Begin Again, and Again, and Again

A luminous illustrated meditation on transformation as practice-for anyone learning to live with life’s cycles of breaking open and rebuilding.

Illustrator and author Alessandra Olanow knows that life never unfolds as you think it will. After divorce, her mother’s death, and the quiet unraveling of a carefully built life, she found herself awake at 3 a.m. with questions that wouldn’t settle: Is this all there is? What do I do when everything comes undone? How do I stay open when I want to close down?

Begin Again, and Again, and Again started as notes to herself in those wakeful hours-a practice of thinking through images and words to map the territory of uncertainty. What emerged is a book about the fundamental rhythm of being human: the constant cycle of questioning, doubt, finding ground, opening, and beginning again.

Through watercolor illustrations integrated with personal narrative and philosophical reflection drawing on Buddhism, Stoicism, and lived experience, Alessandra offers not answers but companionship. The book moves through five movements like a breath-Question, Doubt, Ground, Open, Renewal-holding the particular texture of each stage. The hollowness of Is this all there is? The weight of I think I can’t. The surprising fertility of hitting bottom. The radical simplicity of presence.

Here’s permission to stop waiting for the final version of yourself. To trust that transformation isn’t about arriving but about learning to live with constant change.

It’s never too late to begin again.

Author Biography

Alessandra Olanow is the illustrator and author of I Used to Have a Plan (Harper Design, 2021) and Hello Grief (Harper Design, 2023). Her work explores life’s unexpected turns with honesty and grace, drawing from her own experiences with loss, reinvention, and the courage to begin again. She has also worked as a death doula, an experience that deepened her understanding of life’s cycles of transformation and renewal. She lives in Brooklyn, New York, with her daughter, Coco.????????????????