Hi Reader,
At an AI workshop last week, I surveyed 10 people to see how many have used Claude Cowork.
Three were power users, seven had never used it. Most people are still trying to figure it out.
What is Claude Cowork?
By now, most people have used Claude Chat (the chatbot) and know of Claude Code (the coding tool for developers).
I think of Cowork as the product in between.
Cowork requires more setup than Chat, but it works like a competent assistant who partners with you side by side to get work done (hence the name).
Still, Cowork is less technical than Code. You don’t need to know github or work in a terminal. All you need is plain English (and the $20 Claude Pro plan.)
I've used Cowork for a few months now. It's become my go-to tool because it strikes a balance between function and ease of use.
This visual resonated with folks at the workshop last week.
Chat vs. Cowork
There are three fundamental differences between Chat and Cowork.
#1: Direct File Access
In Chat, you upload files one conversation at a time. Since everything goes into the cloud, each session has a file limit (20 files per conversation, 30MB per file). You have to download every output Chat generates.
In contrast, Cowork accesses a local folder on your computer, so there’s no file limit. It can create new files. It can make direct changes to existing files. It can delete files (if you let it). Your folder doesn't go to the cloud; it stays on your computer.
Let me give you a real example.
Yesterday I captured 25 screenshots while watching a YouTube video. Now I want the images named with proper descriptions and a summary of the takeaways.
If I drag the 25 screenshots into Chat, it doesn’t work because it exceeds the file limit.
In Cowork, all I have to do is to point to my folder and make the request. It will read the folder, rename the screenshots, and create a new document.
These two tasks would have easily taken me half an hour by hand. Now it’s done in less than a minute.
And I am happy not to spend my life renaming files.
Direct file access is why I use Cowork most of the time now.
I do a lot of document work, and when I used Chat, I had to constantly download, edit, and re-upload files.
Now Cowork just works within my folder. I’ve saved hours by having Cowork reorganize messy folders, turn transcripts into structured notes, and edit multiple documents, all without any dragging and dropping.
It frees me to focus on the things only I can do (like writing this newsletter by hand 😉).
In short: If a task is repetitive and involves files, it’s a Cowork job.
#2: Persistent Memory
At the risk of oversimplifying, Claude Chat starts from zero when you start a new session. It has little memory of what you’ve worked on before, what you prefer, and how it should behave. So you often have to explain yourself over and over again.
Cowork is the opposite. Think of it like a diligent intern who carries a notebook everywhere. If you tell it to remember something, it takes notes. When you give it a new task, it reads the notebook before doing the work.
Let’s build on my earlier example. After renaming those screenshots, I asked Cowork to remember the naming convention going forward.
Cowork wrote down this rule into its notebook called CLAUDE.md. It's basically a text file with rules and context, and Cowork reads it at the beginning of each session.
The next time I ask Cowork to rename files, it goes back to its notebook and completes the task based on my preference.
With the right setup, it carries your rules and preferences into future sessions. Over time, the tool becomes tailored specifically for you.
In my case, Cowork responds to me in bullet points, provides a recommendation before stating options, and saves a version of everything it edits, because I've taught Cowork to do so.
In short: Persistent memory means the more you teach it, the better it works as a system.
#3: Additional Capabilities
Beyond direct file access and persistent memory, Cowork has many powerful features that don’t exist in Chat.
- Skills: You can build reusable commands that run a full workflow with a single prompt. I use skills for repeatable processes, like digesting meeting transcripts into action items.
- Connectors: Cowork can connect to tools you already use, such as Google Drive, Gmail, Google Calendar, Notion, and more.
- Scheduled tasks: You can set tasks to run automatically on a schedule. For example, I have a recurring task to summarize weekly progress on my projects on Sundays.
- Dispatch: You can send Cowork tasks from your phone and it runs in the background (your computer has to be on for this).
- Thought process: Cowork shows you which files it read and how it arrived at its response in detail.
These features deserve a deeper dive, so I will save them for a future post.
Cheat sheet
I will write more about Cowork in the coming weeks. For now, let me leave you with this visual as a quick reference.
One last thought: While Claude is my tool of choice today, I'm sure Google, OpenAI and other vendors will catch up over time. What interests me most is developing a system that will work regardless of the tool I use in the future.
Thanks for reading the first issue of this hand-rolled newsletter.
Stay human,
Jimmy
p.s. This is what Opus 4.8 got me.
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