Cave Exploration and Cayman Brac: Living and Leading Beyond the Shadows
On limestone bluffs, ironshore, and what becomes visible when we step past comfort
The final weekend in March has turned my attention to the way an unfamiliar landscape can change what comes into view. We live amid noise, speed, and repeated opinion. Projections can start to look like truth; borrowed certainty can start to feel like our own. Sometimes a harder path or a moment of physical discomfort interrupts that pattern, bringing us closer to what is actually there.
What came into view on the island
We are spending the final weekend in March on a limestone island cut with high bluffs and caves, many miles from our native Maine on Cayman Brac. Over the past days, we have followed narrow footpaths above steep drop-offs and stepped into stone chambers that tighten around the body before widening again. None of this feels natural to me. I have never felt fully at ease with heights. Enclosed spaces make me more conscious of every breath. Still, curiosity keeps drawing us forward.
Unlike the ambling granite shores of Littlejohn Island, the bluff here rises like a towering blade. The cave openings cut dark seams into the porous but unyielding rock known locally as ironshore. We placed one careful foot after another, uneasy but intent on seeing what lay ahead.
That physical experience has drawn me back to an ancient story that has traveled with me for years: Plato’s allegory of the cave.
Plato’s cave, in plain language
For readers who would like a re-introduction, Plato places the cave image in Book VII of The Republic. He asks us to imagine prisoners chained inside a cave from childhood, forced to face a wall. Behind them, a fire burns. Between the fire and the prisoners, others carry objects whose shadows fall across that wall. Because the prisoners have never seen anything else, they take those shadows for reality itself. One prisoner is eventually freed, leaves the cave, and slowly learns that what he accepted as reality was only projection. The image is Plato’s way of showing how readily human beings confuse appearance with truth, and how difficult real education can be because it requires a painful turn toward what is more fully real.
That old image still fits modern life with unnerving precision.
We live among projections. Headlines. Algorithms. Group assumptions. Inherited scripts. Somebody else’s certainty can fall across the wall in front of us so quickly, and so often, that it begins to look like fact. Plato’s cave remains useful because it reminds us that comfort and truth are not the same thing. Familiarity can harden into its own form of confinement.
“Sometimes a different landscape, a harder path, or a moment of real physical discomfort can redirect our attention and bring us closer to what is actually there.”
That lesson felt less abstract after a week of moving through actual caves.
A cave marked by history
One of the caves we visited carried not just geological force, but human grief. A weathered sign at its entrance remembers Rebecca Bodden, one family’s infant daughter whose relatives fled there during the catastrophic hurricane of November 9, 1932. She reached the cave with her family, but died of exposure and injuries received during the storm. She is buried inside the cave, her grave marked by a simple white memorial.
Beyond Rebecca’s Cave, a cross-island path continues across the bluff toward another memorial. Even in good weather, we found the footing treacherous. The ironshore is sharp, uneven, and broken by crevices that require careful footing almost the entire way, so we did not walk the full route between the two sites. We later visited the seaside location honoring the other 19 lives that were lost during the storm.
Reading the memorial markers changed the scale of the experience immediately. The cave was no longer simply a destination on a trail. It became a chamber of survival, loss, and memory.
As we walked, we thought about how quickly a cave can change meaning. In Plato, it represents illusion. In a storm, it becomes refuge. In memory, it becomes both shelter and wound. Stone can conceal. Stone can protect. Context determines which truth we are facing.
“The cave was no longer simply a destination on a trail. It became a chamber of survival, loss, and memory.”
That matters in leadership too.
Leadership beyond the projected wall
Leadership often falters when we mistake the visible wall for the whole room.
A team can become captive to its own shadows just as easily as any prisoner in Plato’s thought experiment. The loudest opinion can masquerade as the clearest one. The most repeated interpretation can calcify into doctrine. Old habits can pass for wisdom simply because they have occupied the wall for a long time.
