If you answered Q1–Q3 above, that already helps a ton. I also made a 3-min survey to aggregate patterns. I’ll share a summary of results and invite early testers if there’s real demand: https://concerns.vercel.app

I quit hoarding. Collecting was the bottleneck, not organizing.

Just get filtered digests now. Needed less input, not better retrieval.

i feel that most of my problems in this space would be solved with better "fuzzy" search integration in obsidian. Some sort of local rag on my daily notes would be very effective.

do you know if such a project already exists?

Maybe I'm not understanding the problem. I just saw mention of obsidian being the only paid app a user had on their laptop. I'd never heard of it. For me, I keep a notes.txt either local to the project (not repo) folder, or named similarly. To find something I grep through them all. It's not perfect but it's very easy. If it becomes collaborative, I push it as a readme or a wiki page. I don't feel a need for anything more. Maybe a slightly better search but that's it.

I just use Logseq and put double brackets around my key terms. Whenever I need to revisit a topic, I can quickly review what I've a already learned about it, when, and what else it was connected to.

My understanding is that Obsidian is pretty similar? The point of my PKM isn't to turn my notes into shipped things. The point of my PKM is that when I do want to work on something, I don't have to repeat all my old mistakes to get back to where I was before, or reinvent all my own wheels.

I attempted to handle some of what you're suggesting via the plugin ecosystem utilizing a vector database for RAG, and LLMs to auto-suggest tags or related docs. None of the plugins seem to get this quite right. The extensions were pretty brittle, and limited in terms of what they could do with the open doc. I now do most of my new note creation/editing and organization through cursor and custom built agent flows. The obsidian app is now just for mobile access and sync.

> What I’m asking from you:

> 1.Where does your “second brain” break down the most?

First and foremost, remembering to write notes or to review them. What do I want? Is there a timeline that requires things to be done before it becomes invalid or increases liability?

Secondly, remembering to do actions instead of sitting down and doing something that gives some dopamine. I decide I want to work on a project on my computer. So I go sit down in front of the computer and... I've already forgotten the project, now it's time to play a game or read Hacker News instead.

Lastly -- it's the things that I "don't know". Let's say I want to build a robotic lawnmower. There are plenty of robotic lawnmowers already but I want to build my own. I know where to find the source code (or I can make my own). I don't know where to find the tools, where to source components, or who to ask for help assembling heavy things; I don't know how to assess risks (what happens if this thing catches fire on my lawn while I'm in the kitchen? what happens if it drives into the street and hits a car? or worse, what happens if it drives into the neighbor's kids?).

> 2.What best represents “active project context” for you today?

In my head, mostly. Documents in random places like ~/Documents/<project-name>, or a todo.md in the project root. Hard to remember what <project-name> is for or when I last did anything of value for it though.

> 3.What’s your hard “no” for an AI that

If the AI does not run 100% on my machine, then it's not getting anything important. That means no notes, no personal projects that have business value. Business value includes comments or ideas to improve other peoples' products! I've seen too many times my comments end up turning into someone else's pay-me project and I see none of the rewards. Speaking of which, here I am giving you valuable information for free.

After that, it's pricing. If I spend $20 on a weekend project, that's fine. If I have to spend $20 for every task, then it'll be yet another project that is only ever half-finished.

I like obsidian, but use Logseq day-to-day. I find it pretty easy to dump information without too much work due to the block / indenting structure. Retrieval isn't too bad, because you navigate to the wikilink you need, and everything is under it (I do sometimes swear I used a specific wiki link and then find I used something else, and have to dig for information).

Something that did work well recently, was creating a node script to gather all text under a given wiki link and copy to a doc with some formatting modifications, and then feed the document to an LLM for consolidation and a summary of everything I have recorded for a given subject.

Do I hoard notes/links? Yes.

Do I struggle to turn them into actions? No.

Do I struggle to keep them organized for later reference? All the time.

Do I use Obsidian? No.

I actually use Joplin, which I switched to after deciding I needed to dump Evernote. And before then (and somewhat simultaneously with), I used a pile of disorganized text files (sometimes shared via DropBox).

I'd say it's more that when I hoard links, a small slice of them end up becoming useful reference knowledge long-term.

Though I don't really have a system for storing them effectively as of yet, and as someone with a strong preference for open source on my critical workflows, I never got on the Obsidian train myself. Current experiment is Silverbullet.md, because I do very much like raw Markdown and file-based notes, but that's different from having a meaningfully fleshed-out setup haha

Yes!

