Minutes before DJ Ca$h Era hosted Lollapalooza's first drag show, the Black queer woman behind the stage name was pacing nervously behind the scenes and listening to a drag queen animatedly remind her they were "making history."
She knew she couldn't cry before taking the stage, so she "tapped into Ca$h" and focused on performing. Once she stepped off the stage and took her first deep breath, she was bawling.
"It was so overwhelming for so many reasons," the 26-year-old said. "For one, I think representation is very real. I'd never seen someone that remotely even looks like me play Lollapalooza. Someone who's a woman, who's Black, who's queer, who's very masculine in their queerness, take the stage at Lollapalooza. Who would've seen this shit coming?"
CaSera Heining, DJ Ca$h Era by night and a part-time WGN producer during the day, didn't predict her life would consist of curating music at various events then waking up in the morning to create radio segments.
A Chicago native, Heining was the first in her family to graduate from high school and attend university, where she studied radio with a minor in television but fell in love with DJ-ing during a required elective course.
"So much of my career still feels like an out-of-body experience," Heining said. "I never envisioned this for myself, so I just continue to struggle with taking limitations off myself and opening my mind."
After graduating college, Heining started working part-time at WGN, producing podcast segments in the early hours of the morning. For months, she'd finish DJ-ing around 3 a.m. Saturday night then pick up food, nap for an hour, and get into WGN by 5 a.m Sunday morning.
"A lot of people never saw that," Heining said. "Some people thought, 'Oh she's DJing tonight' and other people thought, 'she's coming into work this morning,' but they didn't think about the logistics of that, like that I hadn't slept all night."
Over time, Heining developed a certain persona for DJ Ca$h Era that propels her forward when she comes up against performance anxiety, busy schedules and other obstacles. "Ca$h is like, that cool version of me I'd always envisioned for myself, like that older kid you look up to and think is so awesome."
Before most sets, Heining's hands still shake and she gets quiet until she's on stage. But then, she channels Ca$h, "who's out for revenge in the healthiest way possible." Ca$h lives in the moment and has less emotions. She's "the asshole CaSera can't be."
"When someone tells CaSera she can't do something because no one like her has ever done it before, she's quiet and she takes it," Heining said. "Ca$h is like, "Oh really? Well, then I'll show you some shit." That's where Ca$h came from."
Once the mic is in her hand, Heining said she feels like she has to "reiterate and prove" why she deserves to be there and how much work she did to make it there.
Heining doesn't plan anything ahead. She has playlists with her favorite decades of music and others named after Chicago neighborhoods. From these lists, she chooses songs based on her audience's engagement.
"A lot of times, I notice who's not dancing in the crowd and I focus on them," Heining said. "If I'm playing new music and you're not phased, then I'll play '90s music. If I switch to Britney Spears and your head got to bopping a bit, first of all, shame on you. You should be singing Britney Spears, but at least I know I'm in the realm now."
After Heining's professor helped her book her first few events while she was still a studentDJ-ing poetry slams on her college campus hosted by Louder Than A BombHeining's mother pushed her to think more strategically about her hobby.
Heining's mother encouraged her to purchase equipment with a credit card then pay off the debt by DJ-ing various events. She gave her advice about getting business cards, a stage name, a logo, and helped her to build her brand from the ground up.
"My mom really played an integral part in helping me get everything together," Heining said. "I never thought DJing would become a full-time job ever, and I don't think my mom did either, but she would just drop subtle hints. She never pushed anything. She's always just said, 'Find something that you like and do it, whatever you want to do, do it.' She's majorly supportive in that way."
In both her careers, Heining said she "sticks out" and is often the only Black, queer woman in the rooms she walks into. She said she feels "honored to be a focal point for some people," but hates being "put on a pedestal."
"My biggest thing is that I want to see more people like me go even further than me," Heining said.
Heining said she usually doesn't think about her identity until it's brought up to her, but "it hits hard" whenever she has a moment with someone who tells her that her visibility means a lot to them or helps them feel represented.
"I've always looked at it as, this is me, this is who I am as a person," Heining said. "I joke about Ca$h and CaSera being separate people, but they are one person at the end of the day. I am CaSera, I am Ca$h, simultaneously, always and forever. I've been gay, been Black, been woman, been masculine all of my life. At this point, I'm not changing for anyone."