I wasn’t expecting a restaurant to stop me in my tracks.

But last week, — the author of The Art of Gathering and someone whose thinking has quietly shaped how I design every session I facilitate, — had a fascinating conversation with , the chef and owner of Sofreh, a Persian restaurant in Brooklyn.

Nasim opened Sofreh at 59. No restaurant experience. A lifetime of cooking for family, for friends, for anyone who showed up hungry.

She’d been asking herself a question for years before she opened:

I read that, and it gave me pause for a time.

Because that question — what is my role now — is one I hear underneath almost every conversation I have with families navigating end-of-life.

Sometimes it comes from the person who is dying.

More often, it comes from the people who love them, suddenly responsible for decisions they were never prepared to make.

Priya distilled ten lessons from her conversation with Alikhani. And one by one, I kept finding my work in them.

Not metaphorically. Literally.

Seth Godin wrote something recently that I keep returning to alongside all of this:

Nasim knew why. That’s what made the difference between a beautiful idea and a restaurant that actually exists, that people actually walk into, that actually changes how they feel — for one night, maybe longer.

This series is my attempt to sit with each of Priya’s ten lessons and ask what they have to say about the work of dying supported. Not as a stretch.

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Not as a clever pivot. But because I genuinely believe that how we host people through the end of life — whether we show up and simply stay, whether we feed our own people first, whether we stay students of our own work — matters more than any checklist or document.

Over the next ten posts, we’ll take them one at a time.

— Patricia

Next: What is my role now? The question Nasim Alikhani asked before opening Sofreh — and the one most of us avoid asking about the end of our lives.

→ Start Here

This is the fifth and final post in a series drawn from my April 15th conversation with end-of-life doula and author . Start at the beginning if you’re just joining us.

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I did not expect this conversation to give me permission.

That’s not usually how it goes. You sit with an end-of-life doula for an hour, and you expect to come away a little more sober.

A little more aware of your own mortality.

Maybe slightly inconvenienced by the fact that you still haven’t done your advance directive.

Instead, Diane Button said this:

Hmm, that made me pause for a minute.

However long the journey — years of preparation after a diagnosis, or no warning whatsoever, just a heart attack on an ordinary Tuesday — death happens on one day. One delineation, as Diane calls it, from this lifetime.

All the other days are something else entirely.

We got into language, because of course we did.

Patty raised it first — the question of what to call ourselves. Death doulas. End-of-life doulas. Does the name actually matter?

And look, I’ll be honest: This made me think, ‘this was going to be a branding conversation.’ It was not a branding conversation.

Diane’s point was simple, and it landed hard. Death doula grabs attention in the media. It’s loud, it works, it gets the click.

But when she walks into someone’s home — someone who is dying, but not dying today — she is not there for death.

She’s there for life. The name tells the person in the bed who just walked through the door.

Pastor Laurence put it in a way that stopped the whole room:

Dark and blank. That’s what the word does to people. It shuts everything down before the conversation can even start.

End of life opens it.

And then Patty said something I haven’t been able to shake.

She knows someone who, as they were dying, shouted:

Seven words. The whole philosophy, right there.

Preparation and living are not in opposition.

You can be ready and still be completely here. You can know what’s coming and still take in everything that’s in front of you right now.

These are not contradictory positions. I don’t know why we treat them like they are.

Diane does something small every day to stay honest about this. She stops — just for a moment — and actually looks at something. A flower. A bird. Something on her plate. Something ordinary she might otherwise walk straight past.

And she lets it remind her: this is all going away someday. So pay attention. Right now. This one.

Not morbidly. Gratefully.

Before we closed, Pastor Laurence shared something that a minister who was also a psychotherapist had told him early in his career.

This man had a particular gift — he could sit with other people’s grief without being flattened by it. Laurence finally asked him how.

The answer: a wheelbarrow.

I listen to everything, he said. I put it in the wheelbarrow. And when I leave the office, I dump it. And move on.

Diane lit up at this.

He didn’t put it in a backpack, she said. He held it — he was fully willing to take it on. He just didn’t strap it to himself and walk home with it.

That is the distinction that makes twenty years in this work possible. You hold it while you’re there. You set it down when you leave. You come back whole.

That’s not detachment. That’s how you stay.

This series started with a mistake — I forgot to hit record — and ended up being some of the most important writing I’ve done this year.

Not because of anything I said.

Because of what Diane Button spent twenty years learning at the bedside. And was generous enough to bring it into our room.

Death is just one day.

Everything before it is yours.

