Living Fully, Planning Thoughtfully: Moving Beyond the Technical in End-of-Life Conversations

By Kim V. Heyman, JD, LLM, AEP, Director, Wealth Planning Group, Pathstone

As estate planning professionals, we spend our time helping clients prepare for the inevitable – death. (Sometimes we have to break the news to them that it is not a question of “if” but rather of “when.”) We draft documents, structure wealth transfers and try to anticipate eventualities with technical precision. Yet, for all our expertise, we often sidestep or downplay the most human - and arguably the most important - aspect of planning: what it means to live well at the end of life, and how to ensure that vision is known, respected and carried out when one is no longer able to communicate for oneself.

When done correctly, this is an incredibly personal exercise rather than merely a legal one. Yet without prompting, it is not something about which many people think. To truly serve our clients, we must evolve from scriveners or strategists into educators and guides – informing clients of the importance of formulating and documenting their wishes and helping them articulate not just what they own but what they value; not only what medical procedures they do not want, but rather how they want to live and what “quality of life” will mean to them towards the end of life.[i]

For those of us advising clients, there are two parallel imperatives: first, to internalize these lessons for ourselves; and second, to translate them into meaningful, actionable guidance for our clients.

Reframing “Quality of Life”: The Foundation of End-of-Life Planning

When clients are asked about end-of-life preferences, many default to generalities:

“Pull the plug;”

“I don’t want to suffer;” or

“I don’t want to be a burden;” or, less frequently,

“They should keep me on life support. I was there for them and they should have to visit me.”

These sentiments, while sincere, are insufficient to guide decision-making. Similarly, statements declaring what procedures one does and does not want (e.g., no CPR), are too specific directions coming from non-medical professionals (when we do not know what would be required to get from point A to point B).

I have heard from ICU, palliative care and ER professionals that the more productive inquiry is this: What does quality of life, at the end of life, look like to you?

“Quality of life” is inherently subjective. For one individual, it may mean the ability to communicate meaningfully (in whatever form) with loved ones. For another, it may include physical independence, cognitive clarity or simply the capacity to enjoy familiar surroundings. Some clients may prioritize longevity, others, dignity, independence or comfort. And all of this may change as people experience different phases of life. For example, it may mean one thing for people who have children, when their children are young, and another when their children are adults. Our role is to help clients move from abstraction to contemplation and then articulation.

Important topics to consider and answer include:

• Who is the right person to designate to make decisions (referred to herein as surrogate decision maker or health care agent)?

• Comfort preferences (e.g., the level of pain medication you may want - relieve all pain even if I sleep more; I would like moist toilettes to keep cool if I have a fever).

• How one wishes to be treated (e.g., if competent, I want to participate in conversations; I want visitors whenever possible; I want someone to hold my hand when death is imminent).

• What matters more (e.g., living independently or living longer; continuing to eat by mouth if one is a foodie or just really enjoys eating, rather than having a feeding tube)?

• What one wants loved ones to know (e.g., I want my loved ones to know I forgive them; I want my family and loved ones to receive therapy to help them with my dying). [ii]

These prompts help individuals clarify inflection points where treatment may no longer align with personal values and under what circumstances certain treatments would feel like “too much.”

A well-drafted advanced health care directive that includes narrative context is far more useful to a health care agent than a checklist alone. Similarly, one or more conversations with a health care agent and family members may go a long way to clarifying one’s wishes, getting everyone on the same page and reducing potential conflict and misunderstandings when the time comes.

The Necessity of Conversations: More than a Document

Many of us have come across meticulously drafted documents that were never meaningfully discussed or created based on a client’s specific wishes and values. A health care power of attorney and living will (also referred to as an advanced health care directive) are often presented to clients without significant options for describing what quality of life means to them, they are rarely discussed, then signed and checked off. After that, silence.

Advanced health care directives are the most important document to a client. If needed, they will impact a client while they are alive and when the client is at their most vulnerable. This is when advanced planning will help a client “speak,” when they may in fact be unable to communicate for themselves. 

But documents, no matter how well crafted, cannot substitute for conversation. Conversations with professionals who work in this area and the literature on living life at the end of life consistently underscore this point. Often end-of-life discussions are deferred until a crisis occurs, leaving families unprepared and uncertain. [iii] These conversations are difficult to initiate, despite being essential.

As professionals, we are uniquely positioned to normalize and facilitate these discussions. We can:

• Encourage clients to contemplate what quality of life at the end of life means to them.

• Assist them in capturing those values and views in writing.

• Support them sharing their directives with their chosen decision-makers and family (chosen or biological - the people who will be in the room when the time comes).

• Suggest family meetings to discuss values and preferences.

• Provide structured prompts to guide dialogue.

• Reassure clients that revisiting these conversations over time is both appropriate and essential.

