What Grief Feels Like | A Cup of Jo


Alessandra Olanow

Alessandra Olanow‘s new book of drawings, I Used to Have a Plan: But Life Had Other Ideas, chronicles a difficult time in her life. “When I set out to draw the book, I was coping with the breakup of my marriage,” she says. “Shortly afterward, my mom was diagnosed with terminal cancer and given a few months to live.” Ultimately, Alessandra’s book tackles grief, shock, empathy and hope. Here’s a peek inside…


Alessandra Olanow book

On shocking news: I had a one-year-old daughter and I was going through a divorce that knocked me off my feet. (I had not seen it coming.) Then, in late May 2018, my mom wasn’t feeling well and went to get a checkup. They said, you won’t make it through the summer. We thought, that’s impossible, she’s completely fine — vibrant, fun, happy. But she died shortly after the fourth of July.

On final days: She lived an hour away, and I started visiting her every day. My mom was my best friend — we spoke a million times a day — and we also had a complicated relationship. It was incredibly intense. In those final weeks, she just wanted to hold my hand. I’m a terrible ukulele player, but she loved when I would play and sing country and Beatles songs for her.

On connecting internally: After my mom died, I started to draw again. It felt very clunky and cumbersome. But drawing my emotions was my therapy.

On a meaningful poem: Mary Oliver has a poem called Heavy, and I read it over and over and over. A couple lines kept running through my mind: ‘That time / I thought I could not / go any closer to grief / without dying.’ Well, I went closer and I did not die. I realized, there is no other way I would want to feel about losing my mother than tremendous sadness. I learned how to carry my grief; I learned how to respect it.

On time passing: Now it’s been a year and a half since my mom died. But when something happy happens, I still want to pick up the phone and tell her. There are days you wake up and feel great, and days you wake up and don’t feel great, and they’re both okay. When you go through something traumatic or painful — a breakup, a death, a move, anything — it takes time. You can’t rush through it.

On navigating different hard times: I Used to Have a Plan was supposed to be about losing this picture of a marriage, and then I lost my mom — but you can apply these drawings to so many things. Therapists have reached out to me — they say, these drawings are palatable when someone’s going through something very emotional; people might not have the attention span for digesting a lot more. Therapists have told me the book was also helpful for people trying hard to have babies — which I completely identify with because I struggled with infertility — and also newly sober people.

On being vulnerable: Publishing this book is the most exposed I’ve ever felt in my life. It was the most complicated time in my life, and the book captured what I was going through. I hope it helps others.

Alessandra Olanow

Alessandra Olanow

Alessandra Olanow

Alessandra Olanow


Thank you so much, Alessandra! Find her book here, if you’d like, and sending a big hug to anyone missing someone today. xoxo

P.S. How to write a condolence note, and what to say to a grieving friend. Plus, Alessandra and her daughter’s apartment tour.



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