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Dear Jack: Project 180, Day 75

I have to do something today, something that I should have done weeks ago. But whether it was adhering to my principles around student ownership and responsibility or just simply negligence, at this point, it is what it is, and I have to do something about it.

At the end of second period on Friday, after watching him sit there and do nothing yet again, I held Jack (name changed) after class.

“Jack, you gotta help me, man. I gotta understand, so we can get better. I am going to write you a letter this weekend, and I would like you to respond. Okay?”

“Okay, Sy.”

“Have a good weekend, kiddo. See you Monday.”


Dear Jack,

I want to begin by saying that it has been a pleasure getting to know you this year. Every day I look forward to your wise and witty words during Smiles and Frowns. Your peers and I never exactly know what’s going to come out of your mouth, and that’s what makes you…well, Jack. You are truly a unique and valued member of our community. Thank you for brightening our days.¬†And while all that is important and my sentiments are sincere, it is not why I am writing you this letter.

I am writing out of concern. I am writing out of a need to know. As we are both aware, the end of the semester is upon us, and as we are both aware, you are in danger of not earning credit for the course. And this troubles me. Greatly. I lose sleep over it. I want to understand. How is it that such a bright young man finds himself in this position? Is it me? Have I not pushed hard enough? Did I give you too much ownership? Is there something beyond school? Or is school the problem? I want to understand. And so, I would like to make you a deal.

I want you to write me back. I want you to help me better understand the Jack I don’t know. Help me better understand you, so I can better serve you. If you do this, I will accept it as your narrative essay, which moves you closer to earning credit. I want you to earn credit. Of course, there’s more to it than just your letter, but it’s not too late for us to get across that line. But more than the credit, we have another half year together, and I want it to be better than the first. I feel like I can do a better job if I better understand how to motivate and help you. Please consider my offer. I look forward to your response.



Over the years, I have had numerous Jacks–and Jills–who have confused and confounded me in such ways. Bright kids who are reluctant to shine. And over the years, I have dealt with such instances differently. Before I knew better, I failed them to teach them a lesson. As I’ve learned, I have tried to meet them in the middle with flexibility and opportunity. And I am now doing that for Jack, but I want to do more than be flexible. I want be more knowledgeable. I want to understand. Even more, I want Jack to know that I want to understand. I want him to know that he’s worth understanding.

Today’s Trail

Along today’s trail we will…

…begin with Smiles and Frowns.

…work on Passion Papers.

…reflect in Journey Journals.

…end with a Sappy Sy Rhyme.

Happy Monday, all.

Do. Reflect. Do Better.

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