After finishing primary school at H. A. Jack, I started grade eight at Sandringham High School. Even after apartheid, most black people still lived in the townships and the areas formerly designated as homelands, where the only available government schools were the broken remnants of the Bantu system. Wealthy white kids -- along with the few black people and colored people and Indians who had money or could get scholarships -- were holed up in private schools, which were super-expensive but virtually guaranteed entry into university. Sandringham was what we call a Model C school, which meant it was a mix of government and private, similar to charter schools in America. The place was huge, a thousand kids on sprawling grounds with tennis courts, sports fields, and a swimming pool.

Being a Model C school and not a government school, Sandringham drew kids from all over, making it a near-perfect microcosm of post-apartheid South Africa as a whole -- a perfect example of what South Africa has the potential to be. We had rich white kids, a bunch of middle-class white kids, and some working-class white kids. We had black kids who were newly rich, black kids who were middle-class, and black kids from the townships. We had colored kids and Indian kids, and even a handful of Chinese kids, too. The pupils were as integrated as they could be given that apartheid had just ended. At H. A. Jack, race was broken up into blocks. Sandringham was more like a spectrum.

South African schools don't have cafeterias. At Sandringham we'd buy our lunch at what we call the tuck shop, a little canteen, and then have free rein to go wherever we wanted on the school grounds to eat -- the quad, the courtyard, the playground, wherever. Kids would break off and cluster into their cliques and groups. People were still grouped by color in most cases, but you could see how they all blended and shaded into one another. The kids who played soccer were mostly black. The kids who played tennis were mostly white. The kids who played cricket were a mix. The Chinese kids would hang out next to the prefab buildings. The matrics, what South Africans call seniors, would hang out on the quad. The popular, pretty girls would hang out over here, and computer geeks would hang out over there. To the extent that the groupings were racial, it was because of the ways race overlapped class and geography out in the real world. Suburban kids hung out with suburban kids. Township kids hung out with township kids.

At break, as the only mixed kid out of a thousand, I faced the same predicament I had on the playground at H. A. Jack: Where was I supposed to go? Even with so many different groups to choose from, I wasn't a natural constituent of any particular one. I obviously wasn't Indian or Chinese. The colored kids would shit on me all the time for being too black. So I wasn't welcome there. As always, I was adept enough with white kids not to get bullied by them, but the white kids were always going shopping, going to the movies, going on trips -- things that required money. We didn't have any money, so I was out of the mix there, too. The group I felt the most affinity for was the poor black kids. I hung out with them and got along with them, but most of them took minibuses to school from way out in the townships, from Soweto, from Tembisa, from Alexandra. They rode to school as friends and went home as friends. They had their own groups. Weekends and school holidays, they were hanging out with one another and I couldn't visit. Soweto was a forty-minute drive from my house. We didn't have money for petrol. After school I was on my own. Weekends I was on my own. Ever the outsider, I created my own strange little world. I did it out of necessity. I needed a way to fit in. I also needed money, a way to buy the same snacks and do the things that the other kids were doing. Which is how I became the tuck-shop guy.

Thanks to my long walk to school, I was late every single day. I'd have to stop off in the prefect's office to write my name down for detention. I was the patron saint of detention. Already late, I'd run to join my morning classes -- math, English, biology, whatever. The last period before break was assembly. The pupils would come together in the assembly hall, each grade seated row by row, and the teachers and the prefects would get up onstage and go over the business of what was happening in the school -- announcements, awards, that sort of thing. The names of the kids with detention were announced at every assembly, and I was always one of them. Always. Every single day. It was a running joke. The prefect would say, "Detentions for today…" and I would stand up automatically. It was like the Oscars and I was Meryl Streep. There was one time I stood up and then the prefect named the five people and I wasn't one of them. Everyone burst out laughing. Somebody yelled out, "Where's Trevor?!" The prefect looked at the paper and shook his head. "Nope." The entire hall erupted with cheers and applause. "Yay!!!!"

Then, immediately after assembly, there would be a race to the tuck shop because the queue to buy food was so long. Every minute you spent in the queue was working against your break time. The sooner you got your food, the longer you had to eat, play a game of soccer, or hang out. Also, if you got there late, the best food was gone.

Two things were true about me at that age. One, I was still the fastest kid in school. And two, I had no pride. The second we were dismissed from assembly I would run like a bat out of hell to the tuck shop so I could be the first one there. I was always first in line. I became notorious for being that guy, so much so that people started coming up to me in line. "Hey, can you buy this for me?" Which would piss off the kids behind me because it was basically cutting the line. So people started approaching me during assembly. They'd say, "Hey, I've got ten rand. If you buy my food for me, I'll give you two." That's when I learned: time is money. I realized people would pay me to buy their food because I was willing to run for it. I started telling everyone at assembly, "Place your orders. Give me a list of what you want, give me a percentage of what you're going to spend, and I'll buy your food for you."

I was an overnight success. Fat guys were my number-one customers. They loved food, but couldn't run. I had all these rich, fat white kids who were like, "This is fantastic! My parents spoil me, I've got money, and now I've got a way I can get food without having to work for it -- and I still get my break." I had so many customers I was turning kids away. I had a rule: I would take five orders a day, high bidders only. I'd make so much that I could buy my lunch using other kids' money and keep the lunch money my mom gave me for pocket cash. Then I could afford to catch a bus home instead of walking or save up to buy whatever. Every day I'd take orders, assembly would end, and I'd make my mad dash and buy everybody's hot dogs and Cokes and muffins. If you paid me extra you could even tell me where you'd be and I'd deliver it to you.

I'd found my niche. Since I belonged to no group I learned to move seamlessly between groups. I floated. I was a chameleon, still, a cultural chameleon. I learned how to blend. I could play sports with the jocks. I could talk computers with the nerds. I could jump in the circle and dance with the township kids. I popped around to everyone, working, chatting, telling jokes, making deliveries.

I was like a weed dealer, but of food. The weed guy is always welcome at the party. He's not a part of the circle, but he's invited into the circle temporarily because of what he can offer. That's who I was. Always an outsider. As the outsider, you can retreat into a shell, be anonymous, be invisible. Or you can go the other way. You protect yourself by opening up. You don't ask to be accepted for everything you are, just the one part of yourself that you're willing to share. For me it was humor. I learned that even though I didn't belong to one group, I could be a part of any group that was laughing. I'd drop in, pass out the snacks, tell a few jokes. I'd perform for them. I'd catch a bit of their conversation, learn more about their group, and then leave. I never overstayed my welcome. I wasn't popular, but I wasn't an outcast. I was everywhere with everybody, and at the same time I was all by myself.

I don't regret anything I've ever done in life, any choice that I've made. But I'm consumed with regret for the things I didn't do, the choices I didn't make, the things I didn't say. We spend so much time being afraid of failure, afraid of rejection. But regret is the thing we should fear most. Failure is an answer. Rejection is an answer. Regret is an eternal question you will never have the answer to. "What if…" "If only…" "I wonder what would have…" You will never, never know, and it will haunt you for the rest of your days.

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