The passing of a loved one is always hard—especially when it’s a parent. As I write, I am processing the loss of my mom. Before her passing, I served as both her financial and healthcare power of attorney. Now, I’m in the process of being appointed as the executor (or “personal representative,” as we call it in Maine).
SIDETRACK
If you’ve ever carried these roles, you know they come with a heavy mix of responsibility and emotional weight. I’m no stranger to Fiduciary Duty—I live it every day as an investment advisor representative. That’s the regulatory term for what most people simply call a financial advisor. Unfortunately, our industry uses a mess of confusing titles.
Here’s one thing to remember: if your advisor charges a fee based on assets under management, they are legally bound as a fiduciary to act in your best interest. But if that same advisor is also licensed to sell commissioned products—like annuities—they can “switch hats.” When they’re selling the annuity, they’re only partially under fiduciary rules, but instead operating under a different, lower standard know as the Suitability Rule. As I said, it can be confusing.
That’s why I serve as a fee-only advisor. I wear just one hat—and it’s always the fiduciary one. I’ll decode the rest of those industry labels in another post.
Now, if you’ve read my writing before, you know I tend to wander down side paths like this. I do it intentionally. A sidetrack can often shine a light on a concept in a way that feels real. Back to the main plot.
MIDDLE CHILD SYNDROME
I’m the middle child. My older brother is four years ahead of me, and my two younger siblings—born just months apart—were practically raised like twins. Middle children often get pegged with “middle child syndrome”. We’re often the peacemakers. That’s true for me—but with an edge. Sometimes I’ve leaned into peacekeeping; other times, I’ve chosen creative destruction and sometimes, regrettably, just destruction.
When I was younger, my parents had a cartoon that captured me perfectly: two men sitting on a bench, one sitting right on the other’s hat. The man whose hat was crushed sat there fuming, thought bubbles of rage overhead—but he said nothing, because his personality was phlegmatic. My parents thought it was funny because it reminded them of me. Maybe it was true then, but I’ve at least partially outgrown it. These days, I’m fierce about property rights—especially personal space, emotional space, and privacy.
What I’ve learned is this: being a peacemaker is not genetic, it’s learned. And sometimes, peace comes at the cost of your own strength. Looking back, there were moments when I should have stood sooner, hit harder, and ridden closer to the edge.
Not always—because as The Byrds remind us:
To everything, turn, turn, turn
There is a season, turn, turn, turn
And a time to every purpose under heaven
This week has held all of it: a time to be born, a time to die, a time to laugh, and a time to weep. And yes, also a time to kill and a time to heal. Deciding what to do with your loved one is hard emotional work.
Seasons… the truth is, I’ve never perfectly known when to choose which.
Few of us do.
But life is about creative destruction, riding the wave, riding the edge. You only learn by trying.
Fail forward. Keep growing.
