Thanks - that’s great advice. I do something similar but I use Workflowy which imo is better due to its node structure. I have written an MCP server for Claude to use it - the template md file though is critical.
I use Workflowy too (have for years) but don’t know what an MCP server is or how to write one. Wonder if Workflowy can just make the conversion natively — would be a smart business move!
It would be smart. But the ability to use it within a model like Claude is super helpful. Ask a friendly engineer how to install this : https://github.com/dromologue/workflowyMCP
You can check Tana for a similar approach (I’m just a customer ..). Like obsidian it gathers full context, and has a powerful “supertags” (objects) that help to structure a basic ontology. The desktop version has a MCP server, and connecting to Claude code is literally a 2 seconds click … Of course the quality of the output depends on the adherence to the ontology, which in the end may be too much for quick, heuristic, work … Just starting to play with it.
The Obsidian + Claude Code pairing is exactly what I run too. The persistent context through markdown files changed everything for me.
One thing I learned the hard way: the CLAUDE.md file structure matters more than the content. After 1000+ sessions, I found that behavioral rules ("execute first, refine later") beat detailed task instructions every time. The agent needs personality constraints, not step-by-step playbooks.
Also, folder-level CLAUDE.md files are underrated. One root file plus project-specific overrides keeps context lean without losing domain knowledge.
As for claude md - this is such dense topic. I was testing milion different things and outcomes are also - very different. Plus with agentic work - the context window is always problematic :/
How would I plug this into a cloud based email like Outlook please? It seems it needs to be pointed at files and directories? Separately, any thoughts on making this work as a tool for a small team? The starting point would seem to be just give it access to common workspace files, and appoint a “driver”? But there would need to be some instruction to Claude about who’s who in the zoo?
Can we do this with notion vs obsidian? I understand that obsidian is local but I have everything in notion and I need the cloud accessibility. Curious on any specific notion setup to resemble what you described here.
You will likely need to use an MCP to connect to Notion. I haven't tried it yet. But I've seen articles out there on how to set up something similar with Notion.
Thank you for sharing! I started using this system a few days ago and it’s been awesome. I’m getting a lot done and feel like AI finally is truly an unlock.
Thanks - that’s great advice. I do something similar but I use Workflowy which imo is better due to its node structure. I have written an MCP server for Claude to use it - the template md file though is critical.
I use Workflowy too (have for years) but don’t know what an MCP server is or how to write one. Wonder if Workflowy can just make the conversion natively — would be a smart business move!
It would be smart. But the ability to use it within a model like Claude is super helpful. Ask a friendly engineer how to install this : https://github.com/dromologue/workflowyMCP
Thanks for sharing!
Sounds interesting!
That’s awesome!
Thank you for this. You've made the set up really accessible for people just starting out.
Thanks so much - just glad to help 🙏
You can check Tana for a similar approach (I’m just a customer ..). Like obsidian it gathers full context, and has a powerful “supertags” (objects) that help to structure a basic ontology. The desktop version has a MCP server, and connecting to Claude code is literally a 2 seconds click … Of course the quality of the output depends on the adherence to the ontology, which in the end may be too much for quick, heuristic, work … Just starting to play with it.
Thanks for the recommendation! I'll check it out
The Obsidian + Claude Code pairing is exactly what I run too. The persistent context through markdown files changed everything for me.
One thing I learned the hard way: the CLAUDE.md file structure matters more than the content. After 1000+ sessions, I found that behavioral rules ("execute first, refine later") beat detailed task instructions every time. The agent needs personality constraints, not step-by-step playbooks.
Also, folder-level CLAUDE.md files are underrated. One root file plus project-specific overrides keeps context lean without losing domain knowledge.
Wrote up the full structure that survived a year of daily use: https://thoughts.jock.pl/p/how-i-structure-claude-md-after-1000-sessions
Thanks for sharing this. Definitely intrigued by folder level CLAUDE.md
I've gone back and forth on their usefulness.
Love the aesthetics of your SS, btw!
Thanks - I am 90s kid - love pixel-art.
As for claude md - this is such dense topic. I was testing milion different things and outcomes are also - very different. Plus with agentic work - the context window is always problematic :/
Just came across this paper that's got me rethinking my claude.md file: https://arxiv.org/html/2602.11988v1
Really enjoying your stuff!
Thanks much, Ben! 🙏
I think what's missing in the "operational co-pilot" mode is an ability to integrate with email - or have I overlooked something?
No, you haven’t missed anything. I just don’t have it set up that way right now.
BUT…
You can easily plug it into your email and build some workflows around it.
How would I plug this into a cloud based email like Outlook please? It seems it needs to be pointed at files and directories? Separately, any thoughts on making this work as a tool for a small team? The starting point would seem to be just give it access to common workspace files, and appoint a “driver”? But there would need to be some instruction to Claude about who’s who in the zoo?
Hmm. I'm sure Outlook has an API you could use. Regarding cloud-based files, you could probably do that too with Google Drive or Sharepoint
You can do it with the online Outlook. Claude Code can read screenshots of your inbox or any folder you choose. Ask Claude to set it up for you.
Can we do this with notion vs obsidian? I understand that obsidian is local but I have everything in notion and I need the cloud accessibility. Curious on any specific notion setup to resemble what you described here.
You will likely need to use an MCP to connect to Notion. I haven't tried it yet. But I've seen articles out there on how to set up something similar with Notion.
I’m not sure, but probably!
Obsidian does have a feature where you can sync your vaults (kinda like cloud access)
Thank you for sharing! I started using this system a few days ago and it’s been awesome. I’m getting a lot done and feel like AI finally is truly an unlock.
So glad it helped! 🙏
Great advice, thanks!
Glad you found it helpful! 🙏
Thanks for the restack! 🙏