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The next Legacy Leaders Guide cohort begins in May. If this series has opened something in you — a conversation you need to start, a relationship that needs tending, a story that deserves to be told — this is where we go deeper.

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This is the fourth post in a series drawn from my April 15th conversation with end-of-life doula and author Diane Button. Start at the beginning if you’re just joining us.

Diane Button showed up to Floyd Barker’s house with everything.

A doula bag heavy enough to be a travel suitcase. Stationery. Pens. Supplies for every possible thing a dying person might need or want that day. And the clipboard. A hundred questions, just in case.

She was ready for anything.

Floyd was a widower. Still grieving his wife, years after she’d gone. He’d sit on the porch where they used to sit together — and that’s where Diane found him. They sat. They talked. They listened to the birds.

And when it was time to go, Diane walked to her car and realized something.

She hadn’t touched the bag. Hadn’t written a single note. Hadn’t asked a single question from the clipboard.

She’d just been there.

That, she said, taught me everything about showing up without an agenda.

The bag got lighter after Floyd. The clipboard eventually disappeared. What Diane learned — slowly, the hard way, the only way you really learn anything in this work — is that presence is the whole job. Not preparation. Not documentation. Not the hundred questions.

Just being there, fully, with nothing in the way.

But Floyd had more to teach her.

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One day, his son couldn’t take him to a doctor’s appointment, so Diane did. And somewhere in the waiting room of that office, she understood something she hadn’t quite seen before.

Floyd was lonely.

She’d been visiting him regularly. She was there. How had she missed it? Because when she was with him, the loneliness lifted. It was only outside — in the world, among strangers — that she could finally see it.

At the front desk, Floyd stepped up bright-eyed and ready.

“My name is Floyd Barker,” he said — smiling, excited, like he was introducing himself at a party.

The woman behind the counter didn’t look up. Name? she’d said. Birthday? Have a seat.

He sat. He kept talking to Diane. They called him in.

The nurse took his blood pressure. Never looked him in the eye.

And then the doctor came in.

That was it. That was all it took. On the way home, Floyd talked about how much he loved that doctor. How she always made him feel so welcome.

One person looked him in the eye. One person said his name like it mattered.

And it changed his whole day.

Diane has never forgotten that. Neither have I.

Because how many Floyds are out there right now — in waiting rooms, in grocery stores, in the apartment next door — moving through their days mostly unseen? Not asking for much. Just to be looked at. To have their name said like it means something.

Maya Angelou said it plainly: people will forget what you say. They’ll forget what you do. But they will never forget how you made them feel.

Floyd knew that. He just needed someone to notice.

This is what end-of-life work keeps teaching me, over and over, in every direction.

The preparation matters. The documents matter. The questions matter.

But underneath all of it — underneath the clipboard, the bag, and the checklist — is something simpler.

Show up. Put the bag down. Look people in the eye.

That’s the whole thing.

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Ready to go deeper?

The next Legacy Leaders Guide cohort begins in May. If this series has opened something for you — if there’s a conversation you’ve been putting off, a relationship that needs tending, a story that deserves to be told — this is where we do that work together.

👉 Join the Waiting List

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The Start the Conversation workshop is held quarterly, with the next at the end of July, capped at 20, and designed for people who are ready to stop putting this off.

End-of-life planning is an act of love. When you’re ready to start that conversation, the link below has everything you need — including how to hold your spot when registration opens.

Everything You Need

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The Crossbow Problem

There’s a moment in a video game where you find a crossbow with no arrows.

In real life, you’d walk past it. Why carry something useless?

But in the game, you pick it up. Because somehow you just know — the arrows are coming.

Productivity expert Tanya Dalton used that image recently to talk about worry.

About how most of what we’re afraid of isn’t really about our circumstances.

It’s about whether we trust the path we’re on.

I’ve been sitting with that crossbow image for hours now.

Here’s what I know about the families I sit with.

They didn’t avoid end-of-life planning because they didn’t care.

They avoided it because the worry about doing it wrong felt worse than doing nothing at all.

What if I choose the wrong person to make decisions for me?
What if I say I want one thing and then I want another?
What if this conversation breaks something that can’t be repaired?

Dalton calls this catastrophizing.
Fortune-telling.
Stealing responsibility for outcomes that were never ours to control.

I call it being human.

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But here’s the thing about the crossbow.

The arrows always come. Not because the universe is tidy.
It’s because you showed up. You picked up the thing. You started moving.

That’s what starting the conversation actually is.
Not a document.
Not a checklist.
Not getting it perfect.

It’s picking up the crossbow.

Dalton offers three reframes for chronic worriers. I want to borrow one.

