The Match | Generations
Word: Generations
Sentence:
Every generation inherits a story and leaves one for the next.
Passage:
This week, I will stand in a room filled with Sullivan alumni who walked those hallways decades before I ever did.
Some graduated before I was born. Others remember a version of the neighborhood, the school, and the world that no longer exists. And yet, somehow, we all belong to the same story.
Sullivan High School is celebrating 100 years.
I spent nine of those years as its principal. At the time, nine years felt like a long time.
Against a century, it feels pretty small.
Long before I arrived, generations of students had already learned, struggled, laughed, fell in love, made mistakes, graduated, and figured out who they were becoming inside those walls.
By the time I became principal, Sullivan was in another chapter. The school had experienced years of leadership changes, declining enrollment, a difficult reputation, and questions about its future. At the same time, the community around it was changing. Students were arriving from all over the world, bringing new languages, cultures, traditions, and stories into a building that had already held generations of them.
It would have been easy to believe our job was to start over. But you do not start over in a place with history. You inherit it.
You inherit the traditions people love, the systems people built, the wounds people still remember, and the stories people tell about what the place used to be. Then, for a little while, you are given the responsibility of adding your own chapter.
That is what Sullivan taught me.
I did not create Sullivan’s story. I was fortunate enough to become part of it.
During our years there, we changed things. We built new programs, strengthened the school, welcomed students and families from across the world, and worked to create a place where young people felt like they belonged. But even the things we built rested on something that existed before us: a community that had survived, adapted, and kept believing the school mattered.
And now another generation is carrying it.
We all live inside stories that started before us. Families have them. Schools have them. Organizations, neighborhoods, communities, and professions do too. We inherit things from people we may never meet. Someone created the opportunity we walked into. Someone fought for something we now consider normal. Someone made a mistake we are still trying to repair. Someone planted something whose shade we now get to sit under.
Eventually, it becomes our turn.
Not to preserve everything exactly as we found it, and not to erase what came before us. To decide what is worth carrying forward, what needs to change, and what we want to leave for the people who come next.
One hundred years makes that easier to see.
None of us owns the whole story. We just get a chapter.
And maybe the real measure of that chapter is whether the next generation has something stronger to build from because we were here.
Your Turn:
What will your chapter make possible for the people who come next?
I always appreciate hearing what a word brings up for you. Don’t hesitate to comment or email me. I’m here!
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4 Comments
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4 Comments
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on October 9, 2026 at 6:56 am
Chad, thank you for serving as the keynote speaker at the “kick off” dinner to recognize the 100th graduating class from Roger C Sullivan High School in 2027. It was great chatting with you at the event.
You could have picked so many optional words for this week’s message – “History”. “Legacy”… as a couple of other options. But, I like that you chose “Generation”. As I stood at the podium last night to accept my recognition as a “Notable Alumni”, I made comments about my own grandparents, having come from Europe in the early 1900s and then in the 1930s. Their stories about coming to the United States are really very similar to those stories of many of the Sullivan HS student body while you were Principal at the school; so, their stories rang loudly for me. As I have served on the Friends of Sullivan board, supporting the last 12 years of incoming and graduating classes from Sullivan, in a way, I feel like I am supporting my own family, although two generations ago.
I think not only do Sullivan Alumni feel a kinship to the school, I think it is more that they feel a kinship to the Rogers Park Community… either “East” or “West”, we all feel it. It was interesting, at the venue, there was another “100th” event going on… one of the attendees was hanging around our table. I recognized him from a gym facility in my community… I found out he also graduated from Sullivan HS in 1973, one year after I graduated. So, in all those times I have seen him at the gym, I didn’t know our kinship. But, during our chat at the sign in table, I felt our connection. So, this begs the question, is this a “generational” connection, or a fellowship connection having lived in the same community and having attended the same high school? I don’t know, but it is worth thinking about which is a more fitting relevance.
Also, what is worth noting… each student only spent 4 years at the school; but, you spent 9 years there! You have had more generational impact than many / any of us alumni.
It was funny reading that you were born after many of us graduated, myself included. Thanks – now you really made me feel old! And, by the way, happy belated milestone birthday.
And, to close, I really wanted one of those hoody sweatshirts… when are you going to have another raffle event?!
