ThinkTank on the PC w/DOS

There's just no denying or sugar-coating it: I'm getting older. My brain ain't what it once was. How many times have I forgotten to take the reusable grocery bag with me to the store? It's hanging ON THE FRONT DOOR AS I EXIT, and I still forget.

Yet, with age comes ideas. Even good ones sometimes! Like the grocery bag, they too can be forgotten as I scramble to commit them, but get sidetracked by Affinity Designer wanting to apply an update. "What was I doing? Why did I open Designer? Ha! That YouTuber's cat just sneezed!" And thus, the moment is lost.

I've long been peripherally aware of "outliners" which promise to help capture and develop my fleeting thoughts. "Idea processors," "personal knowledge managers," "mind mappers," software of this ilk has multiplied in recent years, but I wanted to try the one that started it all. I'm a "back to basics" kind of guy, after all.

At first glance ThinkTank looks threadbare, but a 240 page manual and a 388 page (!) companion book suggest a richer tapestry. Have I unjustly miscategorized this software as mere weapons-grade text indenters? Is there actually a better way to think?

Historical Record

1979
  - Dave Winer pitches outliner concept to Apple
    - Apple declines, suggests talking to Personal Software
  + Winer joins Personal Software
    - Demo of VisiCalc forces a re-evaluation of his work
    - Work continues under the name “VisiText”

1981
  - Personal Software declines to publish VisiText
  + Winer leaves and founds Living Videotext
    - Settlement from Personal Software gave him VisiText
    - VisiText is re-branded as ThinkTank

1983
  + ThinkTank debuts on the Apple II, $150 ($489)

1984
  + The ThinkTank ports
    - DOS, $195 ($610)
    - Mac 128K, $145 ($453)
    - Mac 512K, $245 ($765)
    - Apple III, $150 ($468)
    - Data General/One, $135 ($421)
      - That is one sexy laptop (link at end of post)
  + The ThinkTank clones
    - KAMAS for CP/M, $147 ($460)
    - PC-Outline for DOS, shareware, $50 registered ($156)
    - THOR for DOS, $295 ($922)
    + Framework for DOS, $700 ($2,188!)
      - Outliner was just one part of this package
      - Word processing, database, communications, more
  - Winer begins work on MORE

1985
  + Living Videotext publishes Ready! for DOS, $100 ($301)
    - Memory resident ThinkTank, minus text processing

1986
  + MORE debuts on the Mac, $295 ($874)
    - An outliner tailored to Mac strengths
    - More visual and mouse-driven

1987
  + Microsoft expresses interest in buying Living Videotext
    + Microsoft instead purchases Forethought, Inc.
      - This is how and when MS acquired PowerPoint
  + Symantec acquires Living Videotext
    - Last version of ThinkTank, v2.41NP, released

1988
  + Winer founds UserLand Software
    - Work begins on Frontier
  + Symantec releases a new product, GrandView
    - Outliner and “personal information management”
    - DOS-only, $295

1992
  + Frontier 1.0 releases for the Macintosh, $295 ($682)
    - System level Mac scripting before AppleScript

1999
  + Winer gets Symantec’s permission to release “antiques”
    - ThinkTank v2.41NP, DOS
    - MORE v1.1c, v3.0, and v3.1, Mac

2000
  + UserLand releases Radio UserLand
    - Early blogging platform, includes an outliner
  - Winer releases OPML, outline processing markup language

2012
  + Winer co-founds Small Picture, Inc. with Kyle Shank

2013
  + Small Picture releases
    + Little Outliner
      - Web app, introductory outliner program
    + Fargo
      - Flagship product, syncs with Dropbox
      - Discontinued in 2017

2021
  - Winer releases Drummer, blogger-focused outliner

2022
  - Winer releases Electric Drummer
    - Drummer, wrapped in Electron

Links of interest

• Winer's "antique" releases
• OPML 2.0 spec
• Drummer
• Concord (Little Outliner's engine)

Testing Rig

• DOSBox-X 2025.10.07, Windows x64 build
  • Default hardware configuration (3000 cycles/ms)
  • ThinkTank folder mounted as drive E:\
  • 2x (forced) scaling
  • TrueType text (sorry to the bitmap purists!)
• ThinkTank v2.41NP for DOS (courtesy Dave Winer's website, link above)

Let's Get to Work

ThinkTank is launched in DOS by the .exe file named tank not think for reasons I cannot imagine. A handsomely arranged text mode splash-screen welcomes me in.

The date prompt happens with every launch, and most likely believes the year is nineteen twenty-five, not twenty twenty-five. Nothing we can do about that, so with an "n" we begin.

This! Is! Spartan!

