I Used to Have a Plan by Alessandra Olanow

Sometimes life doesn’t just change your plans — it erases them entirely. And in those moments, it helps to know you’re not alone.

After her own world turned upside down, artist and illustrator Alessandra Olanow did what many of us wish we could: she made something beautiful out of the mess. Drawing from her experience navigating divorce, single motherhood, and the quiet unraveling of a life she thought she understood, she began sharing tender, witty illustrations on Instagram that said the quiet parts out loud. The response was extraordinary — her following grew from 9,500 to over 157,000 in a single year, drawing fans like Katie Couric, Jennifer Garner, and the team at Goop.

This book is the natural next chapter. With 75–100 original illustrations, it walks alongside you through the full arc of healing — the shock, the denial, the self-doubt, and finally, the tentative, hard-won hope on the other side. Organized into five deeply human chapters, from “I Didn’t See That Coming” to “I Like It Here, Can I Stay a While,” it doesn’t rush you. It just sits with you.

Equal parts commiseration and encouragement, this is the kind of book you’ll dog-ear, return to, and quietly press into a friend’s hands during a hard season. It belongs on the shelf next to your favorite mug and a good candle.

Perfect for anyone navigating unexpected change, loss, or the beautiful, bewildering work of starting over.

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