As Thanksgiving approaches, many families look forward to sitting around the table, sharing traditions, stories, and a sense of togetherness that only the holidays can bring. For many households, it’s one of the few times each year when multiple generations gather in one place. While estate planning might not be the first topic that comes to mind when the turkey is carved, Thanksgiving can actually be the ideal moment to start an important conversation about the future.
At Lane, Lane & Kelly, LLP, we believe estate planning does not need to be a difficult discussion about death or loss. Instead, it can be a positive, thoughtful, and caring conversation focused on clarity, communication, and making life easier for the people that you love the most.
A Season for Reflection and Connection
Thanksgiving naturally invites gratitude and reflection. The holiday gives us a chance to appreciate the people in our lives, recognize what we’ve built, and consider how we can take care of our loved ones even after we are gone.
This mindset makes it the perfect time to talk about estate planning for the following reasons:
- Everyone is together, making it easier to communicate openly and avoid misunderstandings.
- The setting is warm and familiar, helping reduce stress around a topic that might otherwise feel intimidating and difficult to confront.
- The holiday is already focused on family, and planning for the future and the transition of family assets is one of the most impactful ways you can provide for your loved ones.
These conversations don’t have to be formal, heavy, or comprehensive. Even a brief discussion can make a real difference.
It is Never too Early to Create Your Estate Plan
A common misconception is that Wills and estate plans are only for the elderly. In reality, a complete estate plan is about ensuring that your wishes are respected and your family is supported, long before anything unexpected ever happens. Creating an estate plan is all about taking care of your loved ones in the event of unforeseen possibilities, and not probabilities. A recent study showed that only 24% of Americans have a Will in 2025. This leaves roughly ¾ of Americans exposed to Probate Court, added expenses, court fees, potential family or legal disputes, and unnecessary ambiguities that come about after the death of a loved one that does not have a plan in place.
An estate plan is crucial for all Americans, regardless of your age, assets, background, or overall health, to ensure that your wishes are honored and your loved ones and assets are adequately protected in the event that tragedy strikes. For a full overview of what to consider when creating a Will or Trust in Massachusetts, read our full legal blog here. A well-structured estate plan can:
- Appoint someone to make financial or medical decisions in the event that you become incapacitated or unable to make your own decisions.
- Name guardians and conservators for your minor children.
- Maximize potential estate tax savings through proactive planning, and by reducing or potentially eliminating any possible tax bill that may be due to the Commonwealth upon your death.
- Ensure that you avoid the Probate Court entirely, which saves your loved ones unnecessary time, stress, and costs.
- Ensure your assets are transferred the way you intend, rather than based on the Massachusetts laws of Intestacy.
- Minimize potential disputes among family members.
- Provide clarity, confidence, and peace of mind.
Talking about these decisions now, while everyone is well and together, can help reduce uncertainty later.
How to Bring Up the Conversation Gently
A holiday meal might not be the time to pull out legal documents, but Thanksgiving can be an opportunity to start the conversation in a comfortable and respectful way. Some families choose to:
- Mention that they’ve begun updating their estate plan and want loved ones to know where things stand.
- Ask family members if they’ve considered creating or updating their own plan.
- Provide referrals for preferred estate planning attorneys, such as the Award-winning attorneys at Lane, Lane & Kelly, LLP in Braintree, Massachusetts.
- Respectfully ask loved ones if they would be comfortable serving as a fiduciary (such as Personal Representative, Trustee, Power of Attorney) or as the Guardian or Conservator of any minor children.
- Share the reasons behind their decisions and answer questions.
- Talk about what matters most, beyond just finances, such as funeral or burial instructions, personal valuables and family heirlooms, or any other family traditions.
Even a short, informal discussion can open the door to more detailed planning later. No one needs to resolve everything in a single afternoon. Starting this conversation during a time of togetherness can prevent confusion and conflict later and can help ensure everyone understands your wishes long before they ever need to be followed.
Ready to Start Planning?
Whether you are beginning your first estate plan or reviewing one that needs to be updated, our attorneys at Lane, Lane & Kelly, LLP are here to help. We have been guiding families across the Commonwealth since 1938 with comprehensive planning, that is tailored to your specific situation and family needs. For a detailed overview of our estate planning services, click here to read more.
This Thanksgiving, as you gather with family and carry-out your longstanding traditions, consider taking the first step toward ensuring the ultimate peace of mind for both you and your loved ones. Planning today can make all the difference tomorrow. If you’re ready to begin, we’re here when you need us.
This blog is made available for educational purposes only as well as to give you general information and a general understanding of the law, not to provide specific legal advice. By reading this blog you understand that there is no attorney client relationship between you and Lane, Lane & Kelly, LLP.
Matthew B. Lane
Matthew is an Attorney at Lane, Lane & Kelly, LLP. Matthew attended Rensselaer Polytechnic Institute obtaining his undergraduate degree in Business & Finance in 2016, graduating with Magna Cum Laude honors, and later graduated from Suffolk University Law School in May 2025 with Cum Laude Honors. Matthew primarily practices in the areas of Estate Planning, Probate & Trust Administration, and Real Estate Conveyancing.
