How One Family Broke the Ice on End-of-Life Planning
September 5, 2025
We often hear from people that our workshop makes them think of their parents and the conversations that need to be had and planning they may or may not have completed. This was the case with one of our first workshop participants who was willing to share the story of her family.
Laurie knew—even before she attended—that there were definitely some end-of-life considerations her parents hadn’t yet thought about. Like many older adults, her parents assumed they were “all set,” but she also knew they might be resistant to anything that sounded like a class about death. Still, Laurie hoped that by attending the workshop herself and sharing the insights and benefits she gained, they might be more open to the idea.
And she was right.
After completing the workshop, Laurie visited her parents with the workshop materials in hand, ready to gently start the conversation. She shared her own experience—what she had learned, the questions she hadn’t thought to ask, and the clarity she gained from going through the course herself. She flipped through the materials with them and walked them through a few key topics.
What happened next surprised her.
Instead of brushing off the discussion, her parents listened. They saw the materials and realized they might not be as prepared as they had assumed. The conversation unfolded more easily than Laurie had anticipated, and she knows that her own comfort with the topic played a big role in that. She wasn’t tiptoeing around the subject; she was inviting them into it.
One simple, yet effective, nudge that helped was offering her parents a “family discount” for attending the workshop together. That extra incentive made it feel less like a class about death and more like a shared, valuable investment in their family’s peace of mind.
Before, end-of-life planning had been a subject avoided in the family. But now, her parents proudly tell people that they have pre-arranged their cremation with the Neptune Society.
The Peace of Mind Planning workshop gave the family the tools, language, and confidence to have difficult conversations about death.
Thanks to the workshop, they’re more prepared—together.
If you’ve been wondering how to open this conversation with your own parents or adult children, let this be a gentle nudge.
Whether you attend solo or with loved ones, the Peace of Mind Planning workshop can help make these important discussions easier, clearer, and even comforting.
See our new fall and spring dates for Peace of Mind Planning.
Meditating on grief
August 12, 2025
Jen and I often get asked about supporting people who are grieving. Since much of our work focuses more “upstream” – the preparation and planning for death – I tend to shy away from talking too much about grief as an “expert”. While I have my personal experience with grief from losing both of my parents, I will direct people to therapists or grief specialists.
However, I do feel comfortable recommending books that have moved me, especially memoirs in which the author articulates their confusing, sad, and messy emotions in ways that I find beautiful, like Kathryn Schultz’s Lost & Found. (Ezra Klein recently interviewed Schultz on his podcast if you want a taste of her story and its broader relevance to the time we’re living in).
I also recommend the Sojourn Into Grief series that my dear friend Daryll wrote about losing his dad. (He did not ask me to say this.)
Daryll wrote these pieces in the first nine months after his dad died. One of the things that I think make them so powerful is that middle-distance perspective – they capture the confusion of someone a little removed from the acute shock, but still really in it. He shares a eulogy, meditates on grief as an emotion, and explores “the terror of meaninglessness.”
I would recommend this to people who have recently lost someone and people who are supporting someone who has lost someone. Grief can be so different for everyone, but understanding what someone could be grappling with in that first year after a death can help build a bridge during a time of deep loneliness.
The season I was familiar with has left me. The season where I had two parents. The season where one of my treasured soulful recreations was sharing the outdoors with my dad. The season where I never thought much about what link I occupied in the chain of my ancestors or what to forge next. Where we had fresh strawberries and corn on the cob from the garden every summer. Where my sense of home felt intact.
I see the weeds taking over his garden, pained that I didn’t learn all of his ways, but also accepting that my life wasn’t really a fit for them anyway. Tending to the land is a full time job. I appreciated it. I tried to learn it. I could not implement it. This will not be my life.
I’ve always felt an imperative to come from somewhere. It’s probably the introvert in me, but boldly going forth into the world has always required a strong foundation. I won’t go as far as to say that my foundation has been lost, but it has certainly been damaged, necessitating a significant reorientation.
How do I go forth into the world in spite of this?
– From Seasons in the Riverlands, part 7 of the series
photos courtesy of Daryll Henrich
Opening a window for hard conversations
June 27, 2025
We recently received an email from a former workshop participant. She had talked in class about her mom’s unwillingness to talk about preparing for death. Now, a few weeks later, she was excited to share the news of an “unexpected opening” – a window of opportunity to start the conversation about end-of-life planning. It came because her mom had joined a new credit union that offered estate planning guidance. It was a natural segue for her to bring up to her mom some of the other aspects of planning, like an advance directive, and organizing her affairs into a Life File.
This news, to us, was like finding our most anticipated gift under the tree on Christmas morning. We hear all of the time about how challenging, scary, or just awkward it can be to bring up end-of-life planning to your parents. There’s no casual or easy way to ask: how do you want to die?
