December 26, 2025
Front Porch Podcast – St. Paul’s Towers resident David Jackson (Part 1)
Episode 4: Who Shall Live? Growing through Grief
Episode Description
David E. Jackson spent his career as an educator, but some of his most profound “life lessons” have come out of navigating loss and grief. After evacuating his Santa Rosa home during the Glass Fire and relocating to St. Paul’s Towers at the height of Covid, David faced the heartbreaking loss of his beloved wife of 50 years to cancer. Yet in moving through the process of grief, David discovered something unexpected: a spiritual awakening, a new appreciation for life and love and the sustaining power of community.
Tune in on December 30, 2025 for Part 2 of our conversation with David Jackson, “Welcome Love, Welcome the Stranger,” where David reflects on his renewed connection to his faith, the joy he finds in teaching first graders and the journey of opening his heart to a new love.
Chapters
- 00:45 – Episode Theme: Growing Through Grief: Anna opens with a heartfelt reflection on the first resident she lost in her career and the recent passing of her father and how her community has supported her through grief and gratitude.
- 03:30 – Introducing Dr. David E. Jackson: Anna welcomes Dr. David E. Jackson, retired Head of School at San Francisco Day School and now a resident of St. Paul’s Towers in Oakland.
- 04:10 – The Night of the Fire: David recounts fleeing the 2020 Glass Fire with his wife, Phyllis, who was undergoing cancer treatment—and the small act of kindness that helped them escape.
- 05:48 – “Who Shall Live, Who by Fire”: As Yom Kippur dawned the next morning, David found new meaning in an ancient prayer about life, loss and survival.
- 06:36 – A Community That Opened Its Doors: St. Paul’s Towers welcomed David and Phyllis in the midst of the pandemic, offering refuge and compassion.
- 07:36 – Becoming a Caregiver: David reflects on caring for his wife through her illness, the return of her cancer and the emotional intensity of that journey.
- 08:52 – Hospice and Compassion in Community: He describes the quiet, wise support of neighbors and staff who knew how to offer comfort without asking for explanations.
- 10:12 – The Final Two Weeks: David recounts the profound connection he felt as Phyllis neared the end of her life—two souls joined in presence and love. He shares the moment of her passing and how it reshaped his understanding of life, death and the mystery beyond.
- 13:19 – Grief as a Life Force: He explains why he sees grief not as sadness, but as an active, transforming power that happens to us, not by us.
- 14:13 – “This Grief” – A Poem by David E. Jackson: David reads his original poem written three days after Phyllis’s passing, exploring grief as both pain and blessing.
- 16:07 – Learning to Be With Grief: David and Anna discuss how our culture avoids grief and how sitting with it—doing “nothing”—can lead to healing and self-understanding.
- 18:14 – The Necessity of Hard Things: Together they reflect on the inevitability of grief and the human design for emotional growth through hardship.
- 18:26 – The Loss of Ancient Wisdom: David laments how modern life separates us from death, depriving us of the deep connection that comes from being present with those we love at life’s end.
- 19:50 – Closing & Transition to Part Two: Anna thanks David and invites listeners to join Part 2: “Welcome Love, Welcome the Stranger,” where the conversation continues about renewal, purpose and finding love after loss.
Key Takeaways
- Grief is not sadness — it’s a force that transforms. It shapes us, opens us and connects us more deeply with others.
- Community matters. The compassion of neighbors and caregivers at St. Paul’s Towers helped David through unimaginable loss.
- Love transcends life and death. Presence at the end of life can reveal the purest forms of connection.
- Ancient rituals still speak today. The Yom Kippur prayer, “Who by fire, who by water,” took on new meaning through lived experience.
- We are meant to grow through difficulty. Avoiding grief postpones transformation; embracing it leads to wisdom.
Guest Bio
After a career in education, Dr. David E. Jackson retired as Head of School for the San Francisco Day School in 2015. He and his wife joined the Spring Lake Village community in Santa Rosa before moving to St. Paul’s Towers in Oakland in 2020. A widower after 50 years of marriage, David re-enacts his love of teaching by sharing stories from the Torah with young children at his local synagogue.