She says most worry, when you strip it all the way down, is really one thing. Her example: three different worries about her son all collapsed into a single wish —
I want my kid to be happy.

I see this in end-of-life planning all the time.

What if no one knows what I want?
What if my family fights?
What if the medical system overrides everything?

Strip those down. What’s the real thing?

I don’t want to be a burden to the people I love.

I want to be known.

That’s it. That’s the whole thing.
And once you name it — planning stops being paperwork and starts being an act of love.

If you’ve been carrying the crossbow — waiting for the right moment, the right words, the right window — I want to offer you the arrows.

Starting the Conversation is a 60-minute live workshop on April 23 at 8a ET.

Not a course. Not a commitment.

One hour to move from I should do this someday to I know exactly where to begin.

That’s it. That’s the whole ask.

The arrows were always coming. This is them.

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What’s your version of the crossbow? The thing you’re carrying but haven’t quite acted on yet? Drop it in the comments.

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This is the third post in a series drawn from my April 15th conversation with end-of-life doula and author Diane Button. Start at the beginning if you’re just joining us.

When Diane Button first started showing up at people’s homes as an end-of-life doula, she carried a clipboard.

A hundred questions on it. Just in case.

She thought she was being prepared. Thorough. Professional.

What she was actually doing — she realized over time — was interviewing people who were dying. People who already had hospice coming in, asking medical questions over and over. People who didn’t need one more person with a clipboard. They needed someone to put the clipboard down and listen.

So she did. And over years — many years — she distilled a hundred questions into six.

Six questions she asks her clients. Six questions she asks herself. Every single month, without fail. She calls it keeping a clean slate.

I want to give them to you now. Not summarized. Not paraphrased. Just the questions themselves, the way Diane offered them — one at a time, with room to breathe between each one.

1. Who matters most?

Who are the most important people in your life right now?

Diane notes this one doesn’t change all that often. But the act of naming them — out loud, on paper, in your own mind — matters. Because we move so fast we sometimes forget to tell them.

2. What matters most?

This one does change. Week to week, month to month, season to season. What matters most to you right now may be completely different from what mattered most six months ago.

The question isn’t just what — it’s whether your energy is actually going there.

3. What is left unsaid?

It doesn’t have to be something enormous. Diane is clear about that. It might be a call you haven’t returned that’s sitting in the back of your mind. An apology you owe someone. A thank you that never made it out of your head.

Small things left unsaid have a way of becoming large things at the end.

4. What is left undone?

This one lives at the intersection of legacy and procrastination.

Nobody dies with everything done — Diane will tell you that plainly. But there are things that are important to you that you keep pushing to later. This question asks you to look at them honestly.

Later has a way of not arriving.

5. What are you worrying about when you’re lying awake at night?

This is the one Diane calls her most important clinical question. And here’s why: it replaces a dozen others.

She doesn’t have to ask: Are you scared of dying? Are you at spiritual peace? Are you worried about your kids? One question surfaces all of it. Because whatever is keeping you awake at night is telling you exactly where you need support.

Ask yourself that tonight. Really ask.

6. What brings you joy in the daytime?

Not the vacations. Not the concerts. Not the fancy restaurants.

The morning cup of coffee. The walk with a friend. Sitting on the porch listening to birds. Diane has watched joy get simpler and simpler the closer people get to the end of their lives. The big things fall away. What remains is so ordinary it’s easy to miss entirely.

Don’t miss it.

When Diane shared these with our Graceful Lifers, every hand went up at once.

Become a Graceful Lifer

Mary spoke first. She said that what is left undone had already started working on her — she’d begun going through her papers and things, slowly, every day. Not as a chore. As a kind of treasure hunt. She’d been finding photos, notes, small pieces of her life — and sending them to the people they belonged to.

“It’s making me joyful,” she said. “And it’s making other people joyful.”

Diane pointed out that Mary was doing three things at once without realizing it — a legacy project, a life review, and lightening her load. All from sitting with one question.

That’s what these six questions do. They don’t demand grand gestures. They just ask you to pause. To notice. To do the small thing you’ve been putting off.

Here’s what I’d invite you to do.

Don’t answer all six today. Pick one. The one that made you catch your breath when you read it. Sit with it. Write about it if that’s your practice. Call someone if that’s where it leads.

And then come back next month. Ask it again. See what’s changed.

That’s how Diane does it. That’s how a clean slate works.

Ready to start with your own six questions?

Join me on Thursday, April 23rd, for a live Start the Conversation workshop — a guided session where we sit with exactly this kind of work together.

