Tech Life They calm me down

I Think in Outlines

One of the key tenets I talk about regarding understanding the engineering mindset is that software engineers think in terms of flow charts. This isn’t exactly correct – engineers think in code, but most of the planet does not, but, chances are, they understand the concept of a flowchart. You’re in a state. When certain conditions exist, you can move to another state. Sometimes… branches or decisions occur.

A key aspect of a flow chart is that fact it is visual. You can draw it. You can walk up to the white-board and clearly visually describe the part of the system that needs explanation. I find this often a better means of explanation than sitting down how the code is organized and how it works. There’s tool in the domain of explanation and organization which I’m not certain is the domain of engineers, but serves the same purpose: outlines.

I remain in a troubling post-Things world where I’m using a bizarre combination of Asana, Field Notes, and my brain to keep track of the world. This is an inefficient system that until recently has been creating just enough value to quiet the productivity rage. However, stuff has recently started falling through the cracks; it’s not clear what belongs in Asana versus Field Notes versus my brain. Yeah, I recently gave Atwood’s three things concept a try and it did shine a clear light on the three things, but – fact – there are more than three big things to tackle each day.

The current experiment is Workflowy.

As data structures go, a text outline is simple. You have one or more items in a list. An item is defined as some amount of text that may also have one or more sub-items. The only difference between an item and a sub-item is that a sub-item has a parent item. Again, simple.

You can layer all sorts of delicious visuals, features, and meta-data on top of these items, but the mental mode is the same: I have this item and if it happens to have sub-items, it means that the item and the sub-item are somehow usefully related. This simple organization mechanism… calms me down.

I think in outlines. If I’m building a Keynote presentation, I’m indenting slides. If I’m writing in a Field Notes, I’m organizing the page with headers and details. A quick scan of my Sent folder reveals extensive uses of bulleted and numeric lists. Outlines. Everywhere.

My outlining predilection might be genetic. I was organizing things is list and sub-lists for years before I stumbled on ThinkTank and discovered there was actual software for what I was doing in text files. The demand for outline process clearly wasn’t huge since both ThinkTank and its Mac cousin MORE died years ago and have been replaced by… what? Outline mode in Word? It’s crap.

It’s early on, but Workflowy so far hits the sweet spot in terms of simplicity, obviousness, and unexpected power user features. I’ve yet to read a single line of documentation, but I am already well into the development of a large outline for a complex ongoing project. It works exactly how I’d expect an outline to work, it stays out of my way, and it occasionally reminds me that by the way, there are some cool power use features you might want to check out.

While I’m delighted Workflowy exists, I remain concerned. Given the lack of a vibrant outline application market, I am clearly in the minority of humans who find value in outlining, but an outline is how I think.

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18 Responses

  1. You need to check out Dave Winer:

    He’s been talking up outlining software for literally decades.

  2. Aaron 10 years ago

    I also think in outlines; I typically use flat text.

    However – Microsoft’s OneNote didn’t fill me with rage when I last used it, and OmniOutliner is probably good (I do 70% of my thinking and notes in OmniGraffle, including outlines) because everything the Omni group makes is excellent.

  3. Pat Cavit 10 years ago

    2 paragraphs in I was thinking “Does he know about Workflowy?”, hah.

    Workflowy’s awesome, I’ve been using it for a while and really love the way it “just works”. It fits in well with my code-addled brain.

  4. I love reading stories from outliner people. I am one too of course. 😉

    Fargo,, is a descendent of MORE and ThinkTank. It does some things neither of them did, it’s great with editing websites, for example. And if you liked those products you’ll probably like Fargo. It’s got the same command structure.

    Hope you give it a try. 😉

  5. I think in trees, too. I blogged some time ago about my search for the best outlining tool for notemaking when I found (

  6. Karl B 10 years ago

    I’ve never used it, but what about OmniOutliner (

    Also, recently switched from Asana to OmniFocus and love it, just had to take 10 minutes to watch a couple videos on how to use it correctly.

  7. SteveO 10 years ago

    Try Workflowy+Bitrix24=Best free productivity combo in history of humankind. Especially for team collab.

  8. Walter Higgins 10 years ago

    Hi Michael,

    I don’t know if you’re an Emacs guy but both org-mode and markdown-mode in Emacs have great outlining. Headings are collapsed/expanded using TAB key, there’s easy navigation of large documents. I have a 26K word org file and a 38K word markdown file. Markdown-mode in Emacs probably wasn’t meant for such a large file, somewhere between 30K and 35K markdown-mode started getting gippy. I don’t know if org-mode would perform any better with such a large doc.

    Take a look at org-mode

  9. I’ll second the OmniFocus recommendation. No task manager is more outline based, since it was (still is?) based on OmniOutliner.

  10. Don Bateman 10 years ago

    I started using outlines in ’85 with Thinktank and More. I’m using OmniOutliner Pro now. I live in outlines and find it baffling that they haven’t taken over the world. I’d go further and banish linear text altogether.

    My fondest hope is that Dave Winer will get together with Ken Case of the OmniGroup and make the ultimate outliner geared toward a simple consumer friendly and beautiful means of building a website. I know Fargo can do this, but it needs to be more elegant and intuitive for the average consumer.

    I yearn for the dogs breakfast of random navigation schemes dominant on the web to be replaced by outline structure. How did we get stuck with the fixed idea of linear text? How did we miss that the constraints of paper need no longer apply? I know I’m preaching to choir on this site. This is an appeal to Dave and Ken to change the web.

    Oh, and while we’re at it, why not build a search engine with actual context. A giant outline to compete with the keyword approach Google is so fixated on. It is a fallacy to assume the searcher is possessed of the needed vocabulary to have the keyword approach work. Google search is a list of turns. An outline is a map of the territory. We need Jimmy Wales of Wikipedia on board with such an effort.

  11. Nandu 10 years ago

    Emacs org-mode ( is stunning: outlining, task management, scheduling, spreadsheet functionality, and more, all in plain text. If you’re not already an emacs user, org-mode alone almost justifies becoming one. At the very least you’ll find a community passionate about outlining.

  12. Jacob Mattison 10 years ago

    Have you looked at all at Fargo (

  13. Ambient 10 years ago

    It’s terrible what Omni Group did to OmniOutliner. It was such a good product – then the “upgrade” removed one of its most valuable features: the Note Pane. The only way to get it back is to upgrade further, to the costliest version.

    The Note Pane is just a field where you can enter text for any outline item. What a concept. But this should be reserved for their most expensive version, due to customer research, they told me. Feh.

  14. I was using Workflowy extensively but realized that navigating that huge document was painful, so I switched to OmniOutliner which has a navigation panel that lets me jump to the section I needed to work on, extensive key commands and formatting.

    I’m still looking for the tool that will allow me to see the forest and the trees (on drilldown) – it’ll probably look like a mashup of OmniFocus, OmniOutliner, Omnigraffle, Evernote and Numbers. Perhaps I’m just pining for the promise of OpenDoc.

  15. Andrew 10 years ago

    I still desperately miss ShadowPlan for the PalmPilot. I’ve been wishing for a more modern version for a long time now, but the author of the original seems to be allergic to all things “cloud”, and I haven’t found another app that quite hits the right mix of features and usability.

  16. Michael 10 years ago

    I’ve been using Workflowy for over a year now, and I love it. You don’t need any docs, and though the video tutorials are nice to have, you simply don’t need them because it was designed so intuitively. Really simple but powerful app. I use it daily.

  17. Weekly Digest of OCDI Diigo Group Content – Online Learning Experience linked to this.