First impressions don't do much to dissuade me from my gut reaction of, "We need a 400 page book for this?" Don't get me wrong, I like it! The screen is essentially blank, save for the 4-line prompt area. Contextual (sometimes insufficient) help is displayed there. I find it comforting having ever-present guidance on screen at all times, like a helper watching over my shoulder. I like it, even if I think it could be executed better. (spoilers: we'll see it done better in the next post)

Unlike the mnemonics of VisiCalc, ThinkTank keyboard shortcuts almost feel random. Top-level menu commands can be triggered directly without entering the menu, while secondary menu commands (under extra/F10) can mostly be triggered directly. But not always.

With the command menu open, options are chosen by arrow keys or a shortcut key, displayed in the bottom bar flanking the left and right. In the screenshot above, "insert" will "add new headline(s)" and can be activated by the "Ins" (Insert) key on an extended keyboard. "Insert" will "add". Word choices like that are trivial in the long run, but also make me "hmm...." as they did some reviewers.

"Among my other minor gripes are: failure to use consistent terminology and definitions across the various menus and in the manual; inconsistent use of some commands."
- Alan Shalette's review, Peelings II, v4n8 1983

On the level

As a self-professed "idea processor," what precisely does ThinkTank want to help me build? The brainchild of Dave Winer, the core conceit is to surface the invisible computer science notion of a data "tree" into a visual structure. You see this nested structure everywhere now, even just navigating the contents of your hard drive in list view. Folders, which contain files and folders, which contain further files and folders, ad infinitum.

To start entering an outline for this very post, I type a header in Insert mode, hit ENTER, type in another header at the same level, and continue down recording top-level thoughts. Left and right arrow will indent/unindent to capture subordinate ideas. This is fast and efficient for "first capture" of an idea, no doubt about it.

When done, every header is auto-prefixed with either a + or - meaning "has nested data" or not. + headers can be expanded and collapsed to reveal/hide subordinate data; said data may or may not be currently visible. Visually, there is no distinction between "expanded/collapsed" state, as disclosure triangles tend to signify these days.

At this point, even Electric Pencil could serve as a simple outliner if this is all you need, and Pencil's first manual was a mere 26 pages. ThinkTank justifies its existence through specialized tools for preserving and manipulating data as a tree.

William R. Hershey wrote for BYTE Magazine in May 1984, "Computers use trees all the time in their internal workings. Users, however, are seldom aware of them because programs reveal only the forest. With Thinktank's tree structure out in the open, we can expect to see some very interesting uses made of this program." As far as I can tell, ThinkTank led the way on this.

"Folding" data at the tree level really is a nice way to visually simplify a project, to focus on a specific sub-unit of information. Headings can be reordered, "promoted" in hierarchy, and so on. If a heading has subheadings, manipulation of the major heading affects all nested data as a singular unit, like how moving a folder also moves the files it contains. You get it.

We know it can build an outline, but ThinkTank promises much more than that. Can it process my ideas? Can it help me think?

Oil. . . can. . .

In my most humble (and correct!) opinion, the user interface for a tool devoted to ideas and thoughts should be as second-nature as possible. Contrary to a previous post, this is one time where friction really is bad, due to the stated goals of the program. In this case, the friction exists in our minds and ThinkTank is explicitly offering to function as WD-40.

ThinkTank takes a stab at effortless idea recording by adopting the number pad as a kind of central control panel for navigation. The first impression is that this will handle much more minute-to-minute editing than it actually does. It's useful enough for exploring a finished outline, but doesn't prove particularly helpful when trying to process and refine the outline.

In practice, I find I jump around the keyboard a lot, from number pad to main keys to F-keys. There's a lot to remember in the usage of the program, even as I'm simultaneously trying not to forget my good ideas. This is not quite the smooth process I'd hoped for. I'm not feeling flow.

Rules of engagement

Flow escapes me in part due to software usage rules which don't come naturally. The book I'm studying, Mastering ThinkTank on the IBM-PC by Jonathan Kamin, spends an inordinate amount of time talking about two things.

First, it is chockablock with stories about fictional characters in the fictional company Sky High Technologies, and how those people use ThinkTank individually and as a team. Entire chapters are devoted to these people.

Second, it talks about the rules of tool usage, and there are a lot of them. Many describe, with fairly long-winded stories, what will be manipulated at any given moment when enacting a menu action, and where to position the cursor to achieve a desired outcome. For reference, in the command glossary, the "Copy" function has five different entries, with five different keyboard commands, describing the unique rules around copying under various circumstances. "Delete" has six such entries.

For crying out loud, the ESC key alone is so convoluted it has an entire section in the back of the book devoted to its quirks.

Hunter gatherer

Where modern software would have you expect TAB to handle indentation level editing, in ThinkTank it is used to "mark" headers. Marked headers receive a 🔹symbol in place of a + or - , which has the unfortunate side-effect of removing header state identification.

Today we call this "selecting" and here it's been. . . let's call it "overthought."

Marking can be done in three ways: by the TAB key for individual items, by the "mark" m key to mark "all" or "none" of the items in a header group, or by "keyword" k then m to "mark" every item which contains your search keyword. Three ways to mark, all with different key commands and under different menus.

