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.
Most parents who are financially thoughtful eventually ask some version of the same question: beyond saving for college, how do I truly give my child a long-term financial edge? Not just a head start for tuition, but something that compounds quietly in the background for decades and meaningfully shifts their future flexibility. If that question has crossed your mind, there is a strategy that is surprisingly simple, remarkably powerful, and often overlooked.
By the time you’re reading this on Wednesday, you’ve probably had a couple days to process the weekend headlines. Maybe you glanced at them once and moved on. Maybe you read every update.
Either way, when geopolitical tension ramps up quickly, it creates that familiar feeling in your stomach. Not fear perhaps, but certainly tension.
So let me start with the part that matters most. We’re not scrambling. And more importantly, we don’t need to.
Tax season has a way of sneaking up on people. One minute it’s January and everyone is easing into the year, and the next minute your inbox is full of tax forms, “important documents,” and well-meaning reminders to file early. Every year, I see smart people feel rushed, confused, or worried they’re missing something.