Any window of opportunity to broach some of these hard topics, no matter how big or small, is a gift. It opens the possibility for a conversation that can lead to the making of a plan for the inevitable, for themselves and their family. Sometimes the window is open just a crack, but if you can use it to let your loved ones know you want to support them in these later stages of their lives, it’s still a win in our books. The journey is often long, and the steps forward can feel slow. But with intention and patience, you can move conversations forward that will help bring your family peace.
We work with people to give them the tools and support they need to have challenging conversations about end-of-life preparation. Please reach out to us if you want help talking with your loved ones about aging and death.
Did The Pitt make you nervous?
May 20, 2025
“I really want to take your workshop! I just can’t do it right now.”
We hear that all the time. And we know, taking a class on the important things to think about before you die probably isn’t at the top of your to-do list. It sounds a little depressing. And you have 100 more immediate things to think about, like work deadlines, end-of-school stuff, and vacation planning.
Also, TV is so good and distracting right now. Have you watched The Pitt? If you got through Episode 4 and wondered, “What would happen if my family had to decide whether or not to intubate my frail father?”, you should join our workshop.
Peace of Mind Planning is a pretty small commitment: just 4 hours over a 6-week period – way less time than it takes to binge The Pitt, and it will make you feel more comfortable, and way more prepared, to think about death and your own mortality.
We’ve got openings for SUMMER and FALL. Come join us! We’ll leave you feeling enlightened, not depressed. We promise.
Before I die ….
September 18, 2024
I recently read about a global art project started by the artist Candy Chang in which she created a space on a public wall with the prompt “before I die_______. The idea came to her after the death of someone she loved and was imagined as a way for people to reflect on life and death.
It took only a matter of days for the entire wall to be filled with answers. Some that might be considered things on one's “bucket list”: traveling to all the continents, straddling the international date line. Others were more simple desires: to be a good dad, to have a better relationship with my sister.
While they all seem feasible and attainable, we tend to put things off for the future, when we have more time or more money. We dream without doing. When death feels a long way off, it’s easy to say “tomorrow”.
It feels like it's only when we think about the end that we give ourselves the lens to articulate what we really want in our life. If so, how can we keep our mortality top of mind? Not to bring us down, but to help us be bold and brave enough to start to tackle the “bucket list”?
If you were told today that you had only a few short months left, what would you change? How might you approach the decisions you make? Giving ourselves the time and space to think about our death can shed light on how to live in the present with more authenticity and purpose, how to make the most of our finite time, and in the end, create the legacy we’d be most proud of.
How would you finish the sentence, “before I die I want to________”?
If you’re interested in giving yourself the time and space to think about it, check out our fall Peace of Mind Planning Workshop.
Don’t miss out! Peace of Mind Planning Workshops – Fall 2024
Our next Peace of Mind Planning workshop is coming up. Find more information and register here.
For a little bit of a deeper dive, here’s what we will cover in each session:
Session 1: What it means to have a “good death” + completing your Advance Directive Session 2: Everything you wanted to know about body disposition + how do you want to be celebrated and remembered? Session 3: Putting together your Life File + having hard conversations with your older loved ones Session 4: Caregiving + the dying experience
We added Session 4 after learning that many folks were concerned about how to navigate the often emotional and stressful caregiving responsibilities for their parents or partners at the end of life. Which is not surprising – did you know that over 37 million Americans provide unpaid elder care annually? That number continues to increase as the boomer generation is aging.
Also, know that if the price of the workshop is cost prohibitive, we can definitely offer it to you at a reduced rate. We’re passionate about getting this content to people who are eager to participate. Just reach out to jen@theheartwoodcollective.com.
Hope to see you on Zoom or in-person in October! Please share with anyone you feel would be interested.
Karen & Jen
Speaking of caregiving….
We found this piece by Courtney Martin about the art of caregiving incredibly beautiful and insightful. Courtney writes a substack called The Examined Family about many things, including caring for her father who has dementia.
Also, I (Karen) recently finished We All Want Impossible Things at Jen’s recommendation. A gut-punch of a novel about a woman caring for her friend in hospice, that is also very funny and a bit crass. For your To-Read List.
Register now! Peace of Mind Planning Workshops – Fall 2024
We’re excited to announce our next sessions of the Peace of Mind Planning Workshop. This fall, we’ll run the workshop both in-person, if you’re in Portland, and via Zoom. Find more information and register here.
Each session we’ll talk about life, death, and our mortality. We’ll guide you through the necessary paperwork to get your affairs in order, and offer advice on how to talk with older loved ones in your life about their preparation.
This spring we completed our inaugural class. We were sold out! Folks told us they liked the interactive format of the workshop, which included sharing, writing prompts, and group discussions that created a supportive atmosphere where everyone could learn from each others’ perspectives, and personal stories. Conversations were meaningful, sometimes funny, and always rich.
Feel free to reach out directly with any questions, and please forward this email to anyone who may be interested in the workshop!