You know you need to have the conversation.
You’ve known for months. Maybe years. You’ve started to bring it up at Thanksgiving. You’ve thought about it during doctor’s appointments. You’ve drafted texts to your siblings that you never sent.
“We should really sit down and talk about Mom and Dad’s wishes.”
And then life happens. Someone changes the subject. The moment passes. You tell yourself you’ll do it next month.
Here’s what I’ve learned after twenty years as a funeral director: Every family that tries to plan these conversations themselves has the best intentions. They genuinely want to get it done. They understand it’s important.
But intention and execution are separated by a massive gap that most families can’t bridge on their own.
Why DIY End-of-Life Planning Fails (Even for Functional Families)
Let me be clear about something first: The families who struggle with DIY planning aren’t dysfunctional. They’re not communication-averse. They’re not avoiding responsibility.
They’re normal families facing an abnormal task.
Planning for death requires skills that have nothing to do with how much you love each other or how well you normally communicate. It requires navigating emotional territory most people have never mapped, asking questions you’ve never been trained to ask, and documenting decisions in ways that actually hold up under pressure.
Here are the specific reasons DIY planning fails, even for families with every advantage:
1. Nobody Knows How to Start
The first barrier is simply beginning the conversation. Who brings it up? When? How do you transition from “pass the potatoes” to “let’s talk about what happens when you die”?
Most families solve this by not solving it. Someone mentions it vaguely. Someone else says “we should definitely do that sometime.” Everyone agrees it’s important. Nothing happens.
Even families who manage to start the conversation often do so awkwardly, often in moments of high emotion (right after a funeral, during a health scare) when clarity is nearly impossible. Or they try to squeeze it into existing family gatherings where the emotional bandwidth doesn’t exist for deep planning. Peoples’ memories of these discussions if often less than strong as well.
The question isn’t just “how do we start?” It’s “how do we start in a way that actually leads somewhere productive?”
2. The Emotional Weight Derails Everything
Death planning isn’t like financial planning or vacation planning. You can’t approach it purely rationally because mortality is uncomfortable and grief is already present in the room, even before anyone has died.
When families try to have these conversations themselves, emotions surface that nobody knows how to handle:
A parent gets tearful talking about not being a burden. An adult child who’s been the primary caregiver starts expressing resentment. Someone who’s been avoiding thinking about their parent’s mortality suddenly confronts it directly and shuts down. An estranged family member says something that triggers old wounds.
Without guidance, these emotional moments either derail the entire conversation or get bulldozed over in service of “just getting through this.” Neither approach works well.
Emotions aren’t the problem. Emotions are data. They tell you what matters, what’s frightening, what’s unresolved. But processing them while simultaneously making critical decisions requires skills most families simply don’t have.
3. Family Dynamics That Work in Daily Life Break Down Under Pressure
The roles that serve your family well at birthday parties and holiday dinners often collapse under the weight of end-of-life planning.
The family peacemaker tries to make everyone comfortable and avoids asking hard questions. The family organizer takes control and steamrolls over quieter voices. The sibling who lives closest to aging parents feels taken for granted. The one who lives far away feels excluded from decisions. The golden child and the scapegoat replay decades-old dynamics.
These patterns are usually manageable in normal family life. But death planning isn’t normal family life. It surfaces power dynamics, favoritism, resentment, and fear in ways that Sunday dinner never does.
Families need someone outside the system who can see these dynamics clearly and navigate them without triggering defensiveness. When your brother suggests you’re being controlling, it’s a fight. When a professional facilitator gently redirects the conversation to ensure everyone is heard, it’s expertise.
4. You Don’t Know What You Don’t Know
This might be the biggest barrier to DIY planning. Most families have no framework for what needs to be discussed.
You might cover burial versus cremation. You might talk about who gets the house. You might even discuss whether someone wants to be on life support.
But do you know to discuss:
- Terramation (human composting) as a disposition option now legal in fifteen states including New York?
- Aquamation (water cremation) as an environmentally gentle alternative available in twenty-eight states?
- The difference between a healthcare proxy and a living will, and why you need both?
- What “do everything possible” actually means in medical terms, and whether that aligns with someone’s values?
- How long-term care decisions interact with Medicaid planning?
- What happens if the designated healthcare proxy is unwilling or unavailable when decisions need to be made?
- Whether anatomical donation to medical science is something the person has considered?
- Who has access to digital assets and online accounts?
- What the actual cost difference is between disposition options in your area?
- How to document wishes in a way that’s legally enforceable versus just emotionally meaningful?
Most families cover about thirty percent of what actually needs to be addressed. Then they think they’re done because they don’t realize what they missed.
I bring a checklist developed over two decades of watching families navigate crisis. I know which gaps cause problems. I know which assumptions lead to conflict. I know what needs to be documented and how.
