TROY: Death ain’t nothing. I done seen him. Done wrassled with him. You can’t tell me nothing about death. Death ain’t nothing but a fastball on the outside corner. And you know what I’ll do to that! Lookee here, Bono… am I lying? You get one of them fastballs, about waist high, over the outside corner of the plate where you can get the meat of the bat on it… and good god! You can kiss it goodbye. Now, am I lying? If I’m lying… that 450 feet worth of lying!

Death ain’t nothing to play with. And I know he’s gonna get me. I know I got to join his army… his camp followers. But as long as I keep my strength and see him coming… as long as I keep up my vigilance… he’s gonna have to fight to get me. I ain’t going easy.

Such is the literary description of death as masterfully crafted by August Wilson in the play, Fences. Death is to be wrestled with. It is a fight. Indeed, we often read that one lost a courageous battle to death. 

At the end of Act Two, Troy assumes a batting stance, and starts to taunt  Death, “Come on! It’s between you and me now! Come on! Anytime you want . . . but I ain’t gonna be easy.” The actor stands alone on stage, the lights go down, and the scene ends. I have never sat in the audience witnessing the theatrics of this play out on the stage. I have only taught this play to my English students decades ago. I can only imagine the emotion that Denzel Washington could stir in his audience. The heartbreak for this man whom you have grown to love from the third row, fourth seat from the right. When the lights once again come up, Troy is dead. Opportunities are missed. 

August Wilson’s genius lies in showing us that our mortality gives weight to our choices. Every conversation matters because the number of them is finite. Every relationship shapes the future because our time to influence it is limited.

I have often said I didn’t know it was my last conversation with my mom or my dad. My last chance to say I love you or to hear them say it.  What I did know was that the last chance was approaching. Life and literature had taught me to brace myself against death. Life was to be extended as if hours clocked was the metric that mattered most. I watched my father lean into his prescribed medical thinking to extend his wife’s life. I witnessed his frustration then anger as he could not save her… or should I say fix her… or maybe keep her with him. As his hours unexpectedly waned, I did not have the medical background to know how to extend his time or to improve the quality of his life remaining. I turned to a friend from graduate school, William Peters, Bill, as I knew him, who had developed a template for a peaceful crossing from life into death for us both.

Liz: I started to say to you the other day … I think I lose my mind as my dad was dying if I didn’t have you on speed dial. I had very little understanding of how to come to the end of his life and be the main person there. I wasn’t at all prepared. I didn’t feel like I had treated him well as my stepmother was dying. I mean, I would have been a mess. And you, that’s why I called … I had to get the words right. You helped me so much just taking all the nonsense away and literally telling me what to do.

William: I remember. The truth of the matter is I have been so involved with studying and being present to many hundreds and hundreds of deaths. And probably the most important thing that was shocking to me about this was how little people actually know about what happens at the end of life… you have super smart people like you who have an aging parent…

…and all we know is the unwelcome nature of death. The language we use betrays us: we “fight” cancer, we “battle” illness, we “lose” to disease. 

William: You have a medical model who sees death as a failure, and they want no part of that. They are committed at all costs to keeping people alive, even when they know that the quality of life is awful.

Liz: You also… You just called death a failure, but recently in a conversation, you said we have this cultural norm that you fight death.

William: Exactly.

Liz: And that’s wrong, too.

William: That’s wrong, too. I mean, dare say I, because I haven’t, fortunately, at this point, faced my own death. But everything I know about myself is that it is going to be something like this… Well, I have this diagnosis, and I have these choices. And what is the best thing to do here might be that doing a medical intervention is the right thing to do. But as I say that, what really goes through my mind is really very little about me. It’s really about who are the people in my life who need me? Because for me, death is no big deal. I mean, it’s just to transition into another state of being. But for my daughter, for my mother, for my partner, for some good friends, I have to take that into consideration and want to take that into consideration. But I don’t have a personal… How would you say this? Imperative to stay alive. Or even to see my grandchildren. I don’t have that. That, to me, is not… That may not be my destiny. But I do have what I would call a relational imperative to check in with and dialog with my loved ones, honestly, about my situation and make a familial communal decision about what is best for all involved here.

William Peters’ work with the Shared Crossing Project encourages a conscious, connected, and loving experience shared between the dying and their loved ones. Where August Wilson gave us a frantic last stand, alone and without family, Peters’ research reveals something closer to a gentle crossing over, often filled with unexpected calm, bliss, and joy. The three essential expressions he advocates—”Thank you, I love you, Goodbye” as I shared in an earlier walk, allow us to open our hearts for one final act different from the fate that awaited Troy.

Liz: So how did you create the Thank you. I love you. Goodbye. How did you create that? Because if someone else doesn’t have the gift of knowing you or of being part of the work that you’ve done, it’s still so simple that anybody could do it. 

William: So for me, when I first got into this, the work with the shared death experience, my aspiration was, well, I know that if people knew this experience was possible, they’d want to say, how can I have it with my loved ones? So I started developing methods to enable the shared death experience, because in my mind, it was the best death possible. You have a shared death experience. You realize that your now departed loved one is alive and well. They’re happy. They’re experiencing joy. Joy and love. They’re reunited with previously deceased relatives. You have a sense you’ll see them again. So this feels like more of a vacation, if you will. A time apart is temporary, not permanent. You have no question about whether they’re alive or nonexistent. You know they’re alive, and your grief is much better. So your grief is just contextualized in the understanding that death is a natural part of life, but you’ll see your loved ones again. So my goal was to give this to people. The truth of the matter is I didn’t even have to think about it. All of a sudden, it just became three things right away. First was to affirm these experiences. You first have to convince people that the shared death experience and other spiritual end-of-life experiences are normal. They happen with great frequency, and you can anticipate that you’ll have those if you are open-minded, if you’re more accepting of death as a natural human process. The second thing that came into my mind is we have to deal with our unfinished business. So you have to really deal with any sense of relational dissonance, acrimony. Those are emotional blocks that will prohibit the SDE. And I learned that, you’ve got to help people die.

Liz: I think those emotional blocks are where this element of fighting death comes from, because even the person that’s dying, they have unfinished business. 

William: Correct. In a certain way, some people could say, well, I have more to do here. And that could be unfinished business. But that’s also a misunderstanding that at some point we have to die. And your list is less important than your natural life expectancy. Once you realize that you’re not in control of that, then there’s a real freedom. But for some people, it’s a real frustration, something they resist. Like, I don’t want to die now. But that’s also a cultural piece of the Western mind, which is diluted into this notion of rugged individualism and self-determinism.

… to answer your question, specifically, the thank you, I love you, goodbye, is the last step in dealing with unfinished business before you start doing the choreographed guided visualization. That’s the step of saying, Hey, I know you’re going to die, or, Hey, you know I’m going to die. I want you to listen very closely to me. I want to thank you for having shared this life with me. I want to tell you that I love you, and I’ve cherished most moments with you and any tension, disagreements, misgivings, regrets that I have for us, for you, for me. I now forgive myself and you of any of that. I absolve us from our relationship, of any of that. And that we are now free to accept one another 100 %. And with that, I want to let you know that I have no illusions that I am not going to be dying soon or that you’re not going to be dying soon.

So I want to say thank you and goodbye. And now that goodbye, I don’t want to miss the opportunity to say goodbye. I hope that we have more time together. But I want you to know as I look at you, our end is near. And so there’s a really beautiful way of just stepping into that. And so doing that, that opens us up to the next and final step is, how do you prepare for the greatest transition in a human life outside of or equal to birth coming in. So that’s how I came to all that.

This gentler notion of death has its roots in William’s own life.

William: My grandmother was dying and when I was with her, I realized she was having these conversations with people, and they felt real to me. And I’m like, ‘What the hell is this?’ And I started getting interested in what is happening at the end of a human life. I had already had two near-death experiences, one when I broke my back on a ski slope, and a second one when I had a rare blood disease, idiopathic thrombocytopenia, where I was drowning in my own  blood, and so I had an out-of-body experience.

While I was watching my grandmother, I was like, ‘She’s both here and somewhere else.’ And that was very interesting to me. And she was having conversations with what I would call a being from another dimension. I couldn’t see this person. Maybe this person was in this dimension. I couldn’t break through to even get to my grandmother. I walked in, she didn’t even know I was there. So with that, I got interested in the end of life.

I decided to join Zen Hospice in San Francisco. And when I did that, here I am sitting at the bedside of many, many people dying, 24-bed, open ward hospice, public hospice, county run. So indigent people with nowhere to go. And we get the opportunity to sit with these people at the end of life because no one else is there for them. Think homeless people, what have you. So I start having these experiences where I’m sitting with somebody, and all of a sudden, I’m out of my body, looking down at them and my body, and the whole shape and dimension of the room is completely different. I’m in a different dimension. And I’m like, this is really interesting. Well, It’s interesting in and of itself, but it’s also like, hey, wait a minute. I’ve been here before in my two previous NDEs, and this is really interesting. And why isn’t anybody talking about this? So this began a very deep exploration of what really is death and dying, what does happen to us. But it took a while because I was reticent to go off in this direction because it’s pretty extreme. 

Talking with Bill had me thinking about death from a new perspective. One my father didn’t have. As a doctor, death must have felt like the ultimate professional contradiction. He spent years learning to read vital signs as data points—when blood pressure drops, you give pressors; when the heart stops, you start compressions. My step-mother’s death must have been not just a medical failure but a personal one, the moment when all his knowledge and skill proved insufficient. What pain that must have been for him. I am rethinking our final weeks together.

My mother, on the other hand, spent the last decades of her medical career bearing witness to many deaths. Perhaps she understood better than anyone the strange mercy in knowing when to step back from the machines and medications, when to shift from curing to comforting. 

Liz: I think my mom had done her own training throughout her medical career once she left my dad and was working at that state hospital where no one got discharged. Every single patient died because it was major head trauma or end of life or dementia. And what she was so good at was helping the families accept it. And I think it’s a shame that she never got to talk to you about her work as a physician doing that, because I think she would have had a great deal of wisdom.

William: Yeah. Well, your mom sounds like she was one of those angels in the system who had found her place where she was more than her role.

