The title of William Homestead’s most recent book suggests there’s value in bewilderment. In Not Till We Are Lost: Thoreau, Education, and Climate Crisis, a finalist for this year’s Vermont Book Award in creative nonfiction, the Putney author praises uncertainty — in careers, relationships and creativity — for allowing us to embrace new possibilities.
In exploring these gifts of “lostness,” Homestead tries to harness different kinds of writing to illuminate two crises he sees as related: an educational crisis “in a world dominated by financial markets, job markets, and market-model universities” and a climate change emergency.
The issues Homestead investigates are mind-boggling in their range and difficulty. What’s required is a structure that brings a reader step-by-step toward fresh clarity and insight, rather than inducing a more acute sense of being lost. Unfortunately, this author’s approach is all too often roundabout and meandering, jumping from topic to topic and episode to episode.
In its most enjoyable sections, Not Till We Are Lost proceeds like a memoir. As Homestead recounts his own unorthodox route through education and eventually into teaching, his chronicle is personal, not theoretical or didactic. As a youth, he aspired to be a writer but kept losing faith in schooling. He dropped out to hike the Appalachian Trail, followed a meditation teacher to New Mexico and took various jobs, many of them unfulfilling.
Homestead’s early enthusiasm for the writings of Henry David Thoreau grew into a lifelong love, especially for the lucid, companionable Walden. He quotes passages from Thoreau throughout, offering plentiful evidence for why this innovative 19th-century essayist, naturalist and political radical is more influential than ever. Homestead measures his own reaching for self-reliance and authenticity by his predecessor’s “pedagogy of listening”:
For Thoreau, the roots of knowledge, or a more complete knowing within the context of our not-knowing, emerges from listening inwardly and outwardly and living in sympathy with intelligence. To begin, we must “simplify.” We must practice listening when walking, or sauntering, and contemplate the voice and voices of nature … welcoming paradox and contradiction as fuel for critical thinking … integrating the poetic imagination with close observation …
Maybe inevitably, given the contrarianism of his exemplar, Homestead kept struggling with formal education. After “seven years, three colleges, and four majors,” he graduated from Rutgers University in 1985 but with “no sense of accomplishment,” he writes, “… only a momentary sense of relief.”
Years of itinerant work followed, and the account of Homestead’s repeated attempts to return to school is interesting and moving. He taught as an adjunct for seven years, earned a couple of master’s degrees from the University of Montana, then landed a permanent job at New England College in Henniker, N.H., where he taught for 19 years before retiring in 2024. Along the way, he earned an MFA in creative writing from Vermont’s Goddard College in 2013.
The most captivating episodes in Not Till We Are Lost take place in classrooms, with conversations between Homestead and his students delivered in animated dialogue.
“I don’t like talking about religion,” a disgruntled student says.
“Why is that?” I ask.
“I just don’t like it,” she insists with a frown.
“I’m not asking you to believe anything; I’m asking you to think critically about religious language and faith because religion and faith influence our world, whether we like it or not.” …
“I thought we were going to write a research paper about our future careers?” she questions, brow furrowed.
Also fascinating (and suspenseful) are Homestead’s recollections of how he succumbed to and then freed himself from a gambling compulsion, as well as his meditation on the allure and dangers of charismatic gurus. Testifying to his own experience, he memorably contrasts servitude to an idealized “master” with the mutual generosity of a mentoring relationship.
But Homestead’s vigorous first-person narrative is weighed down by scholarly logorrhea — an avalanche of citations from Thoreau, Socrates, Plato, Jesus, Ralph Waldo Emerson, Margaret Fuller, Carl Jung, Rainer Maria Rilke, Mahatma Gandhi, James Hillman, James Baldwin, Rachel Carson, Chögyam Trungpa, Thich Nhat Hanh, Bill McKibben, Howard Gardner, John Gatto and many others.
And the book has a bizarre chronology, jumping in time and location from one chapter to another. While celebrating “wandering” as a philosophical principle, Homestead’s prose ambles hither and yon, continuity be damned. A reader may be perplexed on the most basic level: “Who is who, and what’s happening here?” Again and again, this rambling style disrupts the emotional hold of a well-told story.
Through most of Not Till We Are Lost, the specific urgency of environmental collapse is mentioned only glancingly, but in the final chapter, it becomes more decisively the book’s focus.
“Sometimes I don’t know what to teach,” Homestead admits. “I am lost, or at a loss, given that there is so much to teach and so little time to do right by the earth and ourselves to change course.”
At such moments, he continues, he draws guidance from the liberatory approach of Thoreau, who advised his schoolteacher sister that the most effective way to help a student learn was to place her “in a window, to note what passes in the street … let her gaze in the fire, or into a corner where there is a spider’s web, and philosophize, moralize, theorize … What their hands find to putter about, or their minds to think about, that let them write about.”
From Not Till We Are Lost: Thoreau, Education, and Climate Crisis
The original print version of this article was headlined “Not All Those Who Wander | Book review: Not Till We Are Lost: Thoreau, Education, and Climate Crisis, by William Homestead”
This article appears in Sep 10-16 2025.
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