Stay well, my friend. I enjoy reading your messages each week, and it keeps me connected to you during our gaps in getting together.
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on October 9, 2026 at 7:59 pm
Thank you for this. I really appreciated our conversation that night, and I loved hearing you connect your family’s story to the students and families who have come through Sullivan more recently. I think that is part of what I was trying to get at with “Generations.” The people change, the neighborhood changes, the stories change, but there is still this thread of people finding home, opportunity, community, and connection in the same place.
And I think you’re right that it may be more than generational. There is a fellowship that comes from being shaped by the same school and community, even when you were there decades apart. That moment you had with the 1973 graduate says a lot about that.
Also, thank you for the reminder that nine years gave me a little more time in those hallways than most students get. I never really thought about it that way, but I certainly feel the weight and gift of having been part of that many Sullivan generations.
And yes, I owe you a hoodie.
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on October 9, 2026 at 8:08 am
This chapter for me is bringing about the awareness of legacy. Giving this generation hope for the next and making sure the previous generations take accountability for the current generation. Sowing seeds of hope!
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I love this. “Sowing seeds of hope” is such a powerful way to think about what one generation owes the next. We inherit so much from the people before us, but we also have a responsibility to leave something stronger, more hopeful, and more possible for those coming behind us. Thank you for adding this to the reflection!
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Chad, thank you for serving as the keynote speaker at the “kick off” dinner to recognize the 100th graduating class from Roger C Sullivan High School in 2027. It was great chatting with you at the event.
You could have picked so many optional words for this week’s message – “History”. “Legacy”… as a couple of other options. But, I like that you chose “Generation”. As I stood at the podium last night to accept my recognition as a “Notable Alumni”, I made comments about my own grandparents, having come from Europe in the early 1900s and then in the 1930s. Their stories about coming to the United States are really very similar to those stories of many of the Sullivan HS student body while you were Principal at the school; so, their stories rang loudly for me. As I have served on the Friends of Sullivan board, supporting the last 12 years of incoming and graduating classes from Sullivan, in a way, I feel like I am supporting my own family, although two generations ago.
I think not only do Sullivan Alumni feel a kinship to the school, I think it is more that they feel a kinship to the Rogers Park Community… either “East” or “West”, we all feel it. It was interesting, at the venue, there was another “100th” event going on… one of the attendees was hanging around our table. I recognized him from a gym facility in my community… I found out he also graduated from Sullivan HS in 1973, one year after I graduated. So, in all those times I have seen him at the gym, I didn’t know our kinship. But, during our chat at the sign in table, I felt our connection. So, this begs the question, is this a “generational” connection, or a fellowship connection having lived in the same community and having attended the same high school? I don’t know, but it is worth thinking about which is a more fitting relevance.
Also, what is worth noting… each student only spent 4 years at the school; but, you spent 9 years there! You have had more generational impact than many / any of us alumni.
It was funny reading that you were born after many of us graduated, myself included. Thanks – now you really made me feel old! And, by the way, happy belated milestone birthday.
And, to close, I really wanted one of those hoody sweatshirts… when are you going to have another raffle event?!
Stay well, my friend. I enjoy reading your messages each week, and it keeps me connected to you during our gaps in getting together.
Thank you for this. I really appreciated our conversation that night, and I loved hearing you connect your family’s story to the students and families who have come through Sullivan more recently. I think that is part of what I was trying to get at with “Generations.” The people change, the neighborhood changes, the stories change, but there is still this thread of people finding home, opportunity, community, and connection in the same place.
And I think you’re right that it may be more than generational. There is a fellowship that comes from being shaped by the same school and community, even when you were there decades apart. That moment you had with the 1973 graduate says a lot about that.
Also, thank you for the reminder that nine years gave me a little more time in those hallways than most students get. I never really thought about it that way, but I certainly feel the weight and gift of having been part of that many Sullivan generations.
And yes, I owe you a hoodie.
This chapter for me is bringing about the awareness of legacy. Giving this generation hope for the next and making sure the previous generations take accountability for the current generation. Sowing seeds of hope!
I love this. “Sowing seeds of hope” is such a powerful way to think about what one generation owes the next. We inherit so much from the people before us, but we also have a responsibility to leave something stronger, more hopeful, and more possible for those coming behind us. Thank you for adding this to the reflection!