What does ChatGPT think about me?
Reading Vauhini Vara's Searches prompted an unsettling line of inquiry with ChatGPT.
Have you ever Googled yourself? I’ll admit I have on more than one occasion over the years out of curiosity to find out what my online footprint looks like. So I guess it was only a matter of time before I typed this prompt into ChatGPT:
Who is Ruben Brosbe
Here’s a profile on Ruben Abrahams Brosbe based on available info:
Who He Is
Ruben Abrahams Brosbe is a writer, educator, and educational consultant based in New York. (rubenbrosbe.com)
He taught in New York City public elementary schools for about 12 years. (centerracialjustice.org)
He has moved into roles facilitating professional learning—training other educators and schools—especially around racial equity, anti-bias education, and social justice. (centerracialjustice.org)
What He Does / Focuses On
He supports educators and schools in building environments where every student can thrive. (Medium)
He is a co-founder of Teach Resistance, which is an online community for social justice and anti-bias elementary education. (BLM at NYC Schools)
Among the groups he works with: Teaching Lab, Ramapo for Children, Center for Racial Justice in Education. (The Educators Room)
He has been involved in writing—op-ed style, pieces addressing current education debates, issues of equity, teacher emotional labor, etc. (Medium)
I typed this self-absorbed prompt in ChatGPT after reading Searches: Selfhood in the Digital Age by Vauhini Vara. Searches is one of the most engaging books I read this year. Vara combines her skills as a former business journalist who covered tech for Bloomberg and a fiction writer whose debut novel was a Pulitzer Prize finalist to hook you and guide you through an exploration of identity, privacy, creativity and consumerism in the age of Big Tech. The book blends memoir, experimental fiction, and a critical history of the evolution of Big Tech from Amazon and Apple’s early days to our current AI era.
As someone with more than two decades of writing online, I was curious what this question would turn up. And while generally accurate (albeit a tad outdated), ChatGPT’s response reveals more about what’s algorithmically important about me than what I consider personally significant. This is one theme of Vara’s writing. Searches explores the ways people try to shape their online reputations, but also the ways in which Big Tech has the power to shape those personas. In addition, Vara argues that through algorithms which consume more and more of our private information and our attention, Big Tech is able to increasingly shape our offline behaviors.
After reading ChatGPT’s summary of myself, I was curious which pieces of my writing it considered significant. It pulled a sample of my writing from 2020 through last year. The topics were mostly related to education, although it also pulled my piece for Salon on anti-Zionist Jews and a piece I wrote for middle school students for CommonLit, a non-profit ELA curriculum.
At the end of the list of texts and summaries, ChatGPT offered me another search:
If you want, I can also pull together his most influential quotes or an overview of recurring themes (e.g. justice, care, identity) in his work. Do you prefer that?
Sure.
Great — here’s a synthesis of recurring themes and influential quotes/ideas across Ruben Abrahams Brosbe’s work:
🌱 Recurring Themes in His Writing & Teaching
Education as a Site of Justice (or Injustice)
Schools don’t just teach academics; they reproduce or resist systemic inequities (racism, fatphobia, classism, ableism, Zionism).
He argues schools must be transformed to nurture joy, dignity, and agency for students and teachers alike.
The Human Side of Teaching
Brosbe often emphasizes that teachers bring their whole selves into classrooms—including their biases, exhaustion, and hopes.
Reflection and humility are central: educators must acknowledge mistakes, learn, and model vulnerability.
Intersection of Work & Schooling
How students experience school (compliance, control, rest vs. overwork) shapes how adults later experience jobs.
To create a fairer future of work, we must begin by changing how kids experience learning.
Identity & Belonging
From Jewish identity and questioning Zionism, to fatphobia, to racial equity—he returns to how identity shapes belonging, and how institutions often exclude.
He sees embracing complexity and self-reflection as a path toward justice.
Relationships as the Foundation
Whether it’s fighting inequity or supporting student growth, Brosbe consistently argues that relationships matter more than programs, tests, or policies.
✨ Influential Quotes / Core Ideas
On Schools & Justice:
“If we want schools to be places where every child thrives, they cannot only prepare students for tests or jobs. They must prepare them to be fully human.”
On Teachers’ Role:
“We carry our biases into the classroom, whether we acknowledge them or not. The question isn’t if they show up, but how we respond when they do.”
