Double-sided chalkboard

The Double-sided chalkboard is a folding wooden A-frame from Sugar’s living room, but its importance lies in the way its two sides hold together grief and literary ambition. One bears an idea about self-knowledge leading to humility; the other, a line from Eudora Welty about a woman thinking of her mother holding her hands. Sugar remembers the board as more than a decorated household object: it made visible the two concerns that shaped her effort to write a book after Cheryl Strayed’s mother died, and later became the framework for advice about humility, surrender, and work.

Form and Inscriptions

When Sugar was twenty-eight, she kept the Double-sided chalkboard in her living room. It was a wooden A-frame that stood by itself and folded flat, with a writing surface on either side. The arrangement matters: the board did not gather its inscriptions onto a single face but placed them back to back, making each a distinct yet connected thought. On one side Sugar wrote a statement attributed to Flannery O’Connor about humility as self-knowledge’s first product. On the other she wrote a line from Eudora Welty’s novel The Optimist’s Daughter, about a woman sitting and thinking of her mother holding her hands.

The Welty line had a particular place in Sugar’s reading life. She returned to The Optimist’s Daughter repeatedly, and that passage helped explain why the book mattered to her. The chalkboard therefore joined a literary reference to a personal preoccupation: the remembered woman’s attention to her mother echoed Sugar’s own persistent thought of Cheryl Strayed’s mother. The two inscriptions did not make the board a diary or a finished argument. Instead, their pairing gave a compact, visible form to ideas Sugar was still living through: loss, the wish to write, and the humility required to complete the work.

Grief and the Unwritten Book

Sugar describes her thoughts at twenty-eight as one concern made from two pressed together: how much she missed her mother, and how writing a book seemed the only way she could bear life without her. She had long felt that a book was inside her, but its plot and shape became imaginable only after the death. In her account, grief disclosed the story she felt unable to live without telling. The chalkboard’s juxtaposed quotations thus stood near the beginning of a process in which bereavement and authorship became inseparable, without suggesting that writing erased the loss.

The object also marks the distance between wanting to write and producing a book. Sugar had received grants and awards, published stories and essays, read widely, and filled journals with accounts of her life. She also wrote stories in intense but intermittent bursts, expecting them to become a novel without the sustained effort a book required. As her thirtieth birthday approached, she recognized that the manuscript would not assemble itself: she would have to concentrate for longer and work harder than she had thought possible. The board’s reminder of humility acquired force against the grand expectations that had coexisted with her unfinished work.

From Self-Knowledge to Surrender

In retrospect, Sugar does not treat the years before the book as wasted, even though she had once blamed herself for reaching the end of her twenties without a finished manuscript. She understands those years as part of what made the book possible. Unfinished sentences and stories, voracious reading, extensive journaling, grief, reckoning with childhood, relationships, and growing up all contributed to the self-knowledge she needed. The chalkboard’s two sides gather those elements into a tension: the wish to make a book out of pain and experience, and the humility of accepting that becoming able to write it takes time.

When Sugar finished the manuscript of her first book, she went down to the floor and wept, laughed, and remained there for half an hour. She had turned thirty-five a few weeks earlier and was two months pregnant with her first child. She did not know how readers would judge the book and no longer regarded that judgment as the decisive measure. What mattered was that she had completed the work and no longer carried the book as an unrealized demand within herself. She describes the completion as having given the work everything she had, after relinquishing the expectation that she must be exceptionally talented, young, or assured of publication.

The Board as Advice

Years later, Sugar carries the chalkboard’s lesson into a letter to Elissa Bassist, a young writer distressed by her progress. She imagines writing humility on one side of a similar board and surrender on the other. That imagined use extends the original object’s function: it turns a private arrangement of ideas into a practical counsel for someone caught between self-loathing and inflated expectations. Sugar argues that neither self-condemnation nor the assumption of early success gets writing done; the work begins at ground level, through producing pages despite limitations, insecurity, and jealousy.

The board’s lasting significance comes from this shift between inscription, memory, and instruction. Its original sayings offered Sugar a way to place humility beside the image of a mother’s care; her later recollection links those words to the long labor of making a book after bereavement. When she addresses another writer, the board becomes a model for holding difficult truths together rather than choosing between them. Self-knowledge does not promise effortless achievement, and grief does not itself produce a manuscript. The object points instead toward the patient work through which experience can become writing.