Transcription
Hey everyone. So, what if I told you that I went from drowning in unorganized Apple Notes to having an AI agent that automatically organizes them, creates connections I'd never seen before, and even helps draft my weekly status reports? And here's the best part. It only takes about 10 minutes to set this up. And in terms of AI workflows, this is a real easy one.
So, first of all, for those who don't know me, my name is Jason Seir. I'm currently the VP and head of design for both Cisco's security and AI businesses. I've spent 25 years learning to build software that people actually love to use. And this channel, well, it's where I share things that I found that actually work. It's for designers, it's for product managers, and it's for engineers who care about creating impact and not just shipping features. Oh, and these days, spoiler alert, I'm posting a lot of content related to AI. So, if any of that resonates with you, maybe consider subscribing.
All right, let's get into it. So, look, I know what you're thinking. This is just another productivity system video, right? But listen, hear me out because I've tried everything. I'm a total knowledge management nerd. I've read Building a Second Brain by Tgo Forte multiple times. I've got the PAR structure. I've tried Getting Things Done. I've tried Zetocasten. You name it. For the past few years, I've landed on a pretty good hybrid system using Apple Notes as my digital repository and paper notebooks as my daily catchall. And for the most part, it worked until it didn't.
So, let me show you exactly where it broke down because I bet you'll recognize this. I had thousands of notes in Apple Notes and hundreds of them were sitting in the root directory with names like "untitled," "quick thought," or "just note to self." My PAR structure. Yeah, it existed and it was pretty solid, but probably 60% of my notes never made it into the right folder. A lot of them sat in this main notes directory, main notes folder, and would not get processed properly. Sure, I'd spend some Sunday mornings doing digital housekeeping and literally, literally spend two to three hours filing notes, creating links, processing my my paper notebook. But still, I never really felt like I was on top of it.
Here's a great example. I had three different notes about design system scalability from different meetings that were probably a few months apart. Never connected them. When I actually started thinking about something strategic related to design systems, I basically had to start from scratch because those insights, they were buried in notes titled "Tuesday staff meeting" or "thoughts on components." The breaking point for me was when I finally calculated I was spending hours a month just organizing and not actually using my knowledge. And that's when I knew that the system was running me and not the other way around.
So here's exactly what I did. And I'll give you the actual steps. First, I decided I would go back to a notes tool like Obsidian that would allow me to keep my notes in a regular file system as markdown documents. And you're going to see why this is important in just a minute. The first step to this was exporting notes out of Apple Notes. I needed to get all of that data out of Apple Notes. And Apple does not seem to give you an easy way to do this, but Obsidian does. Obsidian has an importer plugin, and with one click, all 2,000 plus of my notes were exported with all my Apple Notes structure still uh held intact.
Then the next step was setting up my AI brain. And this is where it gets really good. So, I pointed cursor at the Obsidian Vault folder that I had just created, which is all just markdown files. For those of you not familiar with Cursor, it's an AI powered development tool. It has an AI assistant built right into it and you can point it at a project or at a set of files and then you can use that AI to manage those files. In most cases, it's used for vibe coding, but I also like to use it for vibe librarianing. Vibe librarianing, is that a thing? I don't know. Anyhow, what I did next was once I pointed my cursor at my knowledge system, I put in a prompt that said exactly this: "You're my knowledge management assistant. Please analyze my vault structure and note-taking patterns and tell me what you observe about how I organize the information." The AI's response was really eye opening. It found patterns that I didn't know I had. And it also recognized that I was using a PAR system and described things really accurately.
So this was my next prompt: "Based on the PAR method, please suggest where each of my unfiled notes should go and consider projects are active and have an end date. Areas are ongoing responsibilities, resources are for future reference, and archives are for things that are no longer active. Show me your reasoning before taking action." The AI processed this for about 30 seconds, gave me a few different strategies on how it was going to organize things. I picked one, I tweaked a couple edge cases, and boom, 300 of my unfiled notes were organized in seconds. This was amazing.
Then my next step was focused on building out my knowledge graph. So this is what I asked at this time: "Find all potential connections between notes. Create bidirectional links using this format. And focus on conceptual connections, not just keyword matches." Boom. Within seconds, it created 847 new connections between notes. My note about psychological safety in teams was now linked to a note on design critique best practices and another note on remote team culture. These things were obvious in hindsight, but they were invisible before.
