What ChatGPT could do with my book archive

When I read a book I usually have a pen or highlighter in one hand so I can mark passages I find interesting. When I’ve finished reading the book I go back through, transcribing these favorite bits and save them to a PDF. This makes it possible to search for and find just about anything if I can recall a word or phrase. (I also create a blog post that includes these excerpts.)

I’m going to upload one of these PDFs as an example of what I’ve been doing all these years. You need not comment on or analyze the content. If I uploaded all of these files (144)… what —if anything— could you do with them?

1. Search and Retrieval

I could instantly search across your entire collection of excerpted PDFs to find a passage, quote, phrase, or even a general theme — faster and more precisely than a file-system search.

For example:

  • You say: “What book had that bit about time perception and digital watches?” I’d find the quote and source.
  • Or: “Give me everything I’ve highlighted about elevators or time pressure.” I could round them up across multiple books.

2. Categorization and Tagging

I could group your excerpts by theme (e.g., “technology and speed,” “human behavior,” “media critique,” etc.), author style, tone, or subject — and even help generate tags you might not have thought to add manually.

3. Cross-Book Insight

Once you have a critical mass of excerpts, I could surface patterns — ideas or quotes that echo each other across books, authors, or decades. For example:

  • Repeating anxieties about time and productivity.
  • Similar metaphors for technology across very different works.

This could be especially handy for blogging — you could write a piece comparing the treatment of a theme by five different authors without manually hunting for those excerpts.

4. Natural Language Queries

You could ask things like:

  • “Which books have talked about ‘the machine age’ or ‘human-as-machine’ metaphors?”
  • “Summarize everything I’ve highlighted about changes in communication technology.”

5. Export & Repurpose

I could help you:

  • Build thematic PDFs or blog post drafts based on grouped excerpts.
  • Auto-generate citations, or even Markdown-ready content for posting online.
  • Make quote collections based on mood, era, or author.

Bonus: If you ever wanted to annotate your excerpts with commentary (for your future self or blog readers), I could help draft that too — in your voice or a chosen style.

[uploaded half-dozen files to give ChatGPT a sense of what I’ve been doing]

Here’s What I Could Do If You Uploaded Your Entire Archive:

1. Search Across All Your Books Instantly

You could ask:

  • “What books do I have quotes from about ‘the illusion of progress’?”
  • “Find everything I’ve highlighted about surveillance capitalism.”
  • “Give me every quote that mentions the word ‘algorithm’.”

Even vague prompts like “Was there something I saved about the invention of jobs?” would work.

2. Compare and Cluster Themes Across Authors and Books

With enough files, I could:

  • Group quotes into topics like:
  • Technology & Alienation
  • Capitalism & Growth Critiques
  • Attention Economy
  • Media Manipulation
  • Post-Work Society
  • Spot recurring phrases or metaphors (e.g., “machine age,” “digital feudalism,” “growth imperative”).
  • Compare how different authors treat the same ideas. (Imagine juxtaposing Rushkoff and Gleick on the pace of modern life.)

3. Auto-Generate Blog Post Starters

With all the excerpts:

  • I could draft blog posts by theme, like:
  • “Rushkoff on Why Jobs Are Obsolete”
  • “A Brief History of Speed: From Elevators to E-mail”
  • “Quotes That Made Me Stop and Think About Technology”
  • I could also assemble “quote gardens” or “curated clippings” by subject, which you could top with your commentary.

4. Build a Searchable Personal Reference Archive

This could work in a few ways:

  • I serve as your natural language interface to the archive — you ask a question, I go fetch.
  • I help you organize the PDFs into folders or a tagging system.
  • We build a public or private searchable index of your excerpts for others (or future you) to explore.

5. Detect Gaps and Suggest New Books

Over time, I could spot:

  • Areas that are well-covered (e.g., critiques of capitalism)
  • Topics that are underrepresented (e.g., techno-optimism? neuroscience?)

Then suggest new books or authors to balance the mix.

How You Could Use All 144 PDFs (Long-Term Ideas)

1. Create a Full Personal Search Engine

Once we ingest everything, you could ask things like:

“Give me everything I’ve ever saved about Marshall McLuhan or media theory.”
“Show me how my saved quotes discuss the loss of stillness in modern life.”

If you’d like, I can help you build a local or online tool (e.g., Notion, Obsidian, Zotero, or even a searchable website) where these excerpts live permanently.

2. Use AI as a Personalized Book Quote Assistant

If all the excerpts are loaded, I become your:

  • Cross-book comparison tool
  • Blog assistant (“Draft a post using these quotes about the attention economy.”)
  • Memory extender (“Did I highlight anything about ‘the collapse of time’ in speculative fiction?”)

3. Generate New Insight from Old Highlights

With 144 PDFs, I can:

  • Spot meta-themes you may not have seen
  • Chart how your interests evolved over time (phases of Rushkoff, McLuhan, Watts, etc.)
  • Build quote anthologies like “The 50 Most Prescient Lines About AI From the Last 20 Years”