👉 Register here

This Thursday, April 23rd, I’m hosting the Start the Conversation Workshop. Sixty minutes, virtual, for only 20 people. $69.

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The Start the Conversation Workshop may not be for you.

And honestly? That’s fine. Not everything is for everyone. I’ve made peace with that.

But here’s who it is for.

It’s for the person who has been the one everyone else leans on — and who has been quietly, persistently, maybe a little guiltily aware that they haven’t yet made things clear for the people who will one day need to lean on something they’ve left behind.

You know this matters. You’ve said “I really need to do this” out loud. Possibly more than once. Possibly to yourself in the car.

And yet.

Thursday is 60 minutes and a structure.

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Not a lecture.

Not a guilt trip — lord knows you don’t need another one of those.

Just a guided hour where you leave with more clarity than you arrived with and an actual path forward.

If that's where you are, the button is here. I'd love to have you in the room.

Your Registration Link

She Couldn’t Keep Her. But She Could Accompany Her.

I read this piece in the New York Times three times.

Not because it was comfortable. Because it wasn’t.

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Julie Rehmeyer didn’t know her friend Beth was going to die in her casita. She brought her muffins. She massaged her neck. She sat with her by the fire and listened — really listened — while Beth said t…

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This is the second post in a series drawn from my April 15th conversation with end-of-life doula and author Diane Button. If you missed the first one, start there.

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I want to tell you about a smile.

Diane Button held her grandfather in her arms when he died. He wasn’t a man who showed his emotions easily — but she always knew she was deeply loved by him. And when he died… he had the biggest smile on his face she’d ever seen.

She couldn’t stop thinking about it. How do you get to die like that?

What does a person have to have lived, said, resolved, let go of — to leave with a smile like that?

That question sent her to the bedside. Nearly two decades of bedsides. And it all started with a meal.

About a week before he died, Diane’s mother gathered the whole family for one last dinner. His favorites: lamb chops, potatoes, vegetables. And mint jelly — which he loved above all of it. Frank Sinatra played in the background. Everyone was there.

Mid-meal, her grandfather went quiet. He put down his fork and looked around the table — slowly, one person at a time — as if he were saying goodbye to each of them with his eyes, without a single word.

Then he spoke.

“When I die, I’m really going to miss...”

Diane thought he was winding up for something profound. Something about love, or family, or all the years.

“...mint jelly.”

She laughs telling it. You’ve got to be kidding. But she never forgot it. Because what he said without saying it — through the looking, through the meal, through Frank Sinatra and the people he’d chosen to gather around him — was everything. The mint jelly was just the punctuation.

That moment became an exercise. Diane uses it with her clients. She teaches it at UVM — the same program that trained me. And once you hear it, you’ll use it too.

It’s called, simply, the Mint Jelly exercise.

Imagine your final meal. Or if food isn’t your thing — your final hike, your final morning on the porch, whatever ritual most holds your life in it. Then ask yourself:

Who is there? What are you serving? What’s playing in the background?

And then finish the sentence: When I die, I’m really going to miss...

What Diane loves about it — and what I love about it — is that it comes in sideways. It’s not an advance directive. It’s not a hard conversation about unhealed relationships. It’s warm and familiar and almost playful. And yet what it surfaces is exactly what matters most.

I told Diane about a man I worked with not long ago. When I asked him what he wanted his final hours to feel like — the music, the light, the people — he lit up. Nobody had asked him that before.

He had a favorite rock band — wore the t-shirts every day of his life. So I asked him about a playlist of the rock band’s music.

“No,” he said. “I’ve been getting into jazz lately. It makes me feel good. That’s what I want.”

His partner — who had loved him for years, who knew him better than almost anyone — looked at me and said: “I had no idea.”

That’s the mint jelly.

It’s not always what you’d expect. It’s not always what the people who love you most would guess.

Which is exactly why you have to ask.

Finish the sentence. When I die, I’m really going to miss...

I’m going to be honest with you.

On April 15th, I sat down with Diane Button — author, educator, end-of-life doula with nearly two decades at the bedside — and we had the kind of conversation that makes you feel like you’ve been handed something you didn’t know you were missing.

And I forgot to hit record.

I know.

I was still sitting with that — a little gutted, if I’m honest — when my life partner looked at me and said: “You do it for the conversation. Not the recording.”

And just like that, the whole thing reframed itself.

Because isn’t that exactly what this work is about?

We spend so much energy on the documentation — the advance directives filed correctly, the wishes captured in the right form, the conversation recorded for posterity — that we sometimes forget the thing underneath all of it.

The conversation itself is the point.

