Playdates With Death: Spirited Chats on End-of-Life Planning

Editor’s Note: This interview was conducted prior to the passing of Playdates With Death founder Dr. Lea Schweitz, who died on September 24, 2025. We share her story in recognition of her work and contributions, with deep respect for her legacy. Read her obituary.

Every few weeks, Dr. Lea Schweitz brings together a group via Zoom for an online “playdate.” This warm and engaging community gathering, typically a mix of first-timers and regulars, is rather unusual in its focus: planning for the end of one’s life.

Schweitz spent years as a seminary professor, including serving as a director of a religion and science center and as a trauma-informed educator. Despite much of her professional career having taken place in spaces dedicated to exploring profound questions regarding identity, spirituality, and self, she’d never done any concrete planning for her own future.

A Stage IV cancer diagnosis in 2023 became her wake-up call. Schweitz, 48 years old at the time, was advised to get her affairs in order. “It was not the most inspiring way to begin,” she admits.

As a mother to two boys, now ages 16 and 11, she had talked in passing for years about the need to create her will and set up other estate planning documents.

“We know we need to do it, and you’re a little bit ashamed that you haven’t – all of which leads to a culture of silence,” Schweitz says. “It’s a really big project to tackle, so if you don’t have some kind of accountability structures built in to really get to the finish line, it makes it very challenging.”

Doing Hard Things Together

Schweitz had been focusing on her health and healing for nearly 10 months following her diagnosis when, around Halloween, her son invited a friend over for a playdate. The boys came down the stairs dressed for the holiday, and Schweitz found herself face to face with the Grim Reaper, the costume her son’s friend was wearing. The irony was not lost on her.

“I found that hilarious,” Schweitz says. “It was a metaphor for the ‘playdate’ with death that I’d been experiencing all year.”

All of this led her to launch Playdates with DeathTM in early 2024, a series of free, interactive workshops held online about once a month to help guide attendees in tackling different aspects of estate planning in a lighthearted community space.

“I do think we’re built to do these hard things together,” Schweitz says. With these playdates, she seeks to “create inspiring spaces for folks to rediscover or discover what their own best choices really are.”

Past Playdates with Death sessions have covered projects both practical and creative, from setting up a medical power of attorney to writing your own obituary to brainstorming ideas for living funerals or post-death celebrations of life. Schweitz also hosts guest speakers with expertise in specific areas. Sessions have included a Q&A with a funeral director and a presentation by a death doula.

Each playdate kicks off with a few thought-provoking, sometimes tongue-in-cheek questions about end-of-life matters. Often, Schweitz includes time toward the end during which participants can start in on the project of the month or take a few minutes after having discussed what are intensely emotional topics to “dance it out” together to an upbeat song.

“If folks stick with us for a while and come back and do the work, my hope would be that they’d have those 10 or 12 projects most of the way finished, to be ‘death-ready,’” Schweitz says. “It’s ongoing work. The goal is just to keep it going.”

Ultimately, Schweitz says she sees end-of-life planning as a way to “help you live your best life now.” Playdates with Death is her way of fostering a safe space where people can begin addressing these essential to-do tasks together.

An Ongoing Conversation

Many people shy away from conversations about end of life and procrastinate on establishing any kind of estate planning documents. In fact, less than a third of Americans have even a basic will in place.

Schweitz describes end-of-life planning as “generational work.” Getting the appropriate legal and planning documents in place, she says, “really makes such a difference in how families can grieve and heal after [a loved one’s death]. It just takes care of things for them and lets that larger family unit do the work of grieving and remembering and celebrating.”

Yet broaching these topics can prove challenging. Aging parents, for instance, may trivialize the subject or else raise their defenses.

“Sometimes, I think the best way to do this is by sharing a story of something you are doing,” Schweitz says.

For example, you might share that you recently had your power of attorney drafted or read a story about someone who learned they were responsible for making all the medical decisions for their estranged child. From there, you can focus on accomplishing one small task. That might be making an appointment with an estate planning attorney, identifying what kind of funeral service you would prefer, or communicating to your closest loved ones what you wouldn’t want, which can be just as important.

With her own kids, Schweitz also seeks to keep communication open and authentic.

“Kids will provide their own stories if you don’t find a way to let them into yours,” she says. “They see what’s going on with me. Insofar as they can have a truthful version of that, that’s what I’m trying to give them. Not a rose-colored-glasses version and not a dire, doom-and-gloom one, but kind of walking the walk. I am trying to give them a story about what’s happening … and navigate where we really are – because they’re going to tell a story about it if you don’t.”

Fostering better communication, living “brighter, fuller lives,” leaving a paper trail to track your wishes in a legally valid way – Schweitz sees all of this as part of the work.

“It won’t be a one-and-done,” she admits. “It’s really a relationship-building piece.”

Death Can Be Life-Giving

For future Playdates with Death themes, Schweitz hopes to explore increasingly specific topics, including estate planning when you have a child with a disability, a loved one with dementia, or pets you want to secure care for after you have passed away.

In addition to Playdates with Death, for which she always welcomes sponsors, Schweitz runs paid workshops and consults one-on-one with clients on end-of-life planning. Other spaces she sees as “well poised to do this kind of work in community” are senior centers, churches and synagogues, and retirement homes.

One other resource Schweitz cites as particularly valuable for folks in guiding discussions about one’s wishes for care through end of life is the Conversation Project. The site offers free workbooks, prompts, and other tools that can be helpful for families and health care professionals alike.

To Schweitz, facing deep questions about end-of-life planning is not only doable, but can also help one clarify their priorities. Most importantly, perhaps, it “can be really joyful and life-giving,” she says. “That’s the refrain I would want to make sure people heard.”

A Playdates with Death website is currently in the works. For now, visit the Playdates with Death Substack and Instagram account.