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.

Balm for the soul—Alessandra Olanow offers advice, inspiration, and encouragement for anyone who needs a shoulder to lean on during a difficult time.“I Know This Too Shall Pass. (But It Would Be Helpful to Know When).”After a series of events left her a divorced single mother questioning herself, her relationships, and basically, everything she thought was true about her “picture-perfect” life, Alessandra Olanow began drawing and posting illustrations on Instagram that reflected her feelings and struggles to right her life. She chronicled her journey of healing, expressing the shock, delusion, denial, self-pity, and self-doubt she experienced and the self-empathy and forgiveness that ultimately helped her regain a sense of self—but stronger, more fearless, and more hopeful than before. Her charming illustrations and keen, memorable observations—struck a chord. Within a year, her audience grew dramatically, from 9,500 to 157,000 followers, including celebrities Katie Couric, Jennifer Garner, Elise Loehnen (chief content officer at Goop), the poet Joao Doederlein, and Joanna Goddard (founder of A Cup of Jo). I Used to Have a Plan brings Olanow’s soothing sensibility to a wider audience, featuring new drawings and ideas that touch upon the universal experiences of unexpected change and loss. Divided into five parts—“I Didn’t See That Coming,” “It’s OK That You’re Not OK,” “Where’d I Go,” “The Only Way Out Is Through,” and “I Like It Here, Can I Stay a While?”—the book beautifully encapsulates the experience of encountering difficulty, processing it and healing from it, and becoming stronger and with a better sense of self. Full of advice, commiseration, empathy, and wit that is comforting, helpful, direct, and remarkable in its truth, I Used to Have a Plan helps everyone through the painful yet ultimately uplifting process of healing.I Used to Have a Plan includes 75-100 illustrations.

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.

Balm for the soul—Alessandra Olanow offers advice, inspiration, and encouragement for anyone who needs a shoulder to lean on during a difficult time.“I Know This Too Shall Pass. (But It Would Be Helpful to Know When).”After a series of events left her a divorced single mother questioning herself, her relationships, and basically, everything she thought was true about her “picture-perfect” life, Alessandra Olanow began drawing and posting illustrations on Instagram that reflected her feelings and struggles to right her life. She chronicled her journey of healing, expressing the shock, delusion, denial, self-pity, and self-doubt she experienced and the self-empathy and forgiveness that ultimately helped her regain a sense of self—but stronger, more fearless, and more hopeful than before. Her charming illustrations and keen, memorable observations—struck a chord. Within a year, her audience grew dramatically, from 9,500 to 157,000 followers, including celebrities Katie Couric, Jennifer Garner, Elise Loehnen (chief content officer at Goop), the poet Joao Doederlein, and Joanna Goddard (founder of A Cup of Jo). I Used to Have a Plan brings Olanow’s soothing sensibility to a wider audience, featuring new drawings and ideas that touch upon the universal experiences of unexpected change and loss. Divided into five parts—“I Didn’t See That Coming,” “It’s OK That You’re Not OK,” “Where’d I Go,” “The Only Way Out Is Through,” and “I Like It Here, Can I Stay a While?”—the book beautifully encapsulates the experience of encountering difficulty, processing it and healing from it, and becoming stronger and with a better sense of self. Full of advice, commiseration, empathy, and wit that is comforting, helpful, direct, and remarkable in its truth, I Used to Have a Plan helps everyone through the painful yet ultimately uplifting process of healing.I Used to Have a Plan includes 75-100 illustrations.