Having loved her courtroom experiences, Sotomayor wants her next job to include “trial work” (282). She does not want to be stuck in a cubicle, a cog in the machine of a large law firm or a small law firm that replicates that culture. Pavia & Harcourt, a thirty-lawyer firm working largely in international trade and business operations, hires her. The firm is woman-friendly and pairs associates with partners, creating a natural mentor environment. David Botwinik, the partner everyone turns to for advice, becomes her guide through the culture shock she experiences moving to the private sector. He helps her understand complex areas of law in which she lacks experience, especially deciphering contracts, and understanding how and why they have been drafted.

Another mentor she meets is Fran Bernstein, an eloquent writer and speaker. When Fran asks her to draft a brief, Sotomayor feels paralyzed, “still terrified” of writing (288). Her brief, produced during a frantic all-nighter, is “subpar,” but Fran is encouraging (288). She also recommends Sotomayor register Republican, not so much for ideological purposes but to align with the party in power. Sotomayor does not feel the need for a label “that cover[s] all [her] opinions” and registers without “party affiliation” (288).