Host Bio
Anna Hall is a purpose-driven leader with over 25 years in senior living, spanning employee engagement, life enrichment, training and innovation in age-tech and program design. A certified life coach and dynamic speaker, she helps people connect with meaning and motivation at every stage of life. She is the creator of The Purpose Equation®, an evidence-informed framework that empowers individuals to define and activate their unique purpose to enhance wellbeing, engagement and collaboration. As Chief Culture & Community Officer at Front Porch Communities & Services, Anna leads initiatives that foster belonging, creativity and human thriving—building communities where everyone feels valued and inspired to make a difference.
Resources Mentioned
- St. Paul’s Towers – A Front Porch Community in Oakland, CA
- Spring Lake Village – A Front Porch Community in Santa Rosa, CA
- Front Porch Communities and Services
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Disclaimer
The views and opinions expressed on this podcast are those of the speakers and do not necessarily reflect the views or positions of any entities they represent. This podcast is for informational purposes only and should not be considered, legal, health, tax, or professional advice. Always consult a licensed professional for specific advice related to your situation.
Anna Hall: Welcome to The Front Porch Podcast. Join us as we uncover the extraordinary stories of people who are part of Front Porch Communities and Services–young professionals just starting their journeys, lifelong learners pursuing new passions and seasoned storytellers sharing the wisdom they’ve gained along the way.
Together, we’ll explore how purpose and community shape us with stories that will inspire you to discover your own unique contribution.
Views expressed by guests on this podcast are the opinion of the speaker, and do not necessarily reflect the views or positions of Front Porch Communities and Services. Please see our show notes for more details.
I’m your host, Anna Hall. So, the name of this episode is Growing Through Grief. I remember the first resident that I lost early in my career. His name was Irving. He was 89. You know, he was a World War II veteran. He was on the beaches of Normandy and survived and told me about that experience. And I’ll never forget that or him. He had 89% heart function, he would always say, and Irving meant so much to me. And when he passed away, I lost my… I can’t say on a podcast. At his funeral, I cried more than the family. Not because the family didn’t care, but because I was so unprepared for the level of pain that I would feel at losing someone who I loved so much. And it happened again and again. And I, over time, with perspective and experience, came to a conclusion. It’s better to have loved and to have lost than never to have loved at all.
And a wise chaplain at one of our communities told me that the magnitude of grief is equal to the magnitude of love. How grateful am I that I have gotten to have this much love in my life, from these meaningful, beautiful relationships that continue to live with me. I’m seeing Irving in my mind right now. Irving, I love you. Thank you for what you taught me.
And the grief for me is very raw right now. I just lost my father. He was 87 years old. Professor Raymond Hall, the first Black chair of a sociology department in the Ivy League at Dartmouth College. He was my best friend. We talked every morning. I still, a month after his passing, wake up every morning and the habit is like… it’s time to call dad, and he’s not there.
At the same time, I feel him with me. And I’ve had such incredible love and support from my Front Porch community, and I find it’s… I feel it’s important to talk about this because grief is part of life. It’s part of our… all of our human experiences at one point or another. Dad, I love you. Irving, I love you, and I’m so grateful that I get to have this incredibly rich life working in senior living.
I’m excited to introduce you to our guest, David E. Jackson. After a career in education, Dr. David E. Jackson retired as head of school for the San Francisco Day School in 2015. He and his wife joined the Spring Lake Village community in Santa Rosa before moving to St. Paul’s Towers in Oakland in 2020. A widower after 50 years of marriage, David reenacts his love of teaching by sharing stories from the Torah with young children at his local synagogue. David, welcome to “The Porch.”
David E. Jackson: So glad to be here. Thank you.
Anna Hall: So, let’s dive right in. You moved from Spring Lake Village to St. Paul’s Towers in a bit of an emergency situation. Could you tell us about that?