Importantly, we should frame these conversations as the greatest gift to those who may one day be called upon to act. Clear communication while a client is able to participate is the best way to reduce conflict if/when a time comes when people must rely on someone else to make decisions. No matter how well families get along today, working to minimize conflict in the future is something we, as estate planning professionals, need to dedicate more time to doing. Clients may find great comfort from this perspective, and they may find it easier to move forward and engage in the process with a motivation other than focusing on their own disability and death.

The Critical Role of the Health Care Decision-Maker

No matter how thoughtfully a client documents their wishes, it is almost inevitable that unanticipated circumstances will arise. Medicine evolves.[iv] Conditions unfold unpredictably. Facts at the time rarely follow previously played-out hypotheticals.

This is why appointing a trusted person, someone empowered to make decisions when the client cannot, is imperative. Given that we cannot predict the future, a client will almost always achieve better outcomes when they appoint a trusted person and grant them discretion to make decisions based on the client’s wishes, rather than mandating today what should happen at a future time.

Too often clients approach this decision based on obligation and guilt, naming a spouse or adult child without considering if the named person will actually follow their wishes or will be “up” for the job. But the role of a surrogate decision-maker is complex and, at times, emotionally fraught (and, when needed to act, is often followed by feelings of guilt). It requires not only a willingness to serve, but the ability to balance competing considerations: the principal’s stated wishes, the medical realities and the emotional dynamics of family members, including, perhaps, themselves.

The ideal surrogate is not necessarily the closest relative or the  most assertive personality. Rather, it is the person who will be the best advocate for the client and who can best exercise substituted judgment - that is, making decisions as the client would have made them, considering both prior expressions of intent and the circumstances at hand.

This distinction is critical. A surrogate is not tasked with deciding what they think is best, nor with rigidly following a pro forma document that does not describe the client’s actual wishes nor fully capture the present situation. Rather, they must interpret and apply the client’s values in the context at the time a decision is required to be made.

In practice, this means that selecting the right person is only half the job. The other half is ensuring that that person understands the client’s wishes, and perhaps more importantly, feels prepared to implement them. Unfortunately, this is where many plans come up short.

Integrating Health & Wealth: Guided by a Well-Articulated Vision

Financial capital may support a wide range of end-of-life preferences, from in-home care to specialized medical interventions. But without clarity of what quality of life means, when an individual is unable to communicate for themselves, even substantial resources may be deployed in ways that do not enhance the individual's conception of what that means to them.

Conversely, a well-articulated vision may guide a more intentional use of assets. For example, a client who prioritizes remaining at home may wish to allocate resources toward long-term care insurance, home alterations or caregiver support. Another who values minimizing medical intervention may focus on palliative care and hospice planning and may take those goals into account by having discussions with their primary care and specialist physicians.

Our advice should address tax efficiencies as well as the client’s values. This may require collaboration with other professionals - physicians, care managers or counselors - to ensure that plans are both feasible and consistent with the client’s wishes and medical needs.

Shifting the Perspective: Living with the End in Sight

One of the most powerful exercises we should encourage, both for ourselves and our clients, is to consider life from the vantage point of its end.

In guides that help with end-of-life planning, the focus is not on the mechanics of dying, but on the meaning of living with the end in mind.[v]

• What relationships matter most?

• What experiences define a life well lived?

• What legacy - tangible or intangible - does one hope to leave?

• What would you keep with you to remember someone you have loved who has died?

• If you had a limited number of months to live, what would you allow yourself to do?

• When you think about care at the end of life, what worries you more:

  • Not receiving enough

  • Receiving overly aggressive care

  • Other

These questions are not ancillary to estate planning or living well at the end of life; they are central to it. When clients engage with these reflections, their planning often will become more purposeful. In addition to possible changes to their estate plan, decisions about medical care may become clearer.

For professionals, engaging in these types of exercises personally may be equally informing. They may enhance our empathy, sharpen our advisory perspective and remind us that the work we do is ultimately about people, not just plans.

Practical Takeaways

While the concepts discussed here are deeply personal, they may and should be translated into practical steps within our practices.

1.      Additions to Documents You May Consider

Incorporating language into an advanced health care directive that focuses on quality of life will provide helpful guidance to a health care agent and family and should be personalized to each client. I have included language below for your consideration.

I offer the following additional guidance of an advisory but non-binding nature for decisions to be made by my Health Care Agent: 

• I wish to live life to the fullest. However, if I am no longer able to interact with and enjoy my loved ones [and to care for myself], I am okay to end my struggles. It is quality and not quantity that matters. I wish to ease the burden on my loved ones and I have faith that my Health Care Representative will make the decisions I would have made. I am not afraid of death.[vi]

• If I suffer a brain injury or disease such as dementia or Alzheimer’s Disease that does not rise to the level of an end-stage medical condition but that destroys my ability to interact with and enjoy loved ones and to care for myself, my Health Care Agent should strongly consider declining all treatment except that which will alleviate my pain. 

• If feasible (taking into account financial, medical and emotional factors), when the time comes, I would prefer to stay in my home and to have hospice nurses and other caregivers, as needed, come to my home.[vii] 

• In making arrangements for my care, my Health Care Agent should choose doctors, hospitals, procedures and treatment options based upon what my Health Care Agent considers best after investigation and consultation with professionals, rather than exclusively based on what my medical insurance will cover.