5. The Follow-Through Problem
Even families who manage to have a good conversation often fail at execution.
You talk about advance directives but nobody actually drafts them. You discuss estate planning but never schedule the attorney appointment. You agree on funeral preferences but don’t document them anywhere the funeral home will find them. You designate a healthcare proxy verbally but never formalize it legally.
Six months later, when a health crisis happens, you discover that the conversation you had was emotionally meaningful but practically useless because nothing was documented, nothing was executed, and nobody can remember exactly what was decided.
Professional facilitation includes accountability. I don’t just guide the conversation. I provide worksheets, documentation, professional referrals, and follow-up to ensure the planning actually gets completed.
6. Assumptions Masquerade as Clarity
Here’s a scenario I see constantly:
A family sits down and asks Mom what she wants. Mom says, “I want to be cremated and I want a simple service.”
Everyone nods. Everyone feels good. The conversation is over.
Except nobody asked: What does “simple” mean to you? Do you want a memorial service or a celebration of life? Religious or secular? Who should speak? What music matters to you? Should it happen right away or can we wait for out-of-town family? What should happen to the cremated remains? Do you want any portion scattered, and if so, where? How much are you comfortable spending?
One person’s “simple service” is a quiet graveside gathering for ten people. Another person’s “simple service” is a catered reception for a hundred guests with a photo slideshow and live music.
When Mom dies and siblings have different interpretations of “simple,” the conflict isn’t about misunderstanding Mom’s wishes. It’s about never actually clarifying them in the first place.
I ask the follow-up questions. I push past vague language to specific details. I ensure that what feels like clarity in the moment will still be clear five years from now when memories have faded and stakes are high.
What Professional Facilitation Actually Provides
Setting the Table isn’t just “having someone there while you talk.” It’s a structured process that addresses every failure point of DIY planning.
Here’s what changes when you work with a professional:
Structure Without Rigidity
I bring an agenda that ensures we cover everything critical, but I’m trained to follow the emotional flow of your family. If someone needs to cry, we pause. If a topic needs more time, we take it. If a tangent reveals something important, we explore it.
You get the benefit of structure (nothing gets missed) without the constraint of rigidity (emotions and dynamics are honored).
Psychological Safety
As a certified grief counselor, I create conditions where people can be honest about fear, uncertainty, and conflicting feelings without judgment.
When your parent says they’re afraid of being a burden, I know how to hold that fear while also getting practical information. When siblings disagree, I know how to validate both perspectives while moving toward resolution. When someone gets overwhelmed, I know whether to push forward or create space.
This isn’t therapy. But it is therapeutic. Families often tell me they feel closer after our sessions because they’ve been honest with each other in ways they rarely are.
Expertise That Prevents Costly Mistakes
I know what the funeral industry charges for different services. I know which decisions have to be made immediately and which can wait. I know what’s legally required versus what’s optional. I know which choices align with which values.
When a family tells me they want “green burial,” I can explain that this might mean purchasing a plot in a conservation cemetery, or it might mean choosing terramation where the body becomes soil that can be returned to family, or it might mean aquamation as a gentler alternative to flame cremation, or it might mean a natural burial in a conventional cemetery that allows it.
I can explain cost differences, availability in your area, and the environmental impact of each option. I can help you understand whether your values are best served by the option you initially assumed or by something you didn’t know existed.
This prevents the scenario where you make decisions based on incomplete information and later discover you would have chosen differently if you’d known all the options.
Neutral Authority
When I redirect a dominating family member or draw out a quiet one, it doesn’t trigger the same defensiveness that a sibling’s intervention would.
When I point out that someone’s wishes seem unclear, it’s professional observation rather than accusation.
When I suggest that a decision needs more discussion, it’s expertise rather than obstruction.
My presence changes the power dynamics in the room. Nobody can claim later that they were bulldozed or ignored because there was a witness whose job was ensuring everyone was heard.
Documentation That Holds Up
I don’t just facilitate conversation. I create records.
Every participant leaves with completed worksheets documenting wishes, decisions, and next steps. These aren’t just for memory. They’re designed to be useful when you’re sitting in a funeral home or a hospital conference room making decisions under pressure.
I also connect families with estate planning attorneys, financial advisors, and elder law specialists who can formalize what we’ve discussed into legally binding documents.
The conversation is the foundation. The documentation and professional follow-through are what make it actionable.
The Setting the Table Process: How It Actually Works
Let me walk you through what happens when you book Setting the Table, so you understand exactly what you’re getting.
Before We Meet
After you book, I send a brief questionnaire asking about your family composition, primary concerns, and any specific issues you want to make sure we address. This isn’t about gathering extensive background. It’s about ensuring I understand who’s at the table and what you’re hoping to accomplish.
About a week before our first session, I send gentle conversation starters you can share with family members if you want to. These are optional. Some families like the prep. Others prefer to come in fresh.
