Begin Again, and Again, and Again

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. 

• "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."
   
  Yung Pueblo, #1 NYT Bestselling Author
• "Olanow brings readers into her internal world with Begin Again, delicately and beautifully depicting the subtle murmurs of awakening present within us all."
  Sharon Salzberg, author of Lovingkindness and Finding Your Way
• 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. 
  Elena Brower, bestselling author and artist of Practice You and Hold Nothing