I built my own AI agent for that.

I do use it but no idea if it's an habit that will stick.

I just read AI summaries nowadays. I tried Obsidian and didn't find it useful.

I think a super common problem with any todo system is the "capture anything" mindset. They've even redefined what "focus" means, like now it just means to focus on whatever thing you're focused on at that moment.

Focus is supposed to mean you have a clear idea of who you are and what you need to work on, and also what you don't.

So I've taken to follow a (bespoke) process where I identify what my own personal principles are, and what priorities and efforts they imply. Then, of all the "oh I could/should do this" potential tasks that occur to me, I have an out: if it doesn't align with my own personal focus, then I can delete it.

I just keep it simple. I have very simple todo lists and work on them as I feel like it.

A few ruby scripts help a bit automatically cleaning them up, keeping track of their status and what not - but at the end of the day they are just text files really. I would not want to make this more complicated than that. My brain kind of is the real decider what is the main priority.

I had been hoarding links/notes to movies/tv shows for some time, saved to a plain text file. Often by sharing links from other apps (ie. Reddit or Letterboxd), paired with hashtags, using an iOS app I built.

Finally extracted the data for these hashtags and fed it to an LLM to organize. I'm happy with the result https://xenodium.com/film-tv-bookmarks-chaos-resolved

While I do hoard notes I've realized over the years that the main reason I write notes is as a memory aid. If I write it down I remember it better, and I'm more likely to do it. Notes also act as a filter because I write stuff down, sometimes review the notes later, and decide what I wrote down isn't worth doing, so making a note of an idea essentially gives me a delay to review the idea and decide if it is worth doing. I do also record links, keeping them in wiki pages (along with wiki pages for notes about various projects); I started doing that because browser histories today seem to autodelete old links. Putting them into a wiki makes them searchable. I keep journals as well, which are also searchable. I don't necessarily want to be reminded of my notes and wiki/journal entries, I know they are there, I mainly want to call them up when I decide I need them. That's the main drawback of paper notes, I can't search them. I've tried scanning them, but it's tedious and they don't translate to ASCII text well, and drawings are not searchable. I've considered using one of the e-paper notepads instead of paper notes, but I'd need a notepad handy in every room of the house and that would cost too much, and the procedures to automatically sync them to a central location don't seem very reliable (and I don't want to sync personal notes to some public cloud).

So for me, an AI that suggests stuff would be annoying. An AI that could take some vague search terms and my history and could pull old information out of notes that don't necessarily have the keywords I enter, using the context provided by my history might be useful. So for example, I may remember I happened across a design for the DSP algorithms in guitar pedals, but the URL or note may not even mention DSP, so something that could turn a search for "guitar pedal DSP" into finding a link for an audio processing web page I visited would be useful. The AI would probably have to scan all the web pages I visit to be able to store enough context to be useful for a search like that. Doing this for 20 years or more might run into some scalability/cost issues.

> Project context signals (repo/PRs? issues? tasks? calendar? a “project doc”?)

There's a cost to recording what you're working on, so usually the only people who track it in a fine grained way are those that need exact numbers for billing. It's not worth the time otherwise.

There are hints to what people are working on. Connecting to a database means SQL may happen, but maybe not.

It's a big issue with personal assistant ideas in general. It's very difficult to get any real context on things. Even data that seems firm like calendar appointments, isn't in practice. Look at people's calendars, and you'll see them triple booked.

At some point, organisation can become a form of procrastination. Building a second brain is not Doing The Thing.[0]

A note is not an intention. It commits to memory, not to action. I really don't care about having a whole searchable, tagged database; I hardly ever look at those notes again.

At work I have topic-based Markdown notes. Sometimes I collect information about a topic for a few weeks or months, and eventually turn it into a proper guide (making guides is my job).

I also LOVE paper notebooks, because they become a beautiful timeline of sketches, to-do lists, thoughts and plans. When I finish a notebook, I scan it then throw it in a drawer.

I also use Obsidian daily notes to journal, mostly because it's easier to open an app than to write in a notebook. I don't do anything special with those notes, unless I'm trying to "debug" something happening in my life.

[0] https://strangestloop.io/essays/things-that-arent-doing-the-...

I legitimately don't struggle with this. I have the "root" note which opens by default whenever I reset my Obsidian vault and it shows three lists:

1. most recently updated notes

2. most recently created notes

3. notes I've added to my favourites

On top of a search bar that doesn't suck, this is pretty much all I ever need.

