5 insane Claude Cowork + Obsidian use cases (steal them)

Summary

most people using Obsidian and Claude Cowork are doing it wrong. they clip everything they see, build a giant brain, and never actually use it. the vault is not storage. used right, it is leverage.

here are the five systems I actually run:

1. the handoff. Claude forgets. the longer you use one chat, the more its context window fills up, and it starts to hallucinate and lose track of where you left off. the fix is a handoff doc. at the end of a work session I tell Claude to write a handoff into my Obsidian vault, and next session it reads that doc and picks up exactly where we stopped. I use this on jerred.com, which I rebuild in 30 minute chunks.

2. websites. web content is hard, so most people never update their site. with Obsidian plus Claude, every page and post lives as a file in my vault. Claude writes, I publish. it even keeps the site optimized for SEO and AI search, the work you used to pay thousands a month for.

3. the client vault. you have all the content from a client (emails, Slack, meeting notes) but no context. one folder per client, plus a signal file where Claude watches for churn risk, key person risk, and upsell openings you would otherwise miss.

4. the family operating system. running a family is harder than running a business, and more important. calendar, conversations, health, recipes, traditions, and a brief file that surfaces what needs your attention in the next 14 days. a personal assistant for 20 dollars a month.

5. fitness. most programs have no feedback loop. feed Claude your training history and injuries, drop in today’s workout, and let it make the small adjustments that keep you safe. it is not better programming than Garage Gym Athlete, but it is a coach layered on top of it.

the thing that ties all five together is the index. it is the map that turns a pile of notes into an operating system Claude can actually run. without it, the whole thing gets messy.

Transcript

the setup

let’s talk Obsidian and Claude Cowork, because it is the most powerful AI stack out there, but 99 percent of people are using it incorrectly. they build some sort of brain that they are never going to use, and they never unlock the full potential. so in this video I am going to show you five Obsidian and Claude Cowork use cases you can use today, so you can build your own operating systems and unlock capabilities that were not even possible before all of this AI madness.

I am going to save you some time, and probably make you some more money. if you do not know who I am, my name is Jerred Moon. I have hit the Inc. 500 twice, I run five total companies, and I am optimizing all of them with AI one week at a time, showing you the systems that work. so if you are ready to build something cool, let’s dive straight in.

use case 1: the handoff

I do not know why people are not talking more about the handoff. the problem is that Claude forgets. if you have not noticed, Claude gets dumber the longer you use it, and so does ChatGPT. it is called a context window. if you try to use the same chat over and over again, at some point that window maxes out, Claude starts giving you improper responses, it hallucinates, and it does not know where you picked up.

you might have a big project you are working on, and you cannot just keep coming back to the same window doing the same thing over and over. the solve is a handoff doc, and you are not actually going to do any of it yourself. Claude does all of it. sometimes I tell Claude to go do a thing I think will take a week, and it does it in 30 seconds.

what I have here is my actual website, jerred.com. it is a personal brand site, real URLs, all live. the current site is the old one. I am working on a new version, updating a bunch of posts, doing all sorts of stuff, but I am doing it in small chunks, 30 minutes here, 30 minutes there. the first time I started, the problem was obvious: Claude kept forgetting, or it would start making mistakes and lose the scope of the project.

so I started the handoff document. after I work on the site for 30 or 40 minutes and I am done for the day, I tell Claude, in my Obsidian vault, go ahead and add a handoff document for this project, so the next time I open Claude we pick up right where I left off. that is all you have to say. I did not write a single word in it. Claude built the whole thing for itself, 4,260 words, the full project mapped out.

so the next time I log in, I just say, we are working on jerred.com, pull up the handoff document, let’s get into next steps. and we are working again in a brand new window, a fresh context window, with none of the Claude forgets or Claude hallucinates problem. whether you are building something for your company, doing client work, whatever it is, have Claude build a handoff document and store it in Obsidian. that is insane use case number one, and it makes big projects so much smoother.

use case 2: websites

the next one is websites. the problem is that web content is hard. I love how Claude builds the artifact for me and it looks like a caveman did it. yes, web content is hard, Claude. the solve is simple: Claude writes, you publish.

I mentioned jerred.com. in a previous video I showed how to build a website, and we built a client site for a fictitious Coach Marcus following the StoryBrand framework. you can build these amazing things, and all of the files just live in my Obsidian brain. these are the files for the Coach Marcus site, and here is jerred.com, every blog post, every page, all in Obsidian. when I talk to Claude, I am having it build all of those files in the vault. I just say, we are building a website, build out all the files and folders inside my Obsidian brain, and it gets to work.

web content is annoying. usually the reason people do not update things is that you have to go into the web editor, upload the images, change the text yourself, all of it. it is cumbersome, so people do not update regularly, and worse, they are not optimizing for AI search or for SEO. you do not have to be an expert in any of that anymore.

building it this way, Claude does all of it for you. to maintain the site, type up a draft for a blog post and say, publish this. go further and say, update everything to the most up to date, optimized SEO strategies on the planet, implement them, and run them by me one by one for approval. it is making web content so easy it is crazy. you used to pay people thousands of dollars a month to optimize for SEO. Claude will do all of it, you throw it in Obsidian, and it gets updated automatically.

