Month: October 2026

A few weekends ago, Lizy and I packed up the car for what turned into roughly a ten-hour drive to Maryland for a cabin weekend with some of our friends from Washington, D.C. Emmy was asleep in the back seat, which created one of those rare parenting situations where you are grateful for the silence for about twenty minutes and then realize you still have several hundred miles of highway ahead of you.

Eventually, we reached the stage of a long road trip where just about anything qualifies as entertainment.  So naturally, we listened to a Planet Money podcast about the looming financing problem with Social Security.

There are moments in markets when two things that normally compete for attention become interesting at the same time. We happen to be in one of those moments now. The stock market has had a strong year, with the S&P 500 reaching another record closing high on October 6, 2026, while long-term U.S. Treasury yields remained above 5% as of October 7.[4][5] Neither of those facts tells us what happens next, and I would be suspicious of anyone who claims otherwise with great confidence. Markets have been humiliating confident people for centuries. But the combination does create an unusually interesting question for people who are already retired or close to it: if a portion of your portfolio has appreciated substantially, and today’s interest-rate environment can support higher lifetime-income payouts from certain fixed annuities than lower-rate environments, is this a reasonable time to review whether part of that money should be assigned a different job?