Mac apps that support your deep work (Cal Newport's concept)

Hi, we at CogSci Apps Corp. are currently revisiting Cal Newport’s Deep Work framework, which complements my Cognitive Productivity framework, to ensure Hookmark plays well with them (its main aim is to support what @MacSparky calls “contextual computing”). So, we are curious what Mac apps people use to apply Cal’s deep work concepts and stay focused.

Newport is a digital minimalist, meaning he advocates throwing away superfluous tools and sticking with the bare minimum tools that give optimal results. I remember Cal mentioning for instance that he uses Scrivener for writing his books (presumably he uses LaTeX for writing papers but I don’t know). Presumably he likes that Scrivener allows users to include notes and research material in book projects. I tried Scrivener for my first Cognitive Productivity book but switched away towards writing in Markdown with BBEdit for various reasons, including that I like my research material to remain directly on Finder where I can reuse them across projects. (Not that I discourage others from using Scrivener – to each their own).

I’m also curious whether Cal’s readers take his digital minimalism concept to extremes or whether they use as many apps and Shortcuts as needed to be highly productive (not that Cal would object to that frameing). On the extreme tool side I think of Brett Terpstra who uses and reviews a ton of tools.

Before posting this, I tried to find related topics here and found: Too many apps reduce productivity - Software - MPU Talk, and re this Focused episode: 174: Deep Work, with Cal Newport - Focused / Focused Episodes - MPU Talk). Maybe there are other topics here on the subject.

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With the caveat that it’s been a while since I read Deep Work …

In order to focus—which is deep work table stakes—I need to maintain cleanly segregated digital workspaces, each of which is appropriate for the work at hand. The suite of apps that I use for my personal administrative workflows are almost entirely different from the suite of apps I use for my research and learning workflow, which are different again from the apps that I use for my photography workflow—even if the apps do more or less the same thing.

For instance, I use NotePlan for administrative note-taking and task management and Obsidian for research and learning note-taking. NotePlan is for admin; Obsidian is for research. Since I use NotePlan for task management, it’s also where I map out and track my research and learning plans, however.

Readwise Reader is exclusively reserved for intentional reading. It’s where I put the PDFs, ePubs, web content, and newsletters that I’ve made a commitment to reading. GoodLinks is for the read-it-later content that I might want to read, but may not find the time or mental shelf space to get to.

I use Devonthink for both admin and research, but maintain separate databases for each area of concern. For instance, I’m on the boards of two different non-profits. Each gets its own DTP database. I do the admin for a couple of family estates and trusts; each of those gets its own DTP database.

I use Safari and Firefox for personal and administrative web browsing; I use ARC for intentional reading, research, and learning related browsing.

This kind of workspace / workflow segregation is what I need for focus given the way my brain works; it might be cognitive overload for someone else.

PS - I’m still sorting out how I’m going to build AI into all this …

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I imagine there are other reasons you switched, but in case anyone was concerned abut this specific issue: you can keep your research files in any location in the Finder and still have them available in a Scrivener project – just import them as Aliases (File > Import > Research files as aliases…). Many people do this just to keep the Scrivener project file size down.

It’s not quite DEVONthink’s indexing vs import, but the key point is that you don’t lose the ability to use the research files outside Scrivener.

As for the substantive point – I use Hookmark every day, and value it a lot, but really don’t use as many of the features I should, my app ecosystem is chaotic, and Deep Work is on my to read list: I am really interested in the answers to your question!

Thanks…

(BTW, any word on when Hookmark for iPad will be out?)

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I don’t remember if Cal mentions it in his book, but I use an app called Freedom

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I’m a fan of all Newport’s books, but definitely lean more in the Brett direction, with “tools maximalism” for everything I feel helps me work more efficiently or stay more focused. Coincidentally, that includes using Brett’s Bunched app as kind of a Focus Mode enhancer, allowing automatically opening/closing apps (and triggering other cues) for the type of deep-work type session I’ve planned to do.

@krocnyc, I wonder if you’d like Bunch for opening/closing those context-specific apps you talked about? It’s free.

I also like LeechBlock (Chrome, Firefox) for compulsive / distraction-prone browsing, probably similar to Ojanostra’s usage of Freedom. There’s something surprisingly effective about the “splash of water to the face” of being forced to sit through a countdown before being able to continue.

For the actual deep work itself, I’ve been liking Workflowy. Not a very Mac-like Mac app, but I’ve found the ability to “zoom in” to different levels of outline thinking/processing (I wrote about some of that here) is really important for me to be able to kind of “blur out” unrelated parts of my notes while having a place to jot down notes on what I’m currently working on.

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You’re right. I also switched because I decided to publish my Cognitive Productivity books on Leanpub using Markdown, and I found BBEdit and other markdown tools to work better for that. But I’m considering writing a book on sleep onset and insomnolence which would likely not be on Leanpub so I might use Scrivener for it, particularly since as you mention content can be imported by reference (and I can use Hookmark, which we released well after the CP books were first published).

thanks for the tip!

we long delayed this (sorry all!). We’re currently working through a bug (which is not in the version that is available through TestFlight [people can still sign up for our test flight by emailing CogSci Apps at support@cogsciapps.com]). We currently expect to release it next month (i.e., July 2025). (Over on the Hookmark forum we will be asking users for feature requests for the iPhone/iPad version, which incidentally will be called Hookmark Pal. In particular, we’d like to know whether they would value integration with bookmarking services like Pinboard, GoodLinks, Instapaper and Pinboard, which the Mac version has. We’re thinking of adding tag syncing, for instance, where Hookmark would read the tags on Pinboard etc. and create/apply Hookmark tags for them, and vice versa.). But I digress.

