The Match | Ownership

Word: Ownership Sentence: Ownership is the courage to say, “This part is mine.” Passage: Ownership sounds simple. In practice, it rarely is. It is hard to say, I messed that up.But it is also surprisingly hard to say, I did that well. Both require a kind of vulnerability. One risks judgment. The other risks sounding like…

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The Match | Progress

Word: Progress Sentence: What used to knock you down can become the very place where progress takes root. Passage: Progress is hard to see in ourselves. We can be our own worst critic. One setback, one hard conversation, one project that falls short, and suddenly it feels like all the work we have done no longer…

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The Match | Rhythm

Word: Rhythm Sentence: Rhythm is knowing when to push, when to pause, and when to let time do its work. Passage: After leaving the principal role and moving into district leadership, I noticed something I did not have language for at the time. The rhythm of a leader. As a principal, I was a bit like…

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The Match | Humor

Word: Humor Sentence: Humor keeps connection alive when the work gets heavy. Passage: When schools, organizations or companies are under pressure, humor is usually the first thing to disappear. Everything gets serious. Performance meetings. Discipline. Turnaround plans. Adults start bracing before conversations even begin. My first year at Harper High School, I worked alongside another assistant…

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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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