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In 2015, I was teaching high-school students in New York. I worked at a nonprofit that partnered with local schools, and my class taught concepts such as growth mindset, social capital, perseverance—the kinds of ideas that are generally outside of traditional curriculums. The students looked up to me, especially the boys. I fit the bill of a strong, positive role model: an assertive, educated, young Black man who could relate to them. We had heart-to-heart conversations, and they often shared things with me that they said they didn’t feel comfortable sharing with their other teachers. A popular student, John, once sat with me in a stairwell and told me about his struggles at home and how they were affecting him in school. I cherished my role in those students’ lives. Their admiration made me feel good about myself.

Until one day, when the students and I were working through a lesson about planning their futures. They were to set a goal and draw a roadmap that used benchmarks to connect them from where they were today to where they would be when they became their ideal future selves. The most confident kids charted their path to becoming Major League Baseball players or Grammy-winning musicians. But some students didn’t know what they wanted. Others knew what they wanted but not how to get there. One student, Leon, turned the activity to me in a way that I hadn’t expected.

“Are you where you dreamed you would be when you were my age?” he asked.

I was stunned. I hadn’t thought about teenage me in a long time. Am I where I dreamed I would be when I was his age?

Of course I wasn’t. Not even close.

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