This week’s Radio Maine conversation with Tobias Parkhurst brought me back to that point. His path from professional skateboarding to entrepreneurship and community-building in central Maine carries an important lesson about what happens when people bring fresh sightlines back home. His story is about persistence, community connection, and the creation of places where people gather over beverages, pizza, and conversation.
“We have much more in common than I think we get credit for.”
— Tobias Parkhurst, Radio Maine
Strong leaders do not merely manage what is already projected. They test assumptions. They widen the aperture. They ask who has not yet spoken, who has been standing in the dark, and what truths have been flattened into silhouette.
Some of the most consequential leadership mistakes I have seen, in medicine and beyond, began with false clarity. Someone assumed they already understood the room. Someone accepted the shadow and stopped looking for the source.
Patients, margins, and the sentence that comes last
Medicine has taught me a parallel lesson.
Patients do not always begin with the deepest truth. Most of us do not. We start with the version we can tolerate. We describe the symptom, the schedule problem, the fatigue, the pain. Then, if enough space opens, something more central emerges.
That is why this week’s Radio Maine Bountiful Path solo reflection on Working in the Margins felt so resonant. The margins are not empty. They are often where the real thing enters. Those unscripted spaces often carry the truth that the main event could not hold.
I saw that over and over as a physician. Having finished a patient interaction, I would reach for the doorknob. Then I would hear the sentence that mattered most: “There’s one more thing.”
“That ‘one more thing’ was often the heart of the matter.”
— Working in the Margins
That final sentence was often the real cave opening.
Not because it pulled us deeper into darkness, but because it carried us beneath the polished surface and into the place where something truer could be named. Pain concealed grief. Insomnia concealed fear. “Stress” concealed loneliness. The chart gave one outline. The human story supplied the missing depth.
In that sense, medicine is an ongoing discipline of leaving the wall and turning toward the source.
A Healthy Conversation: common ground beneath difference
That same theme surfaces in this week’s episode of A Healthy Conversation, in which my co-host Jeffrey Barkin MD DLFAPA and I interviewed Dr. Jim Jarvis about medicine and medical education. We each bring different versions of professional experience to the discussion. Jim and I are family physicians. Jeff is a psychiatrist. We have all held positions in medical leadership and education.
This context feels deeply relevant to Plato’s cave.
People stand in different places. They inherit different shadows. They bring different histories to the wall. Good leadership does not demand sameness before trust can begin. Good leadership asks us to look carefully enough, and listen long enough, to discover what convictions can hold across difference.
In medicine, that matters enormously. In leadership, it matters just as much. We need people willing to ask harder questions without stripping others of dignity. We need people willing to recognize that perspective shapes interpretation, but does not erase the possibility of shared purpose.
Light, wax, and the gallery opening
This week I have also been thinking about Portland Art Gallery artist Willa Vennema’s encaustic work and the way it builds through layering, scraping, embedding, and return. Our recent Off the Wall feature, Carried by Light, describes a practice shaped by molten beeswax, pigment, improvisation, and repeated revision.
“The beginning is always a little scary. I just say to myself, put the paint down, don’t worry about it.”
— Willa Vennema, Off the Wall
Willa is one of the artists being showcased in this week’s Portland Art Gallery opening. The April exhibition also includes Bibby Gignilliat, Ryan Kohler, and Sarah Verardo. The opening reception is on Thursday, April 2, from 5 to 7 p.m.
A gallery opening is, in its own way, an argument against shadow-life.
It asks us to show up in person. To look longer. To let shape, color, surface, and conversation interrupt the speed of the feed. It asks the eye to work honestly again. In an era that rewards quick judgments and borrowed opinions, that kind of attention feels almost muscular. It is not passive. It is a practice.
Why this may matter to you right now
You may not be standing at the edge of a bluff or stepping into a limestone cave this week.
Still, you may know the feeling of living near a threshold you would rather avoid.
A difficult conversation.
A decision delayed by fear.
A role that no longer fits its old outline.
A truth you have sensed at the edge of awareness, but have not yet turned to face.
