The Match | Agency

Word: Agency Sentence: Agency is when people feel the power to shape what happens next. Passage: When I became a principal for the first time, I knew my ultimate goal was never to run the school. It was to give it back to its community. There were four principals in four years. When a school lives…

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The Match | Loyalty

Word: Loyalty Sentence: Loyalty is staying committed to the purpose, especially when the story gets messy. Passage: Most people think loyalty is allegiance to a person. Stay with them. Defend them. Choose a side. But loyalty is supposed to be bigger than that. Loyalty is commitment to a purpose. When you stay loyal to purpose, you…

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The Match | Integrity

Word: Integrity Sentence: Integrity is the safest value we have and the one that gets misused the most. Passage: He was a new student. Sixteen. Quiet. Zero credits.  One morning, he walked into school, passed through security, and then turned around and walked right back out. By mid-day, a staff member reported their car missing from…

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The Match | Choice

Word: Choice Sentence: Your identity isn’t an inheritance; it’s the sum total of the small choices you make each day. Passage: We start choosing earlier than we realize. At first, it feels simple. Who you sit with. What you try. What you quit. What you keep coming back to. But those small decisions stack up quietly,…

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The Match | Legacy

Word: Legacy Sentence: Legacy is how you leave people, not what you leave behind. Passage: This week, a former student of mine graduated from college. When he came to Sullivan, he had already tried a couple other high schools and nothing had stuck. His mom loved him, but addiction had taken more than it had given,…

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The Match | Humility

Word: Humility Sentence: Humility is when your ego steps back and empathy steps in. Passage: I came to Chicago not knowing what to expect on a lot of levels. I was born in Mississippi, and for a long time my worldview was small without me even realizing it. Not because I did not care. It was…

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The Match | Team

Word: Team Sentence: Team is turning failure into feedback. Passage: I started my sophomore year of high school as the varsity starting quarterback. It was the goal I’d worked for, trained for, pictured in my head a thousand times. We went 0–9. When that season ended, I made varsity basketball. Another dream. Another chance to prove…

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The Match | Renewal

Word: Renewal Sentence: Sometimes renewal is as simple as giving today a chance. Passage: Kids can teach us a lot. One of the biggest lessons is renewal. I’ve met students from all over the world. Some whose schools were literally blown up by war. Others here in Chicago who had to navigate intense neighborhoods just to…

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The Match | Rest

Word: Rest Sentence: The best gift you can give yourself is the space and time to rest. Passage: Exercise science has come a long way. We know now that muscles do not grow from the weight we lift. They grow in the rest and recovery that follows. Without enough rest, muscles get overworked, and over time…

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The Match | Steady

Word: Steady Sentence: Steady is being the calm when everything else speeds up. Passage: In some of my darkest moments I have felt the calmest. My first teaching job in Chicago was built for chaos. The school held over 3,000 students and was notorious for gang fights. I was a teacher on a cart, pushing my…

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