Life & Work with Cara Leoni of Boulder, Colorado

Today we’d like to introduce you to Cara Leoni

Hi Cara, so excited to have you on the platform. So before we get into questions about your work-life, maybe you can bring our readers up to speed on your story and how you got to where you are today?
I grew up in the Northwest Suburbs of Chicago, in a little town called Wauconda, Illinois (I know, Wauconda Forever). I moved to Colorado in 2012 to attend University of Northern Colorado in Greeley before I bounced around on the front range for a couple of years. Landed in Boulder in 2018 and been there since. My little sister moved in with me in 2022, which was exciting, we are the only two people in our extended family to migrate from the burbs of Chicago.

When I was in college I knew I wanted to try stand up comedy but I had never been on a stage before… and that felt like way too much to overcome. In 2014, I started keeping a small pocket journal of silly stories I told friends that made them laugh or joke ideas that I had. Fast forward to Fall of 2023- I am reconnecting with an old friend who was taking a comedy class in Denver. We were riding our bikes in Boulder one day and landed at Vision Quest’s Open Mic accidentally! After watching 3 people go up and get 0 laughs I thought to myself “I can get up there and bomb!” 3 weeks later I got on that stage and went for it. Now I go to 3-5 open mics every week.

Alright, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
I think some of my biggest personal stem from being a queer child and knowing I was different but not quite having the words for that. I grew up in a small town. Coming out wasn’t my choice; I confided in a friend who didn’t keep my secret. It was hard, just starting to understand what gay and bi and lesbian meant, what sexuality was and simultaneously having to defend myself as if I ware the poster child of a movement at 13 years old.

I bore the weight of depression and anxiety, both born from the extreme social isolation I endured at that time, far into my 20’s. As a freshly outed teen- I evolved a sense of humor because if I could laugh at the things that were intended to hurt me, that it would take away their power. I decided if people were going to treat me as ‘less than’ for being gay- that I was going to deploy my charming sense of humor and bring joy into rooms in spite of them. Long before I did comedy, I would be preparing for social situations by having a story of something insane that happened planned and ready to tell. Anything to keep people in a warm/ agreeable mood in my presence.

Once I started comedy one of the biggest hurdles was allowing myself to be vulnerable, to be seen and to be authentic in front of the mic. These old wounds around making myself digestible for others were in stark contrast with the evolving persona I had on stage. In discovering my voice, I also started to see myself in ways I had never before- it emboldened me in every area of my life.

Can you tell our readers more about what you do and what you think sets you apart from others?
Off the stage, I am a special education teacher this is my 8th year of teaching in public schools. I am proud of my role in the community, I believe that public schools are a backbone in equity of opportunity for families and their children. I specialize in supporting students that are experiencing difficulties-I believe that my greatest strength has been in meeting those students where they are at and showing them all the opportunities for their future that they may have not imagined.

In regards to comedy, entering that world was like stepping into a whirlwind. Suddenly I’m immersed in a fast-paced environment I never knew existed. Each area’s scene demands a different set of skills: mastering etiquette, understanding producer dynamics, and tailoring jokes to suit different audiences. Jokes that killed in Boulder might flop in Denver or Fort Collins. Am I admitting that I sometimes judge a book (room/audience) by its cover? Yes, guilty. But it’s more about gauging the vibes upon impact and meeting a crowd where they are at. I rarely have a set list figured out until I get to a venue and get a feel for the people there.

These past 1.5 years navigating the comedy scene have been transformative. Beyond honing my craft, I found my people. In Boulder, I quickly bonded with a group of fellow comics at a local mic. Suddenly, I wasn’t just the “ADHD queer friend”; I was part of a community where my quirks were not only accepted but valued as a strength. Surrounded by kindred spirits who share similar thinking patterns and life experiences, we’ve become each other’s cheerleaders, offering feedback, and riffing off each other’s ideas. Every conversation feels like potential podcast material or fodder for a silly reel.

In discovering true community and ever evolving my voice on stage, I’ve grown into someone who relishes taking up space. I am most ecstatic about getting opportunities to spread queer joy and getting to travel with my friends to new places to perform. Thus far, I am most proud of having the opportunity to Headline the Colorado Queer Comedy Festival last October!

The crisis has affected us all in different ways. How has it affected you and any important lessons or epiphanies you can share with us?
Covid 19 came in the wake of a break up for me. A relationship had ended that I thought never would, to say I was devastated would be an extreme understatement. It was my first big break up and now the whole world was shut down, literally. The lessons I learned during Covid were around my ability to fill my own cup. I know that Covid was traumatic and disastrous to so many, I know that I am fortunate to have had a season of personal growth at that time. I rediscovered my hobbies, which coincidentally were the same things I had loved as a child. Bike rides, shooting hoops, writing poetry, making art, and reading in the sunshine. The quiet that came with Covid was integral in my finding home inside my own body.

Contact Info:

• Instagram: https://www.instagram.com/laughing.leoni
• Facebook: https://www.facebook.com/cara.leoni/

Image Credits
Bryce Peterson
Aaron May
Katie McDonald
Jared Chandler