System overhead (second brain)

By system, I am referring to the personal systems we use to organize our lives. So for example, I use Devonthink for my documents system. Almost daily I move emails to my inbox and I process the inbox about once a week on average. It works for me.
I use Filemaker mainly to track invoices and for some light document assembly (exporting contacts to mail merge for letters and to create some form documents). Filemaker is a powerful application and I am only getting a fraction of its power, but because of my limited development skills, its the best I can do. Again, the system works pretty good for me.
As far as task management goes, I use reminders and I’m not completely satisfied with my performance at task management but Its more about my self-regulation problems than my system.
Using Devonthink, then Bear, and then Craft, I have attempted a “second brain” or personal knowledge base or Zettlekasten type of system (I know someone will probably take issue with my conflating these different things). I have not had any success at this. It’s just too hard to maintain. I realize that Phd researcher types probably make good use of such systems, but I don’t really have a specific use case like that.
Just wanting to know if others have had similar experiences in this or other areas where you just kind of threw up your hands and said “not worth it.”

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“Second brain” is a concept too catchy for its own good.

It’s overwrought. The goal shouldn’t be to create a second brain as in “store everything I’ve ever thought ever.” The goal should simply be to extend your cognition in whatever ways are most helpful to you.

A basic calculator is extended cognition, as is a post-it note, as is the FileMaker system you’ve described, as is marginalia.

The tools you mention—DEVONthink, Craft, etc.—are just other tools. The trick with these more complicated tools is that they help with certain kinds of tasks but depend a great deal on learning how to use them to do those tasks. I think that’s the overhead cost you’re referring to. If you don’t need to do those kinds of tasks, you certainly don’t need to put the work into learning the tools.

But that doesn’t mean you don’t need to—or aren’t—extending cognition in other ways.

Pursuit of a “life operating system”—making and maintaining a “real” second brain—is a fun hobby, but the overhead you describe is a real cost. I bet it’s actually a case of what my Sociology 1001 professor called “rationalizing technology.” We find the tech so cool that, when we appraise its value to us, we forget to include in our appraisal the effort required to make it work.

I have a pretty robust system that I’m constantly tinkering with, but if I’m honest, it isn’t necessary to achieve what I want to achieve in life and work. The main reason I’m working with it is because I enjoy doing so. Maybe, someday, it’ll pay off, and I’ll be free of stress and have serendipitous insights aplenty. But until then, I try to remember that I still need to prioritize what I can do with my first brain.


Can’t agree more! :clap:


I started building a Zettelkasten but realised I don’t have the time to ‘tend the garden.’ If I were a full time researcher AND had a lot of freedom in what sort of outputs I produce, it might have been worth it (although the quality of such outputs is debatable). Day to day I usually have specific tasks to do; I’m not looking to collect information and see what emerges.

I do keep a “throw it in” Devonthink database where I put useful articles and journals and rely on a fairly basic filing system and Devonthink’s wonderful search to resurface content when I need it. That requires very little maintenance and is helpful at helping me retain content I stumble across either to archive ‘just in case’ or to read later without disrupting workflow.

Overall, I’m tending to go more analogue (bullet journal, task management, meeting and lecture notes, thinking) and downsizing my use of digital mindmapping, outlining and linked markdown pages. I drop a text file in Devonthink with the paper notebook number and page number so I know I have handwritten notes in there relating to a topic. Handwriting does seem to help with comprehension and memorising in a way that creating digital notes on the fly didn’t.

(Of course, tomorrow I’ll read about a cool digital knowledge management tool on here and…)


I’m sure many are in the same situation. To me, aimless seems like the default state when one’s ability to collect and organize information has outpaced one’s demand for that information. I think that outpacing should be temporary, but it does depend on what you want to do.

Have you had any successful uses at all? When you find something you feel like you otherwise might’ve lost, or would’ve struggled to track down and recompile, that gives you a much better idea of what and how to organize future information.


I think you’re onto something there. Scotty Jackson on nested folders says “fall in love with problems not solutions.” I think my most successful tech uses have been when I have worked to make a solution that addresses a specific and repetitive problem and then incrementally improve it to the point that I have a good handle on it. When I try to develop something with tech that isn’t directly addressed to a specific problem, the results are sometimes interesting, but its rarely anything that becomes part of my regular work routines.


A subtext of this conversation is perhaps the collector’s fallacy - that having a thing is the same as knowing a thing.
The flip side is that if there is no need to know a thing, there’s no need to have a thing.
Then again, if something will be needed in the future, there is a need for some curation, which requires some “knowing.”


I get the concept, although it presupposes that I can reasonably judge today what I’ll need in a year’s time.

A good search and filtering system should be able to overcome over-collection by surfacing things you want/need.

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Yes, yes! A thousand times, YES!


Two things come to mind for:

  • Paperless documents. I gave up trying to name every receipt and document. The is no amount of Hazel or ScanSnap or Keyboard Maestro that can fully automate this for me, and the manual effort isn’t worth it. I still name some stuff, but a lot of it goes into a giant searchable bucket so I can live my life.

  • Related, what is the formula for evaluating the ROI on this sort off thing?
    Investment + Enjoyment = Return? But tangible + intangible = :man_shrugging:

Some tech/automation/tinkering takes more time than it’s “worth” - then there is the enjoyment factor of nerding out.

So, yes, I"ve had similar experiences where I throw my hands up and walkaway.


