McGovern explains Deborah’s decision to enlist by first showing the limits that remain after her 10-year service with the Thomas family ends. The title “Free—to Do What?” draws attention to the limited practical meaning of freedom when Deborah’s choices remain restricted by gender (23). Her success as a teacher sharpens this tension. A wartime shortage of men creates an opportunity for her to teach, and she proves capable enough to be invited back the following year. The circumstances of her employment reveal that wartime conditions have opened an opportunity that would otherwise have been less readily available to her. McGovern then turns to marriage, presenting the legal restrictions that would accompany it. The text specifies that “a married woman c[an]not have a house or a farm or money of her own” (27), with property and major decisions placed under her husband’s control. For Deborah, who wants to travel and experience a wider world before settling into marriage, these limits make conventional adult roles feel increasingly restrictive. Her growing awareness that men can pursue travel and adventure through military service leads her to ask why the same possibility should be closed to her. The decision to disguise herself therefore develops directly from the opportunities she wants and the gender restrictions that prevent her from pursuing them openly, advancing the theme of Gender Discrimination as a Barrier to Independence.

McGovern develops Deborah’s character by stressing her methodical preparation, which demonstrates the patience and practical skill involved in carrying out her plan. Her male disguise requires careful attention to both appearance and behavior. Deborah uses her weaver’s trade to create the specific items for her disguise, including cloth to bind her chest and fabric for a man’s suit. Her existing skills therefore become practical resources in pursuing opportunities otherwise closed to her. The effectiveness of the disguise becomes apparent when Deborah wears it beyond the privacy of her room. Her own mother fails to recognize her, giving Deborah an early indication that her altered appearance can prevent recognition even by someone who knows her well. Her visit to a local fortune-teller extends this experience into an encounter with a stranger. Speaking in the deepest voice she can manage, Deborah is accepted as an “honest man,” showing that maintaining the disguise depends on how she speaks and behaves as well as on what she wears. The fortune-teller’s warning that “not all of [her adventures] will be successful” foreshadows difficulties ahead (32), complicating Deborah’s anticipation of the adventures she hopes to experience.

Men’s clothing emerges as a symbol of the freedom and opportunities that Deborah can’t access while she’s recognized as a woman. McGovern gives the clothing particular significance by having Deborah use skills she already possesses as a weaver to make the material needed for her disguise. The clothes therefore provide a practical means of acting on the plan she has developed in response to gendered restrictions. Her mother’s failure to recognize her demonstrates how strongly outward appearance shapes the way others perceive Deborah. The disguise changes how other people identify her and, consequently, the possibilities available to her. The clothing gives physical form to the social boundaries established earlier in the biography: Once Deborah is perceived as male, she can travel independently and attempt to enter a sphere from which women are excluded. This also begins to complicate the freedom represented by the disguise. Deborah must learn how to sit, stand, walk, run, and speak in ways that will preserve other people’s perception of her as a man. Men’s clothing therefore begins to carry a double significance, providing access to the wider life Deborah desires while requiring her to maintain the appearance on which that access depends.

The journey to Boston tests Deborah’s commitment to the plan as she begins putting it into action. The difficulties she encounters also introduce consequences of maintaining the disguise once she begins traveling beyond familiar surroundings. When Deborah sees her old neighbor William Bennett, her immediate fear that he has recognized her causes her to hide in the woods. The encounter marks an early development of The Burden of Concealment: Although the disguise enables Deborah to travel as a man, encountering someone who knows her creates the risk that her identity will be exposed and her plan disrupted. McGovern then turns from the risk of recognition to Deborah’s uncertainty about continuing the journey. When Deborah becomes lost and finds herself back in her old neighborhood, she briefly considers abandoning the plan. The narrative gives voice to her conflicting thoughts: “‘Give up!’ one part of her crie[s],” while another urges her to “[g]o on!” (36). Her decision to continue develops The Lasting Drive for Adventure, showing that her desire to see more of the world persists when pursuing it becomes physically difficult and uncertain. Her arrival in Boston, hungry and without money, further complicates the adventure she had imagined from a distance. Deborah has succeeded in reaching the city she long wanted to see, but she now faces the practical difficulties of carrying her plan forward.