Alright – so today we’ve got the honor of introducing you to Jackie Bookstein. We think you’ll enjoy our conversation, we’ve shared it below.
Hi Jackie, thanks for joining us today. Can you open up about a risk you’ve taken – what it was like taking that risk, why you took the risk and how it turned out?
Opening an improv theater is definitely the biggest risk I’ve ever taken. I have worked and played in the improv space for many years, but it was always something I did on the side. I had been working on this project, starting Mockingbird Improv for a while in my spare time, but it got to a point where I either had to go at it 100% or leave it behind. I took a road trip up the coast to Portland with my sibling (we took the coastal route because of storms) and it was about 25 hours of beautiful scenery that sunk the message home: life is precious and beautiful and if something lights up your heart you should do it as much as you can. I got back to San Diego and put in my notice at my full-time job and dove in 100%. That moment was exhilarating and exciting, but the moment I think the RISK part of it really sunk in was when I was at a family member’s wedding and every person I met asked the traditional question “what do you do?”. Saying over and over again that I run an improv theater to a ballroom full of doctors, lawyers, and successful businessmen and seeing their raised eyebrows as they tried to figure out how to respond was when I really knew that my life was now officially RISKY.

Jackie, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?
I started learning improv as a teenager and it instantly began to change my life, making me bolder, more authentic and present in the world. I was a very shy kid. I continued it in college as a means of social connection, stress reliever, and life energizer. College is hard and having a space to play once a week was a life line. I continued pursuing it as a hobby for years. performing and then helping facilitate groups, and then teaching. It slowly dawned on me that nothing made me feel more alive and valuable to the world than sharing play, connection, and flow with others, as a scene partner or a teacher.
Mockingbird improv has two inter connected goals: 1. to share the craft with as many folks as possible and give them a change to play, connect with their own creativity, and grow as humans. And 2. to produce high quality improv performances that really shows off the skill of improv, the magic that happens when people are creating spontaneously and listening and being present with each other authentically. We accomplish this through classes for all ages and experience levels from kids to adults and beginners to experts and through shows that are carefully crafted and honed and always striving for better. In both our education and performance aspects we aim to lower entry-way barriers by offering affordable pricing, scholarships, work study programs and more. We want everyone to be able to benefit from the joy we are cultivating here!
In your view, what can society to do to best support artists, creatives and a thriving creative ecosystem?
Support local. We have big hubs of art like LA, New York, and San Francisco, but these places only exist because of smaller local art scenes.

What do you think is the goal or mission that drives your creative journey?
Selfishly, I want to heal myself. Selflessly, I want to help others heal and cultivate joy.
Contact Info:
- Website: https://www.mockingbirdimprov.org/
- Instagram: https://www.instagram.com/mockingbirdimprov/?hl=en
- Facebook: https://www.facebook.com/MockingbirdImprov
- Yelp: https://www.yelp.com/biz/mockingbird-improv-san-diego