Liz: …she was throughout her career. My dad would be furious with her because she would spend so long talking to the patient and asking the patient questions. She wouldn’t see as many patients in a given day as he had created the business model for them to see.

William: Well, and there you see it. When medicine is a business model, I think you’re at odds with humanity. And then, of course, then again, maybe it’s not on medical doctors to do the rest of that. Maybe the best use of them is to use their training and just do the diagnosis and treatment models and offer them that, but then get out of the way and let someone else engage them in their choices. If that’s the case, I’m perfectly fine with it. 

Liz: As you’re talking, I’m thinking about metrics and how this cancer center tells you working with us gives you five extra years of life. Well, if that’s your metric, that’s great. But is your metric how much quality of life you had in those five years and how peaceful the end was?

William: I always say two years of fun and enjoyment to each other with a swifter, nonmedicalized death is better than five years, of which five of that is on medication, and throwing up, and sweating, and losing hair, and aches and pains… a lot of the dying will say, I don’t want to do this to my partner.

Liz: My mom said all the time, I don’t want to be a burden.

William: Exactly. And that’s not an unhealthy response. Sometimes it can be a little bit based on shame of not feeling they’re worthy of care. But a lot of times it’s just like, yeah, I’ve lived a full life. And I don’t want it to be a burden to my family who’s got bigger fish to fry than taking care of somebody who’s lived their life. Go hang out with the grandchildren and know that I love you and support you. And we’ll be cheering for you from the other side. Let’s do a hug and a kiss. And I love you and thank you. And you go live your life fully and don’t stay a day longer than you have to.

Liz: My mom was ready to die. She would say, the Lord will take me when He’s ready. I knew that, and she said that a lot. And I know in the quiet of her place, she had to pray. Aren’t you ready yet?  And yet it was very difficult to administer morphine at the end of her life.

William: Well, this is a very sensitive area in end-of-life care. 

Liz: I feel like I killed her.

William: So there it is, right there. Terminal sedation is one of those things that happens quite regularly… I always say, treat the pain. And if you end up sedating them so much that it hastens death, then you need to understand that that’s compassionate care. If death comes, death comes. A lot of people come into my office feeling guilty, ashamed, like they did it wrong. And my job in those situations is, “Yeah, I see how you struggled with this. And you did the right thing. You did the right thing.”

Liz: We just all want somebody to tell us we did okay.

William: Exactly. 

Liz: There was a point, and I think even you were surprised how quickly I was calling you because my mom was dying soon after my dad died. And you said, What’s going on? And I told you what was going on. And in the tone of voice that only you can have, you said, ‘Oh, yes, she’s dying.’ And I told you she had just said to me, ‘Elizabeth, everyone will know your name.’ And I had said back to her, ‘That’s because you’re my mama.’ And you said, ‘No, she is trying to give you a gift. You have to accept it.’ And I was so glad you said that to me. 

When my dad died early, early, early on a Sunday morning, and I left Saturday morning when the caregivers got there. I’d spent the night, and I went to his bedside, and he said, Am I dead? And I said, Dad, I know I have the face of an angel, but no, This is not heaven. You are not dead. And he chuckled, and I chuckled. And I went into the kitchen to do the thing you do. Here’s the last time he had his meds. Here’s where we are, all those things. And because he and I had just had this exchange, I expected to come back later that day to still have my father. As I was getting ready to go, with as much strength as I’d seen him have in months, he screamed, Elizabeth, I love you. And I didn’t go back to him. I screamed it right back. I love you, too, dad.

When I got back, he no longer was communicative. 

William: Unresponsive.

Liz: Completely unresponsive. And that night, I was changing his diaper. I was using the glycerin lollipops to moisten his mouth. And he willed his death quickly in my mind because there was no way that was the relationship he wanted with me. You had told me about soft lighting and good music. And I sat down on that bed next to him, and turned the lights down. And I played the music that I played when my son died. And I wouldn’t have done that if you hadn’t told me to. 

Bill walked me through my parents’ deaths. I cannot think of a more profound gift.

William: People say, oh, my God, you’ve made such a contribution. I mean, we go to these conferences and there’s hundreds of people after we give a talk. It’s even sometimes hard for me to take it in because I do what I do because this is what I’m called to do. But when someone comes to you and says, you, your book changed my life. Your talk made all the difference in the death with my mom. And we hear this all the time. I’m grateful that my life has had that effect on people. And at the same time, I say, it’s not really my business. I did what I came here to do. And I think I just followed the breadcrumbs and made the best … I mean, look it. I made the best of it. But I think it’s really important to note that I would be not authentic if I said this was the life I wanted, I planned, I worked hard, I manifested. None of that is true. This was the life that was the process of taking the best available option, knowing what my knowledge base was, knowing what my gifts were, knowing what I was capable of doing. And yeah, I definitely work hard. I was going to work hard no matter what. That’s just who I am. I work hard. But like I said. I don’t know. I just did what I could do.

That’s all any of us can do.

Standing alone on that stage production of Fences, taunting death with his baseball metaphors, the character of Troy embodied everything our culture teaches us about how to face the end. Fight hard. Go down swinging. What if, rather than seeing death as the pitcher trying to strike him out, he had recognized his family as the teammates ready to walk him home? Troy’s defiance, though dramatically compelling, left him alone under those stage lights—isolated in his struggle, cut off from the very connections that might have made his crossing something shared rather than solitary. And for those who’ve never sat vigil in those quiet hours, trust me, it’s there, in the dim light of 3 AM when the rest of the world sleeps, that you discover death isn’t a violent intruder we’ve been taught to expect. Instead, you find yourself not in the audience but in a supporting role for one final act of profound connection.

Thank you. 

I love you. 

Good bye.

---

There is a moment that sneaks up on you that is unexpected and unwelcome. It is the moment the first service personnel calls you ma’am. You realize you present as more mature. You convince yourself it is a sign of respect, but you know it is a slippery slope to senior status. Senior what? In my world that means top of the food chain, extra privileges, a beginning of a new life lying in wait just around the corner. Senior Citizen? Well, there’s something damn jarring about that. Society, it seems, has collectively decided that I have hit the age that marks the beginning of my decline. As if I was handed a script suggesting my vibrant chapters should now gracefully give way to a quieter, more contained existence. Bullshit. I am reclaiming senior status with all its positives from high school vernacular for myself and my contemporaries. We are going to cut the lunch line, decorate our parking spots, and embrace a new chapter of living all with a much slower metabolism. Who says there should be an expiration date for ambition, for reinvention? My most interesting stories are still unwritten. 

Carolyn: Nobody really prepares us for this phase in life. Nobody really talks about it. I mean, I think they talk about it more now than ever before, but there’s a long way to go. And you have to really be your own advocate in this journey at our phase. 

Monica: There’s two big components you guys just broke out. Number one, women aren’t really seen in health care and are often dismissed. Particularly after we pass the age of “productivity,” which is the Western model, to be productive, we can feel put out to pasture. Part of that is, we’re going back to a patriarchal order that does not witness the different ages that women have. We’re way more start and stop with our hormonal rhythms than men are. Andropause is long and slow and gentle. Menopause is abrupt and shocking. We get hot and angry and dry.

Liz: All the things I felt so far today.

Monica: In indigenous cultures, there are rites of passage for teenage girls starting their menstrual cycle. There’s a rite of passage for entering, exiting the motherhood stage and entering the wise elder, the crone stage. 

Liz: The crone stage. 

Monica: The crone stage, yeah. Which doesn’t sound attractive, but it is the embodiment of grandmother wisdom. The grandmother is revered in the tribe and is like a secret wisdom holder. But in the West, we don’t have a place to elevate. There’s nothing that elevates us in this stage. As we’re experiencing this transition, we have a loss of identity. We feel like chopped liver because we don’t have a story that takes us into our wisdom stage, which is what this is.

Carolyn: Well, it’s our wisdom stage, but we’re also a culture which is going, I think, in a really horrifying direction as far as what beauty looks like. And with all the cosmetic surgery and people and women trying to fight aging in a way that I find very uncomfortable instead of women embracing their wisdom and their age, they’re fighting it in a way that re-defines what beauty is.

I embrace my aging reflection in the mirror. Indeed as I walk with my contemporaries,  Monica Williams and Carolyn Greenfield, I see only their passion and spirit, appreciating their style. I am inspired by the less travelled paths they have chosen and at no point am I wondering what beauty products they use. We don’t feel like we fit inside the box that once contained our folded, compliant selves. Carolyn turned a creative hobby into a successful jewelry business. She is the artist behind almost every piece of jewelry I wear. 

Liz: I only wear your jewelry, with the exception of a gift and the ring I designed. And every time someone comments on what they call in my neighborhood, ‘the Liz necklace,’ there’s a moment when you and I are connected. It’s empowering that you chose to do this and that you’ve made so much out of it. 

Carolyn: Well, thank you. That’s very flattering. I like to make things with my hands, and I like to be creative. And although it is not something that anyone “needs,” what gives me great joy is to see people wearing things that I made with confidence and it looks different from one person to the next. I can be in a room of crazy, dynamic women, and they’re all wearing things that I’ve made differently than each other. And nobody knows, except for me, that it came from Carden Avenue. It gives me pleasure just seeing you wear it with confidence. 

Liz: But I think you’re doing more than working with your hands. I think you’re curating a place of joy and calm. I don’t know. There are times I just want to be in your jewelry studio.

Calm was also a destination for Monica as she chose a path out of chaos that walked her right out of the emergency room sliding doors following the pandemic.

Monica: I was a full-time emergency physician during COVID, and I did not contract COVID until October of 2022. And it didn’t put me in the hospital, but it put me in bed for two weeks. And I haven’t had an illness as an adult that took so long to recover from. I was going through menopause at the same time, so a double hit. The joints on my right-hand started to swell up in the second week of my recovery. After I was fully recovered, those joints of my hand would swell up in the middle of a night shift… after a glass of red wine… or after too much stress. I got very clear there was a line that had been drawn in the sand. My body gave me a clear signal that this level of stress is a pathologic state, and it was turning on an acute arthritis, which is another pathologic state. And genetically, we see that one disease state turns on other disease states that are latent. And so I just thought, I need to obey this because this could be a clear sign from my body telling me, ‘You have two pathways here.’ I actually quit full-time emergency medicine practice and spent the next year healing. 