As for "AI", it's never going anywhere near my notes. It's supposed to be my second brain filled with content I've bothered to write down for myself. "AI" doesn't write it, "AI" doesn't process it, and I will never be convinced to change that. I use "AI" extensively, but this is a hard line that I will never cross.

I'm probably in your target audience.

Capture: notion and twitter have been best, obsidian and regular markdown have been worst.

Notion is good because of how they support a calendar view where you can put documents in a day's cell, and then see a list view that's just a stack of those notes. I keep a daily diary or youarehere type doc, where I'll have checklists and notes on small things that don't merit changes to a dedicated page. There's arguably a "retrieval" breakdown in that I don't really go back through these to update them or collate them into bigger pages.

Twitter is good because it's low friction and I can just go off, which is fun, and because they have decent search, so I can quote-tweet a related thing and sort of thread the graph together. If you're talking about BASB you're probably familiar with this corner of twitter. visakanv etc. This method works well if you use it enough to be able to recall your other notes. I think there's something special about the twitter format here too: it discourages whole-page thoughts in favor of sequential pithy bits, which i think are easier to both link and recall.

Execution: I would like a chat frontend (signal/SMS/etc) where I can just talk to my projects, ask the status of things, get suggestions, etc. Push based, rather than pull based, execution.

Active project context: I've dropped todoist-like things since they're limited in what they can express, and notion/markdown can do todolists etc. I tend to have lists in markdown style that live in two places: my daily diary/todo docs, and the actual projects themselves. This is messy and it would be lovely if notion or similar had the concept of a "todo block" and could collate all of them into a single view where I could understand association, prune and dedupe, etc. Even better if there's an agent that does or suggests cleanup whenever a new block enters.

Larger projects will get docs of their own, lots of sprawl and notes etc, and then some formalization around a spec or something. I move these to an archive folder when I'm done with the notes and the final document is fleshed out, but I'd love an agent review that makes sure I'm not leaving things on the cutting board, and that I've handled all the todos etc in my notes pages.

I don't use bidirectional linking/tagging enough, but I really should, since I want to be able to coin keywords for particular concepts inline, and then be able to access their overview and see everything that mentions them in a graphlike way.

Calendar is definitely a much used component day to day. For planning, etc. But it's not a source of truth. Everything on a calendar should just be a proxy/link to a more robust doc.

Hard nos: My take on privacy policies for things like this is "show me your incentives and I'll show you your outcomes". That is to say, any company that can survive an attempt to profit from data fuckery will do so. Your data retention policy should include technically unambiguous red lines that are not to be crossed, and define specific per-user monetary payout in the event that a breach occurs, to include clauses that cause user payout to occur before eg preferred stockholders get liquidation preference and drain the possible payout pool. Routine third party audits of how user data is handled/retained/distributed etc. I recognize that this is a bit unhinged, but that's what signaling credibility looks like. A company says "we won't sell your data" and I say "or what" and there's hemming and hawing because nothing will happen to them. If the answer is "this company dies on the spot and our investors get completely fucked", now we can talk.

I think AI service pricing applies here: generally, if it seems neat I could be in for $20 easy, and if it's genuinely game changing, $200/mo is completely reasonable to ask.

re Migration cost: I expect to be able to get 100% of my data in a reasonable non-proprietary format. If that's some blend of markdown, json, sqlite, whatever, fine.

But the bottom line for me, where does my second brain break down the most? It doesn't talk back to me. I want it to understand what I've got going on, and my idiosyncracies. I want to present it with new information and have it be like "oh, this relates to X" or, periodically, to pop up with something like "I'm noticing this correlation / related idea in areas X, Y, Z... does that resonate? Is there something here?" Again, push vs pull. My second brain should be a proactive chatbot. "Noise" is so often thought about in terms of frequency, but it's really about insight quality. If my response to 80% of push notis is "damn, good call" then you can send one every 5 minutes.

I also hear no mention of one's personal life. I don't really make the distinction. It's all in there. I should be able to bitch to this chatbot about my manager, have it know about that background, and riff with me to navigate hard convos. I should be able to talk to it about side projects I have going on, and let it thread those into my calendar. Etc. Notion is already an adequate second brain for work. Nobody has yet built an adequate second brain for the home. My house, my relationship(s), my side projects, my own diarying and self reflection... these are the contents of my brain that matter.

Email in bio if you want to talk. I'm a design technologist and happy to riff / give feedback.