Russell Helmstedter, a middle school math and computer science teacher at De Anza Academy of Technology & the Arts, began his coding journey with Python during the COVID-19 pandemic in 2020. Inspired by Al Sweigart’s "Automate the Boring Stuff," he quickly immersed himself in the language and integrated PyBites into his school's computer science curriculum. Helmstedter faced challenges in managing student progress and certificates manually, leading him to collaborate with Bob from PyBites to streamline the process by exporting student data into a JSON format. This data was then converted into CSV using Python's Pandas library, allowing Helmstedter to efficiently track and compare student performance. He further developed a command-line interface tool to automate the process, using libraries like Typer, Rich, and Plotext for data manipulation and visualization. The project not only resolved his administrative challenges but also provided an opportunity to engage with data plotting, a personal interest, while planning future improvements to automate grading and certificate printing.