Carolyn: What did that year look like?

Monica: Well, I retrained in genomic-based health. I started seeing patients who were the 15% of people who fall outside of the textbook that are generally dismissed by doctors, those tend to be women, tend to be medically complicated, may not have a classic box or category that their lab work identifies them as having “X.” So they feel very unseen, and they’re very sick. And these were the people I attracted as patients because genetically, we could look at you and say, “This is the blueprint. These are the cards you’ve dealt. And these things are trying to wake up. They just haven’t reached laboratory significance yet. But we can work on them and bring them back down, cool them off.” Because that was my own experience in my own health.

Liz: So the arthritis, you cooled off?

Monica: Yep. So whatever genetic pathways were turning that on, when I came out of my state of distress, it was self-induced and career-induced and COVID-induced. It was just the convergence of all of these different stressors. And my blood pressure was out of control, my kidney function was starting to get abnormal. So my ship was sinking, and I got very clear, “Well, I’m not ready to fully decline. I have three children who are dependent on me only, so I need to change my life if I’m going to not be disabled.”

Liz: You’re talking about a medical IEP. In education, we’re talking about an IEP for everyone, including teachers and administrators because we all learn differently. That’s basically what we’re saying. Let’s stop talking about us as late ’50s women because it’s Carolyn, it’s Liz, it’s Monica.

Monica: Exactly. That’s where traditional medicine is no longer going to apply to us because we have algorithms for your blood pressure. We’ll start with this medication, we’ll move to this one, we’ll add in a third. But those are based on population-based studies, and none of us is a statistic. 

If we looked at our genetic profile, we may or may not fit that Bell Curve. If I’m treating you according to what’s under the thick part of the Bell Curve, and you’re one standard deviation out, well, you’re going to feel like medicine has failed you because it has. That’s the future of medicine, which will make it personalized… construct something that’s good for all people and it’s not leaving anyone out. 

Liz: I love the feeling of hope in what you just said.

I can’t help but think that the fact that you chose to follow a passion and design jewelry, and Monica chose to step off the treadmill and not be a full-time ER doc. And I walked away from the next, and next, and next in the education ladder, provides some role model for things that can be different from the way we were taught to consume and achieve…

Carolyn: I think it’s so important to mirror or to demonstrate your work ethic, regardless of what it is. It’s super important that you’re doing something that you love. I do think that our generation of kids values that more than any other generation that’s come before us.

Liz: Yeah, I love that you give yourself grace there that we grew up differently. 

Carolyn: Well, it’s what we’re learning from our kids. And when you make that shift, you have as much to learn as they do.

Monica: Crone Wisdom 101. 

Always willing to learn but always aware we are modeling and teaching our daughters.

Liz: There was a moment, New Year’s Day a year ago… when I was headed into the last semester of being a Head of school and thought at that moment I was going to be the CEO of a software startup. We were having our philosophical “what’s ahead in the new year conversation” and I was overwhelmed to say, “Girls, I don’t know what will come next, and I may fail, but I want to do this because I want you to know it’s okay to risk, to fail, and to learn.” And my God, if I didn’t fail large.

Monica: I would give you a standing ovation for that talk. 

Liz: Thank you. They both just gave me the daughter nod.

Carolyn: It’s the obligatory daughter “I know” nod. 

Monica: But you know what? That probably unnerved them a little bit since you’re their stabilizing force. But that will give them confidence and bravery and unseen moments in their lives.

Liz: I’ll take that. True or not, I’ll just take that.

Carolyn: No, it’s true. You’re putting yourself in a very vulnerable situation.

Monica likes to say we are individuals, not a population. I like that. I don’t want my failures or my age to be someone else’s cautionary tale or a problem to be managed. I want to be an individual. I want to write my next chapter as an adventure of learning, of unbridled joy all while being grounded and more balanced. I am after all a human being …not a human doing.

Monica: My main sense of loss has been around energy because I was way more energetic when I was younger, but I also abused that. I thought my body could do anything. So now I’m coming to terms with the fact that I’m energetically limited, but I’m trying to find the gift in that, and I’ve interpreted it as there’s less energy for doing, so there’s more space for being. And that really should be what the last phase of life should be about, in my opinion.

Carolyn: Well, that’s what I was going to say. I feel like there’s been a shift for me in that your life doesn’t have to be so task-oriented, but it’s all about, how do you want to spend your time? And what do you do with that time? And that goes to your whole idea of being, right? What is it that fuels you? Because it might not be the same thing it was 20 years ago.

I don’t know about the two of you, but I’m just increasingly aware all the time about how you’re so invincible for a period of time in your life, at least you think you are, right? And then there’s a shift, and I’m not sure when that is, but you all of a sudden, maybe it’s when we become moms, or maybe it’s… I mean, who knows what the shift is, and I’m sure it’s different for everyone. But your viewpoints change because you just realize how fragile life can be.

Monica: We just visited a 75-year-old friend who works with homeless boys in Kenya and raises money for an orphanage there for them. She’s like, I must curate my remaining time and devote my active energy to what matters most, even if I find these other things interesting. So what’s the best use of the action principle that I still have remaining? And she’s an elder, wise, crone woman. I could take that from her. I could see the wisdom from which she was practicing. I found all of that inspiring.

We talk about “managing” time as if it were something we could control, when really what we’re doing is making choices about where we place our attention. There’s something almost sacred about deciding to be fully present with the people who matter most—putting down the phone during dinner, lingering a moment longer in conversation, choosing the walk with an old friend and a new friend over the to-do list with which you arrived.

Liz: I keep saying when I’m writing these walks, that these were the right people. And I don’t really know why some of them were involved, like even this walk, it wasn’t planned. And yet we’re standing in the midst of a conversation and I knew it had to be part of the series. 

Monica: Yeah, the right people. You take the opportunities when they present themselves to reconnect with the people that do make you feel good.

I used to guide parents to think about the adults who were in their children’s windshield. When they look up and around every day, who do they see? Who is serving as a role model. For their most formative years, Grace and Ella had the right people in their windshields. They are still there. I never once thought about my wind shield until I started on this journey of walks. I’ll be honest I have not always had the right people in my windshield, so I’m grounding myself to connect with people who make me feel inspired, calm, happy. These two women fit that bill. I knew I had to walk with them. For me. There were hours of conversation I didn’t record. I wish I did. You would be inspired. But maybe it was enough that we had those discussions. That we inspired each other.

There are rare souls who make us feel more like ourselves when we’re with them. They are the right people for this later chapter of my life. They bring hope. They are present. They fill my soul. 

Carolyn: it’s in your heart.

They see in me what I am becoming: not a woman diminished by age, but one amplified by wisdom and seasoned by laughter. I am at the beginning of the most beautiful chapter that opens the moment you stop apologizing and start celebrating the profound grace of a life fully lived as imperfect as it is. Yes ma’am, I am stepping into my crone, and she is glorious.

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Here’s what I’ve learned from wrestling with a blank page: writer’s block isn’t really about writing…or not writing for that matter. It’s about everything else. It’s about the schedule of the day ahead. It’s about the conversation I had with an old friend moments ago… or even months ago. It’s a voice that whispers, “This one has to be good.” It’s about the gap of expectations – the space between potential and perfectionism. 

Maybe writer’s block is really just a necessary pause – that space between stimulus and response where wisdom edges its way in. We have to walk around our ideas – see them from various perspectives – especially in unexpected ways. 

Liz: We were talking about what I call writer’s block, but you said you get it even in a non-creative situation. Can you say more about that?

JD: Yeah, not so much creative, but I always try to find something unique or different or something that somebody’s not thinking about, deeper insight into whatever the topic or the business or the issue might be to bring something to the forefront. So you’re not always having the same conversation about the same thing. You’re digging in. In an operating environment, you’re actually identifying and solving an underlying problem in the business or taking advantage of something that’s going well. So what are those things? How can you identify them? Then what are you doing about them? Either to fix them or to leverage off of it.

Liz: So do you try to tell the story of the thing that’s going well?

JD: First of all, what is it that’s just out of the norm so we’re not having the same conversation all the time? Then what are you going to do to fix it? Or what are you going to do to lever off of it? Or when I was in the field a lot, I used to call it, give the client a gift. Tell them something about their business that they don’t know and that you have taken the time to understand or draw insights into from them.

Give them a gift. I’ll get back to how that applies in the business world, but I have to pause. When Jon Grandstaff, JD as I still call him, said those words on our walk, I stumbled. They had that big of an impact on me. These walks are a gift. Individually and collectively they have been a gift to me – grounding me, inspiring me…. stoking my curiosities and highlighting the simple magnificence that comes from someone’s story. I didn’t intend for them to be a gift to the person with whom I walk, but I have found that they are. It is a gift to slow down a hectic day for a walk. It is a gift to be seen. It is a gift to know someone wants to share your insights with the world because they are so profound. As JD says, I tell them something about themselves that they didn’t see as remarkable and draw insights for others.

And some walks offer unexpected gifts to readers and listeners. You hear something that screams, “You are not alone” and maybe you see something in your life a little differently. 

Let’s return to JD’s explanation of how this applies to business – perhaps, you are asking yourself what business? – I ask myself that too. I’ll try to get to that answer for you… think of it as a gift coming later.

JD: give the client a gift. Tell them something about their business that they don’t know and that you have taken the time to understand or draw insights into from them.

Liz: Can you think of an example?

JD: In the business we’re in, and you’re in the field with clients, I’d always try to look deeper into the data to tell them something about health care utilization or trend or spend areas or provider behavior that may be questionable, that maybe they didn’t know about themselves. We can be that consultative strategic partner and just not the typical vendor relationship. So you’re of value.

Liz: I love that you were pulling a story from data. Do you live in numbers and data?

JD: All day, every day.

Liz: And yet you recognize that the best connection when you’re with a client or now with your team is more in the storyline.

JD: You have to tell a story from it. What does it tell you? Why? Why do I care about that? It’s the old “so what” conversation.

