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. After the celebrations end and daily routines resume, many are left reflecting on what they observed, unsure of what to do next. The period after the holidays presents an important opportunity for families to regroup and plan.
Below are several estate planning and life-planning topics families may wish to discuss in the weeks following the holidays:
Health, Safety, and Daily Living Concerns
If you observed 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 start of a new 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Even if documents exist, they may be outdated due to changes in family relationships, finances, or health.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 post-holiday review can prevent confusion and conflict down the road.
Long-Term Care Planning
For many families, the holidays highlight questions about future care. Discussing the options available before a crisis occurs is important:
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
Time spent together often leads to a deeper understanding of a loved one’s values and priorities. The weeks following the holidays are an ideal time to continue conversations about:
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.
Turning Holiday Observations into Thoughtful Action
Rather than viewing post-holiday concerns as uncomfortable or overwhelming, families should allow these conversations to serve as a catalyst for planning that strengthens family relationships, understanding and provides peace of mind.
A Final Thought
The holidays often bring clarity- sometimes in unexpected ways. What families notice during time together can reveal the need for better planning, additional support and clearer communication. Addressing these issues after the holidays allows for families to act thoughtfully, without the pressure of a festive but busy season.
If your family notices changes or has questions about estate planning, elder law, or long-term care, our firm is here to help you navigate the path forward with clarity and compassion. I wish you and your family open communication, compassion and good health in 2026!
Lauren C. Enea, Esq. is a Partner at Enea, Scanlan & Sirignano, LLP. She concentrates her practice on Wills, Trusts and Estates, Medicaid Planning, Special Needs Planning and Probate/Estate Administration. She believes that it is never too early or too late to start planning for your future and she enjoys working with individuals to ensure that their plan best suits their needs. Ms. Enea received a B.S. in Business Management from Quinnipiac University graduating Magna Cum Laude and a J.D. from the Pace University School of Law graduating Summa Cum Laude. She is admitted to practice law in New York and Florida. She can be contacted at 914-948-1500 or www.esslawfirm.com and she has offices in both White Plains and Somers, New York.
Lauren C. Enea, Esq. is a Partner at Enea, Scanlan & Sirignano, LLP. She concentrates her practice on Wills, Trusts and Estates, Medicaid Planning, Special Needs Planning and Probate/Estate Administration. She believes that it is never too early or too late to start planning for your future and she enjoys working with individuals to ensure that their plan best suits their needs. Ms. Enea received a B.S. in Business Management from Quinnipiac University graduating Magna Cum Laude and a J.D. from the Pace University School of Law graduating Summa Cum Laude. She is admitted to practice law in New York and Florida. She can be contacted at 914-948-1500 or www.esslawfirm.com and she has offices in both White Plains and Somers, New York.
Sign up to receive our free email newsletter for the latest articles and special notices. Plus we’ll send you a free digital edition of our next issue. Stay connected! It’s easy to unsubscribe at any time.
21 Dec 2025
0 Commentspost holiday conversations that matter
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. After the celebrations end and daily routines resume, many are left reflecting on what they observed, unsure of what to do next. The period after the holidays presents an important opportunity for families to regroup and plan.
Below are several estate planning and life-planning topics families may wish to discuss in the weeks following the holidays:
If you observed changes in a loved one’s physical or cognitive health, it may be time to discuss:
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.
The start of a new year is an excellent time to confirm whether your loved ones have up-to-date documents, including:
Even if documents exist, they may be outdated due to changes in family relationships, finances, or health. A post-holiday review can prevent confusion and conflict down the road.
For many families, the holidays highlight questions about future care. Discussing the options available before a crisis occurs is important:
A proactive discussion can give aging relatives a voice in their future and provide peace of mind to the entire family.
Time spent together often leads to a deeper understanding of a loved one’s values and priorities. The weeks following the holidays are an ideal time to continue conversations about:
These conversations help families understand not just the documents, but the intentions behind them.
In my experience, many conflicts arise from secrecy or assumptions. Families may want to discuss:
Open communication now can prevent miscommunication and stress later.
Rather than viewing post-holiday concerns as uncomfortable or overwhelming, families should allow these conversations to serve as a catalyst for planning that strengthens family relationships, understanding and provides peace of mind.
A Final Thought
The holidays often bring clarity- sometimes in unexpected ways. What families notice during time together can reveal the need for better planning, additional support and clearer communication. Addressing these issues after the holidays allows for families to act thoughtfully, without the pressure of a festive but busy season.
If your family notices changes or has questions about estate planning, elder law, or long-term care, our firm is here to help you navigate the path forward with clarity and compassion. I wish you and your family open communication, compassion and good health in 2026!