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The Sunday Best (07/26/2026)

OpenAI said today it is making ChatGPT Health, a feature that helps users with health-related queries, available to all U.S.-based users over 18 across all plans. The announcement comes a day after a Florida-based pastor sued the company for giving a near-fatal suggestion not to consult a doctor.

This third attempt at tariffs is somewhat likely to survive — not because it’s smarter or more principled, but because it comes wrapped in a process that courts are more likely to tolerate. But they will fail to deliver for the American people.

Failure is under-reported relative to its actual occurrence in every domain. In our age of social media Failure is under-shared. This somehow creates an unholy combination of survivorship bias and availability heuristic, making our collective failure estimations not just wildly wrong, but consistently so, and in the same direction.

There’s a phrase in anthropology called “making the familiar strange.” Try it: describe some aspect of human behaviour as if you’ve never encountered it before. It’s good for wonder, keeping hubris in check, developing perspective, and not sleepwalking through life, and allows you to appreciate the bizarre beauty and absurdity of human experience. 

Quality of life is higher than its ever been, but the internal desire for nostalgia is running the market. And young folks are buying in. 

Kalshi, one of the biggest prediction market platforms, announced last week that it has started letting people bet on the outcomes of clinical trials and FDA regulatory decisions. This would make it possible for investors to bet on more specific outcomes – drug approvals and trial results – than on stock markets.

People want out of the rat race. People take jobs they hate so they can retire young. People put up with work they don’t like so they can save enough to stop doing it.It feels like an answer. It isn’t. Most people don’t know how they’ll fill their days.

If you are dedicated enough to your finances to listen to personal finance podcasts or read this newsletter, you are probably going to die a millionaire. Why? Because we are planners. We stack conservative assumption on top of conservative assumption. We model for historically low market returns, historically high inflation, and worst-case scenarios. Zero things wrong with that. 

Older workers now face two major impediments: looming Social Security cuts and rapidly evolving workplace priorities. Could AI help or make things worse? 

If you have a large net worth but never spend any of your money because you worry all the time, that’s not rich. If you spend all of your money to appear wealthy through status symbols to the point that it causes you to worry all the time, that’s not rich either.

 

Upcoming Event

You Earned It. Now Keep More of It.

Half the year is gone. Blink and it was January, and now August is breathing down our necks with a Q3 that always shows up faster than the last one. That matters for your money more than most physicians want to admit, because the clock on this tax year keeps ticking whether you plan around it or not.

Nobody tells you this in residency: the number on your brokerage statement lies a little. A 9% return sounds great until the IRS and your fund fees quietly walk off with a slice of it, and what actually lands in your pocket is a very different figure. Bill Martin at Earned calls the part you keep “after-tax alpha.” For a high-income physician, the gap between what you earn and what you keep is enormous.

Think about your own bracket for a second. You’re probably paying a top marginal rate that would make your parents faint, plus state tax, plus a surtax nobody warned you about in med school. Every dollar sitting in the wrong account and every fee you forgot you were paying comes straight out of your future. Lower earners feel this. You feel it at a scale that should worry you.

Timing is most of the game. A tax move you make in July has six months to breathe and compound. That same move, scrambled together on December 30th between shifts and holiday chaos, usually costs you choices you no longer have. Midyear is when the real planning happens, while there’s still runway left on the calendar.

So we’re doing something about it. On Tuesday, July 28th, I’m sitting down with Bill Martin, CFA, and Myhanh Hoskin, CFP, both from Earned, for a live conversation built for doctors. We’ll get into why after-tax, after-fee returns are the only returns worth measuring, which tax-integrated strategies actually fit a physician’s income, and where markets sit at the midpoint of a strange year. We’ll also cover the harder judgment call: when a market shift is worth acting on, and when staying disciplined beats chasing headlines.

It’s free, and it runs about 45 minutes. Forty-five minutes that could reshape what you keep for the next decade.

Grab your seat. Tuesday, July 28th, 2:30 PM ET / 11:30 AM PT. Register, then bring your questions.

SAVE MY FREE SEAT

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