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Shall I Compare Shakespeare and AI? Lessons from Two Poets

By Josh Cobb, Head of School
In Daniel Pink’s “A Whole New Mind,” he writes, “Poets [...] contemplate the world in which we live [...] and give expression to it in a way that makes the reader understand how the world turns. Poets, those unheralded system thinkers, are our true digital thinkers.” Provoked by this assertion, I asked participants at my January book club on Pink’s work to compare two sonnets, one written by Shakespeare and another written by ChatGPT.
Throughout the exercise, we explored the attributes—or senses, as Pink describes them—that separate human and machine and discussed which poem demonstrated an understanding of “how the world turns.” Ultimately, we saw an enhanced understanding of humanity in Shakespeare’s work.

To activate the ChatGPT poet, I asked, “Write a Shakespearean sonnet on a beautiful young woman and her aging lover.” Then, seeing that that prompt didn’t fully capture what I was trying to create, I requested, “Revise to show that the writer is trying to keep the young woman’s beauty eternal in poetry.” What this request generated was closer, but surprisingly, not in the rhyme pattern of a Shakespearean sonnet. When I asked it to correct that pattern, it simply added an extra stanza in the correct pattern but left three that were incorrect (see Sonnet 1). Reviewing that poem, I was surprised that the formulaic elements of the sonnet, the abab rhyme pattern, tripped up the computer. Still, though it faltered on rhyme, the iambic pentameter rhythmic structure seems intact, as does the traditional couplet conclusion.

Aside from those poetic devices, where the poems differ the most is in the emotive expression of the human experience. In “Shall I Compare Thee to a Summer’s Day?” (see Sonnet 2), Shakespeare begins with a question that seems to set up a simple metaphor: “Youthful beauty is summer.” However, instead of affirming that analogy, he challenges it and ultimately realizes that this beauty is more permanent than a season. It is eternal. This is the emotional pivot of the poem: “But thy eternal summer shall not fade.” Faced with his own mortality, there is a resolve in these lines—an arrogance even—that poetry itself will grant immortality to the lover. Though the poet may be aging, he still has that power and grasps it confidently in the final couplet:

“So long as men can breathe, or eyes can see,
So long lives this, and this gives life to thee.”
A poem that begins with a question ends strongly with a statement, a declaration of this poet’s ability to transcend impermanence, which would seem absurd if it weren’t true. For over four hundred years, the lover’s beauty has lived on in Shakespeare’s verse.

We collectively came to this interpretation during our conversation that night, and I was struck by how animated people became as they discussed the vulnerability and the hubris of an aging poet who was so desperate and then so confident that he attempted to fend off mortality in words. Were they as moved by ChatGPT’s version? Not that night. That night, they chose humans. But why? In creative writing, there is an age-old edict: “show, don’t tell.” ChatGPT often says: “This poem is a vessel of immortal art.” In contrast, Shakespeare uses personification and imagery: “Nor shall death brag thou wand’rest in his shade.” ChatGPT telegraphs, whereas Shakespeare’s poem surprises. There is no pivot in the AI version. It left us flat.

Admittedly, it wasn’t a fair fight. Shakespeare isn’t any normal human; he is a renowned poetic genius. When I mentioned this activity to others later, they questioned my use of ChatGPT 3.5 versus 4, a much more advanced version. ChatGPT 4 would have performed better, they said. In addition to my version choice, my prompts might have also set it up for failure, as the success of AI relies heavily on its human partner. Which brings us to what may be the most scary thing about AI: humans. If we are ultimately to partner with machines to address problems, problems somewhat more significant than writing a love poem, what traits do we need, and therefore what attributes do we, as educators and parents, need to foster in children? First, if we are going to harness the powerful tool of AI and use it morally and constructively, we will need the character attributes we have discussed all year: curiosity, empathy, responsibility, adaptability, and agency. We will also need intellectual attributes like the ones Daniel Pink describes in “A Whole New Mind.” 