What I do have is the transcript. Every word, every pause, every moment where something landed so hard in the room that nobody spoke for a second. And the more I sat with it, the more I realized: this material doesn’t want to be a podcast episode. It wants to be something you can return to. Something you can sit with one piece at a time, like a slow meal with people you love.

So that’s what we’re going to do.

Over the next few weeks, I’m going to bring you the best of what Diane and I talked about — and what our Graceful Lifers added, because they showed up beautifully that day. Vermont, North Carolina, Texas, the San Francisco Bay Area, all in the same Zoom room, all leaning in.

Here’s a taste of what’s coming:

A story about mint jelly, Frank Sinatra, and a grandfather who looked around the table at everyone he loved — without saying a word — before he told them what he was really going to miss.

Six questions that Diane distilled from a hundred clipboard questions she used to carry into people’s homes. She asks them of her clients. She asks them of herself. Every single month. They will stop you cold.

A man named Floyd Barker, a heavy doula bag that never got opened, and what happened when nobody at the doctor’s office looked him in the eye — except the one person who mattered.

And a wheelbarrow. You’ll understand when we get there.

None of this was lost.

It was just waiting for the right container.

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There’s a particular kind of conversation that only happens when the door is closed.

Not closed to keep people out — closed to let people in. Fully in. The kind of conversation where you can ask the question you’ve been carrying around for months, and trust that the person across from you has actually walked that ground.

That’s what tomorrow is.

Wednesday, April 15th, 4–5 PM ET. I’m sitting down live with Diane Button — and this gathering is for Graceful Lifers only.

Diane brings something to this conversation that I don’t take lightly: real, lived experience at the threshold. I think you’re going to want to hear her, and more than that, I think she’s going to want to hear you.

Because the last 15–20 minutes belong to this community. When the conversation opens for questions, bring what’s been sitting with you. The thing you’ve been turning over. The question you haven’t quite known who to ask.

That’s exactly what this space is for.

RSVP HERE

Seats are capped at 20. When they’re gone, they’re gone — and there’s no recording waiting on the other side.

This is the room. Tomorrow. I hope you’ll be in it.

I’ll see you at the threshold.

With grace | Trish

p.s. NO AI Notetakers Allowed. Thanks for understanding.

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There Is No Alternative

Margaret Thatcher had a phrase: TINA. There Is No Alternative.

Seth Godin pointed out in a recent newsletter that it’s always an incomplete sentence.

The full version:

I hear TINA constantly in my work. It sounds like this:

“There’s never a good time.”
“I’ll do it when things slow down.”
“I’m not ready.”

These aren’t excuses. They’re real. And they’re incomplete sentences.

Here’s what I’ve witnessed in hundreds of hours with families in crisis — and why it changes the calculation entirely.

This post is for Graceful Lifers. Join to read on.

Become a Graceful Lifer

We live inside a culture that has made death invisible — and that system has a quiet vested interest in keeping us from thinking too hard about what happens when we die.

Here’s what I’ve witnessed:

When someone dies without getting their affairs in order, the people left behind don’t just grieve. They search. They sort. They argue about what their person would have wanted.

They carry the weight of uncertainty on top of loss.

That cost is real. And it almost never enters the calculation when a thoughtful, capable person tells themselves there’s no good time.

The risk of doing this work: discomfort, clarity, conversations you can’t un-have.

The risk of not doing it: paid in full by the people you love, in their worst moment.

The complete sentence isn’t “there’s never a good time.”

The complete sentence is:

That’s the sentence that changes things.

Not sure where you actually stand? Take the 5-question readiness check. It takes two minutes and tells you more than you’d expect.

HowPreparedAreYou-Really

If you already know you’re ready to begin, Start the Conversation was built for exactly this moment.

Start The Conversation

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I wasn’t thinking about Singapore. Or Vietnam. Or New Caledonia.

Six months of the podcast on the major platforms. 311 downloads. 21 countries. 136 cities.

Not a metric. A miracle

Diane Button’s work starts with the dying and ends with the living. Her book What Matters Most distills what people at the end of life want everyone else to know: stop sweating the small stuff. Start noticing the ordinary ones.

Wednesday, April 15th, 4p ET. I’ll be joined live by Diane Button.

Diane co-authored The Doula Tool Kit with previous guests Gabby Jimenez and Angela Shook — and it became my bible. She also teaches in the UVM program that certified me. I've been wanting this conversation for a long time.

In What Matters Most, Diane's five components of a meaningful life stopped me: love, kindness, presence, legacy. You already know these. That's the point.

