"Obsidian never touches your files in a way that breaks Cowork."
It's actually the whole reason this setup works. I tried Notion for this. But it added invisible formatting garbage that made Cowork choke on my files.
You don't notice until Claude starts ignoring instructions that worked yesterday. Then you spend an hour debugging something that isn't broken. It was your "better" app quietly corrupting your markdown.
Obsidian leaves your files alone. It's the only feature that matters here.
Actually, it doesn't leave my files alone. Just use it in combination with version control and you'll notice what it does. Granted, it doesn't corrupt them. But being a former developer I hate unnecessary changes to my files that pollute the repository's history.
This is crazy-pants. In the last two days I set up cowork for the first time, created my about me, anti-ai, and my own peer-reviewed science PubMed requirements, created a Nutrition folder and researched my specific protein/fiber/plant minimum goals, installed Obsidian, created a /menu skill and created a menu plan that includes batch-fermentation instructions and pantry requirements. And now I can run this every week to make sure it uses in-season foods to feed a family with diverse nutritional needs.
The Obsidian + Cowork setup solves the right problem, but I'm curious about something practical: once you have 30+ skill files and your about-me folder grows to 50+ files, does Claude still parse everything on session start? There's a point where the 'second brain' could hit context window limits and start silently dropping instructions. Have you hit that ceiling, and if so, what's the curation strategy?
well 50 files are a lot when you only need 3-5 that are extremely clear
1/ my about-me folder has 3 files: me, my anti-AI writing style, and my company. if I need to add something, i don't create a new file. i edit the existing one.
2/ you can have 30+ skills because Claude doesn't read all of them on session start. it only reads the one you call with /
You keep amazing me. Always ahead of everything and everyone. Tnx for doing that. It helps me a lot as a one-person business owner! Keep up the good work. Would love to receive your personal md files in a DM.
Problem was always the .md files. Set up Cowork once, felt good about it, then never touched the md files again because opening one felt like reading source code (and it's quite overwhelming)! Time to give Obsidian a try.
Im so glad you admitted you're not a paid Claude affiliate, because I can tell something is definitely up with it on Social Media... Paid Claude Affiliates Mania literally within the last two weeks. Thats some serious affiliate campaigns happening.
Thanks so much - Interestingly, Skills files (.skill) are not visible in Obsidian so you have to tell it to always maintain them as an .md file so you can read/edit them and tell cowork to read them. (I am using PC/Windows).
Muchas gracias por compartir tan generosamente tus conocimientos, y por explicar tan claramente las cosas. Te agradeceria si me pudieses compartir tus archivos de configuración de Claude.
Hey Ruben! Thank you for all the information shared! Could you please share with me the .md files please? I haven't received the welcome message, so I apprectiate if you could dm me. Thank you!
Hey Ruben, love your work - thanks for putting in the hard yards and serving it up on a silver platter for us. Are you still cool to share your "about me" files as a working base? Thank you!
"Obsidian never touches your files in a way that breaks Cowork."
It's actually the whole reason this setup works. I tried Notion for this. But it added invisible formatting garbage that made Cowork choke on my files.
You don't notice until Claude starts ignoring instructions that worked yesterday. Then you spend an hour debugging something that isn't broken. It was your "better" app quietly corrupting your markdown.
Obsidian leaves your files alone. It's the only feature that matters here.
the tool you use to edit your Cowork files is just as important as the files themselves.
if your editor corrupts them, your entire setup is broken and you won't even know why.
the best tool is the one that stays out of the way :)
Actually, it doesn't leave my files alone. Just use it in combination with version control and you'll notice what it does. Granted, it doesn't corrupt them. But being a former developer I hate unnecessary changes to my files that pollute the repository's history.
This is crazy-pants. In the last two days I set up cowork for the first time, created my about me, anti-ai, and my own peer-reviewed science PubMed requirements, created a Nutrition folder and researched my specific protein/fiber/plant minimum goals, installed Obsidian, created a /menu skill and created a menu plan that includes batch-fermentation instructions and pantry requirements. And now I can run this every week to make sure it uses in-season foods to feed a family with diverse nutritional needs.
Mind. Blown.
this is exactly why I write these guides :)
so you can have a system that runs every week without you re-explaining yourself
keep going and share what you built to others
The Obsidian + Cowork setup solves the right problem, but I'm curious about something practical: once you have 30+ skill files and your about-me folder grows to 50+ files, does Claude still parse everything on session start? There's a point where the 'second brain' could hit context window limits and start silently dropping instructions. Have you hit that ceiling, and if so, what's the curation strategy?
well 50 files are a lot when you only need 3-5 that are extremely clear
1/ my about-me folder has 3 files: me, my anti-AI writing style, and my company. if I need to add something, i don't create a new file. i edit the existing one.