Back to deep work tools, when I first read Deep Work, quite a long time ago now, I was surprised that Cal Newport would manually log his time. With all due respect to Cal, I think this is an example of him going overboard on his digital minimalism. I’ve argued on CogZest (here: Psychological Rationale and Considerations: mySelfQuantifier – CogZest) that even vaguely accurate time-tracking requires software such as Timing.app. I created a free-to-use spreadsheet which I shared on that site ( Main: mySelfQuantifier – CogZest)that can be used in conjunction with an app like Timing and a text expansion tool like TextExpander. I advocate creating a row in the spreadsheet every time one switches projects. It’s very difficult to keep track of where the time goes without such tools. (And if one is billing for one’s time it pretty much ethically calls for using such tools.) I added related points about Deep Work in 2016 over at SharpBrains (i.e., to boost productivity and cognition in the Knowledge Age, prioritize Deep work, avoid the Shallows, and Self-Quantify - SharpBrains). To be clear, I find Cal Newport’s ideas very useful but think it requires more software.

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I totally agree with this. I find the discipline of adding a row to the mySelfQuantifier spreadsheet also constitutes “splash of water to the face”. It takes a while to get into the habit of it. An advantage of using an app like Timing + a spreadsheet is that it can tell you exactly when you got distracted. Using a spreadsheet makes it easy to tabulate time spent on each project and activity at the end of the day, which provides more “splash in the face”, reward or punishment depending on how the day went.

One thing that is missing from the ecosystem of time tracking software, as far as I know, is integration with todo apps like OmniFocus and Things. Basically you want the list of projects in Timing and mySelfQuantifier to be drawn from your personal todo / project management software — that avoids duplication and from a cognitive perspective it helps one instill/reify one’s projects. I’d love to see Timing integrated with OmniFocus.

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While we’re on the subject of intersection of time tracking and Deep Work, after publication of the mySelfQuantifier [I think it was then] sheet, I added two columns for deep work (i.e., I don’t recall if those columns are online yet). One cell is to put a “1” if the row corresponds to deep work time; the other simply copies the duration cell’s value if the DW cell = 1 [default is 0]. That way, one can easily get an estimate at the end of the day about how much deep work time one has engaged in. Also, I find the simple act of putting a 1 in there is a reward for me, having too many 0’s nags me.

I’d be curious to know what people think about software for tracking deep work / projects, or whether they feel Cal’s method of using paper and pencil is enough. And I’m grateful to read people commenting on digital minimalism.

Thanks for the update on Hookmark Pal – I didn’t realise the beta was still open! But as you’re hoping to release in July, I think I’ll wait now.

As I said before, I use a very limited subset of Hookmark (cmd-shift-space to get a link then either link to another document or paste it into text), but as I use it with OmniFocus the lack of the feature on iPad makes OmniFocus feel very limited.

Thanks!

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A bit off topic but in the same spirit:

On iOS (and to be replicated on Mac later), I’m focusing on these apps: app blockers (ironic), focus music and pomodoro timers. I believe these 3 sets of things can help me get into the flow. Sprinkler in some automation and I can activate them all at once.

For app blockers, I’m currently using Burnout Buddy, focus music is (Not Boring) Vibes, and pomodoro is Focus app. Burnout Buddy is set on a schedule, so that during the workday, distracting apps are blocked automatically. I also have a shortcut that activates DND mode on my phone (thus blocking all notifications), starts the pomodoro timer, and plays focus music.

Most of these can be replicated on the Mac, using Freedom as the website and app blocker, Endel for focus music, and Focus for pomodoro timers. But I have yet to build that yet :slight_smile:

Basically, for Deep Work, my requisite tools are:

  • Calendar for appointments
  • Task list (OmniFocus) for projects
  • Notebook (Agenda) for keeping project-related notes during meetings
  • File storage (local, NAS, cloud)
  • PyCharm, BBEdit, iTerm, Tower, etc., for coding purposes
  • Scrivener, Word, Excel, and Preview/PDFExpert for office work
  • Zotero for reference management
  • Email, Contacts, Messages (iMessage), etc., for communication
  • Web browser

A key thing for me is to mirror names for projects and organizational structure across apps, so it’s easy to find the notes for a project, corresponding emails or Teams messages related to it, files for that project, etc. Agenda is useful because it ties notes to calendar appointments.

On my Mac, I use Spaces to separate areas of work and Moom for window layout. I’ve made many custom automations (Alfred, Shortcuts/Automator, BTT, KM, Hazel, and bash scripts) that would be hard to live without nowadays! I program a lot of my own tools in Python, for example my home-brew writing system (lets me write in Scrivener, generate a Quarto Book project, and render via Pandoc to myriad formats). Consequently the terminal (iTerm), homebrew, uv, cookiecutter, Quarto, scientific Python packages, and other CLIs are hugely important for me.

A few utilities make those mundane little tasks easier:

  • Amphetamine to prevent my computer from going to sleep
  • Gestimer (Pomodoro timer)
  • Cleanshot X
  • Dropzone and/or DropOver
  • PastePal
  • SnippetsLab

Could go on and on!