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.
A lot of people think of their Health Savings Account as little more than a medical debit card. Money goes in, prescriptions come out, maybe you pay for a doctor’s visit here and there, and that’s about it.
But HSAs can be significantly more powerful than that if they’re used strategically.
While it’s a blessing to be included as a beneficiary of an estate, it’s not typically something most of us go through more than once or twice in our lifetimes. This makes it tough to be practiced at the complications involved in receiving an inheritance after the death of a loved one. This usually presents itself via a phone call from a sibling, parent or doctor…or maybe it’s something you’ve been preparing for over a long period of time. A parent passes, a trust gets activated, and suddenly someone who has spent their entire life earning, saving, and planning is now on the receiving end of wealth instead of the building side of it.
I was in the middle of cooking maybe the best chicken thighs of my life in the kitchen. One thing you’ll learn as you get to know me is that I love learning and experimenting in the kitchen, and on this particular night, I was working on what I hoped would be my magnum opus of bone-in, skin-on chicken thighs in the skillet. There’s an art to everything, and that includes getting the perfect golden, crispy skin on a tender piece of poultry. I dried the thighs out in the fridge the night before, put them skin-side down on a cold cast iron pan, and was slowly bringing them up to a sizzle. I was Michelangelo, and this was my…. well, you get the point.
About a year and a half ago, we were down in Southport over Labor Day weekend.
My wife and I had our son Kaiden with us, he was just over a year old at the time, and we were there with our family, including my wife’s parents. We decided to book a sunset boat ride together. Nothing complicated. Just a chance to get out on the water, enjoy the evening, and maybe spot a few dolphins.
It ended up being one of those nights you don’t forget.
In the first part of this series, we stepped back and looked at housing a little differently. Not just as a question of where you live, but how care is going to be handled as life changes. In the second part, we focused on continuing care communities and what they really are beneath the surface, not just the price tag or the amenities, but how they shift responsibility, coordination, and long-term risk.
Once you start to understand those pieces, the question that tends to come next is not which option is best, but when you should actually start thinking about any of this seriously.
In the first article, we zoomed out and reframed the housing conversation. The idea was simple, but it tends to land a little differently once you really sit with it. Later-life housing is not just about where you live, it is about how care is going to be handled if and when life changes.
When people start thinking about their later years, the housing conversation usually begins in a very practical place. Should we just stay here? Maybe we downsize. Maybe we move closer to the kids. Maybe we look at one of those retirement communities our friends keep mentioning. On the surface, it feels like a decision about square footage, yard work, stairs, and proximity to restaurants. It sounds like a lifestyle choice.