by Jamal Winchester
Dedication
To the ones who feel the pull to create, to trust themselves again, and to remember that freedom isn’t earned — it’s remembered.
Initially, this short book didn’t have an “About Me” section. But a colleague suggested it might help you see how I’ve applied these same ideas to transform my own life.
I like to think of my journey as moving from System Errors to Self-Mastery—though take the “mastery” part with a pinch of salt. We’re always in motion, always learning new levels of it.
Looking back, I see how much the traditional education system chipped away at my confidence. It trained me to doubt my creative instincts. I was afraid to be wrong, so I memorized other people’s ideas—other people’s truths. That’s one of the system’s great injustices: it teaches dependence, not independence.
I began playing piano at eleven and never stopped. I practiced for hours, performed at school assemblies, and accompanied my church choir every weekend. Those moments built not only skill but also confidence. Singing and playing terrified me at first—but eventually, it became my favorite form of expression.
Still, like many middle-class kids, I followed the “safe” route: get the degree, land the high-paying job, build the life. I graduated top of my class at UWI with a Computing degree and quickly joined the financial-services world. By thirty, I owned a car and a house.
It looked like success.
But I felt trapped in what I now call default mode.
Instead of life unfolding, I was fighting to keep everything afloat—the mortgage, the job, the image. My manager once called it the golden handshake. I called it a golden cage.
Music became my escape. In IT, everything is binary—right or wrong. In music, everything breathes. It’s not about finding the right solution; it’s about being it.
I’d already been performing at church for years, so I knew what it felt like to earn from joy. That kind of money feels different—it feels alive. It’s fun money. And that realization changed everything.
I started visualizing myself performing more—singing, creating, expressing, earning—and slowly, that vision became real. I began booking higher-paying gigs at weddings and funerals, performing at elegant restaurants, and collaborating with incredible musicians. My confidence grew, and so did my income.
Some of my favorite performances so far include: