This chapter offers a close reading of Woolf’s pivotal 1903 diary at age 21—perhaps the most important of all her 38 diary books. In the crucible of family crisis—her father’s slow death—Woolf makes a conscious (saving) move to the outsider’s position. She contrasts London with the country across this diary: London representing for her culture, the male literary tradition, even (social) death; the country standing for nature, the female, and the unconscious mind. The 1903 Diary offers the first sign of the vital role the downs and solitary country strolls will play in Woolf’s creative life. As she rejects London social success and chooses the outsider role, she reads (and praises) James Boswell’s Journal of a Tour to the Hebrides with Samuel Johnson. Boswell’s Journal introduces Woolf to Dr. Johnson. Her 1903 Diary offers the first glimpses of Woolf the uncommon critic of her Common Reader essays.