2/ you can have 30+ skills because Claude doesn't read all of them on session start. it only reads the one you call with /
Put the about and skill files into the specific projects?
You keep amazing me. Always ahead of everything and everyone. Tnx for doing that. It helps me a lot as a one-person business owner! Keep up the good work. Would love to receive your personal md files in a DM.
hi Peter - follow these steps:
1/ search for my welcome email ruben@substack.com
2/ reply with “I’m not a robot.”
3/ you’ll receive a new email from me.
PS: the files are inside the How to AI library - named “.md files”
and if ever there's no welcome email, let me know and i’ll dm you :)
Problem was always the .md files. Set up Cowork once, felt good about it, then never touched the md files again because opening one felt like reading source code (and it's quite overwhelming)! Time to give Obsidian a try.
updating it feels like debugging code and we're not coders here
now Cowork wont work with files that have the outdated version of you
Im so glad you admitted you're not a paid Claude affiliate, because I can tell something is definitely up with it on Social Media... Paid Claude Affiliates Mania literally within the last two weeks. Thats some serious affiliate campaigns happening.
i just really use it for work and i love sharing how its been transforming my life :)
I want a copy of your files pls
1/ search for ruben@substack.com in your email (the one you used to subscribe) to find my welcome email. also check spam/promotion.
2/ make sure to click the “Step 1 - Get Prompt Library” button. it will send me an automatic email then you’ll receive the How to AI library.
PS: the files are inside the How to AI library - named “.md files”
Do you have advice for setting up a similar system on an iPad? Mist this be on a laptop or desktop?
Cowork is desktop app only :)
Thanks so much - Interestingly, Skills files (.skill) are not visible in Obsidian so you have to tell it to always maintain them as an .md file so you can read/edit them and tell cowork to read them. (I am using PC/Windows).
thanks for sharing, Angela
Sir,
I would love to get your setup md files as a good starting points for my own setup !
hi,
1/ search for ruben@substack.com in your email (the one you used to subscribe) to find my welcome email. also check spam/promotion.
2/ make sure to click the “Step 1 - Get Prompt Library” button. it will send me an automatic email then you’ll receive the How to AI library.
PS: the files are inside the How to AI library - named “.md files”
Muchas gracias por compartir tan generosamente tus conocimientos, y por explicar tan claramente las cosas. Te agradeceria si me pudieses compartir tus archivos de configuración de Claude.
1/ search for ruben@substack.com in your email (the one you used to subscribe) to find my welcome email. also check spam/promotion.
2/ make sure to click the “Step 1 - Get Prompt Library” button. it will send me an automatic email then you’ll receive the How to AI library.
PS: the files are inside the How to AI library - named “.md files”
Hello, thanks for this insightful post. You mention you could send a copy of your files - can you DM me with details please? :)
sure :)
1/ search for ruben@substack.com in your email (the one you used to subscribe) to find my welcome email. also check spam/promotion.
2/ make sure to click the “Step 1 - Get Prompt Library” button. it will send me an automatic email then you’ll receive the How to AI library.
PS: the files are inside the How to AI library - named “.md files”
Hey Ruben! Thank you for all the information shared! Could you please share with me the .md files please? I haven't received the welcome message, so I apprectiate if you could dm me. Thank you!
hey - follow these steps:
1/ search for my welcome email ruben@substack.com
2/ reply with “I’m not a robot.”
3/ you’ll receive a new email from me.
PS: the files are inside the How to AI library - named “.md files”
and if ever there's no welcome email - dm me :)
So inspiring! I just realized I could be using Claude more effectively. I would love to get your files for setting up Cowork Ruben.
hi - i replied to your dm
hey Ruben, can I have a copy of your files? and the instructions you added for Cowork in the Settings section of the Claude desktop app?
1/ search for ruben@substack.com in your email (the one you used to subscribe) to find my welcome email. also check spam/promotion.
2/ make sure to click the “Step 1 - Get Prompt Library” button. it will send me an automatic email then you’ll receive the How to AI library.
PS: the files are inside the How to AI library - named “.md files”
i shared instructions for Cowork here: https://ruben.substack.com/p/claude-cowork-20
Hey Ruben, love your work - thanks for putting in the hard yards and serving it up on a silver platter for us. Are you still cool to share your "about me" files as a working base? Thank you!
of course :)
1/ search for ruben@substack.com in your email (the one you used to subscribe) to find my welcome email. also check spam/promotion.
2/ make sure to click the “Step 1 - Get Prompt Library” button. it will send me an automatic email then you’ll receive the How to AI library.
PS: the files are inside the How to AI library - named “.md files”
Thanks Ruben. Unfortunately don't have the welcome email you mention, checked all folders...