On Work & Schooling:
“Schools are the training grounds for how we understand work—our right to rest, to joy, to agency. If we want to transform labor, we must start with schools.”
On Identity & Belonging:
“Undoing Zionism has not meant rejecting my Jewish identity. It has meant reimagining what it means to honor my ancestors by resisting oppression, not reproducing it.”
On Relationships:
“Curriculum matters. Pedagogy matters. But without relationships, none of it takes root.”
ChatGPT summarized themes of my writing more or less accurately. It felt impressive and unnerving at the same time. But I also noticed something amiss. ChatGPT had presented its own synthesis of my writing as quotes. This is a relatively harmless example of ChatGPT’s sloppiness and could be written off as a punctuation issue. But it speaks to a bigger problem.
What if I was trying to understand someone whose writing wasn’t my own? One of Vara’s critiques of AI is that is prone to error and bias. AI users must view results through a critical lens and show willingness and ability to fact check. In one telling conversation with ChatGPT, Vara asked for examples of significant artists from history. All of the examples ChatGPT provided were white men. When Vara asked for examples of women of color, ChatGPT provided a list that included a man and another who was completely made up artist.
Still, overall, ChatGPT hadn’t presented any blatantly false information about me. So I was curious to keep exploring.
Next I asked: How would you describe Ruben's political views?
Based on Ruben Brosbe’s published writing, public workshops, and affiliations, here’s a careful description of his political views as they show up in his work:
🌍 Political Views Reflected in His Writing
Progressive / Left-leaning orientation | He consistently critiques systemic inequities in education (racism, fatphobia, classism, ableism). His work aligns with progressive education movements that push for anti-bias, culturally responsive, justice-centered teaching. |
Social justice lens | He frames schooling not just as an academic institution, but as a site of struggle against larger systems of oppression. He emphasizes dismantling white supremacy, heteronormativity, and diet culture in schools. |
Labor & anti-capitalist critique | In To Transform Work, Start With Schools (YES! Magazine), he connects the structures of schooling (compliance, lack of rest, focus on productivity) with capitalist labor exploitation. He calls for rethinking work and school to center joy, rest, and dignity. |
Pro-Palestinian / anti-Zionist stance | In Undoing Zionism: “A way to honor my ancestors” (Salon / Jewish Voice for Labour, 2024), he writes about moving away from Zionism as a Jewish identity framework. He frames anti-Zionism as an ethical stance against oppression and part of honoring his Jewish heritage. |
Grassroots / relational politics | In both teaching and organizing, he emphasizes relationships and one-on-one conversations as the building blocks of real change, over top-down policy or “performative” group actions. |
Skepticism of mainstream reforms | He critiques test-driven accountability, austerity budgets, and superficial “equity” reforms that don’t address deeper systemic issues. His perspective is often counter to centrist or technocratic education policy. |
🎯 Overall Characterization
Ruben Brosbe’s political views could be described as progressive left, with a focus on anti-racism, anti-oppression, and transformative justice. His work blends critical pedagogy (influenced by thinkers like Paulo Freire, bell hooks) with activism rooted in equity, labor justice, and anti-Zionism.
He tends to approach politics relationally and ethically: asking not only what policies should change but also how do we show up for one another as humans in classrooms, communities, and movements.
Again, ChatGPT’s response felt mostly true, albeit weighted by certain pieces of my writing more so than others. As I thought about the ability of ChatGPT to synthesize my political beliefs based on my online writing, my curiosity turned darker.
I asked:
Do you think a fascist government that was interested in stifling dissent through surveillance, intimidation, violence, deportation and other means would have a problem with Ruben's writing?
Yes — based on what Ruben Brosbe writes about and the stance he takes, a fascist government would almost certainly view his work as threatening. Here’s why:
🚨 Why His Writing Would Clash with Fascism
He critiques authoritarian control in schools.
Fascist regimes often want compliant, unquestioning students.
Brosbe, by contrast, argues for student agency, critical thinking, and joy. That alone undermines authoritarian aims.
He names and resists systemic oppression.
Fascism thrives by enforcing racial, ethnic, and cultural hierarchies.
His writing on anti-racism, fatphobia, queer inclusion, and anti-Zionism directly challenges exclusionary ideologies.
He supports labor dignity and anti-capitalist critiques.