Graceful Lifers [paid subscribers]: 40 minutes of conversation, then 15–20 minutes that are yours for your questions for Diane. I’ll see you in the Zoom room.

If you've been listening since October and you're not yet in the live audience — this might be the moment. You've already shown up for these conversations. Come all the way in.

Join the GracefulLifers community

Before Wednesday: if someone in your life needs this conversation, don’t send a link.

Just say:

That’s how we got to 21 countries.

p.s. We record live on Wednesday, April 15th, 4p – 5p ET via Zoom. Details and link in the calendar invite to the Graceful Lifers community.

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The conversation you keep meaning to start.

You know the one.

You’ve thought about it. Maybe you even brought it up once — then changed the subject.

That’s not a character flaw.

It’s what happens when no one has made this feel possible.

I’m going to change that.

On April 23rd I’m opening 20 seats for Starting The Conversation — a 60-minute live virtual working session where you leave with three things in your hands:

One real conversation you can have with your family this week.

A completed end-of-life planning starter document.

A clear next step — no lawyer required, no crisis required.

This isn’t a webinar. There’s no slide deck to half-watch.

It’s a room where your specific situation gets addressed. Live. With me.

$69 per seat. $120 for two — because some conversations are easier to start together.

Registration closes April 21. 20 seats. When they’re gone, they’re gone.

Because clarity today becomes peace tomorrow.

StartTheConversation Info+Registration

And if you already know you want to go deeper — the Legacy Leaders Guide cohort begins May 21st. Five sessions. Built for people who plan everything except this. More soon.

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The folks at End Well named something in their recent newsletter that I haven’t been able to shake.

They called it the “innovation tax” — the quiet cost of navigating patient portals, password resets, telehealth platforms, insurance forms — all the systems that were never designed for the people who need them most. Or for the family members who step in to help.

“It’s a form of care we don’t often name.”

What I’d add: it gets exponentially harder when no one knows what the person receiving that care actually wants.

Navigating a portal is hard. Navigating a portal while guessing what your mother would have chosen — for this procedure, in this moment — is something else entirely.

That’s preventable.

It starts with choosing the right person to speak for you — and then actually talking to them.

When I work with people on this, I use the 3 Cs:

CHOOSING YOUR HEALTH CARE PROXY

1

Capable. Can they hold a life-and-death decision under pressure?

2

Committed. Will they show up — and keep showing up?

3

Close to your values. Do they know what YOU want — not what they would want?

Choose your person. Then have The Conversation — the real one, where they get to ask questions, and you both leave knowing they can speak for you with confidence.

A proxy who knows doesn't have to wonder if they got it right.

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End Well is right that the systems need to change. And while we wait — the most powerful thing you can do right now is this: choose your person carefully. Then talk to them.

Because then the people who love you won't have to guess.

The Legacy Leaders Guide walks you through exactly this — including how to have The Conversation in a way that actually sticks. April and May cohorts are forming now.

Start The Conversation

The Legacy Leaders Guide

P.S. Save the date — the End Well Summit, November 12, 2026, Los Angeles. Tickets open in early May.

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“I wish I’d done this sooner.”

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Not because they were sick. Not because something had happened.

Just because they finally had the conversation — and it wasn’t what they feared.

It was actually a relief.

Here’s what I know after years of sitting with the dying and the families who loved them:

Most people don’t avoid end-of-life planning because they don’t care.

They avoid it because no one has made it feel manageable.

That’s what I’m here to change.

Introducing: The Conversation Starter Workshop

A 90-minute live virtual working session — capped at 20 people — where you leave with three things:

✓ One real conversation you can have with your family this week

✓ Your completed end-of-life planning starter document

✓ A clear next step that doesn’t require a lawyer, a crisis, or a weekend

This isn’t a lecture. It’s not a webinar you half-watch while checking email.

It’s a working session. Your questions shape the room.

And it’s the only format where you get me — live, in real time — answering your specific situation.

StartTheConversation Workshop

The first workshop is Thursday, April 23 | 8a–9:30a EDT / 1200 - 1330 GMT

20 seats. Registration closes April 21.

Your investment: $99. Bringing a sibling, partner, or aging parent? The Family Seat is $175 for two.

Every registration includes:

✓ The 5 Essential Conversations PDF — your pre-work, sent immediately upon registration

✓ My personal NOK Box recommendation — the organizational system I recommend to every family I work with

✓ Live Q&A you won’t find anywhere else in my work

Count Me In

A note on why I’m doing this quarterly:

The Legacy Leaders Guide (LLG) is my deep-dive program for executives — five intensive, transformational sessions. It’s not for everyone, and it’s not meant to be.