David E. Jackson: Sure. My wife, was diagnosed with endometrial cancer, and she had just completed that treatment of chemotherapy and obviously was in a weakened state. And then the Glass Fire, in 2020, erupted. And over the course of the day, it crept closer and closer and closer to Spring Lake Village. And finally, after dark, we decided we had to leave. Our go bags had been packed and we ran down into our car, got into the car, and left. Outside Spring Lake Village it’s a two-lane road. And, of course, it was packed with cars coming from the west to the east, escaping the fire. I’m sitting there thinking, “I’ll never get on to this road,” but then suddenly the car that’s right there stops and waves me into the traffic.
Anna Hall: Wow.
David E. Jackson: The first act of kindness that I received that night. And, steadily, we got to the highway and came down. The ash was so full, it was raining down on the windshield of the car with the windshield wipers going – just like it was in the middle of a snowstorm.
We have two daughters in Berkeley. We came into their apartment. It was well after midnight and my whole body just started reverberating, and the only thing I could say was, “You have to take care of me now. I’m an old man. I can’t take care of myself.” From the shock of exiting and having a wife who could barely walk from the chemotherapy.
That was the eve of Yom Kippur, the holiest day in the Jewish calendar. And the next morning, as we get up, now feeling safe, we Zoom into the traditional service, and we’re all chanting the ancient prayer which says, “Who shall live, who by fire, who by water, who shall live.” And I’m sitting there saying to myself, I always thought this was a silly prayer, a metaphor. You know, serious, but just a metaphor. But now… “Who shall live? who by fire, who by water?” And that certainly changed me, that experience.
My wife had already had a relationship with the people at St. Paul’s and we called them up. And remember, this is 2020. This is in the midst of the worst of Covid.
Anna Hall: Oh my goodness!
David E. Jackson: You know, the most intense isolation. And they said, “Come on over.” We came over. We drove up. They said, “Welcome, David Jackson.” The gate opened up. They ushered us in. And that’s how we ended up at St. Paul’s Towers.
Anna Hall: So already we have an incredibly heartbreaking, fascinating, and lucky story all in one. Right?
David E. Jackson: Right. All in one.
Anna Hall: Wow.
David E. Jackson: Yeah. So my whole life, you know, I’ve been secular humanist, hardcore materialist, everything science. No belief in anything beyond that. But now, of course, I…. That belief is shattered. There’s definitely something else going on in this world, and somehow it’s got its eyes on me.
Anna Hall: And you ended up at St. Paul’s Towers as a caregiver, with your wife, Phyllis.
David E. Jackson: Yeah.
Anna Hall: What was that like?
David E. Jackson: I had, you know, recently retired, and my job was Head of School. And when you retire from that, it’s like you’re done. It’s like jumping off a cliff. You have no connection. No one takes your phone call. Nothing. So, I had to start, kind of, recreating a life. And then the cancer came back and everything that I had joined, I said to them, “Sorry, I’m quitting because my wife’s cancer came back.” And it became my sole preoccupation, caring for her. First, it was going through the chemotherapy. And then after that, it was just taking care of her. There was a brief time after the end of chemo for several months, where she was pretty much symptom free. We knew the cancer was there. It showed up in all the tests. And then, it metastasized and we learned it had just spread throughout her body.
Anna Hall: I’m so sorry.
David E. Jackson: And within about two months she just got progressively very worse as the cancer just drained everything. She said to me, you know, “My one wish is don’t take me to the hospital. I don’t want to go to the hospital. I want to be in my own bedroom.” St. Paul’s again started their little caregiving and they sent up an aide. So for about an hour a day I could get out and go for a walk knowing that she was safe.
Of course, that time is a time of tremendous uncertainty and fear. You know, I just… “Am I doing the right thing? Should we call another doctor?” Then hospice came in. Everyone who tells you about hospice… they were amazing. The thing about St. Paul’s, which was so amazing, you know, I was relatively new to the community, but everybody was… knew exactly what to do to help me during this tremendously difficult and challenging time.