I love being in the field with clients, understanding what’s working well, what’s not, what their needs are, trying to move a conversation to the next level, get something done with them. 

Liz: Why did you like that?

JD: I always wanted to be seen as a problem solver because I never was a sales guy. But I was always looking for ways to grow businesses and grow work that we’re doing with clients, but more from the perspective of being of value.

Being of value. Isn’t that what we all want? I remember Angi Evans admitting her thoughts on retirement, “I matter. In a certain segment of the world. I matter. People notice if I’m not there. I think I will miss that. I’ve become very used to mattering in the world.” 

There was something about her honesty and vulnerability that has stayed with me. We don’t just want to belong somewhere – we want to belong in a way that matters and not just for our utility but because we made a difference in a project, or in a life. 

I remember thinking years before my father retired, “I wish he would slow down.” I voiced that to a friend of his. He disagreed, “Your father has meant so much to so many people, he wouldn’t know what to do with himself if he didn’t work.” For a brief moment Dad was lost when he walked out of the CEO’s office at Wheeling Hospital. Now what? He didn’t wander far from his patient-centered life. He volunteered at a free clinic and remained a trusted medical advocate for friends and for me. I’d ask him about every ailment my daughters or friends had. I’d ask him for advice on kids at school, for referrals for teachers, and for guidance on our health insurance. The last one always eluded us both.

We should have asked JD. Turns out his business is healthcare finance.  As a woman who just navigated private pay through COBRA for herself and her daughters, I have some thoughts on health insurance, but I thought better of disclosing as much and asked JD for his opinion.

Liz: So what’s your take on health insurance in general as an individual, as a dad, as a family member? 

JD: I guess thinking about it, it’s one of those necessary evils in life. It’s so expensive and so cumbersome and so difficult. But if you didn’t have it, it would probably be pretty awful at the end of the day and detrimental to many of us. So I don’t know.

Liz: That’s an interesting comment.

JD: It would take so many families and individuals down financially and otherwise. They would not take care of themselves because they couldn’t afford to do it. Even with health care itself already being expensive, they would just not take care of themselves.

Liz: There was obviously a time that there was just a doctor and a patient, and there was a transaction. And somewhere along the way, insurance was born.

JD: Now that you say that, I never have really thought about that. But I assume it was somebody thinking they could do it better or more efficiently or more cost efficiently with this concept of accumulating people into groups and group rating individuals to get better cost. That’s the whole structure of HMOs and PPOs and having networks that you can put people together and spread cost around and you can drive volume to providers that justifies them giving breaks on costs.

Liz: The idea is I just pay a little bit regularly, and then I never get blindsided by a big bill, but I’m also in turn helping other people when they need it.

JD: Yeah. This year, you may not have much of a health care need, and you take certain fewer dollars out of the system, but somebody else has cancer this year, and they’re taking a lot out, so they can average that across a number of people, but keep it low for everyone.

Liz: And you work at the level above all that. Your support is of the insurance companies themselves.

JD: For the insurance companies, inherently …but I like to tell the story that we’re actually, to some extent, working on behalf of the individuals and the members. Because to the extent that we can help manage costs for the providers, it means that the health insurance companies now don’t have to charge such high premiums. If you don’t have to charge high premiums, you can care for more people.

Liz: That’s a good spin on it.

JD: Again, how do you tell the story? It’s about tying into what is my client’s reason, what’s their so what and their why, and their mission and objective is to, most always, provide great world-class care for their members. How am I a part of that conversation? How am I supporting their objectives? In terms of that gift and how I tie what I do to what clients need and want. 

Maybe it’s my athletic background or team environment, but I’m all about the team and collaboration. And as I say, sometimes all hands stacked in the middle.

Liz: You mean that moment before you go?

I couldn’t even find the words for the huddle – that moment of pure alchemy before a collective, explosive roar… before hands fly skyward and bodies scatter into formation… before individual goals manifest again. The individual strength in that close circle doesn’t just add up—it can multiply.

JD: Everybody’s got to be on the same page. Everybody’s got know the why. What I don’t do very well… I call it the ‘got you game,’ and I’ve had some very direct conversations with peers and other people about that whole thing.

Liz: In my life, I’ve noticed that direct conversations between people, even if they’re painful, are the only way to move forward. And if you can’t have those direct conversations, then it’s probably not the right place for me. Rick likes to say, ‘Bad news only takes so many minutes, and then it’s over. Stop fretting about it.’ 

JD: I mean, to the point, whatever I said earlier about being willing to face the brutal facts, whatever they are. I mean, we used to have a saying in my old company. We’d say that bad news doesn’t get better with time. So just speak it and live it and be brutally honest with yourself.

Liz: Oh, be brutally honest with yourself. Say more about that.

JD: You, as an individual, have to be willing to acknowledge and accept whatever it is, good or bad. Everyone will always accept the good, but you have to be willing to look at the bad as well and then challenge yourself with ‘Why was it bad? What am I going to do about it?’

Liz: Except sometimes, can’t we, without someone else… an outsider helping us, can’t we pick the wrong answer to ‘Why was it bad?’ Pick the victimization role? It was bad because of them instead of what I did? 

JD: Sure. I try and not always make it about someone else. But all right, so what was our role in what they did? Someone else may have ultimately done whatever. But aren’t we ultimately accountable with them?

Liz: And you can’t change them. You can only change you.

JD: But if we had a better process, a better tool, a better way of this, a better that … better whatever… could we have kept them out of that scenario altogether? Maybe not always, but we should always challenge ourselves.

Liz: I think if I’ve learned anything in the past two years is just to hold space because you don’t have all the information, and if you’re quick to judge or act without all the information, you’re going to be wrong. So if you hold space, there’s something else coming and I can work within this parameter of what I have, you’ll be more successful. 

JD: Well, and a lot of that comes from a certain level of trust as well. 

One invisible thread weaves through every successful collaboration, productive meeting, breakthrough innovation or just a good walk: trust. Whether you’re leading a team or navigating a difficult conversation, trust serves as the fundamental currency in the transaction. Without it, even the most talented teams crumble under miscommunication, and defensiveness. With it, trust creates a safety net that allows people to take risks, share ideas, and navigate hard times. During one of my hardest times, it was JD I trusted to be a steady, logical presence. It was he who was my safety net.

Liz: I think I’ve learned more about you on this walk than I even knew I would learn. But there was no question in my mind when I felt lost in a storm, You were a lighthouse. And it’s not just because you’re so much taller than I am… There’s going to be a moment where we stop and take a picture, and it’ll be clear to anyone who hears or reads this that we are not of the same size. 

JD: We’ll find a rock for you to stand on. 

Liz: Yeah, right. Might need more than a rock… but I just felt like, here’s a steady hand that I can hand the controls to. And I’m very appreciative of it.

JD: Well, thank you for trusting me in that. I don’t know that I deserved it. I’m appreciative that you trusted me.

Liz: No, of course you did. And the truth of the matter is, none of us think we deserve those, I don’t know, recognitions, or acknowledgements. But you said yourself it works better when you see the transaction between people as a gift you’re giving. And I don’t think we all think that way… but should. 

Maybe writer’s block isn’t about having nothing to say. Maybe it’s about learning to listen to what wants to be said, and then finding the courage to say it imperfectly, authentically, one word at a time…or two.. such as thank you. JD, your steady consistent rational hand gave me peace and helped me navigate through a storm or two. Never as loudly or as clearly as the time you leaned forward as we rode an escalator and you whispered, “as long as you have your girls.” Now those seven words were his greatest gift.

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Are you old enough to know Mary Tyler Moore? Do you remember the still image of her broad smile captured as the video freezes on her throwing her hat into the Minneapolis sky while spinning around to look into the camera with eyes that welcomed you to join in her joy? 

When I look at the image I am struck by the woman in the background. You can almost feel the generational clash radiating in the moment. There’s Mary in the center, practically glowing with liberated energy, while the woman in the blue headscarf embodies the boundaries she wouldn’t dare to cross. Her whole ensemble contains her – the opposite of taking up space. You can see the generational fault line. Tension creeps in. The writers could only push so far—they’d give us a professional woman, but she would have to be palatable and gracious. Even as Mary blazed trails as a career woman, she still apologized time and again for taking up space. Still…it was a step on the continuum. Obviously, it touched my young heart as the song serenaded, “We’re going to make it after all.” 

I hadn’t thought of that moment of television history in decades until I witnessed Luke Felker make almost the same gesture in Chicago a few years ago. He was joyful – no resplendent –  to be walking the streets of the windy city reveling in a quick respite from being a Head of School and the weight of expectations that accompany it. As heads we lead and influence that generational continuum – it’s heady work – pardon the pun – so we need time to find ourselves relishing the joy of a moment – Mary Tyler Moore-style. 

Luke is my Head of School soulmate. He is my 2 AM call… which is awkward because we have been on very different time zones for 11 years now. He is my Mary Tyler Moore with a lilt in his voice as his words flow unrestrained in pure excitement for the work. When life kicks him in the teeth, as it does all of us, I swear the entire world tilts off its axis. And being a Head of School at The Bay School in San Francisco, CA – especially during COVID – knocked the wind out of him a time or two. His silence would cause alarm momentarily.

Luke: Even if we haven’t spoken in the last month, whatever the case is, knowing you’re out there in the world generally makes me feel better. It’s going to be okay. She’s out there.

We’re going to make it afterall.

Liz: When things were really rough at one point during my divorce, I remember I got a card from you and you said, “I wish I could take you for coffee.” And you sent me just enough on a Starbucks gift card for a cup of coffee. It was just the simplicity of, ‘I see you. I know this is a hard time. I wish there were something I could do. Have a cup of coffee.’ 

We buoy each other. We build on each other’s energy. It has been crucial to me to have a colleague that I trusted with my strengths, my ideas, and the depths of my challenges and my fears. He shares many of them… as do many of the colleagues who live as heads of schools. Listen in.

Luke: Life is fragile. Schools are fragile, and some schools are more fragile. When you have no money in the bank, it’s a really logical fight or flight… it embeds in us in ways that… One of the things I share with a couple of really wonderful leaders I work with all the time is we’ve all got to take ourselves… in the balloon again. 

