Claude Cowork: The Ultimate Engine for Objectively Viewing Your Own Thought Evolution
I had been pondering whether Claude Cowork actually has any practical uses.
Then I discovered yet another new way to use it. Cowork is a work companion that autonomously executes multiple tasks based on massive amounts of data that surpass what chat can handle.
Claude Cowork: The Ultimate Engine for Objectively Viewing Your Own Thought Evolution
As you know, Claude Cowork is not merely a chat tool. It is an AI agent that directly accesses your local file system (in my case, Obsidian) and autonomously completes tasks.
You can either place Obsidian in a folder that Cowork can access, or use the combination of Local REST API + Obsidian MCP Tools to have Cowork retrieve information via MCP—both approaches work effectively.
What makes this tool truly disruptive is its ability to execute against three years of my living thought data with precision and speed comparable to the Observe and Orient phases of the OODA loop (Observe, Orient, Decide, Act). Sounds pretentious, right?
Enabling High-Dimensional Differential Extraction Across Time—Something Difficult to Do Alone
Why bother using Claude Cowork? Because I know how vague human memory is and how conveniently it gets rewritten.
Breaking Through the Limits of Observe: It is humanly impossible to extract every single description on a specific theme from three years of notes numbering in the thousands. Information obtained through word searches is only a fraction. You need to extract information while considering intent as well. Cowork autonomously repeats searching and browsing, comprehensively observing all data.
Deepening Orient: The thinking habits of my three-years-ago self versus my current self, the subjects of interest, and changes in word choice. By having AI identify these differences, I can confront my own growth or stagnation as objective facts that I could never have noticed on my own.
This is not for reminiscing about the past, but for gaining an advanced metacognitive environment to use my past self as a stepping stone toward new ideas.
This is an effective environment that I could not achieve simply by using Obsidian as RAG with Dify. What was limited to merely retrieving information has now evolved into comprehensive information retrieval and analysis.
Using Three Years of Obsidian as Fuel to Gain Insights for the Future
I have actually shared my three years of Obsidian data with Claude Cowork and am running workflows like the following:
Step 1 (Observe): Scan all notes containing my views on generative AI from 2023 to the present (2026).
Step 2 (Orient): Analyze chronologically at which points and through which technological breakthroughs my thinking changed.
Step 3 (Insight): From that trajectory of change, have it present blind spots in thinking that I should focus on in the next year.
[Image of spinning the OOA loop with Cowork]
Previously, doing this required spending several days reading through past notes. However, with Claude Cowork, while generating intermediate analysis files in the working folder, it writes up a map of my own thinking in just minutes. This is not mere summarization—it is prototyping for the future through dialogue with my past self.
This is an efficient and effective way to reuse PKM (Personal Knowledge Management).
Continuously Updating Your Thinking Together with an AI Colleague
In these uncertain times ahead, there is no time to cling to past success stories. On the other hand, data about what you thought in the past and how you experimented is your own unique asset that belongs to no one else.
Stop using Claude Cowork as just a summarization tool.
Cowork is literally a partner for increasing the speed of your thinking and running the OODA loop faster than anyone else. Whether you let three years of data sleep as mere records or turn it into a power plant for your next ideas—that key depends on how you master Cowork as an agent.
I will continue to gaze into this abyss of the ultimate mirror and refine my thinking day after day.
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