Alessandra Olanow: Begin Again, and Again, and Again w/ Kerry Diamond

Event guidelines:

• Each ticket will include either a copy of the featured book or a $10 Books Are Magic gift card.
• Additional copies of the book will be available for purchase at the event.
• A signing will follow the talk.
• Home address is collected for contact tracing purposes; it will not be used otherwise.
• The event will also be livestreamed for free here: https://youtube.com/live/sagqogVBCEk
• As a reminder: If you are not feeling well, please do not come to the event, even if you have a ticket; email us and we'll work it out.

If you have any questions regarding these guidelines or to request accessibility accommodations, please contact [email protected].

A luminous illustrated meditation on learning to live with life’s cycles—for anyone in the middle of breaking open and rebuilding.

Artist and author Alessandra Olanow knows that life never unfolds as you think it will. 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—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 renewal.

Through watercolor illustrations woven with personal narrative and philosophical reflection, Alessandra offers companionship rather than answers. The book moves through five movements—Question, Doubt, Ground, Open, Renewal—each holding its own texture.

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.

Alessandra Olanow is a writer and illustrator beloved on Instagram as @aolanow. 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 an end-of-life doula, an experience that deepened her understanding of life’s cycles of transformation and renewal. Her books include I Used to Have a Plan, Hello Grief, and—coming in March 2026—Begin Again, And Again, And Again. She lives in Brooklyn, New York, with her daughter, Coco.

Kerry Diamond is the co-founder and editorial director of Cherry Bombe, a biannual indie magazine about women and food. She's also the host of the Radio Cherry Bombe podcast and co-owner of the Brooklyn eateries Nightingale Nine, Wilma Jean, and Smith Canteen. Previously, she was an editor at Harper's Bazaar and Women's Wear Daily.

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