Plato’s cave endures because it names a human tendency that never quite disappears. We accept shadows. We inherit them. We repeat them. Then life, if we are fortunate, places us in circumstances that make a larger reality harder to ignore.
For me, this island has done that through physical discomfort. The body has made the lesson plain. I do not need to adore heights or confined spaces in order to learn from them. I do not need to erase fear in order to move. I need only refuse to let fear become a fence around what I am willing to know.
That feels like a useful threshold for late March, with spring gathering force just beyond the calendar’s edge.
Closing reflection
This week has braided several truths together: Plato’s old warning about shadows, the cave history carried by storm memory, the leadership lesson of looking past consensus, the patient lesson of listening for the sentence that comes late, the conversation on A Healthy Conversation about common ground beneath difference, and the artistic discipline of layering toward light.
Together, they make the larger pattern easier to see.
Truth rarely arrives as a spotlight. More often it comes as an adjustment of sight. A longer look. A harder question. A step past the point where comfort tries to halt us.
Pause + Reflect
Where in your life are you accepting a shadow in place of a fuller truth?
The limestone caves, ironshore, and high bluffs have pressed that lesson into my body as much as into my thoughts. I have felt it in my ribs, in my breath, and in the careful placement of each foot.
What lies beyond familiar fear is not always comfort.
Sometimes it is simply clearer vision.
That is enough.
✨ Thank you for walking this bountiful path with me.
Lisa
P.S. This week also marks the release of the first Bountiful Path Seasonal Reflection, a guided companion for reflection, emergence, and creative flow.
For the inaugural release of our seasonal toolkits, we’re sharing our spring version widely—at no charge— with this community. We hope you will let us know what you think.
This and future toolkits will also be included in our upcoming course, The Life that’s Asking to Be Lived. Future seasonal toolkits will become part of the broader Bountiful Path subscriber experience.
Get the Spring Seasonal Reflection Toolkit Here.
Radio Maine Live: Emergence and Light
Join us for Radio Maine Live: Emergence and Light on April 16, from 5–7 pm at the Portland Art Gallery. Our spring panelists bring music, art, home, community, and medicine into the same frame, creating a rich conversation about emergence, light, and the forms of connection that come into focus over time.
Dr. Emily Isaacson is the artistic director of Classical Uprising, where she reimagines classical performance as a more collaborative, democratic, and deeply social artistic experience.
Christopher O’Connor is a Portland Art Gallery artist whose paintings of rock, water, and abstraction invite us to slow down, look more closely, and let place open into a different state of mind.
Heather Shields is an island-born real estate leader and longtime community-builder who understands Maine not only as a market, but as a place where belonging, beauty, and human connection shape how people want to live.
Dr. Deirdre Heersink is a family physician and medical leader specializing in post-acute and long-term care. Her work restoring life stories to elders reminds us that health care is not only about needs and diagnoses, but about identity, dignity, and being truly known.
The panel conversation will run about 45 minutes, followed by a social hour focused on conversation and connection among attendees.
Attendance is free, but space is limited.
We hope to see you there!
Spring Virtual Book Circle
Awaken to the energy of spring and spend an evening with fellow readers who want companionship without homework.
Spring can feel like a threshold, with longer light, softer air, and the slow, steady work of thawing. My co-host and friend, Karen Longfellow, and I invite you to gather with us in that in-between space for the Bountiful Path Spring Virtual Book Circle on April 21. Attendance is free, and there is no required reading: simply be willing to share whatever pages you’ve been turning with our friendly little group!
Meeting you along the Bountiful Path
We appreciate the opportunity to be part of your world.
If you’re wondering where to find us, here’s where we land during the week: Solo episodes on Monday, Radio Maine on Tuesday, Off the Wall on Wednesday, Books on the Boat on Friday, and The Bountiful Path Foundational Posts on Sunday.
See you on the path!
The Bountiful Path: Offering seasonal practices for real connection, rooted in medicine, leadership, and art.