Behind the shiny squares of Instagram, we all live real lives and deal with real shit. For many of us, none of that stuff will ever make it onto our feeds – it’s far too raw and personal – but for others, it’s cathartic to share their highs and lows with their followers...
For New York illustrator Alessandra Olanow, discovering her “picture-perfect” life was anything but – a divorce, which came out of nowhere and the reality of being a single mother – inspired a new creative direction, albeit one that led her to open up and express her vulnerabilities and fears. Alessandra began posting illustrations on Instagram that reflected her feelings and struggles. She explored healing, expressing the shock, delusion, denial, self-pity, and self-doubt she experienced.
Her personal journey also inspired her newest book entitled I USED TO HAVE A PLAN. Featuring more than 75 illustrations, the book offers advice, inspiration, and encouragement for anyone who needs a shoulder to lean on during a difficult time (as in, probably all of us right now). And Alessandra openly touches upon the universal experiences of unexpected change and loss, the struggle to build oneself up again, and the evolution of pain as it moves toward healing.
As we enter a new year that is filled with all the myriad challenges 2020 created for us (and many more), this book is a nurturing read, which is something we could all do with.
Here, we speak to Alessandra about her new book.
You can also read her TALE here.
A series of events left you a divorced single mother questioning yourself, your relationships, and basically, everything you thought was true about her “picture-perfect” life - tell me about this time in your life?
When my marriage fell apart I was a mess. I didn’t see it coming. I had thought my relationship was solid and that we were happy, so when my partner confessed that not only was he not in love with me anymore, but he didn’t feel any love from me – it shook my confidence in everything I knew. How had I been so clueless? And if I had missed such a big one in my own marriage, what else was I glossing over in life? I became completely insecure in who I was and what I was doing with my life.
How did you build yourself up again? How did you heal?
I stopped everything. I just pushed pause. I stopped drinking. I stopped moving forward on a big project I was meant to launch. I just let myself off the hook. Some days I lay in bed and cried, if my work and my kid allowed it. And other days I surrounded myself with friends and family.
The healing began by being honest with myself and examining what was really happening. I dove into yoga and meditation and as predictable as that may sound, it was a positive, healthy outlet for me. But my true healer was my art. I started drawing my emotions and sharing them, and this process proved to be a cathartic release for me which then grew into a new creative path.
What is your advice to someone who is going through a divorce with children?
It can be really hard to set aside your own anger and hurt but try not to look at your ex as your enemy – rather the person that loves your kid as much as you do.
How has art changed your life?
It hasn’t changed my life necessarily, but art has allowed me to observe and process how I’m doing. My art and my life have evolved together.
In your new book, you touch on the universal experiences of unexpected change and loss - what did you learn about unexpected change and loss when you were working on the book?
When I set out to draw this book I was focusing on the breakup of my marriage, but during the book development my mother became terminally ill and passed away. That’s when the real loss showed up. What I learned was that difficult moments arise again and again, and part of life is navigating our ever undulating emotions.
When we last interviewed you, you said the book was going to be an illustrated tribute to letting go of what you thought was going to happen and embracing what actually is happening. Little did we know what was going to happen in 2020 - what has this year taught you?
People need people. From covid to the political state to racial and gender issues, we need each other and we need to be good to each other – it’s a hard business being human. 2020 has been an incredible reminder for me to take look at how I’m living and how I want to continue to live and contribute to the world around me.
How do you unwind?
I draw, I play music, I dance with my daughter, I cook, I stretch and I sing while playing terribly on my ukulele.
What has been the most challenging stage of motherhood for you and how have you overcome any challenges?
The hardest part was definitely when she was a newborn. I didn’t know what I was doing and I found myself feeling like a failure all of the time. I had to remind myself that she didn’t come with a handbook, that no matter how much you read online (and god knows I scoured the internet), every baby is different and it takes time to figure it out – you’re doing ok, mom.