But I kept hearing from people who wanted a place to start.

This is that place.

The Workshop is where you start. The Legacy Leaders Guide is where you go deep.

If you’ve been reading this newsletter, listening to the podcast, or thinking “I really need to do this” — this workshop was built for you.

20 seats. Four times a year.

The next one is April 23.

Reserve My Seat

Registration closes April 21. After that, the next workshop isn’t until July.

Questions? Hit reply — I read everything. | Trish

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They are. Mostly. And I’d rather tell you where we’re headed than wait for the last few details to land.

Here is who is coming to In Conversation with an End-of-Life Specialist for the rest of 2026.

Every episode records with a live audience of Graceful Lifers on the third Wednesday of the month, 4p –5p ET via Zoom.

Graceful Lifers receive the link directly and get to ask questions in the final 15–20 minutes — which, if you’ve been to one of these, you know is where things get really good.

Become a Graceful Lifer

Let me introduce you to everyone.

April 15 — Diane Button
Death Doula | Author, What Matters Most | UVM Instructor

Diane and I share a UVM thread — she teaches in the same End-of-Life Doula Certificate Program that certified me — and I’ve been hoping to have this conversation for a long time.

Her book What Matters Most was written at Maria Shriver’s personal invitation and published by Penguin Random House. But here’s what it actually is: two decades of bedside work distilled into stories about the people Diane calls her “wisdom keepers.” The clients who, when everything else fell away, knew exactly what mattered. Floyd, who taught her to put the clipboard down. Rosie, the six-year-old who made every day feel like a party. People who didn’t set out to teach anyone anything — and did anyway.

I have a feeling this one is going to stay with you.

May 20 — Dr. Ken Gorczyca DVM
Veterinarian | Companion Animal End-of-Life Doula | Artist | UVM Faculty

Here’s something I don’t say enough: I am also a UVM-certified Companion Animal End-of-Life Doula. And Ken Gorczyca was one of my instructors.

So when I say this invitation felt personal — I mean it literally.

Ken has practiced veterinary medicine in California for over 40 years. He learned to be a death doula not in a classroom, but by accompanying friends through the AIDS epidemic — sitting with loss before the field had a name for what he was doing. He now brings ceremonial, sacred farewells to animals and the families who love them: in living rooms, in gardens, at the ocean’s edge. He writes obituary poems. He paints commemorative portraits. He teaches — and apparently some of his students go on to start podcasts.

Here’s the thing nobody says out loud: grief for an animal is real grief. Not a lesser version. Not something to get over quickly. Real, bone-deep, reshape-your-days grief. This conversation is for everyone who has ever been told otherwise.

June 17 — Barbara Karnes, RN
Hospice Pioneer | Author, Gone From My Sight | End-of-Life Educator

If you have ever sat at a bedside with someone you loved who was dying, there is a good chance Barbara Karnes’s “little blue book” was somewhere in that room.

Gone From My Sight has sold over 40 million copies. It has been in continuous print since 1985. It is still the most widely used resource on the signs of approaching death — because nothing has come close to replacing it. Barbara has been educating families, caregivers, and healthcare professionals about the dying process for four decades, since before most people could pronounce the word “hospice.”

Welcoming her into this community is something I have wanted to do for a long time. June is finally our month.

July 15 —
Death Doula | Emmy-Nominated Writer | Author, Never Can Say Goodbye

Darnell began sitting with dying people at thirteen. He went on to write for children’s television, earn a PhD in cultural anthropology from Howard University, and accompany the dying across four continents — all without ever leaving the bedside. His debut book Never Can Say Goodbye (HarperOne, 2026) is already one of the most important things published in this field this year.

I finished it and sat with it for days.

That’s all I’ll say. Read it before July if you can.

August 19 — Dr. Karen Wyatt
Hospice Physician | Author, 7 Lessons for Living from the Dying | Host, End-of-Life University Podcast

Karen Wyatt left clinical medicine to become a full-time educator, author, and podcaster. Since 2013, she has built End-of-Life University into one of the most respected platforms in the field — now past 535 episodes.

I have been a student of her podcast for years. This August, if the dates align, I’m hoping to turn that around. Two podcasters. One conversation. The same conviction that talking about death is one of the most life-affirming things we can do.

September 16 — Dr. Kevin Dieter, M.D., FAAHPM, HMDC
Hospice Physician | Palliative Care Educator | Certified Listener Poet

Dr. Kevin Dieter built a nationally recognized palliative care curriculum at NEOMED around a single radical idea: that dying patients are the faculty. His “Hospice Patient as Teacher” model has been described by students as life-changing and career-changing. After 35+ years at the bedside, he is also a Certified Listener Poet and a trained Anamcara — which is to say, he brings both clinical rigor and something harder to name into every room he enters.

