Word: Bittersweet Sentence: Bittersweet is knowing it is time to go, even when part of you still wants to stay. Passage: Graduation has always carried a strange kind of weight. It is joy and fear in the same room. A marker of progress.A door closing.A road opening.A version of yourself ending before the next one has…

Word: Hold Sentence: Hold is knowing that what matters most is meant to be carried with care, not clenched with fear. Passage: In our most stressful and uncertain moments, the instinct is to squeeze. We squeeze our plans.We squeeze our people.We squeeze our expectations.We squeeze ourselves. We tell ourselves we are just trying to keep things…

Word: Identity Sentence: Identity gets lost when what we do becomes the only place we know to find our worth. Passage: I know what it feels like to disappear inside the work. When I was a principal, the job asked for everything. My mind, my energy, my heart, my body. I carried the school with me…

Word: Fear Sentence: We have all been more fearless than we have been afraid. Passage: We forget. For me, it started in the classroom. Standing in front of students while still feeling like one myself. In a lot of ways, I taught myself how to teach. Every day felt uncertain. Every day asked something of me…

Word: Tension Sentence: Tension is what we carry when two truths exist and neither lets go. Passage: This week held both joy and heartbreak. I ran into a former student who told me he wants to become a principal. In the middle of the conversation, he turned to someone else and said I was the reason…

Word: Resonance Sentence: Resonance is what remains when the role ends, but the meaning still rings true. Passage: Leaving the principalship was harder for me than I expected. For a long time, I focused on what was unfinished. The dreams that felt so close. The ideas that had life in them but would now belong to…

Word: Connection Sentence: Connection begins when we look past what is different and stay long enough to discover what is shared. Passage: Connection often comes easiest when we can see ourselves in someone else. When the story feels familiar, the bridge is already there. I feel that with other principals all the time. There is an…

Word: Momentum Sentence: Momentum starts when the vision becomes shared and belief starts to spread. Passage: By year five, I could feel something changing at the school. What once felt heavy started to feel lighter. What once took constant pushing began to move with more ease. The vision was no longer just mine. It had become…

Word: Forward Sentence: Sometimes the thing that moves us forward is not success, but what failure shows us. Passage: In my third year as principal, Mayor Rahm Emanuel asked us to take part in XQ, a national high school redesign challenge backed by Laurene Powell Jobs. We would be the only Chicago school to submit a…

Word: Values Sentence: Values are what people carry with them after being with us. Passage: Recently, I ran into three former students, and each time I walked away with the same feeling. Pride. The quiet kind.The kind that sneaks up on you.The kind that stays with you longer than the conversation. At the school I led,…