Now, this is the cool part because this part was totally unplanned, but it became probably one of the most valuable aspects of this. The next thing I did was I asked it, "You've read all my notes, my challenges, my thinking patterns, my goals. If you were an executive coach specifically focused on design leadership, what questions would you ask me?" It generated 64 questions in seconds. Not generic stuff, but things like, "Your notes mention a tension between innovation and stability in a number of different places. How are you bouncing these?" It also told me that I've captured 12 different definitions of what great design is, and it asked me, "What's your definition?" Wow, these were great questions. I didn't want to let these slip away.
So, what I ended up doing was asking, "How do I maintain these or or how do I take action on these in a systematic way?" And the AI actually recommended that I create an N8N workflow, which I did. So now every Friday afternoon at about 3:00, I get an email and it has one of those questions in it along with a link that creates a new note in my file system. I spend about 10 or 15 minutes reflecting on that question, capturing my notes, and all of that reflection goes back into the system. And so it's like having a coach that actually knows all of my context all of the time. It's really powerful.
So let me tell you a little bit now about my exact sort of system and how I use it. So on a daily basis in Obsidian, there's a a notion of a daily note and it's based on a template in the system. So every day I create my new daily note and this becomes the place where I capture everything. Everything goes in there. Meeting notes, random thoughts, links to things, no filing, no organizing. I just capture it.
Then on Saturday mornings, I take about 15 minutes and I run through my weekly agent routine and Cursor. And it does four things for me that are really important. First, it files all of the notes that are sitting in my inbox and puts them into the proper proper PAR folders. The next thing it does is it goes through all of those notes and all of my daily notes looking for all the action items that it can find or things that look like action items and it creates Apple Reminders for those things with due dates. Then it goes through all my daily notes and pulls out all of the important knowledge snippets, permanent notes, and files them in the most appropriate places in my system. And then lastly, it goes and it creates a first draft of my weekly status report that I send to my boss. And it doesn't write this report, but it gives me a list of items that I should consider putting in the report, just bullet lists that I can then build on and choose to put in or or take out.
And then monthly, I ask it a couple other questions. One, "What patterns do you see in my thinking this month that I should think about?" And then the other question that I ask it is, "What questions am I avoiding based on what you're seeing in my notes?" And then I ask it to go and archive completed projects and stuff.
So let's talk a little bit about return on investment here ROI. First of all, I would say that my time spent organizing notes has gone from probably 8 to 10 hours a month to less than two hours a month. My time spent preparing and writing my weekly status that I send to my boss has gone from 45 minutes or an hour every week down to probably 15 or 20 minutes. And most interestingly, the number of insights that are surfaced to me through my notes has become probably three or four valuable connections per week that I wouldn't have seen before. And that's probably the most important thing or the most valuable thing that I'm getting from this. But the biggest change, I'm not afraid to capture all my messy thoughts anymore. Before I'd sort of self-censored things because I knew that I'd have to try and organize it later. But now everything goes in. It's forcing me actually to take better notes during the day because I know that there's a ton of value in that knowledge entering into my system and being used. The AI is going to help me make sense of it.
For those who are wondering about the cost breakdown to all this, it's actually next to nothing. So, Obsidian is totally a free tool. Um, Cursor that I use as my brain is about $20 a month, but you could also use Code directly if you're already using Code. And then the time to set this up was like literally just a couple hours on a Saturday. It is very, very easy to get up and running.
I also want to focus a little bit on a quick reality check because not all of it has worked incredibly well. And I think the biggest thing that I would call out as a failure is having AI write my notes for me. This just doesn't work. It completely loses my voice. I lose the benefit of of thinking and processing um the things that I'm that I'm writing and thinking about. So, I think the key as I'm using this system is really leveraging AI in terms of where it shines, which is to organize and connect things, but still focus on, you know, me doing all the creation and thinking.
Look, if you've made it this far, you're probably like me. You know that there's gold in your notes, but you can't access it when you need it. So, here's my challenge this weekend. I want you to export your notes, start using Obsidian, and connect an AI to it, just like I explained. Even if you just take the first step and use it to file all the random notes and make sense of things, even if you stop there, you're going to be ahead.
And if you want to see the subsequent system that I built, which is the next step to all this, which takes Claude Code and takes it even further, including agents that do research on topics essentially while I'm not even paying attention to it. Um, let me know in the comments because I think that my next video is going to be uh on on that system of agents which is taking this whole system to the next level.
So before I log off, tell me what's your biggest note-taking frustration. Drop it below in the comments. I read everything and honestly your problems might just inspire my next batch of automations, that's kind of how all this works. So look, before letting this video get way too long, I'm going to end it there. But I just want to say thanks for watching. Please make sure you're share the please make sure that you're sharing your experimentation with me because I'd love to learn from them. And I'll see you at the next one.