While we explored Shakespeare’s sonnet at the book club, I emphasized Pink’s sense of symphony, which he describes as “the capacity to synthesize rather than analyze; to see relationships between seemingly unrelated fields; to detect broad patterns rather than deliver specific answers; and to invent something new by combining elements nobody else thought to pair.” Shakespeare’s initial question, “Shall I compare thee to a summer’s day?” is his effort to show literary symphony, and that query leads him to personify death and to deify poetry, all engaging intellectual acts of synthesis and creativity. 

In Pink’s chapter on symphony, he purports that those who are going to succeed in the future “must become adept at analogy—at seeing one thing in terms of another.” He details three ways of seeing relationships: the metaphor maker, the inventor, and the boundary crosser. Another reason Shakespeare’s poem may show a greater understanding of the human experience is because of metaphor. Pink asserts, “The more we understand metaphor, the more we understand ourselves.” Shakespeare skillfully sets up the poem by introducing a metaphor, only to challenge it throughout. Then he shows his inventiveness, what Pink describes as “the ability to forge [...] inspired, inventive relationships,” as he plays with the metaphor throughout, introducing new elements of nature—wind and sun—as he arrives at another analogy: the impermanence of the seasons reflects our own mortality. It is here, at the pivot, that he becomes a boundary-crosser and in Pink’s words, “he sees the relationships the rest of us never notice.” A poem is not usually seen as a vehicle for immortality. That is more in the realm of religion, or maybe even science, but not poetry. Still, he steps across that line and asserts that words can stop mortals from wandering in death’s shade. 

This capacity to find the intersection between seemingly incongruous concepts is an attribute that is distinctly human and a catalyst for creativity. In Frans Johansson’s “The Medici Effect,” he claims that “When you step into an intersection of fields, disciplines, or cultures, you can combine existing concepts into a large number of extraordinary new ideas.” He, like Pink, argues that this ability will be a distinct advantage now and into the future: “The advantage goes to those with an open mind and the willingness to reach beyond their field of expertise. It goes to people who can break down barriers.” The inventiveness that Shakespeare displays in this poem is not uniquely his own. I believe that we can all discover and refine symphony. As an educator, I strive to foster that capacity “to synthesize rather than analyze; to see relationships between seemingly unrelated fields; to detect broad patterns rather than deliver specific answers; and to invent something new by combining elements nobody else thought to pair,” all in an effort to help our students thrive. 

Sonnet 1 by Chat GPT 3.5
In youth’s fair bloom, thy visage pure and bright,
A radiant sun, thy grace doth brightly gleam.
Yet time, relentless, casts its shadow’s stream,
Aging this frame, once vibrant in love’s light.
Oh, dearest muse, let not thy beauty wane,
Preserve thy charm, as roses keep their hue.
Eternal youth, thy countenance imbue,
In every line, let love’s sweet verse sustain.
This poem, a vessel of immortal art,
Shall cradle thee in verses ever true.
Through ink and time, thy beauty shall renew,
A timeless echo of our love’s sweet start.
Though age may touch me with its withering hand,
Our love, a timeless flame, shall brightly burn.
In memories, let youth forever stand,
A testament to the passion we discern.
For in our hearts, where love shall ne’er expire,
Thy beauty blooms, a love that shall inspire.
Sonnet 2 by Shakespeare
Shall I compare thee to a summer’s day?
Thou art more lovely and more temperate.
Rough winds do shake the darling buds of May,
And summer’s lease hath all too short a date.
Sometime too hot the eye of heaven shines,
And often is his gold complexion dimmed;
And every fair from fair sometime declines,
By chance, or nature’s changing course, untrimmed;
But thy eternal summer shall not fade,
Nor lose possession of that fair thou ow’st,
Nor shall death brag thou wand’rest in his shade,
When in eternal lines to Time thou grow’st.
 So long as men can breathe, or eyes can see,
 So long lives this, and this gives life to thee.

Graland Country Day School

Graland Country Day School is a private school in Denver, Colorado, serving students in preschool, kindergarten, elementary, and middle school. Founded in Denver in 1927, Graland incorporates a rich, experiential learning approach in a traditional classroom setting, emphasizing the development of globally and socially conscious leaders who excel academically.