From the Stage to the Classroom
- 3 minutes ago
- 5 min read
Kay Cheytanov on purpose, pain, and the years nobody sees
There was a moment in a car that changed everything. No audience. No spotlight. Just exhaustion, a radio playing in the background, and the quiet realisation that something wasn't right.
At the time, Kay Cheytanov had what many would call a music career. A band. A life built around performance. But something in that life was no longer aligned, and she knew it.
She was touring the country, singing in clubs and pubs. And she was miserable. Exhausted, disillusioned, deeply unfulfilled. By day, she worked as an IT consultant. By night, she came home to a house full of musicians lying on couches, playing guitar. She was carrying everything.
She made the decision to walk away from the band and start again, alone.
Within a year, she had a No. 2 hit single. Solo. On her own terms. One month after giving birth to her son Dylan.
May 2002. A chart position and a newborn in the same breath. It was the kind of moment that should have felt like arrival.
Instead, it became the beginning of a longer, quieter question.
Because what Kay realised wasn't that she needed a new career. She needed a different kind of purpose.
The Idea That Started with a Rock Band and a Baby
The concept was bold from the start: perform at schools for free but bring colleges and career information along, creating a self-sustaining model that served students while generating revenue through educational partners.
The first 25 schools were done with her full band, Fly. "In hindsight, a terrible idea," she laughs. "Principals definitely don't want a full rock band in their hall."
But something significant happened on that first tour. Kay fell pregnant with her son, Dylan. "When I got back to Johannesburg, everything shifted. I had left my consulting job, and now I didn't have the luxury of figuring it out slowly. I had to make it work."
She went solo, found a producer, and released her first album as KayVee. The following year, she was back on the road, pregnant, with a No. 2 hit, Time, on Five FM.
"But this time it felt different. I wasn't chasing a dream anymore. I was building one."
And Then Life Added Pressure She Couldn't Ignore
Dylan arrived at 34 weeks, weighing just 1.8kg. "Suddenly everything became very real," she says.
What followed was the kind of chapter that never makes the highlight reel. But it should.
Breastfeeding behind stage curtains at schools. Waking up in Bloemfontein to snow and leaving her baby behind because she was too scared to take him out into the cold.
Celebrating his first birthday in Cape Town, just four people on the road, no family, no party.
"I remember sitting on his second birthday feeling completely overwhelmed with guilt. I wanted to be present. But I was always building. Chasing something that hadn't paid off yet."
A messy divorce added to the weight of it all. The business was surviving, barely.
This is the part of the story most people never see. Not the success. Not the impact. But the years where nothing is guaranteed, and everything costs something.
"The first five years were incredibly hard on all fronts: emotionally, financially, physically. But what I didn't realise at the time was that I wasn't choosing between being a mother and building a business. I was becoming both, in a very real, very imperfect way."
The turning point came in 2006, when her husband Lubo entered her life. "Up until then, it felt like I was carrying the weight of everything on my own. He brought stability, perspective, and a sense that I didn't have to fight every battle alone."
The Night That Changed Everything
If 3RC was born from an idea, the High 5 Wellness Show was born from a wound.
In early 2020, Kay moved her daughter from a small, nurturing school to a new one closer to home. It made logistical sense. Then lockdown happened. When things reopened, her daughter returned to an environment where she had never had the chance to belong.
"Things became more difficult when she moved into the high school environment," Kay says carefully. "She was questioning her identity, including her sexuality, and instead of being met with understanding, she was met with rejection and cruelty."
For a while, it showed up as headaches and stomach cramps. Kay reassured her. Told her it would get better. Called her, her "strong girl."
"That's something I wish I could take back."
Because behind that strength, something was breaking. The bullying escalated until the night Kay's husband found their daughter on her bedroom floor in crisis. What followed was a long road to recovery, a diagnosis of PTSD and depressive psychosis, caused by the actions of other children.
"There are so many children sitting in classrooms every day carrying pain they don't have the words for. Not all of them have access to the support we were able to find. That thought terrified me. And it gave me purpose."
High 5 wasn't built from strategy. It was built from that moment. A school wellness programme designed to reach children before they reach breaking point, built around five pillars: Kindness, Safety, Resilience, Bravery, and Individuality. It now reaches over 55,000 students every year.
The One Thing She Still Struggles to Give Herself
Of those five pillars, Kay admits there is one she struggles to extend to herself.
"Kindness, without a doubt. I can be incredibly hard on myself, especially when I feel like I'm falling short as a mom, as a leader, as a business owner."
After 25 years at the helm of a company, her definition of wellness is not a morning routine or a productivity hack. "It's the ability to recognise when I'm running on empty and give myself permission to stop, even briefly. I listen to my body and my emotions sooner, not later."
The rockstar hasn't disappeared entirely. Music remains a private anchor. "There's something about music that allows emotions to move. To connect with things, you can't always say out loud." She channels that creative energy into the shows themselves, the storytelling, the way her team engages with students. "It's still performance. Just with a different purpose."
What She Wants You to Know
For the woman reading this, holding more than she shows, questioning whether she's getting it right, Kay's message is simple.
You are not failing. Even on the days it feels like everything is slipping, showing up still counts. Building something, raising a family, holding it all together in ways no one sees, that counts. Because the truth is, there is no perfect way to do this. There is only your way. And that has always been enough. |
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