When I would go down to pick up a meal, people would come up to me and they knew not to say, “How are you doing? They knew that was the very wrong thing to say. And they would just, you know, put a hand on my shoulder, give me a gentle hug, say, “I’m thinking about you.” They knew how to give the level of support and awareness that was just what I needed and didn’t burden me with trying to explain things to them. And that was a really amazing solace to me during that time of really fear and uncertainty.
And then over the last maybe two weeks as the cancer got more and more spread and she became in and out of consciousness. And I believe that was the most profound two weeks I’ve spent with any person in my entire life. In and out of consciousness, every once in a while, she’d come out and say something. And it wasn’t her that was saying something. It was her deep inner being that was saying something. Something just would bubble up from inside her being and say things like, “Come closer.” I said, “I’m here, I’m here.” She said, “No, no, come closer. You know I have separation anxiety.” I said, “Okay, I’m here, I’m here.” And then she would say to me, you know, “Don’t you think I should be dead by now?” And I would try and just say, “Well, are you ready? Are you okay with, you know, dying?” And, then she would fall back. And I realized during those two weeks that I was connecting with her at a level that was beyond consciousness, beyond, you know, day-to-day. It was just somehow, two souls connecting. And that experience being there as she came closer and closer to death has just enriched me as a person, experiencing that mystery.
And then that one morning she stopped breathing and I was there with her, and I could feel her slipping away. And, you know, once upon a time, I believed, okay, she’s dead. You know, the body decays. Now, I know that there’s something about every person as they slip away from this life, there’s… they go someplace. I don’t know where it is. I don’t have access to it. Every once in a while, you know, it breaks through, and that, that something touches us and we can feel it. We doubt whether it’s real, but the experience of it is very visceral when that breaks through from that realm to this realm. And I’m forever grateful to St. Paul’s that they enabled this to happen, grateful for the opportunity to be with her during those last couple of weeks. And I… this is crazy to say, but it wasn’t until after her death that I realized how much she loved me and how much I loved her. It’s just a crazy thing to say, to know. But, you know, life is busy. We’re raising children. You know, we have to go to work every day. Somebody has to take out the garbage. Somebody has to pay the bills. And you sometimes, you know, just let that go and you just don’t realize that you’re two souls connected. And I didn’t realize that until after she died.
Anna Hall: I’ve heard that the level of grief one feels is often equal to the amount of love that one feels. It almost seems cruel in a way, but also beautiful.
David E. Jackson: Yeah.
Anna Hall: You’ve described grief as a life force.
David E. Jackson: Yes.
Anna Hall: That it can be a growth process.
David E. Jackson: Yeah.
Anna Hall: Can you talk more about that?
David E. Jackson: Sure. The phrase, you know, “I am grieving,” is wrong.
Anna Hall: How so?
David E. Jackson: Grief is its own separate force that happens to you. You are not grieving. It… you know, it’s something that, humans are capable of, something that happens to us, and it just takes hold of us. Can I read that poem now?
Anna Hall: Absolutely. Absolutely.
David E. Jackson: So this poem I wrote, three days after her death. Tomorrow is the four-year anniversary of her death… tomorrow.
Anna Hall: Oh my goodness, David.
David E. Jackson: Entitled, “This Grief”
“This grief is not sadness nor sorrow.
This grief is a force forming within me,
a storm, its solidity swirling, erupting from deep.
This force grows steadily into a looming wave,
crashing onto a rocky, abandoned shoreline,
releasing projectile spray
that plunges into every pore,
muscle, sinew and synapse
tremors, streaming tears,
throat choking sobs overtake my physical being.
They ebb and flow, unanticipated, unregulated,
successive waves of intensity
into relief, exhaustion.
This force, its own dynamic,
Mocks my intentional efforts
to control or understand.
May I have the sense and strength to let it be.
Let it fill and shape my being.
