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BEGIN AGAIN, AND AGAIN, AND AGAIN

Alessandra Olanow

Notes on the Art of Perpetual Renewal

A unique, beautiful, hopeful illustrated meditation on the unfolding of life, and a perfect gift for every woman facing the beginnings of midlife and all of its changes and challenges.
Illustrator Alessandra Olanow knows all too well that life never unfolds as you think it will. After divorce, grief, and career transformation, BEGIN AGAIN, AND AGAIN, AND AGAIN started as notes to herself at 3 a.m., when questions would arise: Is this all there is? Am I doing it right? What comes next?

For everyone, midlife is a time when new challenges arise and when the vision of life's expectations and reality come crashing together. This book offers a new perspective on this time - while it can be a tumultuous time full of change, it can also be a time for renewal. By letting go of preconceptions, Alessandra illuminates for readers the continuous cycle of transformation - being open to possibility, questioning your current state, finding ground, beginning again, and finding the joy in starting over.

BEGIN AGAIN, AND AGAIN, AND AGAIN grants you permission to start over as many times as you need to - it's never too late.

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 lives in Brooklyn, New York, with her daughter, Coco.
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Published 2026-03-17 by Workman Publishing

Comments

With reminders to relinquish our grasp, choose our focus, and select which thoughts we believe, Alessandra's words and illustrations are an invitation to rewrite the narrative and remember that the ache is a good place to Begin Again, and Again, and Again.

Olanow transforms the pain of unraveling into the art of becoming with words and illustrations that make you feel deeply seen. This book holds space for all the versions of yourself you've been and all the ones you're becoming.

Olanow brings readers into her internal world with Begin Again, delicately and beautifully depicting the subtle murmurs of awakening present within us all.