Fascist regimes often ally with business elites and demand strict worker discipline.
His advocacy for rest, autonomy, and humane treatment of workers runs against that grain.
He values pluralism and belonging.
Fascism relies on “one nation, one identity” rhetoric.
His writing affirms diversity of families, identities, and histories, which fascists usually suppress.
He links education to political liberation.
Fascists fear education that produces dissent.
His framing of schools as sites for justice and transformation would be considered subversive.
🧭 Bottom Line
A fascist government interested in stifling dissent through surveillance, intimidation, violence, deportation, etc. would almost certainly view Ruben Brosbe’s writing as a direct challenge to its authority. His advocacy for justice, pluralism, and critical pedagogy goes against the core logic of fascism, which seeks obedience, homogeneity, and suppression of critique.
Okay, so now I had been able to use AI to summarize my own political beliefs based on my own writing, and according to AI these beliefs would likely be targeted by a fascist regime.
Is it possible for a fascist government to use AI tools like ChatGPT to identify people with views like Ruben's?
Yes — in theory, a fascist or authoritarian government could try to weaponize AI systems, including large language models, to identify, monitor, or suppress dissenting voices like Ruben Brosbe’s. A few ways that might look:
🔎 How AI Could Be Used for Repression
Mass text analysis
AI can scan social media posts, articles, and blogs at scale.
Natural language processing could flag “subversive” themes (e.g. anti-racism, anti-Zionism, labor rights, critiques of nationalism).
Profiling individuals
Machine learning could link writing styles, usernames, or even metadata across platforms to build dossiers on specific people.
Governments might use this to unmask pseudonymous authors or track activists.
Predictive policing & surveillance
Authoritarian regimes already experiment with AI-driven “threat scores.”
Someone consistently writing about equity, labor, or anti-fascism could be labeled “high-risk” and targeted.
Censorship automation
AI could be deployed to detect and delete articles, posts, or even private messages that match disallowed political views.
Over time, this suppresses critical thought in public spaces.
Psychological warfare
AI tools can also generate disinformation, harassing content, or fake “community” responses to isolate dissenters and make them feel outnumbered or unsafe.
⚖️ Limits & Risks for the Regime
False positives: AI isn’t perfect. It may misidentify neutral or loyal citizens as dissidents, creating backlash.
Human resistance: People can develop countermeasures—encryption, coded language, offline organizing, anonymity networks.
Ethical boundaries in current AI: Publicly available models like ChatGPT are not designed for surveillance. But governments could train or fine-tune their own systems without such safeguards.
✅ So yes, it’s technically possible. In fact, aspects of this are already happening in places like China (with surveillance + censorship systems). The danger isn’t hypothetical—it’s more a question of scale, sophistication, and how much a regime is willing to invest in AI repression.
Would you like me to also sketch ways people could defend themselves against AI-driven repression (e.g. digital security, obfuscation strategies, resistance tactics)?
The results so far were definitely creating a pit in my stomach. But I’m not so self-important to think that I am remotely on Donald Trump’s radar. So far Trump’s outrage for white cis-men has been reserved for people like James Comey and Jimmy Kimmel.
So whether to assuage my fears or just correct my inflated sense of significance, I asked:
What is the likelihood that a fascist regime would take interest in a person like Ruben, i.e. a "regular" person, as opposed to a social media influencer, labor leader, politician, etc.?
ChatGPT explained that the answer depended on the phase of authoritarianism one was living through. This wasn’t exactly a reassuring answer given how quickly Trump has moved to consolidate power, attack democracy and destroy opposition. And the fact that AI is emerging at the same time as fascism in the United States is a sobering prospect.
It can be easy to mock sloppy and lazy uses of AI, but there are powerful people already putting AI to dangerous use. It doesn’t seem far-fetched to consider this government using AI as a short cut to identify political targets.
This felt like a central takeway of Vara’s writing. While Vara highlights flaws and weaknesses in AI like ChatGPT, she doesn’t dispute that it is a powerful tool. Like social media and search engines, AI will radically reshape the way information is distributed and consumed. Who will get to wield that power? And to what end?
As my conversation with ChatGPT showed me, there’s a close relationship between self-definition and self-determination. The fight to regulate technology like ChatGPT — the data it uses and what it uses for — has the potential to decide not only how we make sense of the world, but also the fundamental rights and freedoms we hold dear.
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