Michael Holland
Writer | Strategist | NomadExploring culture, history, and modern life, one month at a timeAbout I Curiosity I Essays I Collaborate I Connect
About Me
Welcome
Hi, I’m Michael, a writer, strategist, and nomad guided by an insatiable curiosity to explore how people and place shape each other and what that reveals about ourselves, our capacity for transformation, and our search for belonging.For the last three years, I’ve called more than 40 places “home” across three continents, eight countries, and 23 U.S. states. What began as a leap into the unknown has become a slow, intentional practice of immersion: listening, observing, and learning from the stories and undercurrents most people only read about.Before this odyssey, I spent three decades as a strategist, launching start-ups, navigating international crises, and contributing to efforts as far-ranging as the Irish Peace Process, the Paris Climate Accords, and humanitarian relief. I’ve advised Fortune 100 CEOs, government leaders, and Nobel laureates, always working at the edge where clarity and trust matter most.Today I write about what happens when culture, history, and modern life intersect, and how curiosity can transform not only how we see the world, but how we see ourselves.
A Guiding Principle
Curiosity, Practiced
Curiosity, when practiced deeply, is transformational. It sounds simple to say, but in reality, it’s difficult work. It forces you to confront your beliefs, priorities, and blind spots, to challenge your own assumptions, and, oftentimes, to sit in discomfort.For me, it started with the decision to leave stability behind. With my sons off in college, I had a choice: stay in the home the three of us had built together or pack up two decades of memories, attachments, and routines and begin again. I chose the latter.What unfolded was a journey of constant discovery. Slow travel became a method by not rushing through places, but staying long enough for them to reveal themselves. Every city, every crossing of a border, asked me to begin again, to see with fresh eyes, to listen more closely, to move with humility.This rhythm became energizing—a reminder that the greatest opportunities for growth often lie in the spaces between what we know and what we have yet to learn.What I discovered is that curiosity isn’t passive; it demands risk. It requires us to give up certainty in exchange for possibility. And in that trade, we don’t just see the world differently; we change how we live within it.
My Writing on Substack
Life, Uncontained
Stories from the road, and the deeper terrain beneath it.Life, Uncontained is where I explore what slow, immersive travel reveals about culture, identity, and ourselves. Shaped by more than 40 homes across three continents, these essays move between fieldnotes and reflections, personal narrative and cultural commentary.Some ask what it means to belong. Others test ideas about home, transformation, or travel itself. Together, they form four through-lines — America, Reconsidered; Home, Reimagined; Life, Reframed; and Travel, Redefined. Each is a way of making sense of a fractured world, and of finding clarity in motion.If you’re drawn to stories that bridge the personal and political, the global and the local, I invite you to read along and to see the world and your place in it with fresh eyes.
America, Reconsidered
Finding America
A journey through the landscapes, myths, and contradictions of the United States, exploring how history, culture, and lived experience shape a nation still wrestling with its identity, and what it means to belong here today.
Home, Reimagined
Finding Home
Reflections on “home,” and how walking away from permanence challenged my assumptions of stability, forcing me to reckon not only with physical shelter, but with the deeper, often unexamined home within myself.
Life, Reframed
The Curiosity Compass
An approach to life that embraces curiosity, adaptability, and the lessons of discomfort as catalysts for growth, reshaping how we see ourselves, connect with others, and reimagine the work we do.
Travel, Redefined
A Nomad's Guide
Practical wisdom from life on the move—field-tested lessons on slow travel and exploration, offering guidance for anyone seeking not just to see the world, but to inhabit it more deeply.
Collaborations
Working Together
At the intersection of story, strategy, and curiosity, I help people and organizations rethink how they see the world, and how the world sees them.Writing & Storytelling
From essays and thought leadership to ghostwriting and brand narratives that move people.Speaking & Facilitation
Talks and dialogues that weave narrative, culture, and belonging, inviting audiences to reflect and reimagine.Leadership & Coaching
One-on-one or small group sessions to build clarity and confidence across cultures, communities, and contexts.Travel & Cultural Immersion
Curated journeys and experiences that shift perspectives and spark new ways of seeing and creating.
Scenes from the Road
A journey isn’t just measured in miles, but also in its moments. These are fragments that left their mark: quiet, fleeting, and unforgettable.
Palenqueras at sunset, Cartagena
Mornings on the canals, Utrecht
Through a telescope, Gamboa
Stone and sky, Crazy Horse Memorial
Immersive Traveling
Slow Travel, Defined
Slow travel is a deliberate choice to make a temporary home in a place. Unlike traditional tourism, slow travel invites you to immerse yourself in one location for weeks at a time, typically four to six for me.Stay still long enough, and you notice how a city wakes, where conversations gather, and which histories are remembered or silenced. What you gain is measured not in landmarks checked off, but in texture, depth, and memory, including:• Cultural Immersion: absorbing customs as they’re lived.
• Authentic Experiences: finding experiences not in the guidebooks.
• Personal Growth: learning to navigate, adapt, and belong.
• Mental Health Benefits: trading urgency for the space to notice.
• Financial Benefits: living, not just visiting, often costs less over time.Slow travel doesn’t just show you the world: it shows you your world, reframed. It reminds you that belonging isn’t about how long you stay, but how deeply you engage.
My Writing on Substack
Life, Uncontained
Stories from the road, and the deeper terrain beneath it.Life, Uncontained is my ongoing chronicle of identity, disconnection, culture, and rediscovery, shaped by living and working in more than 40 cities across three continents.This isn’t just travel writing. It’s narrative fieldwork: stories with soul, drawn from barrios and borderlands, city halls and hostels, conversations with Uber drivers and civic leaders alike. These essays challenge surface narratives and ask us to rethink what proximity, perspective, and belonging mean in a fractured world.I write for those who care about culture and context. For anyone navigating disruption or searching for a truer sense of home, in your work, your story, or yourself.If you’re drawn to stories that bridge the personal and political, the global and the local, I invite you to read along, and to see the world, and your place in it, with fresh eyes.
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Places Teach Us Things
Every journey, across geographies, cultures, and ideas, reshapes how I see the world and how I help others see it. Places teach us to slow down, notice what’s hidden, and tell truer stories. Those lessons travel with me into every project, workshop, and conversation.
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