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Check Out Jesse Greenfield’s Story

Today we’d like to introduce you to Jesse Greenfield.

Jesse, we appreciate you taking the time to share your story with us today. Where does your story begin?
I’ve always been obsessed with possibility, with openness, with playing, with living and being available to the now. Being on the improv at Scripps Ranch High School was fun and silly, and being on the improv team at Tufts University was everything to me. Building worlds in the basement of the performance arts building for 8 hours a week with 7 of my closest friends taught me what time travel and true love really felt like. I felt my ability to take whatever life threw at me expanding, and I was a more confident communicator- not as terrified to be vulnerable. And it was FUN, like “beaming on the walk back to my dorm room after rehearsal ended at midnight and again in the morning right when I woke up” kind of fun.

I’d been working in health communication since I finished a public health masters degree in 2020 (yikes). I held and witnessed so many feelings- fear, frustration, relief, etc.- and held and witnessed my colleagues struggling with how to communicate hard and emotional things to members of their community. “Yes I can tell you what’s inside the vaccine, but what do I do/say when this person is coming at me crying after losing a loved one and is unsure of how to protect herself?” There was clearly a gap in training that was causing suffering. At the time, I knew that my dream job probably didn’t exist yet, (I think it still doesn’t!) and I’d have to create it. I knew how much the practice of improv built my confidence and ability to connect and communicate, and imagined it could be immensely supportive to others, especially during the isolation and confusion of the pandemic. As soon as I heard the term “Applied Improv,” which is using improv games to develop skills relevant to life/work/etc. instead of to perform on stage, I started to research obsessively and apply to teach these kinds of workshops wherever I could in the public health domain.

After a couple years of doing that on the side of my full time job, my best friend/soulmate/love of my life, Sabrina, died in an accident. Everything about the world inverted and blurred. There was no possible way I was going back to a desk job to sit in front of my computer when I knew I felt most alive, joyful, and magical doing this play-work of applied improv. Sitting on the jouch (jean couch) in my living room with my bestie, Jenie, I knew that’s what I wanted to do, but was heavy with grief and not wanting to do it alone. They said something along the lines of, “I’ve always wanted to start a business, but just needed a cause to believe in.” A few weeks later, Jenie had registered us to be an LLC, Kaleidoscope Training Center (the name came to them in a dream). That was November of 2023. With Jenie running the business side of things and me planning and teaching the workshops, we’ve been working with organizations all over the country to help them play their way to healthier communication and relationships as well as hosting workshops open to our community here in San Diego at least monthly.

We all face challenges, but looking back would you describe it as a relatively smooth road?
The path that we’re moving on feels like a spiral- it’s not always moving forward, and the way forward often looks different than what we might have imagined. My 12 years of improv training really helps with that, actually! One of the core principles of improv is adaptability and being ready to change course when needed. Things that might first appear as mistakes/failures are great opportunities to get creative. I’m not new to teaching improv, but we are new to running a business, and there is so much to learn.

One of our constant struggles is in describing this work (let me know how I do by the end of this interview!). How do you describe the magic that happens when someone has an epiphany about their relationship with their wife and starts to cry while playing the role of the creme filling of an Oreo? Most people I’ve talked to haven’t heard of applied improv before, and finding the words to capture the essence of this dynamic, ever-changing thing can be difficult. Honestly, I was expecting more pushback for the work; I wasn’t sure how open conferences full of medical professionals, for example, would be to trainings based on play, but people are hungry for it, for connection.

The other main challenge in the infancy of our business is making the time to do the work while having multiple other jobs so we can keep living and loving in our beautiful and pricey city of San Diego. As people with chronic pain/illnesses and in my immense grief, we have to be human first and understand our time and energy to be our most precious resources. The more we are honest about our values and what we are able to do with the time we have, the more we find people who share those values of collective care, compassion, and mutual support. It was a bit slow to start, to advocate for learning through play, and we are still growing and changing. We are in no rush- we know that our garden, just like improv, has to grow at the speed of life and the speed of trust. We are just now seeing the sprouts of trees we planted that will take time to grow roots and layers of thick trunk, and will hopefully be around and fruiting for a long time.

Appreciate you sharing that. What else should we know about what you do?
I teach workshops using applied improvisation, where we play improv games not with the intention to get on stage, but to learn, grow, connect, and for the sake of play itself. I don’t know of anyone doing something quite like this in our city. (If you are, let me know! I’d love to work together!) It’s a beautiful set up to practice deeply important interpersonal (with each other) and intrapersonal (within ourselves) skills in a low-stakes, supportive environment. Even though I did sit in communication classes in school where I was told on a PowerPoint slide to “be a good listener,” my classmates and I would often reflect that we didn’t know what good listening really meant/looked like/felt like. Getting to actually practice doing that in a way where you can step outside of yourself and play as a wise frog, for example, and then hear how your listening landed on the person you were playing with is an experience that can feel way more meaningful and embodied than words on a slide.

The games we play together are delightful, of course, but the real magic of these workshops is in the conversations afterwards, where we talk about what happened and how we will apply what we’ve learned to our lives outside of the session. Sharing about our embodied experiences and hearing from others about theirs is a powerful reflective tool, as well as a chance for people to celebrate each other. It is a gift to see and be seen in our vulnerability.

Kaleidoscope Training Center is a queer-owned, accessibility-focused, anti-capitalist organization that is working to make this play-learning available to all who are interested. We want to be a meaningful and integral part of the San Diego community, and it’s important to us that our offerings are sliding-scale (for organizations who are booking us as well as for community events). We are also highly interested in bartering/trading, knowing that each of us has valuable offerings to share with each other, and that it takes way more than money to have a flourishing community. A friend paid for a recent community workshop with citrus and avocados from their garden, and I have never felt more nourished.

Because the nature of this play-work is very flexible, I am able to apply it almost anywhere. We’ve been hired by medical schools, queer camping festivals, museums, and organizations supporting foster parents, to vaguely name a few of our clients from the past month. We teach frequent community workshops, like “Embodied Play,” “Improv for Creativity,” and “Giggles for Grief” (May 13 6-7:30pm at the Bravo Family Mortuary). I am so inspired by my loved ones, community, mentors, and the world around me to co-create new offerings that seem needed, interesting, and/or super fun.

We love surprises, fun facts and unexpected stories. Is there something you can share that might surprise us?
Shhh! Come closer!

Only my dearest friends and family know that I am a time traveler from the future and the past that wears luxurious silk robes and lives inside a lavender flower.

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