Liz: In the balloon? 

Luke: In the balloon. Well, imagine our work as heads or our work as educators. We’re often right on the ground with kids, whatever the case is. And on occasion, we all need to come up to see. I have this amazing CFO who has not been in schools before Bay, and I feel like he has the ability to ask a question where I’ve forgotten that was possible because I’ve been in schools so long, or let’s say, not exceptionally wealthy schools.

And I’m like, Oh, my God, that could happen here.

Liz: But to the balloon, we think of a hot air balloon, and so you think of blue sky. So I think there’s two reasons to get in the balloon. 

Blue sky thinking is like giving your imagination permission to soar without limits, a creative space where you temporarily set aside budget constraints, technical limitations, and that little voice saying “but that’s impossible” – while embracing the hint of “what if it weren’t?”

Luke: Oh, my God. Yes. Well, that’s part of the work that… I mean, that’s what’s been so much fun about working with you is that I feel like we readily go back and forth from land to sky, and there are people in your world who are going to do that with you and that allow you to pause to see things you wouldn’t have seen otherwise. And I think that’s part of what keeps me sane. And why did I come back to ISACS all those years when I was in California? Anything that gets me out of my bubble allows me to see things from a different perspective. 

Liz: Just get out of the typical box, for lack of a better word.

Luke: It’s myopic. I adore my CFO. I have to resist talking to him every day. This might be crazy, and… Sometimes he’s like, Okay, I’ve learned more about how the school works, and this is a craziness that is. Sometimes I’m like, ‘Oh, my God, you’re right. Why have we done this? Why does every other school do this?’ He’s like, ‘It’s insane.’

Liz: I like that you said, “This might be crazy, and” instead of, this might be crazy but.

Well, because… AND accepts the crazy. 

Luke: … tension is not a negative, it’s a descriptive phrase, and that’s some of the best work we do … If we’re not in tension, we’re probably too far on one side of the spectrum in terms of how we might be leading as a school or a program. You can’t have tension all the time, and you can’t have people being mad at each other all the time, blah, blah, blah. But it’s been like a self-help skill for me ”Oh, tension is a part of my day.”

Not just any tension…we are talking about generational tension. It isn’t the enemy—it’s the very curriculum of our schools. Of course Mary’s breakthrough joy carries the weight of what came before. Of course there’s friction between the woman who tosses her hat in the air and the one who keeps hers pinned down with a proper scarf. I shouldn’t smooth over these differences or dismiss them as obstacles, but rather lean into them with curiosity.

Why does Mary still feel she has to smile apologetically for taking up space? What complex inheritance makes her grateful for scraps of opportunity? Why does her very accommodation—that lingering need to make everyone comfortable with her liberation—stir something unsettled in me?

This is where growth lives: in the uncomfortable space between generations, where the old rules haven’t fully died and the new ones aren’t fully born. Each generation carries both the wounds and wisdom of those who came before. The headscarf generation knew survival; Mary’s generation dared to dream beyond it. Both truths can coexist, creating productive friction.

As educational leaders, we’re constantly navigating these generational crosscurrents—honoring what sustained previous generations while clearing space for what the next generation needs to flourish. How could there not be tension when we’re literally midwifing the future while honoring the past? That tension can be our compass, pointing toward the essential work of helping each generation build on what came before while becoming fully themselves.

Luke: We’re doing generational work around which the communities of the world have been built. I mean, I’ve said things like this to our staff before in a slightly more focused way.  I just want to name it, it’s no wonder we might feel fill in the blank, because this isn’t even just about teaching or the way America doesn’t view teachers. I’ve really actually tried to hit the word generational because I think it also reaffirms for teachers that this is something far more than the moment. We’re not just serving ice cream. Not that that’s not an important job, but we’re trying to connect past and future. That’s really heavy.

Liz: At times, the very best thing we can do is serve ice cream.

Luke: Yes, that’s true.  If ice cream is your jam, Godspeed. For those who have chosen education, how do we help them experience and see the larger arc? Because day to day, it can feel like #$%. We need ice cream. We need snow cones. Something that I’m really proud of. This is a year, too, where I feel like I’m coming to terms with the things I can be proud of and that I can name without being bashful or like, Oh, well, I tried my best. I think I’ve really brought some joy to a very intense philosophical school that took everything really seriously. We have four snow cone days a year that happen on random days. During the pandemic, I was like, On Amazon, we’re getting a #$% snow cone machine for the first day we got back.

Liz: Isn’t that funny? I promised a popsicle party our first day back.

Ice cream cuts straight through the complexity of life, untainted by cynicism or fear.  It offers uncomplicated joy that can be measured in scoops.

Luke: And again, it’s not about the snow cone, per se. We need little bursts of things, and kids need it. And to be really clear, adults need it, though they’re less quick to admit it. I think that’s part of the complexity. I mean, it’s part of the beauty of the role. Why do I stay after this many years? Where else could I travel from the dirt all the way up to the blue sky, back and forth with all of these different people dealing with the future of our world, while actually also working with the board where I get to experience really interesting people from a whole bunch of other industries. 

Liz: Angi Evans says nobody else gets to work with three-year-olds to 70-year-olds on a daily basis.

Luke: Yeah, and God forbid, you run out of coffee at Grandfriend’s Day. I learned that lesson once, never again. Grandparents eat coffee. It’s an indelible life lessons. I think that’s, again, part of the challenge of the role. It is partly pastor, it is partly tactician, it is partly business manager. 

Liz: I think that goes back to support. I can create all kinds of head networks, but it’s still that person that you need that knows the job, that you can say the things you’re not allowed to feel, and they’ll say the things back, whether it’s hard or not.

Luke: Yes. Time a Million. 

The Head of School simultaneously holds space for the older board member who believes “children today need more discipline” and the young parent demanding restorative trauma-informed practices. You’re constantly translating between generational languages, validating the lived experiences that shaped each perspective – including your own – while gently nudging everyone to move the needle forward for the sake of generations to come. No wonder we need an unhurried hug hello as I found in James’ office a walk or two ago.

Luke: That’s given me another level of access to sanity… it is finding those two or three people that are always there.

The two other people who are always there and who know the work. Our trio: James, Luke and Liz. In the life-changing work we do, you need a team with which to face off against the generational forces at play.  It’s not quite superhero work, but I swear every Head I know deserves a cape. For our trio, I like to think of Batman and Robin, who were incomplete with Batgirl. I’m Batgirl.

Luke: You’re that friend. You make the connections with people.

Luke: I’m constantly reflecting on what you do, how you do it, what you did with Edge, I found and find so inspiring. And there’s still a piece of me who’s like, I can’t even… It scares me. But my point is seeing what you’ve done with Edge or seeing how you lead a WCDS or just talking with you about other schools. It builds the capacity to believe like, “Oh, wait, I could do that. It’s not insane”

Liz: Let’s look up and see. Let’s put a man on the moon. 

Luke: Well that’s again part of it, that is the inspiration. On some level, if we zoom out, whatever percentage of things are going to make it or not, we move forward.

The percentages of things that will make it. 100% isn’t feasible. We wouldn’t want it to be. There would be no failures from which to learn. Still, we are timid before we leap into that sky which isn’t always blue. 

I love the quotation from Erin Hanson,

And you ask “What if I fall?”

Oh but my darling,

What if you fly?

I always wanted to write those lines on the beams of the shelter where parents waited for our youngest students at WCDS. I thought it would be good inspiration for them as there was always a bird’s nest balanced atop one of those beams. I liked working at a K-8 because it was all about childhood – the innocence of possibility – the hope for the future – the joy of what the day brings as embodied in a bird’s nest. Luke understands. He taught…

Luke: First grade, I taught it for five years. I loved it. I don’t think I could have done it for my whole life. I clearly love crazy jobs, which first grade is. But I don’t think I would have been professionally fulfilled forever. And those years formed me. And it’s so #$% joyful. The whole world is opening up to them, learning how to read. How #$% cool is that?

Liz: And it makes you learn all over again. Yes.

Luke: And we can tell her how to read and go to the pumpkin patch on the same day.

Liz: But come on. When the first graders are still on the playground and not in music when they’re supposed to be because they found a bird’s nest. 

Luke: I know. 

Liz: It is as exciting to the teacher as it is to the first graders.

Luke: Damn well it should be.

Liz: I woke up this morning with this feeling of, I’ve got to tell Grace she should teach for a little bit. I don’t know. I think everybody should spend a little time teaching somebody something they don’t know for a year …or five.

Teaching lets you embrace the joyful complexity of standing at the generational crossroads— you’re part of an ancient chain of learning. This generation of students teaches you as much as you teach them, reshaping your understanding as you guide young people toward their potential. You become a living bridge between what was, what is, and what could be. It matters…one student at a time.

Luke: To be able to have this conversation today feels so cleansing and empowering, coming back to the reality that if someone doesn’t like it, God speed. Like, great, all good. 

Liz: If the head isn’t well, the first grader is affected. And that’s not okay, because to Ella Landini, junior year is not a dress rehearsal for senior year. It is the only junior year she ever has. And the teacher she has damn well better care that my kid learns. I walked with a guy who used to be a teacher… I said, what do you want the teachers of your children to know or to do? And he got real emotional and said, ‘love my kids when they’re not with me.’ And isn’t that what our job is? – we make all the employees feel loved and supported and happy so that they make everybody feel like it’s okay.

Luke: You need people to bring you back to love, to get you out of the policies, the procedures, the fact that we deal with the 2% worst of whatever is happening, because the kids can feel it. I think about how I want to show up. This walk helps to renew the “I can’t wait to be there tomorrow,” I’ll say something ridiculous and silly that they don’t completely understand. But they’ll know, “Okay, that guy, he’s looking out for us.” 

Liz: And when you talk about tune back into that love, it’s tune back into that childhood that still lives within us.

