For a long time, one of the easier assumptions to make in financial planning was that a reasonably desirable house, priced reasonably well, would sell reasonably quickly.
I am using the word “reasonably” three times because the housing market appears to be testing all three of them at once.
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?
Many of you know this, but earlier this year I was involved in a car accident on I-485. Thankfully I walked away mostly unscathed and my two sons were not in the back seat. I was rear-ended, and my reliable, trusty red Honda Accord was totaled and officially laid to rest. So this became the year of getting a new car.
Thankfully, knock on wood, I shouldn’t have to worry too much about warning lights coming on in the new car anytime soon. But it did get me thinking about how we respond when one does. If a warning light comes on in your car, there are two bad responses. The first is to ignore it completely and keep driving as if nothing happened. The second is to panic, slam on the brakes, pull over, and assume the engine is about to fall out.