The life span of Silver Oak High School, a public charter Montessori Secondary program located in Hayward, California, can be likened to Montessori's planes of development, which span the years from birth to age 24. Montessori educational practice pays special attention to the evolving needs of the individual within each plane of development. Although the planes of development Silver Oak has experienced do not directly mirror the developmental planes described by Montessori, dividing the school's journey into four "planes" of development provides a structure to which Montessorians can relate. This article will discuss the school's triumphs as well as its growing pains as it passed from one stage to the next. It will also include testimonies from founding faculty members, parents, and students; they illustrate Silver Oak's colorful journey from then to now.