Those familiar with Douglass’s Narrative of the Life will readily recall his creative, improvisatory maneuverings as he strove toward his goal of literacy. Given that the authoritative discourses did not even permit serious discussion of the possibility of a slave being formally educated, Douglass employed his creative intellectual and imaginative powers to create his own “school” by transforming his daily tasks into opportunities to improve his reading and writing skills. Whether it involved playing on white boys’ pride in not wanting to “lose” a writing game to a slave or bringing extra bread on an errand to gift impoverished white children in exchange for a “stealth” reading lesson, Douglass created educational sites out of mundane tasks—and more extraordinarily, he created these within a context of oppressive, unjust, and demeaning social relations. 
Douglass takes advantage of this antagonism and creates educational sites wherever he goes. Having utilized fences, brick walls, and pavement as make-shift copy-books, Douglass states that his writing lessons were at last completed when could copy “the Italics in Webster’s Spelling Book” by memory. . In addition to improvising with the objects just mentioned, Douglass notes that he had also make good use of little Master Thomas’s (Mr. Auld’s son) old and quite used copy-books. As Douglass explains, while Mrs. Auld attended her weekly Monday afternoon meeting, he would “spend time in writing in the spaces left in [little] Master Thomas’s copy-book, copying what he had written.” . After seven long years with the Auld family, Douglass achieves his goal of literacy through intentional, creative acts of resistance. In other words, Douglass, well before Derrida and other deconstructionists, seeks those left over spaces, the in-between, silenced, erased and already “written” spaces in order, as Sisco puts it, “to exploit their rich potential.”
However, Douglass’s attainment of literacy, just as Auld predicted, proves painful given Douglass’s status as a slave—one living yet socially dead. Having read and studied various essays and speeches arguing against slavery and promoting universal human rights, Douglass’s anger and hatred toward his oppressors intensified. As he explains, his new found ability to articulate with the utmost clarity why slavery was unjust and his increased knowledge regarding matters of justice and human rights gave rise to a deep discontentment—the “very discontentment which Master Hugh had predicted would follow”. Commenting further on the double-sidedness of literacy for a slave, Douglass writes:
The more I read, the more I was led to abhor and detest my enslavers. I could regard them in no other light than a band of successful robbers, who had left their homes and gone to Africa, and stolen us from our homes, and in a strange land reduced us to slavery. […] I would at times feel that learning to read had been a curse rather than a blessing. It had given me a view of my wretched condition, without the remedy. It opened my eyes to the horrible pit, but to no ladder upon which to get out. 
Douglass goes on to say that he at times wished himself ignorant or a beast—in short, he preferred any condition that would rid him of his incessant thinking. “It was this everlasting thinking of my condition that tormented me.”  However, he could not make his mind stop. “It was pressed upon me by every object within sight or hearing, animate or inanimate. The silver trump of freedom had roused my soul to eternal wakefulness. Freedom now appeared, to disappear no more forever.” In other words, wish as he may, there was no turning back to blissful ignorance. Douglass’s literacy made him aware of his wretched condition as a slave in a way that was not possible before. Listen, as Douglass continues his eloquent description of how his deep longing for freedom was ever before him, bidding him draw near yet leaving him bound, boxed in, and unable to reciprocate.
[Freedom] was heard in every sound, and seen in every thing. It was ever present to torment me with a sense of my wretched condition. I saw nothing without seeing it, I heard nothing without hearing it, and felt nothing without feeling it. It looked from every star, it smiled in every calm, breathed in every wind, and moved in every storm. I often found myself regretting my own existence, and wishing myself dead; and but for the hope of being free, I have no doubt but that I should have killed myself, or done something for which I should have been killed .
At this stage, Douglass came to the painful realization that for the slave, literacy, how ever good and necessary its attainment may be, is not sufficient for true freedom. True freedom requires the ability to participate as a full citizen and to have equal opportunities for education, employment, housing, and other rights granted fully functioning citizens qua social and political agents. This realization in no way diminishes Douglass’s extraordinary achievements in the midst of a hostile and oppressive society. As we have seen, Douglass’s resistance to and reharmonizations of the authoritative (white) discourses and unjust socio-political practices highlight his creative ability to reconfigure his environment and re-narrative his subjectivity. However, Douglass’s freedom through literacy was partial, and, paradoxically, the limited nature of his freedom become painfully apparent as a result of his literacy.
 Douglass, Narrative of the Life, 41.
 Ibid., 44.
 Ibid., 44–45.
 Ibid., 45.
 Sisco, “Writing in the Spaces Left,” 201.
 Douglass, Narrative of the Life, 42.
 Ibid., 42–3.
 Ibid., 43.