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Lost Diamonds: How our current system is failing underprivileged talent

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Second Chances

I might have given up on myself, but Mrs. Harris refused to give up on me. When she found out that I didn’t get into Head-Royce, she went to work on a back-up plan. Maybe she knew what really happened with the financial aid. Maybe she just believed in me that much. We tried to get into a better public middle school in the wealthy part of Oakland, but nothing came of our efforts. Undeterred, Mrs. Harris contacted and pushed to get me into the Heads Up summer program, which offered free classes at Head-Royce for underserved kids.

I remember sixth grade feeling like a lost year. I can’t remember any of the teachers’ names. I just have memories of the English teacher who the kids made cry and the substitute math teacher who yelled at me when I corrected him on how to do long division—never mind why a sixth grade classroom was being taught long division. But I had been given hope. During summer classes at Heads Up, I felt challenged academically for the first time ever and really started to love school. That newfound appreciation for education also rubbed off on my parents — they somehow saved up enough from their minimum wage jobs to pay for a math tutor whose house I went to twice a week that year. Mrs. Harris changed everything. I hope she’s reading this, since I don’t think I ever even said thank you. Thank you.

I applied again to Head-Royce, this time for seventh grade. We applied for financial aid as soon as it opened up and had several people check over the forms to make sure everything looked right. Thanks to the generosity of the Malone Family Foundation, I received a financial aid package that allowed me to attend Head-Royce. Head-Royce felt like paradise. Everyone there was smart and loved to learn. The coursework was actually challenging. I loved it. Even so, I never felt like I fit in. I never, ever told anyone about what had happened when I had previously applied to Head-Royce— it remained a huge, shameful, dirty secret. I don’t think I ever got over that feeling that I wasn’t good enough, though it certainly motivated to me to work my butt off. Years later at Stanford, where a large percentage of the student body receives some financial aid, I maintained that internalized feeling of not belonging in this world, of not being good enough. I never talked about it. Not at Head-Royce. Not at Stanford.

I never graduated from the Heads Up program. After enrolling at Head-Royce, I still spent my summers in Heads Up classes and attended the monthly meetings that continued through ninth grade, but I eventually stopped going. I remember Mr. McCoy and Mrs. Gee, who ran the program, being disappointed in me. As a high school freshman, I couldn’t quite explain to them why I dropped out of the program: I just didn’t want to be there anymore. Years later, I realized that it was because I was ashamed. Way back in fifth grade, Heads Up didn’t feel like an opportunity — it felt like a consolation prize for not actually getting to go to Head-Royce. I was very self-conscious going to Heads Up meetings after I enrolled at Head-Royce. I felt like an outsider when everyone talked about their schools, and I didn’t want to brag about how great actually going to Head-Royce was. I think part of me almost wanted to erase the fact that I was in Heads Up because I just wanted to fit in at Head-Royce. I remember making it a point to never mention to any of my classmates at Head-Royce that I was a “Heads Up kid” because I had once heard someone describe it as charity for poor public school kids.

Isn’t that crazy? Somehow, despite everything, I had been fortunate enough to be a part of the Heads Up program and then attend Head-Royce on a full scholarship from grades seven through twelve. But rather than talk about any of it, I tried to hide or forget everything— like Carlos, I tried my best to not remember any of these incidents. Out of shame, but also motivated by something else Gladwell points out: survival instinct. Once you see a way out, an opportunity for what he terms capitalization, the ability to reach our potential in a meritocratic society, you become laser-focused on that opportunity. It doesn’t matter whether it’s a scholastic or sports scholarship, or a less traditional path. Being poor, you cannot afford to fuck up the opportunity that comes along. You don’t take it for granted because you understand you’re playing by someone else’s rules. Even today, Ricky and I often feel like that. Given the long odds we beat to get here, sometimes in our heads, our world feels very fragile; at any moment, the clock could strike midnight. We’ve encouraged each other to talk more openly about these feelings, in an effort to strengthen and reinforce the reality of what we’ve built.

As Gladwell pointed out, capitalization is generally only possible when you have a champion who can not only show you the way, but help carry you there. Mrs. Harris was that hero for me. She wasn’t a big-shot lawyer in this case; she was just a teacher who believed in me. She made opportunities happen for me, and she persisted when things hit unexpected roadblocks. But not every kid is lucky enough to have a Mrs. Harris. Or an Eric Eisner. Remembering that and thinking about how many underprivileged kids must be experiencing this on a daily basis is why Carlos’ story brought me to tears.

We as a society need to do more to not only find these lost diamonds in the rough, but to dig them up, champion their cause, and push open doors for them, like Mrs. Harris did for me. We always need more Mrs. Harrises and Eric Eisners, but this isn’t just a call for champions. I believe that in order to level the playing field for underprivileged, minority or other disadvantaged groups, providing opportunities is not enough — we need to start talking openly about the differences in background, mindset, and opportunities that persist even after you attempt to level the field. When discussing diversity, people often bring up the idea of a pipeline, where the focus is on bringing in as many qualified, underrepresented or underprivileged candidates as possible. But perhaps we should start thinking about it as less of a pipeline and more of a leaky funnel.

The fact is, when you grow up poor or disadvantaged, there are innumerable places where you might drop off before you have a chance at capitalization, at a better life. As Gladwell points out, many of the brightest students in Carlos’ hometown end up gang-affiliated as early as the eighth grade, long before free SAT prep courses, scholarships, and admissions officers can open up doors for them. We have to do more to ensure that the underserved know what opportunities are available to them and help them through every step of realizing those opportunities.

In the face of adversity, you have far fewer chances, far less margin for error. I cannot speak on behalf of people of color or women in tech, but I would imagine they experience similar drop-offs in the funnel due to discrimination. The oversights and slights you internalize over the course of many, many years make the rare opportunities you find even rarer and leave you unable to capitalize on what’s left. If we want to start to spot and seal the cracks and leaks that leave people behind, we need to begin the dialogue on unseen inequalities and unexpected drop-offs.

To everyone who has experienced this— who has felt like they don’t belong or aren’t good enough— the world needs to hear your story. Only then, can it begin to give current and future underdogs a better chance at a better life. And just remember: you ARE good enough. You DO belong.


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