Sunday Memo Library

Why Tax Filing in 2026 Isn’t Business as Usual

  Tax season is officially underway.  Erin Collins, the National Taxpayer Advocate, explains that the IRS is beginning this tax season under significant strain and filing taxes this year could be a little more chaotic than usual.  Taxpayers should be extra careful.   Why this season is different The IRS

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Chutes & Ladders – The Market Edition

  When you were a kid, did you ever play Chutes and Ladders? Land on a ladder—up you climbed! But hit a chute and… whoosh—back down you went. The stock market can feel exactly like that. One headline hits and stocks jump.  Another surprise shows up and—yep—down they slide. So let’s play

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The Lottery Effect

  What could possibly go wrong if your neighbor won the lottery? A 2018 Philadelphia Fed study found that when someone wins the lottery, their neighbors often start spending more, borrowing more, and bankruptcies rise!   Turns out “keeping up with the Joneses” isn’t just a joke—it’s a financial hazard. Ouch. You’d hope

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What Did Venezuela Teach Us About Market Reactions?

  What crossed your mind last weekend after news broke that Venezuela’s Maduro had been captured? Did you wonder how markets might react? The S&P 500 didn’t hesitate. It rose 1.07% for the week, closing at 6,966.28 — another record high. I expected markets to shrug. I didn’t expect them to respond

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A Modest Proposal for 2026

  2025 was quite the year. I’ll let you be the sole interpreter of that phrase. Year-in-review recaps and predictions for 2026 are everywhere. Depending on your news feed—and its built-in biases—things may look either terrific or terrible, with very little room in between. Oxford University Press even named “rage

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The Mega-Rich, Rethinking Luxury

 The ultra luxury market is going through a profound shift.  It seems that rare wines, status watches, and private jets are losing their appeal.  The best vacation spots, restaurants, and experiences are now the “in” thing. Luxury goods sales have fallen globally since 2023, while ultra-luxury experiences are up nearly 90% since

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All I Want for Christmas

  We’re getting mixed signals from the economy right now. On one hand, things look…pretty good. Corporate earnings are still rising. Inflation is easing. Interest rates are drifting down. And if forecasts are right, the effects of lower taxes should start showing up in early 2026, with refunds giving the economy

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A Smarter Way to Support What You Love

  When is the best time to give money to a favorite charity?   …. well … anytime! Charites need our support.  Ask the same question from a tax standpoint, and the answer changes.  The ability to deduct charitable donations is changing in 2026. Let’s talk about how to get the

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A Modern St. Nicholas Moment

 December 6th is the feast of St. Nicholas, the patron saint of children. For centuries, kids placed their shoes outside hoping he’d fill them with small treasures—coins, oranges, bits of chocolate. One legend says that Nicholas threw a bag of gold into the home of a poverty-stricken family so the

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Is Your Commute About to Change?

  I remember when driverless cars first hit the news.  I read news articles from across the US about cars that lost connectivity – creating wicked traffic jams that needed human intervention.  My favorite was about a robotaxi that got stuck in wet concrete in San Francisco. Who on earth

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Where Will All The Pennies Go?

  The U.S. finally stopped minting pennies.  Each 1-cent coin cost more than 3-cents to make. In 2024 half of all newly minted coins were … pennies! Hardly anyone uses them. They languish in checkout trays or pile up in jars at home. It doesn’t take much to see that

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When the Economy Hits Reset

  I’m curious; how many times did you pick up a news feed this week, and didn’t see something about a looming AI bubble or market crash? I think this next downturn – whenever it happens – could be the most predicted correction in the history of the market. Recessions,

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This Week’s Market Dysfunction

  This week my inner critic had a lot to say about my questionable market mindset. Why would I ever wish for a stock to go down?  Maybe it was the full moon. More likely, it was Michael Burry’s $1.1 billion short. Burry was the guy who famously bet against subprime

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Lessons from My Dad

  Eight years ago today, on November 2, 2017, my dad passed away.  It also happens to be All Souls’ Day—a day the Catholic Church sets aside to honor those who’ve gone before us.  The night before, his favored Houston Astros won the World Series. And the moon hung huge,

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Is The AI Bubble About To Burst?

  There is a lot of discussions about Artificial Intelligence these days. AI can balance your books, spot skin cancer, plan your next trip, and tell you which houseplant you’re about to kill. AI only arrived in 2022, yet the next generation could design cities that think for themselves, prescribe

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Irrational Exuberance, Revisited

  Let’s take a quick ride on a stock market roller coaster. As you read this, check in with your emotions. In December 1996, Fed Chair Alan Greenspan warned of “irrational exuberance” in the markets. In plain English, he thought stock prices were way too high. So, what happened next? Stocks rose 105%

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Government Shutdown Trivial Pursuit

  This week the government shut down—and yet the Dow and S&P 500 pushed to new highs.  With headlines full of layoffs, rising healthcare costs, and relentless finger-pointing, that outcome felt almost surreal. Were you surprised?  I was. Let’s play quick game of Government Shutdown Trivial Pursuit to see how previous shutdowns

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The Joy of Missing Out

  I’ve just returned from a beautiful two-week trip to Italy, grateful for every moment —and aware of a few I missed. Some experiences I didn’t even know to look for until the opportunity passed. Darn! That familiar tug of FOMO (Fear of Missing Out) crept in. Could I have

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Family Trust Issues

 Hey Succession fans! Have you seen the latest Murdoch news? After losing a court fight to change his trust, Rupert still got his way—Lachlan will take sole control of the media empire when he’s gone.  What happened?  Here’s a quick sequence of events: After his 1999 divorce, Rupert locked his

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Confessions of a Tomato

  My mom always said, “the most expensive vegetable you’ll ever eat is the one you grow.” No joke. This year I turned my entire backyard into a garden. I planted nearly every vegetable Walter Anderson had to offer. Most of them gave me nothing. A did get a few

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