August 27, 2017

Pride, Work and Necessity of Side Projects: CEO Claire Lew Complements the Art of Leading a Business with the Art of Painting



What are you working on—on the side?

I spend my days as the CEO of Know Your Company, a software company that helps business owners overcome growing pains. We help 15,000+ employees at companies, like Airbnb and Kickstarter, build more open, honest workplace environments.

On the side, I love to paint. I typically paint with acrylics, but lately have been focused using oil on canvas. You can view my paintings on my personal site.

I grew up painting and drawing—thanks to my mother who is an artist and designer. I feel insanely lucky that she exposed me to creating things with my hands. Almost every day we were doing some sort of art project: making models of clay, doodling with markers, glueing masks, cutting out prints, you name it.

To this day, that exposure to art has affected the way I think and see things: space, color, light and perspective matter to me, because of it. I can tell art influences the choices I’ve made in running our software company, Know Your Company—whether it’s in how I design our powerpoint slides for my talks, or the design choices we make within the software itself. In fact, I illustrate all of our blog post images myself.

How do you manage to work
on your side project(s)?

Whenever I’m in the mood for some alone time, I paint. This often happens on a Friday or Saturday night. Sometimes, I’ll do it on a weeknight. I’m an introvert, so alone time is key for me to feel recharged ツ

I try not to pressure myself to produce a certain number of pieces or finish something by a certain date. Running and growing a software company is hard and stressful enough, at times. So I try hard to make sure my painting never feels that way.

That’s the beauty of a side project: It’s supposed to be fun. Nothing more.

Why have a side project?

Painting is very much “therapy” to me. I try to paint whatever it is swirling in my mind or I’m feeling at the time. It is my way to give my emotions or thoughts a visual, physical manifestation of what they might be. The same way journaling or writing can help a person think through something more clearly, I see painting as being very similar.

Especially, being in front of a computer screen for 8 hours a day, if not more…I crave doing something physical with my hands, away from anything involved with technology.

Painting is also one of the few things I do for myself. It’s sole purpose is to make me feel good, and no one else. I think I have a tendency to want to give, give, give…which is a good thing! But it can wear you thin. Painting is one way I make sure I’m still giving something to myself.

• • •

Diptych courtesy of Claire Lew.

• • •

Read more about the joy of side projects.


This series, devoted to side projects, is delivered in association with Chicago creative agency 50,000feet—dedicated to helping brands and businesses soar.


Please consider supporting Design Feast
If you liked this lovingly-made interview, show your appreciation by helping to support my labor of love—Design Feast, which proudly includes this blog. Learn more.