The Three-Session Dinner Series (Recommended)
Session One: Foundation and Trust (Two to Two and a Half Hours)
We start with the basics, but “basics” doesn’t mean easy. We’re establishing how this family communicates, what ground rules everyone needs, and what the easier topics reveal about harder ones to come.
We cover disposition preferences. Not just burial or cremation, but the full range: traditional burial, green burial, cremation, terramation (legal in fifteen states including New York), aquamation (legal in twenty-eight states), above-ground entombment, anatomical donation to science. We talk about what matters to each person and why. Environmental impact? Religious tradition? Cost? Family expectations? Simplicity?
We discuss funeral or memorial service preferences. Religious or secular? Intimate or large? Immediate or delayed? Who should speak? What music matters?
We create notification lists. Who needs to know right away? Who should be invited to the service? Who should absolutely not be contacted?
By the end of session one, families usually realize two things: they knew far less about each other’s wishes than they thought, and they’re capable of having these conversations without falling apart.
Most families leave hungry to continue.
Session Two: The Deep Work (Two and a Half to Three Hours)
This is where we earn our money.
We go into medical decision-making: advance directives, healthcare proxy designation, living wills, DNR orders. We define what “quality of life” means to each person. We discuss what “do everything” actually entails medically. We talk about what “don’t let me suffer” looks like in practice.
We address long-term care: home care versus facility care, assisted living versus nursing home, hospice preferences, caregiver expectations. Who will be the primary caregiver if that’s needed? What financial resources exist for care? Has anyone considered Medicaid planning?
This session is where family dynamics show up hard. The sibling who’s been the primary caregiver for years expresses resentment. The one who lives far away feels guilty. The parent who doesn’t want to burden anyone struggles to accept they might need help.
My grief counseling training is essential here. We don’t avoid the emotions. We move through them. We acknowledge fear and resentment and grief while still getting to clarity.
Families leave this session exhausted and relieved. The hard part is done.
Session Three: Integration and Action (Two Hours)
We review everything decided in sessions one and two. We confirm that everyone is clear, that nothing was misunderstood, that no critical questions remain unanswered.
We discuss next steps with legal and financial professionals. Who needs to draft or update a will? Who needs to formalize their advance directive? Who needs to meet with a financial advisor about estate planning or long-term care costs?
I provide referrals to trusted professionals in each area. The planning doesn’t end with our conversation. It becomes legally binding through proper execution.
We also create space for the legacy conversation. What do you want to be remembered for? What values are you passing on? If you could tell your family one thing they’ll carry forward after you’re gone, what would it be?
This session often feels less like planning and more like honoring. It’s a celebration of having done something most families never do.
The Single Dinner Option
Not every family needs three sessions. Some can accomplish everything in one intensive evening.
Our single Setting the Table dinner runs two and a half to three hours and covers the essential ground: disposition wishes, service preferences, medical decision-making, long-term care, family roles, and professional referrals.
It’s condensed but comprehensive. You’ll leave with documented wishes and a clear action plan.
For all Setting the Table dinner experiences, whether single session or three-session series, you can add optional upgrades: a private chef who prepares a beautiful meal in your home (two hundred fifty dollars per person), or curated wine pairings (one hundred dollars per person) that create a warm, elevated atmosphere for difficult conversation.
The Essential Conversation (For Couples or Individuals)
If you prefer a streamlined, business-focused approach without the dinner element, The Essential Conversation offers ninety to one hundred twenty minutes of expert planning facilitation.
This is designed for up to two people doing actual planning (typically a couple or an individual) with the option to include up to two additional family members as listeners.
No meal. No wine service. Just focused work getting your planning done right.
Who Benefits Most From Professional Facilitation
Setting the Table isn’t for everyone. Some families genuinely can handle these conversations themselves. They have exceptional communication skills, low conflict, clear roles, and someone with expertise in estate planning or end-of-life care who can guide the process.
If that’s your family, you don’t need me.
But you probably do need professional facilitation if:
Your family has any history of communication difficulty or conflict, even minor. These conversations amplify existing dynamics.
You’ve tried to have this conversation before and it didn’t happen or didn’t go well.
There are complicated family dynamics: blended families, estranged members, favoritism, unequal caregiving, past resentment.
The person whose wishes you’re documenting struggles with being vulnerable or asking for help.
You want to ensure nothing critical gets missed and you’re not confident you know what all the critical elements are.
You value peace of mind enough to invest in expert guidance rather than hoping you get it right on your own.
You’ve watched other families fall apart over estate and funeral conflicts and you’re determined to prevent that in yours.
The Cost-Benefit Analysis
Let’s talk about money, because I know you’re thinking about it.
Setting the Table costs anywhere from several hundred dollars for a virtual Essential Conversation to several thousand dollars for the complete three-session in-person dinner series with premium upgrades.