use case 3: the client vault

here we have the client vault. what I put together for this video is fictitious, because I am not going to show you my real clients. the problem is we all have content. if I am working with a client, I have emails back and forth, Slack messages, and notes I can generate with something like Granola. it is great that we have transcripts, emails, and messages, all the content to work with clients well. but we have content without context, and this is where it gets insane.

you build out folders in Obsidian and tell Claude to start dumping everything in there. that becomes your client brain, one folder per client, and then Claude gets ahead of things and looks for signals. I had Claude mimic what I actually do and build out some fake companies. Apex Manufacturing has all the emails, all the meetings, the about the company file, a running list of everything I have ever done with them.

the most important file is the signal file. right now it says the churn risk is high, estimated window 72 days, three converging signals across the file set, none obvious in isolation, together they are loud. you set up the signal file and tell Claude to get ahead of all the data coming in: is someone unsatisfied, are they not making progress, are they about to churn. use all the data I give you to keep this signal file current so I can stay up to date with my clients.

another one, Bright Line Studios, flagged key person risk as severe. the account is healthy, but the problem is structural: every pillar holding the customer up is the same person, Marcus Webb. if Marcus leaves before August 14th, nobody there can or will authorize a renewal. one more, North Star Logistics, flagged an upsell opportunity: all the problems they are expressing are solved in your upper tier plan, they do not even know it exists, and you have not pitched it yet, so go do that.

this takes the content you already have and puts context behind it, so you are not constantly trying to remember what is going on, especially with a lot of clients. there are other examples where it notices that when someone started working with you their emails were around 140 words, and now they are sending you four and 15 word emails. not sure it is a signal yet, but something to watch. things you might not catch right away, Claude catches when you set up the signal file.

use case 4: the family operating system

use case four is the family operating system. I am married, I have three kids, and running a family is like running a business. honestly it is more complicated, and it is definitely more important. the solve is to build a family brain. this was one of the first things I tackled. again, I will show you fictitious stuff, because I do not need you in my personal business.

you can set up a family OS in Obsidian: the calendar, conversations you had, connect iMessage if you want, health, people, recipes, stories, traditions, and the brief. the brief is the important one. it says, this week, here is what needs your attention. Wren’s preschool spring program is happening. date night with Mara is Saturday, May 30th, and you have not picked a place, here are the last three you mentioned. then it looks forward at the next 14 days.

something that happens to me, and just happened toward the end of school, is the kids had recitals and plays and talent shows all popping up. I needed those on my calendar, not just to know they were there, but to be nudged to prep for them, plus an anniversary and everything else going on. it is really helpful to have something pulling all of that together.

it also becomes the family history book, which as a big family guy I think is really cool. I can dictate a story and it puts it in there. you could hand this off to future family members to read, or have Claude write a book about your family if you put enough in. putting in calendar, conversations, the health of your relationships, and recipes, then having the brief file surface what to pay attention to, is like a personal assistant reminding you to grab flowers before you head home. that is the level, for 20 dollars a month.

use case 5: fitness

the fifth and final use case is fitness. I am a big fitness guy. if you did not know, I run the company garagegymathlete.com. this is something I am starting to recommend our athletes do. the problem is that most fitness programs have no feedback loops. sometimes I have so much coaching information, or I work with advanced athletes, that I do not realize what beginners do not know. the solve is to let Claude be the coach.

our Garage Gym Athlete programming is 25 dollars a month, some of the best programming on the planet, but it is not one on one coaching. I have tried multiple times, and I do not think Claude can write better programming than we do. where we do not help athletes as much as we could is the feedback loop. if you hurt your back two years ago, that needs to be accounted for when we program deadlifts this week. if you have a shoulder issue and we are going overhead a lot, you need to adjust.

so you take solid programming and create a feedback loop file. first you work through Claude to build an intake file about you: your goals, your injuries, your limitations, what has worked, what has not. then you say, here is my workout for today based on everything you know about me, what adjustments would you make. it might see a barbell row and say, based on your hinge limitation, do a one arm kettlebell row supported on a bench.

it makes those small adjustments while you stay inside the program that was set for you, and now you have a feedback loop. it makes fitness so much better, like adding a coach on top of really solid programming. if you follow any workouts that are not one on one coaching, this is a phenomenal way to add a feedback loop that keeps you safe and healthy, for 20 dollars a month.

the vault is leverage, not storage

the bigger takeaway is that the vault is not just storage. what I see online about Obsidian and Claude is people saying to clip everything you ever see and throw it all in there, and maybe someday it will be useful. that is not helpful. the vault is not storage, it can be turned into leverage.

if you are a business owner, get your wheels turning about how many systems you could build. I gave you the website, the handoff, the client vault. you can build systems Claude can run, notice patterns in, and get ahead of trends with. this gets really powerful when you combine Obsidian, used the way it should be, with Claude. after that, you are creating leverage, not building a brain that stays useless.

here is the deal. these five use cases work, but you need to understand one concept, and I call it the index. you can build the most powerful AI stack on the planet, but if you do not follow the index method, Claude and Obsidian get messy at some point, I promise you. the index is what turns a pile of notes into an operating system Claude can actually run. it is the map, and without it you end up lost.

I broke down exactly how to build your index in the video, How I Use Obsidian and Claude to Run My Life. watch that one next, then go build some more cool stuff.