I Used to Have a Plan

INterview By Daniela Jung
February 21, 2021

Alessandra Olanow

Photograph by: Jessica Antola

If the name Alessandra Olanow rings a bell, chances are, you have probably come across her poignant illustrations on social media.

The Brooklyn-based artist, who has worked with a variety of clients such as Urban Outfitters, Wall Street Journal, Oprah Magazine, Vogue and Uniqlo among others, first started sharing her illustrations as a coping mechanism after her ‘picture perfect life’ fell apart, and she hit the proverbial “rock bottom”.

Cue to 2020, when the world was suddenly brought to an abrupt halt. Most of us confined to our homes for weeks, that turned into months, making pandemic Instagram-scrolling a veritable way to connect to the outside world.

Alessandra’s poignant, witty and super vulnerable daily musings hit a collective nerve, and started to be shared widely by thousands, amassing a huge following seemingly overnight.  

The Sun Came Up Today

In a time where many of us have a love/hate relationship with social media, finding solace in her simple, yet profound daily reflections on getting through this ‘thing called life’ - maintaining routines, and questioning the “WHAT NOW” - felt like mini doses of daily therapy.

We chat with the single mom about her reluctant Instagram “fame”, her minor obsession with coffee, and the publishing of her first book “I used to have a plan”.  

I Used to Have a Plan Book Cover

Was illustration always your favorite go-to medium?
Yes, I’ve been drawing since I can remember. It’s something that comes naturally to me, and I love that all I need is my paper and pencil. I can be comfortable almost anywhere as long as I can sit in a corner and draw.

When did you first start sharing your work on Instagram and was the intention to post daily, or did this just happen organically?
I guess I was a bit of a latecomer to Instagram. At first, I mostly posted cute pictures of my family and me. It wasn’t until my marriage fell apart that I shifted focus and started drawing my feelings. Organically, I began sharing every day because it became an emotional purge, and now it has developed into a creative habit.

Your book is called “I used to have a plan” with a drawing of you face-down lying on the floor. Coming out of 2020, to say this resonates, would be an understatement. Does it make you smile, that so many people re-create the cover pic on Instagram?
I love it, it absolutely makes me smile. It’s my reminder that we are all figuring out how to make our way through this crazy life.

Reading your book, and scrolling through your posts, stirs up so many moments of complete relatability. Were you surprised that your personal struggles, and life experiences struck a chord with so many of your followers?
Not really. I know the ups and downs of life couldn’t possibly be unique to me. But it certainly feels good to connect with so many others and remind each other that it’s okay to not have it all figured out. We can ‘not have a plan’ together.

Some of my most favorite witty posts of yours, revolve around my number one beverage - coffee! Can we surmise that you have a special relationship with coffee? What’s your go-to coffee routine, and has it changed during the pandemic?
I love coffee, and making it, is my morning ritual. I treasure the process of making my cup the start of the day, where I pause from whatever’s going on in my head. It’s my little meditation. I grind the beans, boil the water and patiently wait as I brew my cup. The aroma gently wakes up my senses, and I ease myself into the day.

I personally love pour-over, but I’ve strayed here and there. Still I always come back!  

Neruda Poem

There is a lot of talk about self-care these days. What does self-care constitute for you? Do you have any rituals, besides your work, that you can share?
I am a massive proponent for self-care, it helps my mood and focus; and as a creative being, I rely on these qualities. I have a daily yoga practice, which I enjoy. If I have time, I will join a class online, but mostly I have my own routines that I flow through, and I can adjust depending on time constraints. Combining stretches with conscious breath just makes me feel better. 

I think I can circles

When it comes to your beauty routine, what is your fave beauty hack?
I like to keep things very simple when it comes to my beauty routine. As I’ve gotten older, I’ve really ditched most makeup to concentrate more on keeping my skin healthy. This means a gentle wash and occasional exfoliator, a nice Vitamin C serum, and a hydrating oil or cream for my face. This winter I’ve been loving Kat Burki’s super peptide firming creme

Super Peptide Firming Creme

Lastly, what are 5 things on your post-pandemic bucket list?

1. Dance party with all my friends, on a beach that we have to fly to.
2. Crawl into bed with my grandma and watch bad telenovelas.
3. Take a yoga class at Prema in Brooklyn.
4. Go to the movies and eat popcorn with raisinets.
5. Hang out in a coffee shop, draw and talk to strangers. 

Grow through what you go through