I Used to Have a Plan

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.