2.      Expand the Scope of Conversations

Incorporate questions about quality of life, not just assets and beneficiaries. Even a brief inquiry, such as “What matters most to you? And would that change if you were seriously ill?” - may open meaningful conversation.

3.      Connect with Outside Resources

Tools such as Five Wishes and The Conversation Starter Guide provide accessible guidance for clients. Offering these resources may help clients begin thinking about issues they may otherwise avoid (and that you may feel uncomfortable about discussing in detail).

4.      Emphasize the Selection of the Right Decision-Maker

Guide clients through the attributes of an effective surrogate decision-maker. Encourage them to consider not only trust, but temperament, availability and ability to navigate complex situations. Most importantly, dissuade them from appointing someone out of guilt or obligation (for example, their oldest child).

5.      Encourage Communication, Not Just Documentation

Make it standard practice to ask clients whether they have discussed their wishes with their chosen agents and broader family and friends. If not, recommend they do so, and if possible, provide guidance (or resources) on how to do so.

6.      Revisit and Update

End-of-life preferences are not static. Health status, family dynamics, life experiences and personal values evolve. As people evolve through different life stages, their views about life and death may very well change. Regular reviews should include not only legal updates, but reaffirmation (or revision) of wishes.

7.      Lead by Example

Professionals who have engaged in their own (or a loved one’s) end-of-life planning are often more effective in guiding clients. There is credibility - and authenticity - in speaking from experience. I know that my views are greatly influenced by my experience with my father’s prolonged illness and his much later death.

Conclusion: Planning as an Act of Humanity

At its core, estate planning is at the intersection of planning from both the technical and human side. A plan may save all the taxes in the world, but if it does not consider the fact that people have to live “in it,” it will likely fail. Planning to live life well at the end of life and then dying will include a discussion of assets, but also of values, relationships and dignity. If needed, advanced health care directives will have the greatest impact on our clients personally.

By assisting clients articulate what quality of life means to them, by ensuring they appoint trusted decision-makers, and by fostering open, ongoing conversations, we may elevate our practice beyond technical expertise.

We may assist clients to live more intentionally in the present, and we will ease the burden on those who will one day be called to act on their behalf. In so doing, we are reminded that the true measure of a plan is not only how efficiently it transfers wealth, but how faithfully it reflects the life and values of the person who creates it.

Kim V. Heyman is a Director in the Wealth Planning Group at Pathstone, a multi-family family office. Kim focuses on advising ultra-high-net-worth individuals and families on legacy, wealth and philanthropic planning. Before joining Pathstone, Kim has over 20 years of experience advising ultra-high-net-worth families on estate, gift and generation-skipping transfer tax issues, philanthropic structures and special needs planning, most recently (before Pathstone) as a partner in a boutique trusts and estates law firm. She has authored articles and spoken locally and nationally on estate planning, charitable planning and trust and estate administration topics. She sits on the Board of the PEPC. Kim is the Co-Chair of the Fiduciary Administration Committee, and was previously the Co-Chair of the Emotional and Psychological Issues in Estate Planning Committee, of the American Bar Association’s Real Property, Trust and Estate Law Section.

[i] Over the years, several organizations and authors have created frameworks to help individuals navigate these questions. Among them are “Five Wishes,” Aging with Dignity (fivewishes.org) (“Five Wishes”); “Your Conversation Starter Guide,” The Conversation Project (https://theconversationproject.org/get-started) (“Your Conversation Starter Guide”); and “ Hello - The Conversation Game for Living and Dying Well” by Common Practice (https://commonpractice.com/products/hello-game) (“Hello”); Rev. Dr. Elizabeth T. Boatwright, The Last Things We Talk About (2018) (“The Last Things We Talk About”); Anita Hannig, The Day I Die: The Untold Story of Assisted Dying in America (2016) (“The Day I Die”) and Coventry Edwards-Pitt,  Aging Healthy, Wealthy & Wise (2017) (“Aging Healthy, Wealthy & Wise”). Each invite us to consider end-of-life planning not as a clinical or transactional process, but as an opportunity to define and to communicate what quality of life means to us.

[ii] See e.g., “Five Wishes” or “Your Conversation Starter Guide.”

[iii] The Last Things We Talk About.

[iv] See, e.g., Adam B. Kushner, “What Do Vegetative Patients Know,” The New York Times Magazine, April 12, 2026.

[v] The Day I Die and Hello.

[vi] Only include the highlighted statement if it is true for the client.  My father told this to my older siblings, and it made an awful situation that much easier when the time came to make the decision to place my father on hospice.

[vii] It is more standard for someone to have hospice in the home than at a facility, but sometimes there is an option.  It is important to explain to families the limited role a hospice services provider plays, and the necessity of hiring additional care givers, unless the family is able and willing to take care of the physical needs of the patient.