I Went From Street Hacker to Prison Inmate—Mentors Inside Prison Helped Me Build a Legal Tech Career

At 2:07 a.m., Pollsmoor roared like an animal, and the letter in my hands could get me stabbed before sunrise. A job offer sat in my lap like contraband. Meanwhile, footsteps crept closer down the corridor, slow and confident, as if they already knew what hope looks like in Cell 24, Section B, tonight too.

Metal gates clanged. Someone argued in the passage, then went quiet, the way men do when a blade appears. I circled back to the first line, willing my eyes to focus.

"Sipho Jacobs, we are prepared to employ you as a junior compliance developer upon your release."

A job. A salary. A chance to step outside without looking over my shoulder.

But good news in prison attracts predators. A gang runner named Vuyo had clocked me attending the coding sessions. He called it "acting clever". He said clever boys get humbled. The last guy who tried to keep to himself left the clinic with stitches and a warning he never spoke about again.

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Footsteps stopped at my door.

"Jacobs," a warder barked. "Yard."

I folded the letter and slid it under my mattress, fast and neat, like hiding a weapon. In the corridor, Vuyo watched me and smiled, as if he could smell the future I was trying to claim.

I walked towards the yard with calm on my face and panic in my bones, praying I would live long enough to deserve that letter. I promised myself I would not waste this chance.

I grew up in Mitchells Plain on the Cape Flats, where the wind carried sand into your mouth and danger into your choices. My mother, Nomsa, cleaned offices in Claremont during the day and scrubbed private homes in Rondebosch on weekends. She came home smelling of bleach and fatigue, yet she still checked my homework as it mattered.

My father left when I was eight, and the house never felt whole again. He did not slam doors or throw punches. He quietly stopped coming back. His silence trained me to expect abandonment without explanation, and it oriented my mother to survive without asking anyone for help.

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The men around us filled the gap with bad examples.

Uncles sat on corners, unemployed, drinking cheap beer and arguing about respect. Boys my age joined gangs for protection and status. Teachers warned us not to "waste our lives", but nobody showed us what a life could look like.

School felt like a crowded warehouse. Classrooms overflowed. Textbooks were older than we were. Computers existed, but half the keys did not work. When I asked questions, overworked teachers rushed through answers, as if curiosity was another burden.

Still, I loved electronics. I collected broken phones and cracked tablets from neighbours' bins. I sat on our floor at night with a screwdriver and a torch, taking things apart and learning how pieces fit. When something powered on again, even with a dim screen, I felt like I had proved I was not trapped.

I taught myself from public library computers and whatever tutorials I managed to open before the Wi-Fi cut out mid-sentence.

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YouTube became my teacher. It also became my temptation. I watched people talk about hacking, security, and "systems" as if they were puzzles. Nobody sat beside me to draw a clear line between understanding and exploiting.

In my street, money came fastest from risky moves. I began to believe being savvy meant finding shortcuts. I told myself I was not hurting anyone. I was only outsmarting faceless machines, only making a plan like everyone else.

That story felt safer than admitting the truth. I was scared of staying poor forever. I wanted control over life.

Once I reached twenty-one, people stopped calling me Sipho. They called me "Ghost" because I moved quietly and made money without appearing to lift a hand. I bought groceries for my mother and paid the electricity bill. I fixed neighbours' phones for free to earn goodwill, then took cash from strangers who never asked questions.

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I walked like a man with options.

But I lived like a man on the run.

Every siren tightened my chest. Every unknown number made my stomach sink. Respect in my neighbourhood was never a gift. It was a loan with brutal interest, and the collectors always arrived.

My friend Keenan found me near a spaza shop in Delft, grinning like trouble was a party.

"We've got a big move," he said. "Quick money. Clean."

I hesitated. "We said we'd slow down."

He laughed. "Slow down for what? You want to live on coins forever?"

Coins were my mother's life. Coins were the reason she limped after work. So I nodded, even while my instincts screamed that I was running out of luck.

The operation went wrong. I refuse to describe it, because I will not teach the road that wrecked me. What matters is the moment I realised I was not a mastermind. I was a scared boy playing with fire in a township full of petrol.

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Blue lights cut the street.

Someone shouted, "Run!"

I ran. I jumped a wall and cut through an alley. My lungs burned, and my legs turned heavy. I thought I could still vanish and live up to my nickname.

A hand grabbed my shoulder and slammed me down.

My cheek hit tar. Dust filled my mouth. Cuffs snapped shut on my wrists, and an officer said, almost amused, "So you're the clever one."

At the station in Athlone, they took my belt, my laces, my phone, and my pride. I sat on a plastic bench with my hands shaking, pretending I still had control.

I did not.

My mother arrived hours later in her cleaning uniform. Her face looked older than it should. She gripped my arm like she could pull me back into childhood.

"Sipho," she whispered. "Why?"

I wanted to say poverty is loud. I wanted to say nobody showed me another road. Instead, I stared at the floor and said, "I'm sorry, Ma."

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The court moved fast. Shame moved faster.

When they sentenced me, the judge's voice sounded far away. But the handcuffs were real, and Pollsmoor was waiting.

The cell stank of sweat and old urine. Men watched me the way dogs watch meat dangling just out of reach. A tattooed man leaned close and asked, "Which side are you with, Ghost?"

"I'm not with anyone," I said.

He smiled. "Everyone's with someone."

Survival demanded choices I hated. If you acted soft, people tested you. If you worked hard, they recruited you. I learned to move carefully, speak less, and sleep with one ear open.

Weeks later, I saw Keenan in the yard, thinner but still arrogant.

"Ghost!" he shouted. "We'll be out soon, bru. Back to business!"

My chest tightened: back to business meant back to cages, even if the bars were invisible.