I like the idea of child-like wonder: that Mary Tyler Moore-ish unabashed joy that comes from seeing the world through each new generation’s eyes while carrying forward the wisdom of those who came before. I am grateful to think about tension – the ‘both and’ of yesterday and tomorrow. The reminder that all of our generational crossroads are embedded with learning and therefore growth… and that we never navigate these transitions alone. We can send out the bat signal to those colleagues who understand that we’re simultaneously keepers of tradition and agents of necessary change. With them we can take off into the blue sky – how lucky to be accompanied by a creative and strategic genius like Luke Felker.

We are going to make it afterall.

And speaking of the sky… I’ve been trying to articulate the simplest moonshot message as to the purpose of the work Luke and I do. I know it involves the essence of joy. I know it involves a better future. I know it uplifts potential. I don’t quite have it, but then again I haven’t quite finished my walks even though I’ve done 51 of them.

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This is a walk where the lines between teacher and student blur. 

This is the walk that made me understand the Zen philosophy of “beginner’s mind.” In leadership, beginner’s mind is that rare gift of approaching each challenge with fresh eyes. Unencumbered by the weight of “how we’ve always done things,” we can have bold vision. It’s the strategic humility to learn something new. Such leaders understand that the moment we stop being students, we stop being effective teachers. 

This is Kermit Cook, the CEO for Penn Foster Group, who finds himself reimagining education for the 80,000 students who walk through their digital doors each year—students the traditional system couldn’t quite reach. 

The first word describing him on LinkedIn is teacher. Mine is learner. It’s ironic because I was Kermit’s teacher. Within two years of graduating college, Kermit decided to be a teacher himself and applied to Teach for America (TFA).

Kermit: It turns out if you put St. Louis as your top choice for TFA, you get St. Louis. I coached basketball. I taught physics, and I ended up coaching tennis, even though I’m not a tennis player. I’m a terrible tennis player. The athletic director comes up and says, ‘Hey, Coach Cook, will you coach tennis for me this spring?’ And I said, ‘Well Coach, if you can’t find anybody else, I’ll help you out, but I don’t really know what I’m doing with tennis.

Liz: You know that’s a yes in a school.

Kermit: Exactly. He responded, Great, you’re hired. 

There is a line in an independent school contract…and other responsibilities as assigned by the head of school – the catch all. It means you’re driving the van through the parking lot on Grandparents’ Day even if you are the Director of Admissions or folding chairs after the assembly… or coaching tennis.

Kermit’s school wasn’t in the independent ecosystem, it was Gateway Tech magnet school.

Kermit: The school had a very good career education program. That actually directly leads to where I am today. But they had a health care pathway where you had retired nurses who were teaching students. They could roll right into an apprenticeship as a medical assistant.

They had this really cool partnership with the airport, Lambert Airfield, where we had old airplane engines in the basement of the school. And again, retired airline mechanics would teach these kids. And the kids when they finished that program went straight into an apprenticeship at the airport and ultimately became a licensed airline mechanic. It opened a door.

One of my tennis players, 

yes…I am laughing at his ownership of coaching tennis all these years later when he was admittedly a reluctant coach at best. 

Kermit: One of my tennis players, Keith, is a senior engineer of GE Aviation today. He was a C minus physics student. He had a learning disability. He really struggled with math, with physics. He got through with a C minus because he just worked hard and got in all the assignments on time and came in at 7:00 in the morning before school started. But the airplane engines he just got and he loved it. That experience was just so eye-opening to me about the importance of a path that it wasn’t a traditional two or four-year degree… ultimately, that’s why I’m at Penn Foster. 

That is one of those other “duties” that we willingly perform in education – show up at 7:00 to walk a struggling student through the maze of learning because none of us want to be in the business of surviving school. In my first six years of teaching, a day didn’t go by that Denny Hon’s wasn’t the first car in the parking lot. He identified struggling students throughout the school, and he tutored them. One of those students became one the best teachers I know, Joe Jividen. He credits Denny with getting him through math although Joe was never in one of Denny’s classes. Joe has told me that Denny had one non-negotiable – show up. The day you missed was the last day he would work with you. Now “Coach Joe” – so named in that same vein of other responsibilities as assigned by the head – sorry Joe – is carrying on that tradition – he shows up; he cares.  

Not everyone has Denny Hon pulling them in before school.  There are so many roadblocks to making that a reality. Our traditional systems, for all their good intentions, are riddled with spaces between the floorboards—places where a kid can disappear without anyone noticing the absence. We’ve built these elaborate structures with their rigid schedules and predetermined pathways, but have we installed enough safety nets for the ones who stumble? 

Kermit: I would argue in the world of education, I’ve seen a lot of stifled innovation in what the actual education model is … because there’s so much constraint around the infrastructure and the way the funding works and the legacy of something. But taking the traditional system and saying, ‘Okay, we need to be able to get somebody all the way through a high school degree for a total of $1,500,’ you’re insane.

How insane? You should know the public school average to educate a child is $13,500 per student per year.  If you are doing the math in your head, that’s $54,000 over the course of a high school career. Penn Foster’s price tag is only 3% of that.

Liz: Well, the other thing I’ve learned is you have to put limits on for true innovation. It’s within the constraints that you can get creative. 

The constraints: from my limited research we have 2.1 million students ages 16 – 24 that did not complete high school or earned a high school credential. They did not find their way in public schools. Their socio-economic status left private school out of reach. As a high school drop out their economic forecast is bleak… thus our economy’s forecast becomes bleaker. Who drives innovation that meets students with what they need in a radically different model? Who can navigate that dilemma? Who possesses the beginner mind to see a bold vision? A man whose

Kermit: …collisions of experiences are taking you where you need to go.

Kermit Cook, the son of two educators, a teacher himself, and a professional with 13 years in private equity asks those questions. Clearly, private equity is a different path than most school leaders take. When he was faced with the decision to follow his passion at TFA or follow a radically different path, he found inspiration from his mother.

Kermit: Right at that time, mom and dad moved, and mom decided to retire from teaching and go to seminary full-time. I distinctly remember the conversation when she said, ‘Let’s cut through it this way.  I have, God willing, another 20 years, and that’s plenty of time for a whole new career.’ She was almost 60 at the time.

As his mother had the courage to follow a new path after a full career in independent education at The Linsly School,  Kermit made a career choice that would stretch his thinking, but ultimately led him back to his passion for teaching and learning.

As my friends in education said, I decided I could do better for the world in private equity for 13 years.

Liz: I fully believe that the path you take leads you to where you’re supposed to be because you can’t be doing what you’re doing if you don’t understand private equity.

Kermit: That was the conversation I needed at that moment to just have this perspective that careers are long. The choice I make tomorrow doesn’t define who I am for the rest of my life. And exactly what you said, going to KKR, the doors that would open from there compared to TFA were just massive. 

… and with KKR in Hong Kong, Australia and the United States and

Kermit: at a factory in Malaysia, getting food poisoning every now and then. And so that is one of the beauties of that experience … I would work side by side with companies like that for a year and a half to two years. And then we get to a spot where I work myself out of a job. We hire the right permanent person, and then I get to see another leader’s style because I go work with the next company. So I worked hand in hand with 13 CEOs and leadership teams who I worked with over that time really intensely.

Liz: All right. So you know this is coming. Distill it. Thirteen CEOs, what were the top qualities that took you aback? I mean, wow, this works.

Kermit: I reflected on this a lot before I stepped into my current role. The qualities that I thought really worked actually came back to TFA’s Teaching as Leadership course. So it was 

1. Set a big hairy audacious goal. 
2. In the TFA context is to know your students and know your students’ families. In the corporate context, I think of that as knowing your people and investing in the culture. Have a culture that’s aligned to what the big goal is. 
3. Work purposefully and relentlessly towards the goal… 
4. and then learn. You’re going to screw stuff up along the way. It’s not going to be perfect. Pull up on a regular basis and create that as a real mechanism for the organization that people are comfortable with screwing up as long as you learn from it and share it broadly.

Liz: The big, hairy, audacious goal needs a really clear story around it. I would assume in your comment on culture, you’re putting clear communication and trust in culture.

Kermit: Yes.

Liz: Because that’s what makes the culture.

Kermit: You absolutely need clear communication and trust. 

A BHAG asks, ‘Wait, what if we actually could?’ It’s an audacious dream that refuses to be reasonable. When John F. Kennedy declared we’d put a man on the moon, he wasn’t just setting a target—he was issuing an invitation to reimagine what was possible. The beauty of a BHAG isn’t in its achievability but in its power to pull people beyond incremental thinking into transformational action. But to understand the vision of the BHAG, you have to know the context and respect the history of the organization.

Kermit: So Penn Foster was founded in 1890 as a correspondence course for coal miners to help them get more safe jobs. Primarily serving immigrants in the Scranton, Pennsylvania, area. And I tell you, when I go to Scranton, it feels a lot like Wheeling. The mission …even today, while we’re now online and reaching many more people… is still fundamentally the same. It’s helping people who are in positions where the traditional system isn’t really built for them get to better jobs. And so we will enroll roughly 260,000 students this year. We’re an accredited high school and career-focused college.

Liz: What’s the big hairy audacious goal? 

Kermit: The big hairy audacious goal, we graduated 70,000 students in 2023. We’re going to graduate 150,000 by 2029. And we’re not going to do it by enrolling more students. We’re going to do it by improving the outcomes for the students who are already enrolled. Our goal really comes down to doubling our completion rates within five years. It would get us to a roughly 60% completion rate, which is on par with two and four year schools across the country as a fully asynchronous program, serving learners with some of the circumstances that are most challenging to continue to progress in their learning. That’s the BHAG.

All of these students who’ve never realized, ‘Hey, failure is how you learn.’ They’ve internalized failure means I can’t do it. That’s probably the biggest challenge we have in getting people through.

Liz: Give me a tangible example of what support you now give to students or you plan to give to students.

Kermit: A tangible example that is both the support, but also just actually giving a great learning experience. Our vet tech program … in the first semester, you have to pass biology… our 90-day completion rate for that biology course was 8%. Imagine most of our learners are working parents, working one or two jobs, minimum wage, squeezing it in, studying at night. You get to the sixth course for a four semester program, and three months later, you’re still stuck in it. How long are you going to stay? You’re going to quit. 

