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Why I started SAINT KAY MEDIA (and why it’s named after a patron saint of sidekicks)

March 22, 2026

Welcome to the Gray Zone!

Founder of Saint Kay Media, mom of three sons, and someone who has never once taken the safe route. I write about the stuff your therapist charges you $200 an hour to say out loud.

Meet Kenda

The surgery or the check. That was the choice.

I was standing in a bank line seventeen years ago, phone pressed to my ear while my father, a chiropractor, explained that the numbness spreading through my pelvic girdle meant I had maybe hours before permanent damage. “Get to the ER. Now.”

I looked at the teller windows. The line wasn’t moving. I was holding a check that needed to be deposited before another one bounced. I was on welfare, in the middle of a divorce, with a baby, living in my mother’s basement, pouring everything I had into an organic skincare company that was somehow in Whole Foods and scaling internationally, while I could barely keep the lights on. There were no reserves. No safety net. That deposit was the only thing between me and another bounced check.

Check or spine. Money or body. Urgent or important.

My dad said there was no time.

I left the line.

The Myth of Arrival

The trajectory is supposed to go like this: struggle, breakthrough, arrival. You hit rock bottom, do the work, and emerge transformed. Cue the Instagram post with the sunset and the inspirational quote.

Except that’s not how it works.

I got the emergency surgery. The doctors told me I’d need a catheter forever, probably a colostomy bag. The night before my birthday, desperate to feel normal, I did what any rational 31-year-old would do. I went to YouTube. And lo and behold, there was a video showing me how to remove it myself with a syringe. So I did. My mother and my doctor were floored. They could not believe I would do such a thing. Clearly, they had misjudged my determination and blatant disregard for safety. What could go wrong? Only my kidneys, if I couldn’t pee. I spent years lying in bed talking to my body, begging it to work.

It took years. Not weeks. Not months. Years.

And I’m still managing it. Weekly colonics. Ongoing protocols. It didn’t end when I could pee again. It just continued.

That’s the pattern. Every time I thought I’d arrived, life handed me another choice.

Three years ago, I was finally in a place that looked like arrival. Financially successful. Assets, investments, a portfolio my husband and I built from nothing. Highly respected in my field. International business trips. A meeting with government leaders in Costa Rica the next morning. And then I got a call from my son’s school counselor. He was suicidal. I called my business partner, told him I wasn’t coming, and quit everything. Walked away from all of it. Because none of it mattered if my kid didn’t make it.

The Sidekick Thing

My best friend Georgia calls me Kay. Always has. She’s the kind of person whose energy is electric. People just want to be near her. I’m the one next to her saying, “Yes, and what else?” Hyping every idea, matching her energy, and being absolutely insufferable about it. I recently showed up unannounced at the senior bingo she goes to every week with her mother-in-law just to sit next to her. Life got busy. We hadn’t seen each other in a while. Sometimes showing up is the whole thing. I just wanted to see her face.

When I was naming this company, I Googled “Saint Kay” on a whim. Turns out he’s the patron saint of sidekicks in some obscure text called The Hidden Almanac.

Perfect.

What We Are All Doing Here

Nobody has it figured out. Not me. Not the therapist. Not the woman whose book is on your nightstand.

Even when things are good, they’re fragile. One kid gets sick. Your husband hits a wall. You miss four workouts and suddenly the whole system feels like it’s unraveling.

That’s why I built Saint Kay Media. Not because nobody is having the conversation. Because I had to. Because I watch Kylen, my cohost and family, get up every morning and try to figure out how to be a person in a world that gave him bad instructions. Honest conversation is part of what gets people through. So I built a place for it. Loud, imperfect, and on purpose.

Surgery or check. Costa Rica or son. Comfort or truth.

You just keep choosing.

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