“I Know This Too Shall Pass. (But It Would Be Helpful to Know When.)” Inspired by a personal experience that abruptly 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 a cathartic experiment. She began drawing and posting illustrations that were reflective of her feelings and struggle to turn herself right side up and posted them on Instagram. She touched on the shock, delusion, denial, self-pity, and self-doubt that made up the beginning of her healing to working through her feelings, giving herself a break, and ultimately, regaining a sense of self—but stronger, more fearless, and more hopeful than before. Her charming illustrations and her keen, memorable observations—often delivered with deeply affecting, minimal language—told of her daily ups and downs as well as a bigger-picture struggles struck a chord and she has developed a large and growing audience very quickly. In the last year alone, Olanow’s Instagram account following has grown quickly and organically from 9,500 to almost 157,000 between February 2019 and February 2020—and includes notable creative directors, designers, and artists with their own social media followings, including celebrities Katie Couric, Jennifer Garner, Elise Loehnen (chief content officer at goop), and Joanna Goddard (founder of A Cup of Jo). Olanow’s I USED TO HAVE A PLAN is a volume of 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, not only processing it and healing from it, but becoming stronger and with a better sense of self. Read as a narrative or flipped through, every spread delivers a combination of advice, commiseration, empathy, and wit that is comforting, helpful, direct, and remarkable in its truth. Olanow has distilled the process of healing into an accessible, entertaining, and comforting volume that is sure to make it a classic in this genre of gift book.