09/18/2026
Boston this morning. Vermont next.
This annual September trip is a little different. Plus the flights like to get delayed.
I’m headed home to keep working through my own family’s estate planning which is something we’ve been slowly pecking away at since my mom passed in 2021.
Our family situation isn’t particularly complicated. We know we want to keep the farm. We know what matters to us. There aren’t many people involved.
My mom was the planner. For my dad, part of this process has simply been overcoming the weight (and ego) of having to make decisions she would have once simply made. That was her contribution.
What happens to the property? The stuff? The accounts? Is everyone on everything as beneficiaries? I’ve been the fiduciary and power of attorney for a few years now, but it’s time to get it firmed up.
These aren’t complicated questions because we don’t know the answers. They’re complicated because they’re uncomfortable to talk about. I’ve got a lump in my throat even just writing this.
Something I’ve learned both personally and through working with families in transition: the paperwork usually isn’t the hardest part. Starting the conversation is.
If you made a will or trust years ago and life has changed since then, whether through a death, marriage, divorce, new property, a move, or simply the passage of time, it may be worth pulling it back out and having the awkward conversation.
Apparently this weekend, it’s our turn. After Violet’s Birthday and the Tunbridge Fair , of course. Transitional LIFE Specialist Ericka Grygowski ❤️
