Sharing Values, Wishes, and Plans: Conversations for the Holiday Table
By: Lauren C. Enea, Esq.
The holiday season is often thought of as a time for celebration, tradition, and gathering with family and friends. Yet, year after year, between Thanksgiving and New Year’s, our office receives an influx of calls from concerned children, nieces, nephews, and other family members who have just spent time with an aging loved one and noticed a decline in health, safety, or overall well-being.
For many, the holidays are the only time of year when everyone is physically together under one roof. And while this should be a joyful time, it can also bring to the surface difficult realizations: a parent seems more forgetful than last year, an aunt no longer manages her home as well as she once did, or an elderly relative confides that they are feeling overwhelmed, isolated, or vulnerable. While this can be emotional, it also provides an opportunity: a natural opening for meaningful conversations about the future.
Below are several estate planning and life-planning topics families should consider discussing during the holidays:
- Health, Safety, and Daily Living Concerns
If you observe changes in a loved one’s physical or cognitive health, it may be time to discuss:
- Whether they feel safe living at home;
- Whether they need help with driving, shopping, bathing/ dressing or managing medications;
- Whether they have had any recent falls, hospitalizations, or moments of confusion; and
- Whether they have a plan if something unexpected happens.
These conversations can be difficult, but approaching them from a place of concern, not criticism, can open the door to planning that preserves dignity and independence.
- Reviewing Essential Estate Planning Documents
The end of the year is an excellent time to confirm whether your loved ones have up-to-date documents, including:
- Last Will and Testament;
- Durable General Power of Attorney with Gifting Authority (if applicable);
- Health Care Proxy / Living Will;
- Assignment of Agent for Disposition of Remains;
- Revocable and/or Irrevocable Trusts (if applicable); and
- Beneficiary designations on retirement accounts and life insurance.
Even if documents exist, they may be outdated due to changes in family relationships, finances, or health. A quick review can prevent confusion and conflict down the road.
- Long-Term Care Planning
Discussing long-term care options before a crisis occurs:
- Discuss In-home care versus assisted living benefits available;
- Discuss Medicaid Planning and/or Applications to be submitted;
- Discuss Long-term care insurance to purchase or implement; and
- Discuss how to pay for care without jeopardizing one’s life savings.
A proactive discussion can give aging relatives a voice in their future and provide peace of mind to the entire family.
- Understanding a Loved One’s Personal Philosophy
The holidays offer rare uninterrupted time to talk about the values that shape one’s future planning. Encourage your loved ones to share:
- Their philosophy on money and financial independence;
- Their views on charitable giving and legacy;
- Their priorities for quality of life as they age; and
- Their hopes and expectations for how family members will support one another.
These conversations help families understand not just the documents, but the intentions behind them.
- Planning for Communication and Transparency
In my experience, many conflicts arise from secrecy or assumptions. Families may want to discuss:
- Whether adult children know where important documents are stored;
- Who the trusted advisors are (attorney, financial advisor, accountant);
- What role each family member might play in the future; and
- Whether the person wishes their estate plan to be discussed openly or privately
Open communication now can prevent miscommunication and stress later.
- Using the Holidays as a Healthy Check-In
Rather than viewing these conversations as solemn or uncomfortable, families and friends can reframe them as part of caring for one another. Just as holiday traditions bring families and friends together, honest dialogue about the future can strengthen relationships and reduce uncertainty.
A Final Thought
While no one wants to spend Christmas dinner talking about legal documents, the reality is that the holidays often highlight the need for better planning, safer living arrangements, and clearer communication. With empathy and the right guidance, these conversations can help ensure that aging family members are protected, supported, and heard.
If your family notices changes or has questions about estate planning, elder law, or long-term care during this holiday season, our firm is here to help you navigate the path forward with clarity and compassion. I wish you and your family good health, prosperity and joy this holiday season!
