I was on a flight last weekend, tired but wired, folded into a middle seat with my elbows tucked in like I was trying not to exist. The cabin lights were dim, the seatback screen was glowing with that particularly dizzying shade of airplane blue, and for reasons I can’t fully explain, I decided to watch The Princess Bride for the first time. (I know I am late, but we all have our gaps.)
Somewhere amidst the sword fights and the Rodents of Unusual Size came the line I already knew by heart despite never having seen the movie: “Hello. My name is Inigo Montoya. You killed my father. Prepare to die.” I laughed out loud because of how absurdly direct it is. There is no warm-up, no small talk, no easing into it.
“Do You Always Begin Conversations This Way?”
Wedged there between a dozing woman whose head kept drifting uncomfortably closer to my shoulder and another stumbling through a Sudoku with clear exasperation, it hit me. This is probably what I sound like to some clients when I bring up estate planning as a new party entering the conversation. “Hi. Here’s your will. Let’s dissect your powers of attorney. Who makes decisions if you can’t? Who gets what? What happens if you don’t come home?” It matters. And it’s brutal to talk about when life feels full and tomorrow feels far away. So, people flinch. I get it. I flinch too.
Most of us would rather talk about markets, which feel somehow friendlier, despite the frequent whiplash. Even taxes, frustrating as they are, have rules and levers and a sense that if you’re thoughtful enough, you can optimize your way through them. Estate planning is different. It makes you say the quiet part out loud.
“Inconceivable!”
Some families engage quickly because there’s a glaring motivator: a looming estate tax bill, a complicated business, something that puts a dollar sign on procrastination. Others come to it after walking through probate with a parent or sibling and deciding, very clearly, that they never want to put the people they love through that again. Meanwhile, plenty of people look at their balance sheet, feel reasonably comfortable, and wonder if this is really necessary right now. Maybe later, when things slow down, and there’s more time.
I know how that movie ends. I’ve seen clients move through loss with clarity and calm because the work had already been done. Documents were in place. Assets were titled properly. The people responsible for making decisions knew they had been chosen, and they knew what their loved one wanted. Grief was still there, as it always is, but it wasn’t layered with confusion or court dates or frantic phone calls asking, “Do you know where they kept that?”
And I’ve seen the other version. The scavenger hunts for passwords. The outdated beneficiary forms. The account that was supposed to be retitled but never was. Siblings trying to be gentle with one another while also trying to agree on a matter that feels impossible and incomprehensible. Decisions layered on top of sadness, uncertainty piled on to shock, loved ones left guessing about things that never should have required a guess. When there is no plan, the burden does not disappear. It just gets handed to the people you love most.
A few weekends ago, I was talking with two close friends whose lives have taken off in the best possible way, with great jobs in medicine, their first home, and their first baby all arriving in quick succession. They asked me what kinds of stocks they should be buying and how they should be thinking about retirement now that life feels bigger and more complex. I had an answer to that question, but my first response was a different one. “Do you have an estate plan, and if something happens to both of you, who takes care of your son? Who’s empowered to make decisions if you can’t?” They work in hospitals. They watch high-stakes moments unfold every day. They know exactly how much it matters to have the right people clearly named before things get urgent.
“Death Cannot Stop True Love.”
That is the lens that matters here. An estate plan isn’t dramatic. It isn’t morbid. It isn’t a “wealthy people” thing. It’s paperwork with a pulse. It’s love expressed early, in a boring font. It’s you, while you’re still here and clearheaded, deciding to carry a little weight now so someone else doesn’t have to carry it later.
Everyone needs an estate plan, not because everyone has a tax problem waiting in the wings, but because everyone loves someone. It belongs in the same category as the ways we already show up for the people who matter to us, whether that looks like cooking an extravagant dinner for your spouse on a random Tuesday night, coaching your daughter’s basketball team when your calendar is already full, or just listening for hours while your friend works his way through a breakup.
You do not second-guess those moments. You show up because love calls for action, and estate planning is the same. It is unglamorous work done quietly and in advance so that when life does what life inevitably does, the people you love are protected, supported, and spared unnecessary pain. It’s a deeply human gesture. A way of saying, “I’m going to make this easier for you.” No sword fights. No dramatic monologues. Just middle-seat energy: uncomfortable, but over before you know it.
Put it on the calendar. Send the text or email. Start the process. Future-you will be grateful. Your people will be, too.
Matt Gregory
Director, Integrated Planning
Trevor Cummings
PWA Group Director, Partner
