Begin Again, and Again, and Again: Notes on the Art of Perpetual Renewal

by Alessandra Olanow

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  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 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. 

Genres: Nonfiction, Poetry

164 pages, Kindle Edition

Published March 17, 2026

Reviews

[Erika · Rating 5 out of 5]

A profound and powerful illustrated meditation on beginning again and life’s inevitable cycles, this book is an invitation to take stock and slow down.

✨ Book Review: BEGIN AGAIN AND AGAIN AND AGAIN: Notes on the Art of Perpetual Renewal by Alessandra Olanow
📅 Publication Date: March 17, 2026

What a renewing read. This book felt like a ray of sunshine providing just the right amount of warmth. The writing is lyrical and the illustrations charming. I especially enjoyed the drawn type and illustrations throughout the book because they forced me to slow down and linger. True to the book title, I anticipate returning to this short-but-powerful book again, and again, and again.

I’ll leave you with two favorite passages that really resonated with me, at least on this first read.
- “Perhaps the question is not what more, but what deeper awaits you.” - page 33
- “Breathe. Look up. Step outside. Be still. Your worth isn’t in what you produce. It’s in how you exist. It’s okay to be soft in a world that wants you hard.” - page 143

Rating: ⭐️⭐️⭐️⭐️⭐️ (5/5 stars)

🥰 Thank you to WorkmanPub for the #gifted copy of this book. I received a free copy from Workman Publishing in exchange for a free and unbiased review.

[Kathy · Rating 4 out of 5]

Review of Begin Again, and Again, and Again by author and illustrator Allessandra Olanow. Four Stars

Begin Again, and Again, and Again, is a beautifully written, illustrated and thoughtful book about finding your way through the cycles of life. Nestled among the pages is the realization that life continually brings us the pain of endings as well as opportunities for growth and joy in our new chapters. Our journeys depend on our willingness to accept, adapt, and try new things even when hesitant.

I thoroughly enjoyed Olanow's talent and read the book in one sitting. It would make a lovely gift. I would love a hard-copy of the book myself!

My sincere thanks to the author, and Workman Publishing for allowing me to access a DRC of the book via NetGalley. Publication was March 17, 2026. All thoughts and opinions expressed in this review are my own and are freely given.

[Maya Patel]

We’ve all had those 3am thoughts—those quiet, restless moments that seem to arrive so easily, especially after having kids and waking in the night for feeds. The “what ifs” and “should haves” feel almost inevitable.

‘Begin Again And Again And Again’ by Alessandra Olanow is a beautifully illustrated reflection on navigating change, particularly during midlife.

Change reshapes us. And sometimes, it asks us to begin again, no matter where we are or how we got there.

Through a combination of artwork, personal writing, and poetry, this book is a journey of self-discovery. If you find yourself in the middle of a big shift, this is the kind of book you’ll want to reach for.

Thank you @workmanpub for a #gifted copy in exchange for a free and unbiased review. Keeping this one on the coffee table!

[Jahnayah · Rating 4 out of 5]

I hope to read this again in a different season of life with a different set of eyes. 3.75 ⭐️
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I was looking forward to this release. I liked around 75% of the book, it was difficult getting past the initial pages. The quote “Life is not happening to you. It’s responding to you” made me wince. I had a visceral reaction to write in my kindle notes that life is very well happening to people. Horrible things happen every day to people who don’t deserve it, didn’t ask for it, or somehow will it to happen to themselves. Fortunately, I was able to move on and explore more of the book. I was pleasantly surprised - particularly with the ground chapter and the later discussion of Sisyphus and Camus.

[Emily · Rating 5 out of 5]

This book was absolutely beautiful and such an uplifting read. Begin Again, and Again, and Again came at the perfect time for me. It was a much-needed and much-appreciated pick-me-up. The illustrations were gorgeous, well placed throughout the book, and paired well with Alessandra Olanow's words. The book has six sections, five of which are based on five movements—Question, Doubt, Ground, Open, and Renewal. Each section was amazing, filled with drawings, graphs, and words of encouragement.

This book is perfect for those who are facing new beginnings in major parts of their lives. The blurb says it's perfect for women facing the beginnings of midlife, but I also think it's perfect for every woman facing a new beginning, a new start, regardless of their age. This book was absolutely perfect and a breath of fresh air.

*Thank you, NetGalley, for providing an arc in exchange for an honest review.*

[Cheyanne · Rating 4 out of 5]

This book was stunning. It's a deeply reflective work that helps readers consider the tough parts of themselves that are often forgotten and pushed down. A highlight of this work is the beautiful illustrations that are pieced in throughout the text. It adds another element that makes the book stand out.

[Leslie · Rating 5 out of 5]

Beautiful book. Reading it felt like a hug from a friend and a reminder that everything is going to be okay, maybe even better than before. Loved the artwork.

[Jade Melgar · Rating 5 out of 5]

This book taught me to stop chasing the “best version of myself” and to let myself transform and change everyday. Find beauty in living and in being present.

[Sinduja Krishna Kumar · Rating 4 out of 5]

It’s a beautifully illustrated book with meaningful insights. I liked it so much I’ve kept it to reread. I think you can come back to this book at any phase and it’ll still feel fresh.

[Elfiana NF · Rating 5 out of 5]

Too relatable. Chef kiss.