Let it take me along the path to transformation.
This grief is a blessing.
My own crooked path to soulful existence.”
So I say to myself, “Does grief scrub my soul?” It opened me up. It It made me less afraid of human contact, less restrictive with my own emotions. And, you know, what a gift from my wife, this grief.
Anna Hall: And indeed, and an incredible transformation for you.
David E. Jackson: Yeah.
Anna Hall: What do you think happens for people who might be afraid of grief? You know, I’ve… I’ve learned as a life coach that you can’t, like, put grief aside cause it will wait for you. It’s something you have to move through. And it’s not moving through to get back to your old life. You’re moving through it to get to a new normal.
David E. Jackson: Yeah, you know, our society is pretty ignorant about the ancient wisdom of the grief process. And we don’t support each other in going through it and leaning into it and letting it have its way with us. And there are lots of ways to avoid grief. Getting back to work and suppressing the emotions. But, you know, in my view, that’s, that’s not a good thing for a person, for a human. And I was lucky, you know, my kids were raised. I was… didn’t have work responsibilities. I was alone. So I could just be with myself and my grief. I spent a lot of time walking along the seashore here in Oakland. I had a really good therapist. It’s always helpful. She said, “David, okay, do nothing for the next… I’m not sure how long, but do nothing.” And I would say, “Well, I’m just sitting here daydreaming.” She said, “Good, that’s exactly what you should be doing.
Anna Hall: Being. Processing.
David E. Jackson: Just being. Just let it, you know. Let it be.
Anna Hall: Yes.
David E. Jackson: And, you know, it does subside and… but it’s always there. And then you find yourself… I found myself just open to, to people in a way I had not been open to people before. Just so eager to hear what’s going on with them, to hear their stories. You know, not actually… I didn’t need to tell people my story. I really was curious about their story, what they were feeling. That’s what this process helped me grow into. You know, obviously, I’m a way better person now than I was then.
Anna Hall: You know, I’ve learned in life that we can’t really avoid the hard things.
David E. Jackson: No.
Anna Hall: We can’t avoid the challenge. We can’t avoid the grief. It is part of the journey. And it sounds like you’re telling us that it is, indeed, a necessary part of the journey.
David E. Jackson: It’s beneficial, you know, somehow we were constructed, you know, biologically, you know, psychologically to go through this process so that we grow.
Anna Hall: Yes.
David E. Jackson: emotionally, soulfully through it.
Anna Hall: Yes.
David E. Jackson: You know we think about how, ancient humans lived. They lived in extended families. They were much more aware of family members dying. They were much closer to the process of life and death. Now with families separated, you know, and the medicalization of death, we often are not with the person who’s dying during those final two weeks or a month. That’s a loss. That’s a real loss. And when you speak to people today, here, those who were fortunate enough to be at the bedside during the last two, three weeks and hold someone’s hand and have them squeeze the hand back, have the person emerge from unconsciousness and say a few words and then slip back. They talk about that experience as, you know, wonderful.
And then the person whom… who lives across the country and couldn’t get there and has work responsibilities, you know, they don’t get to have that experience. And that’s a loss for them.
Anna Hall: Thanks for tuning in to part 1 of our conversation with David E. Jackson. We invite you to stick around for part 2: “Welcome Love, Welcome the Stranger” where we’ll talk to David about what he’s up to now.
You’ve been listening to The Front Porch Podcast. I’m your host, Anna Hall. Our theme music was composed by Geoven Snaer and Dianne Kae Enriquez. Carmen Elena Mitchell is our producer and editor. Our recording engineer is Jeff Gall. Special thanks to Laura Darling for production and marketing support. And to Joseph Escobar for our show art design.
The Front Porch Podcast is a production of Front Porch Communities and Services. If you enjoyed today’s conversation, please share it with a friend and help others find us by subscribing and leaving a review.
We’ll be back soon with more stories from the fascinating folk who live and work at Front Porch. Until then, stay connected and inspired.
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