We basically had taken a college-level biology textbook, put it online, attached some assignments and essays and writing assignments that had nothing to do specifically with vet tech because the organization was using biology across a few different programs. They just used that same course and said, ‘Good luck. Here you go. Here’s your biology text.’ 

Kermit: So no wonder. We redesigned that course to be vet tech-specific. You’re not spending time writing essays about the Krebs cycle…with that new biology course… we launched it. Big surprise. You go from a completion rate of 8% to 62% within the first few months. And then our team keeps working on it and refining it, and seeing where people get stuck.

From a culture perspective, one of the principles we spend a lot of time talking about is discovery – don’t think you know what the right answer is. Go put it in front of learners, see how they engage and learn! Learn from that and then continue to refine. So our learning design team now has a principle. Instead of, oh, we’re going to update a course, we’ll put it out there. And then in five years, when re-accreditation comes up, we’ll revisit it and see how it’s working. We put a course out, and with the data that we have, we can watch how students are engaging… Where are they getting stuck in the process? Where do we need to add proactive support rather than waiting for them to call us?

Liz: And that’s part of the beauty of this asynchronous learning, because you literally know compared to… I had no idea what you were going through when I put a blue book in front of you.

Did I mention Kermit was in my Junior English class? I loved watching a student come alive with ideas during an in-class essay. Blue books carried the weight of everything my students poured onto those pages in some allotted time. Each one was a window into a mind at work—unfiltered, unrehearsed, smudged, at times illegible and always authentically human. I knew which students had truly grappled with the material and which ones were bullshitting their way through unprepared territory. AI will give us insights into the data – the content that stumped the argument – the patterns of sentence structures… but will it match the confidence, hope, support and resilience swirling in the air as it did when Kermit sat in my classroom? Will an AI tutor session feel like it did at 7:00 a.m. in Denny’s classroom?

Kermit: We’re now using AI agents that can reach out and say, ‘Hey, Liz, I see you submitted your English essay, and it didn’t pass. Would you like to set up-time with one of our writing coaches?’

Liz: Is the writing coach a human? 

Kermit: Yes. 

Liz: Okay. But it could be…

Kermit: Well, we actually now have just partnered with a company called Learnosity to build an AI writing tutor to do scaffolding. What’s most amazing is how we see learners engage with it. I saw one learner, well I saw the transcript, one learner literally put in, ‘Are you really an AI?’ And he said, ‘Yes, I’m an AI, Powered by Penn Foster.’ He’s like, ‘Okay, because I’m really nervous about writing. And I always failed in school. I’m not sure how I’m going to do with this.’ And then it’s like, ‘Okay, well, let’s just get started. What’s on your mind?’ And so that they have a chance in a very low stakes way to throw things out there and not feel judged.

Did you catch it? Kermit referred to the AI as he and then it. A brave new world indeed.

Liz: Interesting, that piece of, are you AI? Because I don’t want to be judged by a human.

Kermit: A hundred percent. That’s very true.

And this goes back to your point of talking with some of the learners. I call half a dozen learners every month who graduated to say congrats and talk about their experience. We just had an in-person graduation in Atlanta. Every chance I get, I try to talk with learners. One of the things I took away is, “Man, I got to that writing assignment, and I haven’t written anything that didn’t have an emoji in it in five years.”

Most of the students we are serving hit a wall in the traditional classroom, so they have learned that they can’t do it.

Liz: There wasn’t a Denny to grab them and put them in front of him at 07: 00 AM. It was just an F.

AI will never replace Denny Hon, but isn’t this a powerful use of it? I’m impressed not only by Kermit’s work for students, but his honesty about what’s missing.

Liz: My only question is, are you paying attention to the fact that I would guess you have a large percentage of students with an undiagnosed or diagnosed learning difference?

Kermit: No, we do a terrible job of it today. Absolutely terrible.  And we do want to work on it. It’s very front of mind, but it’s like we’re getting a foundation right. That’s next. 

Penn Foster is a for-profit education company. That means it needs to make a profit while serving the mission of educating under-served students. 

Kermit: Because Penn Foster’s financial model is a pay-as-you-go model. 90% of our students enroll for $20 and pay effectively $50 a course as they progress. And if they drop out, they stop paying.

Dropping out hurts mission and profit. Kermit, the teacher and coach at heart, isn’t going to quit on one of his students any more than Denny Hon did…even if there are 80,000 of them. To prepare for that,

Kermit: I went online. I read every student review I could. I enrolled in high school in medical billing and coding and in elementary education. And I said to myself, ‘Holy cow, there is so much we can do better. There is so much we can do to improve the experience for these learners.’ But at the same time, I saw videos of students who are holding up their credential saying, I’ve got this job as a pharmacy tech because I went through this program, I never thought I would be here.’ And so I knew there was this goodness underneath. And it’s just if we could get the culture of the organization focused on outcomes, where we could go.

He became a student of his school. To all my friends and colleagues who are in school leadership, I ask, have you done that? I hadn’t…yet.

Kermit: When I kicked off my presentation to the board of Penn Foster as part of the recruiting process, I started with, first thing you need to know: I’m a teacher and a coach at heart. And so this is not going to be a presentation. This is going to be a class discussion. 

And everyday is yet another class discussion – a discovery of what the students need. Every day is a reimaging of the traditional educational system where students learn that failure is just part of the process of learning. Where students don’t survive school, but find pathways to their passions… like aviation engineering.  And that leaves us…

Kermit: …where we started with Keith becoming an airplane mechanic.

Keith and Kermit are still connected today and I would dare to say Keith has taught Kermit a thing or two about learning, about constraints, about creative engineering, about an innovative model for education. The teacher became the student… and 80,000…soon to be 150,000… other students are benefitting every single year.

My best teachers —whether in classrooms, boardrooms, across my dinner table or just walking next to me —share one unmistakable quality. They approach each day as if they’re still figuring it out. It is a courageous “beginner’s mind”—a state of wonder to ask questions – to learn and to help others learn.  

Indeed there is more to learn. Maybe 50 walks wasn’t quite enough.

---

“Ready All.” 

All eight flexed at the catch, blades squared and almost buried by water. The slide compressed, knees bent, bodies coiled. Eyes locked on the shoulder of the teammate in front of you – save the stroke whose eyes are locked with the coxswain. 

“Row.” 

Eight oarswomen simultaneously lock onto their riggers as legs explode against footboards—legs, back, then arms. The shell, initially dead in the water, lurches forward. At the finish of the first stroke, blades feather cleanly emerging from the spring water in unison, hands dropping away as bodies slide forward for the second stroke. A process that will be painfully repeated for six minutes without recovery.

As the coxswain, I feel the boat respond —that initial jerk gives way to flight as the hull begins to run between strokes, the bow cutting through the water as momentum builds stroke by stroke. When the oars catch precisely as one, the boat lifts and seems to fly on top of the water. It is transcendent to experience the propulsion of such collective power. To increase hull speed, the race plan calls for a power ten at the 500 meter mark of this 2000 meter race. As if not already giving everything they have trained for since September, the rowers are asked to dig deeper for ten strokes. 

“Power ten in two. One. Two.” 

And we lift out of the water as if beginning again.

To sustain the effort, knowing full well the competition can hear my voice, I look across the lanes and begin naming the seats in the opponent’s boat. 

“I’m even with the seven seat and climbing.”  

“I’m walking through their engine room.” 

The collective power moves us through the seats of other boats like climbing rungs on a ladder. 

“Yes,” I scream with a guttural echo that now makes my dog cower.  

Then, I nod, cock up the left eyebrow and smile slyly at the stroke, who is doing her best to control the stroke rate as the power surges at her back. I turn my neck just enough to ascertain I no longer sit across from a rower, but am almost equal to the bow of the closest competitor. 

“Bow ball!” 

We have taken the lead by a boat length. Thoroughbreds a full length across the finish line at the derby. “Bow ball” connotes our race plan, our collective effort is working. 

Jane: When I look back at it, just the willingness to be disciplined, so disciplined, especially at that age, and then achieve really great things and surprising things, I can always lean back on that. Because life does, as we just said, life does life, and there are challenging times. I remember that because we rowed and because we committed to something so completely, and we achieved great things, anything is possible.

Liz: And there has to be trust. When I think about the fact that you, as a rower, can’t even see where you’re going, it blows my mind. We don’t ask many athletes to perform backwards.

Jane: Backwards, tied in, like literally injured if you stop. You can be thrown from the boat.

Jane Fleming was the third seat in that boat I was coxing. While we were only teammates for four years, we lived a lifetime in that boathouse and on the water of Lake Carnegie.

In 1904, Princeton University President Woodrow Wilson was courting steel magnate and philanthropist Andrew Carnegie for a major donation to support academic programs—specifically hoping for funding of a law school. His tour of Old Nassau took a turn when Carnegie announced, “I know exactly what Princeton needs, and I intend to give it to her.” Carnegie told the surprised Wilson, “It is a lake.” The cooperative effort of Rowing, Carnegie hoped, would provide a better model for global relations. I tend to think he was correct, but of course I am biased. That lake attracted a different type of person. 

Jane: It was in us. I know you enough to know that you like to win, and you like the challenge of trying to figure out how to win. And I think I’m the same way. My competitive edge has softened as I’ve gotten older, but I think that I like to be excellent, and I like to push myself into new experiences. I think that rowing, of all things, was always a new experience because you were never physically or mentally the same every day, and yet you were being asked to achieve at the same level every day.

Liz: And add to that the weather. We rowed in some conditions that there shouldn’t have been a race.

Jane: Absolutely.

Liz: Including the one when we won the national championship.

Jane: Yeah, I’m convinced it’s because we were allowed to eat.

Liz: But you know what? That’s selling ourselves short. That’s not right.

Jane: Talk about that experience. That was a choice. We did not need to row that race. A bunch of us got together because we all wanted to challenge ourselves. For me, at 6 foot, dropping to weight was no easy task. But I think there was just something so fun about trying to achieve a national championship. I must say it’s one of the greatest bragging rights ever.

Liz: I couldn’t agree more.

Jane: Achievement is wonderful for everything we’re talking about. It’s the work put in. It’s about mission accomplished,  working as part of a team to do something. But then you get it, and it’s great, and it goes into a bragging somewhere in the past. But really in and of itself, it isn’t a thing.