He reached out to me. I said yes immediately. Now I get to return the energy.

October 21 — Shaka Senghor (to be confirmed)
NY Times Bestselling Author | TED Speaker | Founder, The Atonement Project

I’ll be honest: Shaka Senghor is not my typical guest.

My podcast lives in the world of end-of-life care — hospice, grief, death doulas, the conversations most people still struggle to have. He is a resilience expert, a bestselling author, and a criminal justice reformer. And yet.

His work has always lived in the places most people refuse to look: solitary confinement, shame, atonement, and the person we become on the other side of our worst moment. That is end-of-life terrain, even when it doesn’t carry that name. Nineteen years in prison. Seven in solitary. What he found there — literature, forgiveness, the capacity for transformation — is exactly what my listeners are searching for at the threshold.

There’s a line in How to Be Free I keep returning to: it doesn’t have to be perfect. But it does have to be a process. It has to be progress.

That’s this conversation.

December 16 — Aurora Leonard
Documentary Filmmaker | Former Associate Director, The Living/Dying Project | Hospice Volunteer

Aurora Leonard uses story and presence to bear witness to life’s most tender transitions — which is a description that could also fit half the guests on this list, except she does it through a camera lens. She is currently producing Living to Die Now, and she brings a Filipina American perspective to a conversation that has for too long been shaped by a single cultural frame.

We are still finding our date. But this conversation is coming.

Eight doorways. Same territory. I hope you’ll walk through as many as you can.

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With grace | Trish
Certified End-of-Life Doula | Founder, Graceful Transitions
Creator & Host of the Podcast ‘In Conversation With An End-of-Life Doula’

Graceful Lifers: Live Audience

James Clear on perfection:

“The last 5 percent of quality almost always costs a disproportionate amount of time and money.”

The leaders I work with are not people who do things halfway.

Precision matters to them. Completeness matters. And that very quality — the commitment to doing it right — becomes the reason it doesn’t get done at all.

The perfect plan becomes the enemy of the plan that actually exists.

This is exactly why people don’t start end-of-life planning.

They want the perfect plan. The right moment. The complete picture before they begin.

But perfection isn’t the point. Progress is.

Five sessions in the Legacy Leaders Guide won’t give you a perfect plan.

Nothing will.

What it gives you is 95% of what matters — the values conversations, the Decision-Maker chosen and briefed, the information your family can actually find, the legacy you’re living now rather than leaving later.

That’s not settling. That’s the best possible use of your time and energy.

Progress over perfection. That’s the whole principle.

You don’t need to be ready. You need to begin.

What LegacyLeadersGuide Is

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James Clear on trades:

“Saying yes to one thing is always saying no to something else.”

Here’s the trade most leaders don’t see:

• Yes to “I’ll handle this later” = no to the conversation your family deserves now.

• Yes to leaving it unorganized = no to the peace of mind that comes with having it done.

• Yes to waiting until you’re ready = no to the time you could be spending fully present, not carrying this.

The cost of a bad yes isn’t just the time it takes.
It’s whatever could have grown in that space instead.

That’s the trade. Is it a good yes?

I’ve watched people complete this work and describe something I can only call lightness.

Not because death became less real. But because the weight of everything unresolved — the documents unfiled, the conversations unstarted, the people left to figure it out alone — that weight lifted.

The trade they made five weeks earlier was the best yes they’d said in years.

The Legacy Leaders Guide is five sessions, small cohort, everything you need to finally make the good yes.

What LegacyLeadersGuide Is

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“Your habits will hold you back more than your enemies ever will.”

I think about this constantly in the context of end-of-life planning.

It’s not that leaders don’t care. It’s not that they don’t know it matters. They’ve built careers on strategic planning — they understand better than anyone the cost of being unprepared.

The thing holding them back isn’t knowledge. It isn’t time. It’s the habit of treating this as “someday.”

Someday when things slow down.
Someday when it feels more urgent.
Someday when I’m ready.

Someday is a habit. And habits, unlike enemies, can be changed.

The leaders I work with are not avoiders. They are planners, strategists, people who have built contingency protocols for events with a 2% probability of occurring.

And yet the one event with 100% certainty sits untouched in the “someday” pile.

That’s not a knowledge gap. It’s a habit. And habits — unlike enemies, unlike mortality itself — are entirely within your control.

What would it look like to make one different choice this week?

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