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.
A couple of days ago, I was scrolling through Facebook when a post caught my attention. It showed the Charlotte skyline through a series of snapshots taken over the years. The first was from 1940, then 1960, 1985, 2006, and finally 2026.
I found myself stopping on each picture for a while.
Charlotte was still Charlotte, of course. But the changes were remarkable. Buildings appeared. Familiar landmarks changed and new ones took their place. The city grew upward and outward, and with every picture you could see another chapter of its evolution. What struck me most was how different the change looked when compressed into a handful of photographs.
Most of us have used an AI tool by now. You type in a question to ChatGPT or Google Gemini and it gives you an answer. Then it waits.
AI is already becoming part of everyday life. Even Kaiden, my three-year-old, has started trying to talk to our Alexa at home, asking it questions and expecting an answer. To him, speaking to a computer already feels normal. Not quite sure how I should feel about that, but I digress!
My wife and our two boys spent last week in Southport, North Carolina, celebrating the Fourth of July with our family. It’s become one of those traditions we genuinely look forward to every summer, and it’s become even more meaningful now with a three-year-old and one- year-old.
The streets are draped in red, white, and blue, American flags sway from nearly every storefront, boats fill the waterfront, and the smell of sunscreen, salt air, and backyard cookouts seems to linger everywhere you go. The parade is still one of my favorite parts of the week. Watching veterans, first responders, scout troops, local businesses, and families make their way through downtown is a simple reminder that, despite everything happening in the world, there are still plenty of reasons to be optimistic about our future.
This year felt especially meaningful as our country celebrated its 250th anniversary. I couldn’t help but reflect on where we’ve been as a nation, the sacrifices that made those celebrations possible, and the resilience that has carried America through generations of uncertainty. Our history has never been a straight line, yet time and again we’ve found ways to innovate, adapt, and move forward.
Last week, I attended a wealth symposium in Washington, D.C. and one of the more
interesting takeaways had little to do with stock prices, interest rates, or election
forecasts.
During discussions featuring former Federal Reserve Chair and Treasury Secretary
Janet Yellen, Democratic strategist James Carville, and Republican strategist Karl Rove,
a common theme kept emerging. Despite their different backgrounds and perspectives,
all three spoke about the resilience of the American people, the strength of our
economy, and the unique ability of this country to innovate and create opportunity.
As I listened, I could not help but think about one of the biggest investment stories
capturing headlines today: the growing space economy.
Most retirees have never heard the term IRMAA until they enroll in Medicare or begin discussing retirement income planning. Once it enters the conversation, however, it often becomes a major focus. Questions about Roth conversions, capital gains, retirement account withdrawals, and other income decisions suddenly take on added importance because of their potential impact on Medicare premiums.
Growing up, my family always went to Oak Island, North Carolina, a tradition that still stands to this day. If you’ve never been, it’s not the polished, energetic, high-rise version of a bustling beach town. Oak Island is different. It’s quieter, more lived-in, and unapologetically real in a way that feels harder and harder to find along the Carolina coast.
It’s the kind of place where faded beach cottages sit on stilts beside newer homes with wide porches and rocking chairs, where golf carts drift down side streets carrying sunburned kids with sandy feet and melting ice cream cones, and where seafood restaurants still write their specials by hand out front while seasoned fishermen crowd the piers swapping stories about tides and bait like they’re discussing the stock market.
This weekend, I was reminded that even the best routines need a little flexibility.
At our house, bedtime with two young boys usually has a rhythm. Bath, snack, books, calm voices. Lights down. The whole thing is designed to gently land the plane after a busy day.
But this weekend, with my almost-three-year-old, the routine took a detour.
Before the books and quiet voices, we ended up wrestling on the bed. Nothing fancy. Just dad and son, laughing, rolling around, and making one of those little memories you hope you never forget. And I will admit, I was emotional that evening thinking about my little boy and how he will one day be a young man.
Eventually, we still made it back to the routine. Books were read. The room got quiet and bedtime happened.
But the best part wasn’t the schedule.
It was the adjustment.