The jump from middle school to high school can feel overwhelming; especially for first-generation students who lack access to critical information about academic, expectations, resources, and opportunities. Many struggle with navigating course selections, extracurricular involvement, and high school expectations without guidance from experienced family members. Our project addresses these challenges by giving these students the correct resources, presentations, and acting as their older sibling that's trying to help ease this transition. Using qualitative research methods, we conducted interviews with a first-generation college student to understand common struggles and support systems. We also utilized content analysis to identify key themes from personal narratives. By applying action research, we continuously refine our project based on feedback from our target audience. Essentially, our goal is to empower these students with knowledge and confidence to ensure they step into high school feeling prepared and supported.