Earlier than most families do. That’s the honest answer, and most people who’ve been through it will say the same thing.
The conversations that go smoothly tend to happen before there’s any urgency. When your parents are still sharp, still independent, and there’s no particular reason to be having the conversation except that it’s sensible. Those conversations are easier for everyone. Parents are more open. Options are wider. There’s no pressure, and no one is trying to make decisions under difficult circumstances.
The conversations that go badly tend to happen after something has changed. A fall. A diagnosis. A hospital stay. By that point, capacity may already be in question, which changes what an attorney can legally do. It also changes the emotional temperature in the room, and decisions made under pressure rarely reflect what anyone actually wanted.
There are moments that make the conversation easier to start. A health scare in the news, or the death of a friend’s parent, creates a natural opening without it feeling like a direct challenge. Tax season, a property sale, or a new grandchild are all practical prompts. The key is finding a frame that positions it as your parents controlling their own wishes, rather than anyone else rushing them toward an outcome.
One thing worth raising carefully: siblings don’t always react well to this conversation. Some interpret it as pressure, or as a family member making a move on the estate. If that’s a risk in your family, consider letting your parents raise the topic themselves after you’ve planted the idea privately, or framing it around what they want rather than what the family needs. An elder law or estate planning attorney who regularly works with families can often help navigate that dynamic too.
Once a parent’s capacity becomes uncertain, the number of things an attorney can do on their behalf shrinks considerably. New trusts become harder to establish. Beneficiary changes require more documentation. Some options close entirely. The earlier a proper plan is in place, the more of those doors remain open.
There’s also a less obvious benefit. Adult children who arrive at a parent’s later years with documents already in place report significantly less conflict with siblings, less stress dealing with institutions, and less time lost to paperwork during an already difficult period.
The right time is when your parents can still have the conversation comfortably. For most families, that time is now. A first meeting with an estate planning attorney costs a few hundred dollars and takes an hour. It’s considerably less expensive than the alternative of acting after things have already become complicated.