The Tale of Two Lisas: A Story About Finding Freedom When You Least Expect It
In 1999, I learned something profound about human freedom from a woman holding a dishrag in a chain restaurant kitchen. Later, that lesson would be echoed by another Lisa — this one writing from a cafe in Thailand — though in ways I couldn’t have imagined during that first steam-filled conversation.
But I’m getting ahead of myself.
Let me take you back to that summer evening, when my soggy shoes left wet footprints across the steaming asphalt outside Macaroni Grill. My clothes carried the familiar scent of dried marinara sauce, but my mind was elsewhere, turning over questions that had followed me from the Borders Books next door. I’d spent my nap break between shifts reading Rich Dad, Poor Dad, and wrestling with an unsettling revelation: there were people moving through life, guided by hidden knowledge, operating under different rules than the rest of us.
What determines the shape of a life? Despite having eight aunts and uncles and over thirty cousins, we didn’t have a single millionaire in our family. Uncle Rich had tried, but couldn’t live up to his name. Most people, I observed, lived where their parents lived, believed what their parents believed, and made about what their parents made. We’re told that hard work and education can change everything, but how often does that actually happen? Are we truly free to choose our path, or are we merely playing out roles assigned by circumstance?
This question haunted me as I pushed through the restaurant’s heavy doors, entering a scene that played out nearly every night. Chad, our lanky master of ceremonies, was finishing his Sinatra tribute — “That’s Life” delivered in the style of Jim Carrey’s “The Mask.” Not to be outdone, another waiter (who claimed to be a vampire and maintained a strict diet of raw Bistecca alla Fiorentina) launched into the Barenaked Ladies’ “One Week,” competing with our busser, Mac Lethal, for the title of world’s fastest rapper.
Their performances were like tiny rebellions against the clockwork routine of restaurant life — trying to write their own stories even within the rules they had to follow. But were they really free choices, or just the predictable results of personality and conditioning playing out according to invisible rules?
These questions erupted into heated debate while closing down the restaurant. Lisa, a veteran server who carried herself with the quiet authority of hard-won wisdom, grabbed a mahogany chair leg and flipped it onto a table draped in two white sheets of paper.
“If you’re so smart, Matthew,” she challenged, “then explain me.”
We’ve all had moments like this — when life suddenly presents us with a teacher disguised as an ordinary person, in an ordinary place, doing ordinary things. But wisdom, I would learn, often arrives in exactly this way: not in meditation halls or philosophy lectures, but in dish pits and late-night conversations.
Fresh out of college and sure I had all the answers, I tried to explain how human minds work, as if life could be reduced to a simple formula of cause and effect. “We’re each just the sum of our experiences,” I declared, “filtered through biology and genetic predisposition, then strained through environmental factors. Shake it up, and you have the cocktail that makes ‘you’ you.”
A smile crossed her face — the kind that suggests wisdom earned through intimate acquaintance with life’s deeper currents. Following me down the serpentine hallway to the dish pit, she challenged the neat boundaries of my philosophy. “By your logic, I should be in some mental hospital, not serving pasta and debating the nature of consciousness.” Steam rose as she opened the dishwasher, creating a ghostly curtain between us — between my theories about life and her lived experience of it. “How does free will fit into your neat little theory?”
“Free will is an illusion,” I declared, catching the damp towel she tossed at my face. “People use it to shield themselves from the harsh reality of living in a deterministic universe.”
Her hook was set. Like a Zen master ready with a perfect koan, Lisa began to dismantle my certainties with the quiet authority of lived truth.
What Lisa Taught Me About Freedom
The story she told next would haunt me for decades. Not just because of its content — though that was haunting enough — but because it challenged everything I thought I knew about human nature and free will.
“Let me tell you a story,” she said, her voice steady as the rhythm of dishes passing between us. “When I was a little girl, my father was an alcoholic — a mean sonofabitch. Every day after school, I’d come home to find him waiting. On the end table sat a pistol. He’d wave me over, grab the gun, and press the cold muzzle against my soft temple. ‘Today, Lisa,’ he’d say, ‘Today just…might…be…the day.’”
The steam swirled between us as she continued, her words cutting through the humid air. “Each day, I waited, not knowing if that day would be my last. Finally, I had enough. One day, I walked over, picked up the gun, and handed it to him. ‘Do it. Just do it,’ I told him. ‘I can live with dying, but I won’t live in fear any longer.’ I waited for the sound, but nothing came.”
She paused, letting the weight of her words settle like stone. “That was the day my life began.” Her eyes met mine through the rising steam. “So, try again. How does my choice to override the most basic human instinct — self-preservation — and stand up for myself fit your worldview? A mere illusion? To say that is to deny your own experience of being human.”
I wracked my brain, searching for an explanation that would preserve my philosophical framework. “Someone must have modeled standing up for yourself, showing you it was possible. You followed that pattern and realized he was bluffing.”
Lisa wasn’t having it. “You’re missing the obvious,” she said, closing the dishwasher with a decisive click. “Sometimes, you gotta face your fear of losing everything to find the courage to live.”
Thirty Years Later: Another Path to Freedom
Sometimes life has a way of teaching us the same lesson twice, though rarely in the same way. Three decades after that steam-filled conversation about free will, I would meet another Lisa whose journey would illuminate a different facet of transformation.
In those digital spaces where modern seekers gather, I connected in a online book club with another Lisa through shared questions about consciousness and healing — those eternal mysteries that pulse beneath the surface of ordinary existence. As our conversations deepened, we discovered a shared history: both raised in the rigid certainties of evangelical fundamentalism. She had studied at Moody Bible Institute in Chicago, the same institution my father had attended, where questions often met with answers that failed to satisfy the soul’s deeper longings.