I am struggling with my “first brain”, so there is not much time left for the second …



I’m not a Phd type but I get great use out of the life organization system I am developing. I have many areas of interest, I gather lots of stuff about things I am interested in and I have to provide info out to all sorts of different people so for me I get value from a well organized idea/task/reference management system. What I have found is that I need to spend a fair amoout of time setting up and defining a system but then I can usually work with it for years or decades.

It takes a lot for me to change the system and I’m going through that right now with my out of DEVONThink/Omnifocus system into Obsidian/Omnifocus/Zotero system. I used the old way for over 12 years so the investment in time to get it going was well worth it.

I don’t find it hard to maintain once I have it set. I know exctly where certain types of information will be put. I know how to get to the location I stored the data and I know how to get it out and reformat or summarize or use as I need to for future uses. What takes the time is setting up and learning all those workflows.

I find the second brain analogy very useful. To me your second definition of extension of your thinking is exactly what a second brain means to me. I see it as an auxillary storage and retrieval system so that I can quickly use and access with enough hooks so my organic brain can get to the pieces I want to use when I am working other problems.

I agree that there is real cost in developing a system but using it is or should be simple and no harder than not using it and in fact should make it easier. Time saved looking for stuff for example.


The Zen of Zettelkasten


Won’t call it a second brain, rather a passive brain extension. It needs to be “triggered” to come to action.

A logical file naming convention, folder structure, OCR, backlinking and Hazel rules in combination with Drafts, Devonthink and Omnifocus enable me to find anything I want in a heartbeat.

Still think understanding how complex search queries work is the best way to “extend” human memory and find what you need when you need it. A lot of what is on my computer is happily “offloaded” from my brain to make room for the more important stuff. The awareness that you can find anything quick and have universal access to it, takes a lot of the other brain activity that creates anxiety away.

As simple as the concept to create a shopping list as it is a better tool than your brain to use and store the essentials you need to bring home. Your brain is wired to think about what needs to be on the list, not to be the list. That said: every system needs discipline to function well and the human brain is not known to excel in that …where was I? sorry got distracted…

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I agree with that. I find my mastery of Google Scholar and academic library advanced searching makes up for my general lack of memory/knowledge :smile: I really should delve deeper into DevonThink’s searches and search results too.


@wvu_mtneer, I stumbled upon August Bradley’s Pillars, Pipelines, and Vaults framework that he implements in Notion. I am not recommending another app, just sharing an insight that may help you. PPV struck a chord with me because Bradley’s underlying approach is to work on things that are meaningful to you. Apps are the tools we use to develop the aspects of our lives we find most important.

I would ask you why are you keeping a PKM or Zettelkasten? Does the effort and time invested enable you to develop yourself into who you want to be? If it’s too hard to keep up with, stop. I suggest first determining what are your “Pillars”? Once you clarify to yourself who you want to be then collect, sort, and synthesize the information that aligns with your ideal self.

The overhead you mentioned is real. I have felt it myself. Similar to your experiences, I love the idea of PKM and Zettelkasten, but do not have a genuine purpose for one. The friction between wanting and needing has caused me to excerpt unnecessary effort toward something that hasn’t yielded any self-development. Based on the ideas represented in PPV, anything that doesn’t align with developing myself is, as you say, “not worth it.”

Check out Bradley’s PPV introduction on YouTube. Eduardo da Silva wrote a summary of PPV that is worth reading, too.

I sincerely hope you find a methodology that you can connect with.


Yes. Although I have to admit that I’m not fully satisfied with any currently available solution. I like DEVONthink’s AI to help with filing, and I like that their sync solution is fully encrypted end-to-end, but there’s just so much to the application.

What I’d like to see is Apple enhance macOS with features of DEVONthink and Hazel.

  • Fully encrypt iCloud Drive end-to-end
  • Enhance Siri and the “Today” view to show filing options and associated documents to the current selection.
  • Enable easy export in an open format from Notes (and make it easier to add code snippets)
  • Just buy Hazel and add it to Settings.

If I had sway at Apple with the direction of macOS, I’d push them towards making it the best environment for knowledge workers to get work done. My job depends on me knowing things. Or at least having the required information on hand. So far the easiest, most low cognitive overhead, and most reliable means of keeping this information has been a nested hierarchy of files and folders. No management app, just Finder and Spotlight.

Sounds like Apple has already nailed it for you :slight_smile:


Relevant article by Eleanor Konik.
I don’t agree with everything she’s written, but it’s a thoughtful post.


The rumors that an app would do my thinking for me are greatly exaggerated, Mr Twain would say.

So would be the rumors that numbered index cards, a common book, or a bullet journal, would do that, specially for ME. :slightly_smiling_face:

Index cards might help enhance my thinking, provided I could find them, write down good, relevant questions (for whom?), and remembered to write down good, relevant answers, after managing to locate the box with the cards with the questions, and the (sub) atomic, numbered (and) related thoughts.

My experience has been that the cards, the boxes, and the numbering trick are not the issue. On a good day, they help, so I keep coming back to my little boxes, hoping they help me make sense.

Back in the day, I started with notebooks, then moved to index cards, because of the PoIC box and index cards system. That was pretty clever, and fun.

Anyway, my little boxes are now stored in a beautiful Mac, as are my little cards. Someone suggested I should keep them close, and never store them out there in the “Cloud”. OK. Another fellow - can’t remember his name, said they should be “evergreen”. I prefer them black and white, so never mind. In any case, I wrote that down.

I miss the boxes, the little 3x5 cards, and the PoIC system.