Law with Lauren by Lauren Glynn

The Gift of Clarity: How To Start ‘The Conversation’ This New Year

For many of us, the holiday season is a time of joy and reunion. But for others, sitting around the family dinner table this past month may have revealed a sobering reality: Things are changing. Perhaps a parent seemed more forgetful, a grandparent more frail, or the house a little less managed than years prior.

These moments are often the first signals that big life shifts are on the horizon. Yet, knowing a conversation needs to happen and actually starting it are two very different things. When it comes to estate planning and future care, the transition from “Pass the gravy” to “Who is your power of attorney?” can feel impossible.

If you’re realizing it’s time to talk, here is how to navigate those waters with grace and effectiveness.

Speak Their Language

The biggest hurdle is often the “death language” itself. Many people feel discarded or “pushed out” when children bring up estate planning. To lower the stakes, mirror the language your parents use. If they prefer humor and talk about “kicking the bucket,” meet them there. If they use softer terms like “when I’m gone” or “taking a long nap,” follow their lead. Using the words they find comfort in prevents the conversation from feeling like a clinical or cold confrontation.

Identify Their Priorities (Not Yours)

It is easy to enter these talks with our own anxieties—avoiding probate court, managing taxes, or dealing with a messy house. However, for the conversation to be successful, you must identify their priorities.

Ask yourself—and then ask them—what they value most:

• Is it their personal security and staying in their home?
• Is it the fear of becoming a “burden” to the family?
• Is it the desire to ensure their children don’t fight over heirlooms?
• Is it the protection of assets from potential healthcare costs?
  When you center the plan on their goals, you aren’t taking control away; you are helping them secure their legacy.

Focus on Roles, Not Dollars

A common mistake is asking, “How much is in your savings account?” This can immediately trigger defensiveness. Instead, keep the focus on roles. Everyone, regardless of wealth, needs a team. Frame the discussion around support.

• Medical Decisions: “If you couldn’t speak for yourself, who do you trust to make health decisions?”
• Financial Power of Attorney: “Who should help keep the bills paid if you’re under the weather? What can we do today—like organizing passwords or automating bill pay—to make that person’s job easier?”
• The Executor: “Who is responsible for winding things down later, and do they know where the insurance policies are kept?”

Choosing the Right Tool

The “why” determines the “how.” If the goal is simply to have a plan on paper and the family is comfortable with a bit of court work later, a will combined with a Transfer on Death Deed may suffice. It’s often the simpler, more affordable route upfront. However, if the goal is to avoid the expense, time, and public nature of probate court entirely, a trust might be the better option. You don’t have to have all the answers. You can let a qualified attorney help identify which legal tools fit the situation. But an attorney can only build the bridge; you and your family have to decide where it’s going.

This New Year, give your family the gift of clarity. Keep the tone light, weave in happy memories, and remember: This isn’t a conversation about dying. It’s a conversation about how we take care of each other while we’re living.

Lauren Glynn is a local attorney and town justice, dedicated to helping neighbors. She can be reached at (607) 303-6554.

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