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Winston's Bright Future is NOW!




Winston's Bright Future is NOW!
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Head's Messages


By Dr. Jenn Milam, Head of School

The life of a school is not unlike the life of a young person. There is an incorporation date (a birthday!), then the awkward teenage years when the school and those who work in it are trying to figure out exactly who and what they want to be. Next come the early adult years where the future comes into clearer view and things stabilize a bit with experience and wisdom. And then hopefully, what comes next is a settling in and a perfecting of the vision that enables a school, as it does a person, to really enjoy the next stage in their life, having worked hard, refined their goals, and served proudly those around them. 

For nearly fifty years, Winston has been serving young people who learn differently in the Dallas community. Even before the word “neurodivergent” was common, our intentionally small school was educating the whole child, not only in the core curricular areas, but also in the fine and performing arts, athletics, and STEM-related fields, like engineering, physics, and design-thinking. As a school that holds inclusion and acceptance as fundamental to its mission, Winston has graciously welcomed and served children and their families from widely diverse backgrounds and communities as close as Preston Hollow and from as far away as Corsicana. Indeed, families have even relocated from out of state for their children to be at Winston! 

By now you have all received the announcement that our Re-Enrollment timeline and Tuition Assistance application process begins on November 1.  We are shifting our processes earlier in the academic year so that we can move not only prospective students through our process more efficiently, but so that we can ensure that our current families are given priority consideration for tuition assistance if needed. We are experiencing a marked increase in admission inquiries and admission applications, alongside shrinking availability in many grades - in our Lower School especially. It is clear that Winston’s future is bright and the secret is out - Winston is a special place where young people can feel safe, seen, and cared for while receiving an exceptional, college-preparatory experience. 

I urge you to carefully note deadlines in your family calendar, to make sure you are completing appropriate steps and submitting required documents, and if you need assistance, please reach out for support. We are happy to help you meet those deadlines so you can ensure your student’s place at Winston for the 2025-2026 school year. While it seems early to be thinking of next year already, we are hopeful that these revisions to our process will ensure our current families are well-served, ahead of our work with prospective students and families. 

Since my official beginning on July 1 of this year, I have been joyfully and wholeheartedly reminded, daily, of the power and promise of Winston. I have met families in challenging moments, not sure of their next move or school community, and I have helped to mend hearts that are hurt by the ebbs and flows of adolescent friendship. I have seen athletic teams rally together, even in the face of adversity, and students for whom academic success doesn’t come easily, commit to improvement and learning and find a win. Winston’s future is bright - Winston’s future is NOW! And we’re so happy you’re a part of it!







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Winston's Bright Future is NOW!