Something about her presence in our online discussions felt different. Each question she asked opened up new ways of seeing things, like ripples spreading across water. Like many who leave strict religious backgrounds, she had traded one set of rules for another. The rigid demands of wellness culture had replaced the strict rules of faith. Just as steam had once veiled profound truths in that restaurant kitchen, the digital space between us held its own kind of mystery, where stories of transformation could emerge in their own time, like dawn gradually illuminating a landscape.
As a former proof-reader for Poetry magazine, Lisa offered a hand on a memoir I’d been writing. Through our emails, her story unfolded slowly, piece by piece. She had spent years living in two worlds — one focused on just getting by, the other reaching for something more, even if she couldn’t say exactly what it was. Working as a nanny for wealthy families in Nashville, she witnessed daily the hollow victories of material success, while her own life felt increasingly confined by invisible walls far more subtle than the ones the first Lisa had faced, yet no less constraining.
She treated healing like a battle plan, as if she could become whole by following the right steps in the right order. The first Lisa had faced a real gun. The second Lisa had turned self-improvement into her own kind of weapon, trying to force herself to change through pure willpower.
“I tried everything,” she wrote to me one day. “Every decision was filtered through the lens of mental health — ice baths, morning sun exposure, meditation, carefully timed supplements. At home, my life became a carefully constructed regiment: no sugar, no alcohol, no dairy, no gluten. I thought if I could just get the formula right, I would finally heal completely.” Her days unfolded as a masterclass in self-optimization: strenuous exercise, breathwork, therapy, shadow work, plant medicine ceremonies. Yet beneath this scaffold of wellness practices, a deeper loneliness persisted — the kind that comes from trying to outrun your own shadow.
What Freedom Really Means
Her catalyst for change wasn’t a single moment of defiance but a gradual awakening to possibility. It began, ironically, with a lesson I’d shared with her from Rich Dad, Poor Dad — the same book I’d been reading that night at Macaroni Grill. Where I had first learned the mechanics of inequality, Lisa discovered a door to liberation. Her house, once a burden, became more than just an asset — it became a key to unlock a different way of being in the world. Just as the first Lisa had found life by accepting death, the second Lisa found freedom by releasing her grip on certainty itself.
At fifty-two, she made her move — not in one dramatic gesture like her Macaroni namesake, but in a series of small surrenders that added up to radical transformation. It began with renting out a room in her house, then came an RV, soon she was on the road — each step a quiet rebellion against the life she thought she was supposed to live. She left behind her rigid routines, her careful strategies of self-improvement, and set out to discover what lay beyond the boundaries of her known world. From Quebec’s apple orchards to crystal-clear Balinese waters to Indonesian volcanos at dawn, she followed an inner compass that pointed toward authenticity rather than achievement.
Her journey challenged conventional narratives about transformation. Instead of trying to reach some perfect version of herself, she was learning to sink roots into who she really was. From Italian farmhouses to rustic villages, she discovered communities where her sensitivity — once seen as a flaw to be corrected — revealed itself as a gift. When a Workaway host’s impatience triggered old wounds, instead of retreating into self-doubt, she leaned into her truth: “Am I imagining this? On a scale of 1–10, how frustrated did that make you?” What had once felt like weakness became a way of perceiving the subtle textures of existence that others might miss.
In these off-grid communities, she found people who valued presence over perfection, who could sit with life’s complexities without rushing to solve them. Her questions about consciousness weren’t met with blank stares but with eager exploration. Her tendency to feel deeply wasn’t seen as a weakness but as a natural way — - maybe even supernatural way — of being human.
Lisa saw the irony: after years of trying to fix herself through strict rules, she was finding peace in simple, unexpected moments of joy. In a Thai cafe, with Christmas music playing and the hum of air conditioning washing over her like a gentle tide, she allowed herself dessert. In community gardens, her hands deep in soil, she found connection without trying. Walking narrow streets in Bali, she discovered that her sensitivity — once a burden to be managed — had become a way of touching life’s deeper currents. The very experiences she had denied herself in pursuit of wellness became unexpected doorways to genuine well-being.
Both women had found, each in her own way, that freedom comes not from fighting harder, but from letting go. The first Lisa found it in that crystalline moment when she handed her father the gun, choosing to face death rather than continue living in fear. The second Lisa found it gradually, in the quiet acknowledgment that being human — with all its messy imperfections — might be enough. Their stories, separated by decades but united in wisdom, suggest that perhaps transformation isn’t about becoming someone new but about releasing our grip on who we think we should be.
In that steamy restaurant kitchen thirty years ago, I had argued that we’re all just products of our circumstances — that free will was just an illusion. Life, through these two women, offered a more nuanced teaching: that while we may not choose the conditions of our existence, we can choose how we meet them. The first Lisa’s story seemed at first to validate my position — wasn’t her father’s alcoholism, his daily terrorizing, precisely the kind of environmental conditioning that shapes a life? Yet in that moment when she handed him the gun, something transcendent emerged — a choice that defied both survival instinct and circumstance.
Both Lisas, in their unique ways, demonstrated that freedom isn’t found in perfect control or complete release, but in the courage to remain open to life in all its messy, imperfect glory. Sometimes that means staring down death itself; sometimes it means eating dessert in a Thai cafe when all your careful rules say you shouldn’t.
Their stories suggest that free will isn’t an illusion after all, but something more mysterious and profound than our philosophical frameworks can contain. In the end, both women discovered the same truth: sometimes you must face your fear of losing everything — including your ideas about freedom itself — to find the courage to truly live.
