passwords — they aren’t vulnerable to phishing attacks. I’d make the switch as soon as your bank makes this option available.
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Determining an appropriate stock allocation can often be far more nuanced than standard rules of thumb suggest. In a recent paper, Yale professor James Choi highlights why simple formulas based solely on age or net worth overlook critical variables. Asset level and spending matter, but they are only part of the equation.
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This is an underappreciated and counterintuitive point about the inflation protection of TIPS.
Very different outcome if you chose short term, medium, or long dated maturities for your TIPs...
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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. I’d view it as an almost obvious choice to proceed with a conversion up to the top of the 12% bracket.
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Interest rate movements are inherently unpredictable over any given horizon. Even when rates look like they’re heading in one direction, unexpected reversals have happened. Rather than attempting to forecast where rates will head, a more durable approach can be to hold bonds across multiple categories and maturities. That structure would allow a portfolio to benefit in some measure regardless of whether yields rise or fall.
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In building a bond portfolio, the most important thing, in my opinion, is simply to be diversified enough that you could reliably draw on these holdings in years when stocks are down. Recognizing that even short-term bonds carry some amount of risk, you might add some cash holdings, in a government money market fund.
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Jonathan Clements often observed that after decades of disciplined saving, learning to spend in retirement can feel unnatural. It’s the people who are the best savers who tend to accumulate the largest portfolios who are in the best position to spend more. But because they’re natural savers, they’re the least willing to spend. There’s no obvious solution to this conundrum, but if you find yourself in retirement with more savings than you expected, it may be worth further thought and analysis.
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One of Jonathan Clements’s best insights was to book trips months in advance. Anticipation can often be the best part of an experience, he said, and the additional runway doesn’t cost anything more.
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Benjamin Graham noted that markets are weighing machines over time. Day to day, though, the market behaves much more like a pinball machine. Reacting to every bounce and headline is exhausting. Stepping back from the noise tends to serve retirees far better in the long run.
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A buyer’s guide to life insurance:
Not everyone needs life insurance, and not every policy is worth buying... @AdamMGrossman explains how to determine if you need coverage, how much, and which type to choose. humbledollar.com/2026/10/lif…
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If you’d like to help your children, making modest gifts incrementally can serve two purposes. As a parent, it gives you the opportunity to see how your children handle these smaller sums. Making gifts incrementally can also help the recipient — modest gifts provide children the opportunity to acclimate and hopefully to adjust.
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