Final answer:
Jess relates to Douglass's concerns about speaking abilities because both wish to use their literary skills to influence others and gain societal acceptance.
Step-by-step explanation:
Jess identifies with Douglass's concerns about his own abilities as a speaker because, like Douglass, Jess is uncertain about his own ability to write a speech that will increase his popularity with classmates. This echoes Douglass's experience as detailed in his narrative; he provides an account of his pursuit of literacy and how he used it to advocate for himself and others, reflecting his sophisticated thinking about the societal impacts of slavery and his ability to influence his audience through effective speech. Both Jess and Douglass understand the importance of literacy and oration as tools to influence society and gain recognition.