That’s real money. I’m not pretending it’s not.
Here’s what you’re comparing it against:
DIY Planning That Fails: You spend months trying to coordinate schedules. You finally get everyone together. The conversation lasts fifteen minutes before someone gets uncomfortable and changes the subject. Nothing gets documented. You feel like you tried and failed. When crisis hits, you’re exactly where you would have been if you’d never tried at all.
Cost: Free, but also worthless.
Estate Planning Attorney Alone: A good estate planning attorney charges anywhere from two thousand to five thousand dollars (or significantly more for complex estates) to draft wills, trusts, and advance directives. That’s money well spent and you absolutely should hire one.
But the attorney can only document what you tell them. If you don’t actually know what your parents want, if you haven’t had the conversations about values and priorities, if family members have different understandings of wishes, the attorney can’t fix that. They can create legally binding documents, but they can’t prevent family conflict if the documents don’t reflect clearly understood wishes.
Crisis Management After the Fact: When someone dies or becomes incapacitated without clear planning, families face contested estates, guardianship proceedings, medical decision litigation. Legal fees can reach tens of thousands of dollars. Court battles drain estates and family relationships simultaneously.
Even families who avoid legal intervention pay in other ways: rushed funeral planning that costs more than it should because decisions are made in crisis mode, medical care that continues for weeks or months because nobody knows when to stop, family conflict that leads to estrangement.
Setting the Table Prevents All of This: What you’re paying for isn’t just facilitated conversation. You’re paying for:
Prevention of legal conflicts that cost far more than our fees.
Medical clarity that prevents unwanted interventions and associated costs.
Funeral planning knowledge that helps families make cost-effective choices aligned with values.
Family relationship protection that has no price tag but infinite value.
Peace of mind that the people you love will know what to do when crisis hits.
When you frame it that way, professional facilitation isn’t an expense. It’s one of the highest-return investments a family can make.
Available Wherever You Are
I personally serve families in the Hudson Valley region of New York, throughout the NYC Metro Area, and in the Philadelphia Metro Area. For these locations, I come to your home and facilitate in person.
Through my network of carefully vetted licensed funeral directors who share my approach and training, Setting the Table is also available in the Washington DC Metro Area and Tampa Bay, Florida.
And for families anywhere in the country, virtual Setting the Table sessions provide the same expert facilitation through secure video conferencing. Virtual works beautifully for families spread across multiple states or for anyone who prefers the convenience of video facilitation.
What Families Say After
I want to share something I hear constantly from families after we complete Setting the Table.
They tell me they expected it to be difficult, uncomfortable, maybe even painful. And parts of it are. Talking about death and mortality and loss is inherently heavy.
But they also tell me it was meaningful. Intimate. Connecting.
They tell me they learned things about their parents they’d never known. They tell me their siblings showed vulnerability they rarely see. They tell me the conversation brought them closer rather than driving them apart.
One daughter told me, “I finally felt like my parents saw me as an adult capable of handling hard things. That mattered more than I expected.”
A son said, “My brother and I have never talked about anything real. This forced us to. I didn’t realize how much I needed that.”
A mother said, “I’ve been so afraid of burdening my kids with this. Telling them clearly what I want felt like giving them a gift, not a burden.”
The conversation you’re avoiding because you think it will be awful might actually be one of the most meaningful your family ever has.
Ready to Stop Trying to DIY This?
If you’ve read this far, you already know DIY planning isn’t working for your family.
Maybe you’ve tried and failed. Maybe you’ve been meaning to try and can’t seem to make it happen. Maybe you’re realizing that even if you could get everyone in a room, you don’t know how to navigate what comes next.
Here’s what I want you to do:
Book a discovery call with me. We’ll spend twenty to thirty minutes talking about your family’s specific situation, what you’re trying to accomplish, and whether Setting the Table is the right fit.
No obligation. No pressure. Just a conversation about whether professional facilitation makes sense for you.
The families who benefit most from Setting the Table aren’t the ones with the most money or the best communication skills or the simplest dynamics.
They’re the families who recognize that some things are too important to leave to chance.
Is protecting your family relationships worth one phone call?
About Michelle
Michelle is a third-generation licensed funeral director, certified grief counselor, and end-of-life planning expert with over twenty years of experience in death care and family services. After watching countless families struggle with DIY planning that failed when crisis hit, she created Setting the Table to provide the professional facilitation, expertise, and structure that makes difficult conversations successful.
She serves families throughout the Hudson Valley, NYC Metro area, and Philadelphia region in person, with virtual services available nationwide. Her approach combines funeral industry knowledge, grief counseling expertise, and practical planning skills to ensure families get clarity, documentation, and follow-through.
Questions about whether your family would benefit from facilitation? Schedule a discovery call / Learn more about Setting the Table