Why the Holidays Are the Perfect Time to Talk About Estate Planning

The holiday season is one of the rare times when families can slow down and truly spend time together. While the focus often centers on food, tradition, and celebration, it also provides an opportunity to connect with loved ones on a deeper level.

One topic that often goes unspoken, but shouldn’t, is estate planning. While these conversations can be difficult, they help prevent confusion, reduce future stress, and ensure that your wishes, or the wishes of a parent or spouse, are clearly understood.

At Harper Law, we help families throughout Connecticut create and update estate plans that align with their current needs and future goals. We also remind clients that the best time to have these conversations is before a crisis arises.

Why These Conversations Matter

Many people put off estate planning. Some don’t know where to begin, while others feel uneasy discussing legal or medical decisions. But beginning the conversation now gives everyone the chance to ask questions, understand what is already in place, and prepare for the future.

If you already have an estate plan, you can lead by example. Simply sharing that you have a will or trust, and explaining why, can encourage others to take the same step. For parents or aging relatives who haven’t yet made a plan, a thoughtful conversation now can help prevent unnecessary stress later.

If it feels difficult to bring up, you can introduce the topic by mentioning a recent news story, a family milestone, or a change in health or living arrangements. The most important thing is to approach the conversation gently and without pressure.

Essential Estate Planning Documents

A complete estate plan involves more than just a will. Below are several documents every family should have:

·       Last Will and Testament
Specifies who will receive your assets and designates the person responsible for carrying out your wishes.

·       Durable Power of Attorney
Appoints someone you trust to handle financial or legal matters and make decisions on your behalf if you are unable to do so.

·       Healthcare Directive and Living Will
States your preferences for medical care and name a healthcare representative to make decisions on your behalf.

·       HIPAA Authorization
Permits healthcare providers to share medical information with the individuals you’ve chosen.

Together, these documents ensure your wishes are respected and that someone you trust can act for you when needed.

Planning for Medical and Long-Term Care Needs

Estate planning also involves discussing future healthcare decisions and living arrangements. Though these conversations can be uncomfortable, addressing them early provides clarity and peace of mind for everyone involved.

Consider the following questions:

·       Would you prefer to remain at home if your health declines?

·       Are you financially prepared for long-term care?

·       Do you have long-term care insurance, or would you need to apply for Medicaid?

These discussions are especially important for aging family members and can help prevent confusion and stress later on.

Not Every Conversation Has to Happen at Once

You don’t need to cover everything in one discussion. Sometimes, simply starting the conversation is enough. What matters most is giving your loved ones the chance to feel heard, supported, and encouraged to take the next step, whether that’s beginning a plan or reviewing what’s already in place.

We Are Here to Support You and Your Family

At Harper Law, we understand that estate planning can feel personal and emotional. Our goal is to help you approach these important decisions with care and confidence.

Whether you are reviewing your own plan, encouraging a parent to begin, or navigating next steps after a life change, we are here to guide you forward with clarity and compassion.

Visit our office in Milford
Call us at (203) 883-1656
Schedule a consultation online

At Harper Law, we provide estate planning with the personal touch of a hometown practice, helping Connecticut families prepare for the future one conversation at a time.

Disclaimer: This blog is for informational purposes only and does not constitute legal advice. Please consult an attorney for specific legal guidance.