I started avoiding him. Avoidance made him suspicious. Suspicion made him dangerous. His crew watched me when I walked past, whispering as I owed them loyalty.

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Some nights, I heard screams and prayed my name would not be next again.

Then I saw a poster near the library: Coding and Cybersecurity Mentorship Programme.

It sounded ridiculous in a place built to break people, but I wrote my name down anyway.

I expected prison to finish what the streets started. I expected to come out harder, colder, more dangerous. Instead, the mentorship room became the first place where adults stayed long enough to teach me anything.

The man who ran the programme introduced himself as Mr Naidoo. He spoke calmly, as though calm was his craft.

"I did time here," he said. "I work in tech compliance now."

I stared at him. "How?"

He held my gaze. "I stopped lying to myself."

That was the twist. I had built my whole identity on a lie. I told myself I was clever, not criminal. I told myself I was providing, not harming. I told myself systems had no faces.

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Mr Naidoo refused to admire my shortcuts. He demanded clean work. He made me document every step, explain every decision, and take responsibility for every error.

A volunteer named Thando Maseko brought lessons on cybersecurity ethics and software safety. She spoke about hospitals, schools, and legal clinics that needed protection, not exploitation. She said, "If you can break things, you can also secure them. The skill is neutral. The choice is not."

Those words rearranged something inside me.

I started building a portfolio of legal projects, small tools that organised case notes, controlled access, and flagged risks. I wrote reports like a professional, not a hustler. When I finished an assignment, I felt a kind of pride that did not come with fear.

One afternoon, Mr Naidoo slid a printed email across the table.

"You're ready to be seen," he said. "Not as Ghost. As Sipho."

The email came from a civic tech NGO in Salt River that supported youth after release. They offered mentorship, a laptop grant, and interview coaching if my parole was approved.

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I should have felt relieved.

Instead, I felt exposed.

Because I realised the danger was never my past. It was pretending I could outrun it. If I hid my weaknesses, they would grow in the dark. If I named them, I could manage them.

For the first time, I stopped dreaming about escape.

I started planning a life.

I left Pollsmoor at twenty-four with a plastic bag of clothes and a new rule: I would not negotiate with the life that almost buried me. Cape Town looked the same, but I felt different inside my own skin. The taxi ranks still shouted. The Flats still waited with familiar corners and familiar offers.

My mother hugged me outside the gate, eyes wet, shoulders tense.

"Come home," she said. "Please."

"I will," I replied, "but I'm not coming back to the same life."

The first test arrived fast.

Keenan found me near our block in Mitchells Plain three days later. He leaned against a wall as if he owned the street and smiled as if nothing had happened.

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"Ghost is out," he said. "Let's eat. I've got something lined up."

I kept my voice steady. "Don't call me that."

He laughed. "You're still you, bru."

"No," I said. "I'm choosing different."

His smile dropped. "Different doesn't pay."

"It pays slower," I answered, "but it pays without handcuffs."

He stepped closer, anger warming his eyes. "You think those people in town will trust you?"

I swallowed, then spoke the boundary out loud, so my body could hear it too. "If you bring me work like that again, I will walk away. Every time."

Keenan spat on the ground and muttered, "You'll come back."

I did not argue. I went inside and locked the door. My hands shook, but my feet had moved in the right direction.

I treated my new life like recovery. I woke early. I travelled to Woodstock for training sessions. I met Mr Naidoo at a community centre in Salt River twice a week, where he checked my progress and my honesty. I kept my phone clean, my circle small, my days structured.

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Through the NGO, I interviewed with a legal aid organisation in the city centre. They needed someone to help secure client records, digitise intake forms, and build simple tools that stopped data from leaking. The work felt quiet, but it mattered. The people walking into that office carried fear I recognised.

When I received my first payslip, I bought groceries for my mother again, but this time my money did not smell like panic. She looked at the receipt and whispered, "Thank you, my boy," as she could finally unclench her whole life.

That was my karma.

Not wealth. Not fame.

Peace I could keep, finally.

People love neat stories about bad boys turning good, as if prison flips a switch. My change looked like repetition. It looked like choosing the slower option each morning, saying no when my stomach wanted quick money, and my pride wanted quick respect.

I did not become dangerous because I lacked talent. I became dangerous because I had talent with no direction. In the Cape Flats, survival lessons arrive early, and guidance arrives late. When nobody teaches you how to build, you learn how to take.

Inside Pollsmoor, where I expected to lose myself, I met mentors who refused to let me hide behind excuses. Mr Naidoo demanded accountability. Thando demanded empathy. The NGO demanded structure. They treated me like a man who could choose his own path out of chaos.

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I still carry my past in my body, etched into muscle and bone. Sirens still tighten my chest sometimes.

I still scan rooms for danger. But now I build safeguards the way I once engineered trouble. I keep routines. I ask for help. I walk away before temptation becomes a decision.

Legal work did not erase my record, but it gave me the dignity to keep moving forward. Each time I protected a client's file, I repaired a small piece of harm. Each honest payslip told my mother she had made more than a mistake.

The lesson I live by is simple: skills are neutral, but choices are not. If you want a different life, you need more than willpower. You need guidance, structure, and a boundary that does not bend when fear speaks.

So, at last comes my question for anyone who feels trapped in a story that keeps repeating like a loop you can't escape.

When the fastest road leads back to a cage, will you keep running because it is familiar, or will you stop, ask for guidance, and choose the more challenging path that finally lets you breathe?

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This story is inspired by the real experiences of our readers. We believe that every story carries a lesson that can bring light to others. To protect everyone's privacy, our editors may change names, locations, and certain details while keeping the heart of the story true. Images are for illustration only. If you'd like to share your own experience, please contact us via email.

Source: Briefly News