The Greek mythical story of Icarus leaves us wishing to equip our children with the character and skills to navigate through life and change course when flying too close to the sun. Our author experienced an uncertain, troubled, and somewhat rebellious childhood within the divorced environment of his parents. Time away from this environment while living with his Aunt and Uncle, a "Fly Navy" commercial, and a joyful flying experience with his father altered the course of his life. Uncertainty was replaced with his mission to fly fighter jets. 25 years later while flying an air combat training mission at night over the Gulf of Mexico, he became disoriented, ejecting from his F-16 with less than a second left to live. This near-death experience inspired him to write down lessons learned for his four young children should he not be there to guide them in the future. 12 years after the accident and after several years of experience mentoring high school students as an Admissions Liaison Officer, attending 'career days', and observing his own kids encountering the challenges of Covid and our nation's 455:1 student to guidance counselor ratio (2019); he was inspired to provide guidance counselors with more resources. This life-changing book serves as a manifestation of his hopes and desires to help the next generation navigate doubt, uncertainty, and imperfection.