Liz: There was agency, there was confidence, there was collective risk-taking, and then a dedication of time because we were done.

Jane: It’s time and choice, and choice at a time when all of our peers were wrapping up and celebrating and partying and doing all the things that college kids do, we decided to go left when everybody was going right.

Our small crew made a different choice—while everyone else was sleeping off another night of beer pong, we were up at dawn, lacing feet into a shell, chasing something that made no sense to anyone else. There’s something intoxicating about being part of this small band of the obsessed, this little group that’s willing to sacrifice reunions for something bigger, something that most people will never understand until the day we crossed that finish line first. A crazy left turn away from ordinary paid off and ruminates in your mind as you face every choice thereafter.

Jane: But I think life is choices, right? I think our life is a result of the collective choices we’ve made, good or bad. I think that the willingness to, when they’re bad choices, to remedy is the stuff that makes a satisfying life, at least.

At 37 or something, I said to myself,  I’m good with making mistakes. I just don’t want to make the same mistakes. 

Liz: I love that. Fail forward.

Jane: Fail forward because making the same mistakes over and over again at some point, I think it does crush the spirit. 

Liz: Right. I had a lot of good friends say, You can’t change what happened. So go back and decide how you chose the people you did that with. So you make good choices of who you’re going to go right with when everybody else is going left. So that you don’t follow the wrong people or have the wrong people follow you. I’ve always thought about making choices and wanting a team. 

Jane: So interesting you talk about that because my business partner and I talk about that all the time, that success is 99% picking the right people. Because the other thing I was thinking about how rowing resonated for me is that it was a really wonderful lesson in being part of something rather than the something. And I think that I have a big ego. I think we all do. And my whole life has been about eviscerating that and realizing that all I can do is be part of a team. Another wise woman always says, I just want to be another bozo on the bus.

That brings me to the most salient memory I have of crew. It’s not the adrenaline rush of walking through Radcliffe to their bow ball.  It’s not the exhausted collapse looking up into the sky after crossing the finish line first. It’s not being pulled from the icy waters of the Connecticut River after beating Dartmouth. It’s hearing Curtis Jordan’s voice emanating from the megaphone, “Pull the boats together.”

Liz: The other piece that I think is humbling in a way that I don’t know any other sport has is when you pull the boats together and switch a single person and head race again. 

As coxswains we ease our shells alongside each other in the middle of the lake, oars lifted on the near side and stabilizing against the water on the other. Rowers reach for the oar of the corresponding seat and pull the two shells together as one. 

“Hands on.” 

Oarswomen reach across and hold the gunnel of the other boat. And then we collectively wait to hear what pair is unlacing and trading seats in a feat of balance and grace while your heart beats out of your chest across the fragile shells. Your eight had just won a head-to-head race. If he switches you, just you, will it change the outcome?

Jane: Always. Because I was never the strongest, and I was never the lightest. So it was one of those positions where I was a combo player. So I got switched a lot so that Curtis could figure out what the combination of human beings would work the best. I loved those. I loved that. I did. There was something about the truth of it that I really appreciated. I really appreciated that there was a purity in it. We’re going to switch one person and we’re going to see. Because I also realized that even though it was me being switched, it wasn’t just my job. All I could do is do my best and hope I work well with the teammates that I was rowing with. 

I was coxing the JV boat. Our captain was coxing the Varsity eight. We had just lost a head race by a seat. Someone was about to be tested. Some change was coming. The anticipation hung in the air. Curtis instructed, “Switch the coxswains.” All 18 heads lifted, 36 eyes turned toward his launch in amazement. The coxswains?

Liz: I can tell you, I was switched. I did a head race, which was not typical, and that’s how I landed in the varsity boat. Curtis pulled us together, and you never knew who he was going to switch until you were pulled together. And I got in that boat.

You know how you crunch down? Well, as a coxswain, you crunch into the smallest ball, right? 

As we pushed away from the other boat, I found myself looking straight into the eyes of Sarah Horn, varsity stroke.

Liz: I remember it just being eye to eye as if we were little kids in a blanket fort, and I had to have been as doughy-eyed as possible. And she said, “Get us there. We’ll get you there.” 

You know when you wish you could fill someone with all the confidence you have in them. You want to instill in them the mountain of faith that they might be questioning.

Liz: That’s what she was doing. She was giving me all her confidence. And, man, I remember we won. And I remember you were in that JV boat and I was looking over and thinking, ‘No, I don’t want to lose them. I like them.’ I liked being the underdog. I liked being the JV coxswain. I didn’t want to switch up, but I got called and I had to go.

Jane: What a lesson, right? To step up into what you’re supposed to do. We all have things we’re excellent at and things we are mediocre at. I’ve always thought that it’s a bit of a shame when people walk away from what they’re excellent at.

Liz: Mmm. Ouch. That lands hard. Because I was a good head of school, and I did walk away. It’s been a rough year of, at times, thinking, did I leave too soon? But I really did feel that same calling for, there’s something else I’m supposed to be doing now.

Jane: Well, I guess, what I’m talking about is not necessarily the actual task, but the spirit of what somebody is supposed to be doing on this planet. And you’re still teaching, and you’re still showing up in a form of education and showing up for yourself. And I think all of that’s so invaluable.

I think we’ve all achieved great things. We’ve been, I hope, in service to the world in a way that’s positive. All we can do is to pick ourselves up every day and show up and let life happen and show up in ways that are positive. I know that that sounds trite, but actually… For all the thinking and all the words and all the philosophies, I do think showing up is probably nine tenths of it.

Liz: I don’t think it’s trite in this day and age. To show up positively, that’s a big calling.

Jane: So I believe if I walk out the door and participate in life and participate in the world, things get shown to me. And opportunities come up to be positive, to affect people.

Liz: What’s an example that is salient to you right now of an opportunity that showed up for you?

Jane: I think it’s really interesting. I just finished this Disney Kids project. Zombies 4. And it showed up in the middle of the strike.

Oh right, I should tell you that Jane Fleming is a founding partner, executive and producer at Court Five Productions which develops and converts diverse intellectual property into filmed entertainment. Previously, she was a senior executive at New Line Cinema, ultimately holding the position of Senior Vice President, Business Development. Since that time she has been a prolific producer of independent films with her partner Mark Ordesky including the EMMY-winning Disney+ series, “THE QUEST.”

Jane: We had developed a relationship with the team over at Disney, and they had called and said, ‘Would you ever do this kid’s franchise?’ And if you watch it, it’s a really fun integration story for kids, but it’s for kids 8 to 12. And my business partner did Lord of the Rings. So we sat there and we looked at it and we were like, ‘You know what? For this thing, it’s the best in class. It’s really good at what it does.’ And so, of course, we’ll say yes. And honestly, it was one of the best jobs we’ve ever had.

Liz: Really? Say more.

Jane: It was, again, a really great team. And we were finding young talent, 14 and 16-year-olds, who got to step into themselves in such a spectacular killer way. We got to set the table for all of that to happen and then to support them all the way through this process. It’s been just so gratifying to watch young people step into something pretty extraordinary.

I really love what I do because there’s this moment that happens when you’re about two weeks before production and you walk around all the different departments and everybody is doing the most amazing work all in service of this one end goal. And it’s just electric because as a producer, you’ve played a pretty big role in hiring them and getting them there, putting them together. And they’re having joy as they work towards something that somebody dreamt up and wrote down. That’s amazing. So for the kids, it’s especially salient because the excitement is so infectious. Many of them, it was their first big movie for Disney. It was just joyous. It was a musical, which, come on.

It’s doing gangbuster business. I’m nervous right now, but again, it’s like winning the national championship. It’s great. You get a little charge off of it, right? It’s great bragging rights, but it doesn’t necessarily make the quality of your life better. What makes the quality of our life better is the opportunity to keep doing what we love, the opportunity to connect with old friends like we’re doing right now. 

Jane: I have to say, I’ll do this on the record, on the recording, you are one of those really special people in my life who I never see. But it’s so funny. I was thinking how naturally, I didn’t ask you what you were going to talk about. I was like, ‘No, I trust Liz. We got it.’ And even though we haven’t talked in, I don’t know, two years, three years. It’s just like yesterday.

Liz: Or really talked in 35 years.

Jane: Well, that’s the truth there, which is pathetic because I adore you and I really respect you and I’m inspired by you, honestly.

Liz: I have to tell you, when I was leaving the independent school and I wasn’t going to be starting an EdTech software for learning differences, I was really trying to figure out, where do I go? Who do I reach out to? And immediately, the muse, the universe, whatever, put your name in my mind. You have to talk to her. And I didn’t know why. Here is a connection you have put down in your life that you need to pick back up. And it’s inexplicable why some people are like that in our lives.

Jane: I know. It’s just if you quiet down enough to listen and you go with the flow like we did with rowing, we start flying. You start flying.

And in the boat when you find the rhythm that looks effortless from the shore, you fly. Just beyond the bow ball is open water. That’s the true moment of flight when the coxswain proclaims, “Open Water.” Now there is space between one boat and another. Our boats started even and now there is open water between the stern of our boat and the bow of theirs.

The call “open water” doesn’t mean you can relax. We have this race won. Instead, “open water” translates into the next step – reach farther, stay together, push harder – but with open water it no longer feels punishing on the body – it is exhilarating. It is flying.  It is no longer about the competition and where they are in relation to us. It is just the nine of us. It is intoxicating. Just as open water inspires, it demands more. And with these people on this race day, there is inexplicably so much more to give.

Jane: And as you said, when it works, I don’t know if anybody can describe that feeling. I know a lot of writers have, I think, tried to do so, but I don’t think anybody’s actually ever achieved it because it’s one of those transcendent moments that you can’t really describe to anybody.

It was never about the win. It was always about being part of something bigger than ourselves. 

In the years that followed, I have quietly carried the truth of that palpable anxiety of proving my worth head to head, and that tangible ecstasy of the whole being greater than the sum of its parts. 

Everything I needed to know about leadership and life, I learned in the back of a boat with a microphone strapped to my sweatband. 

“Let it run.”

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