Once we have our marked elements, we can "gather" them. This means to cut all marked items out of their current positions and paste them into a new top-level group with the fixed name "gathered outlines." In this way, it is proposed, we can quickly rearrange our outline to reflect new insights gleaned by inspecting the ideas committed during the initial capture.

Keyword mark-and-gather presumes the user has applied keywords to headers carefully, so as to facilitate this impromptu rearrangement. Put bluntly, to get the most out of ThinkTank we must meet it halfway, subtly changing our way of thinking to more align with the program. The book explicitly acknowledges this.

The "cloning" function further opens up the possibility of using ThinkTank more like a database. Clone a header to another spot and those two headers maintain a quantum link, signified by the & symbol. Once again we lose insight into the + or - status of cloned items. That said, changing one clone instantly changes all clones, a nice "could only be done with a computer" enhancement over paper methods.

You got your peanut butter in my chocolate!

Outlines are not restricted to mere "headings with subheadings." While full-blown media attachments cannot be embedded, as later, more advanced outliners (and operating systems) allow, we can add long-ish chunks of text.

At any level of an outline, tap F5 and an inline word processor, complete with rulers and tab stops, springs to existence. Yes, ThinkText has word processing functions built right in, with caveats. There's no spellcheck or thesaurus, and formatting options are restricted to whatever you can do with a tab key and the space bar. Additionally, each subhead can hold only one block of text, up to a maximum of about 20,000 characters each.

Once typed, those text blocks can be moved around at the header level easily. Moving text between blocks, or between headers, is basically easy if you remember that F4 is "paste." (the program will not inform you of this, unlike other tools where it will inform you of the state)

Hershey's review in BYTE notes, "Differences in the sequence of commands for creating and editing paragraphs is bothersome. Within the same paragraph, the New mode, for example, requires a different set of cursor moves than the Edit mode..."

My intention was to write this entire article in ThinkTank and once again, Hershey and I agree, "I originally intended to write this review entirely with Thinktank. But the editing routine for Thinktank paragraphs is so cumbersome that I decided to use the Word Juggler program from Quark, which now has me spoiled. I still believe, however, in the value of Thinktank for organizing information and writing outlines."

In essence, arranging top-level thoughts in an outline form is a good way to mentally organize ideas. As a way to write a fleshed out document, it's frustrating having to break up longer texts into dozens of little chunks. But, I did use this tool to capture a fleeting sentence here and there. At the end of the day, the document editor is a delightful addition while simultaneously being too much to bother with. Is there a German word for this?

Opposite day

There are quite a lot of fumbles in the user experience. I'll start with how a simple toggle state for a header has three separate keys for expanding and collapsing. Just hitting + should collapse/expand as applicable, no? No. We need - to collapse and + to expand. F8 almost functions as a toggle, because why use the two existing keys when you can assign a third key while also subtly altering its usage?

There is a very nice function called "hoisting" which "zooms in" and filters out everything but the selected header level and its sub-items. "dehoist" zooms back out. "promote" will shift a selected header (and sub-data) "up" a level but there is no "demote" equivalent. Doing that requires a "move" which might not capture all previously promoted data. "delete" a header can be undone by counterintuitively selecting "delete" again, then "undo."

ThinkTank also offers alphabetic sorting, which feels counter to a tool framed around the organization of ideas rather than lexicon. At whatever level your cursor is at in the tree hierarchy, the "alpha" function will sort all headers of the same level in ascending order, dragging their subordinate items along with them.

No, you can't do the opposite and get descending sort. Outside of last name, first name database-style header entries, I can't see how to work this into the creative process. But, it's available and does give the program flexibility to be used in non-obvious ways.

Of course, every time I say "opposite" I mean "opposite to my personal way of thinking." Like grammar, software also has the concepts of "verbs" and "nouns." "promote" is a verb, which we can select as our intended action, then we select a header, the "noun" in this case, onto which to apply that verb. action -> object

The "opposite" way to consider this would be to select a noun, then choose which verb to apply to it. This, for example, is how marking keywords works. Choose the noun "keyword" then the verb "mark." object -> action

ThinkTank is inconsistent in choosing one approach over the other. Sometimes it's verb-first, sometimes it's noun-first. I am not proposing either is "better" than the other. I simply want to note this as a philosophical difference in how two people may approach the same problem.

In fact, this all points to the core, central matter which lingers over this entire software genre. It's a deep question not even a Juggalo can answer.

Brains. How do they work?

This gets to the heart of my interest in, and frustration with, this software. When it works like me, it's great and when it doesn't, it's annoying; there's not a lot of in-between. In fact, I bristle when it works counter to intuition. It's almost a personal insult.

But why? Could this be a driving force behind so many attempts to re-envision and/or re-create such software? Have you seen how many apps there are today?

Drummer, OmniOutliner, Workflowy, Dynalist, Checkvist, TreeLine, Scrivener, Cloud Outliner, Capacities, Logseq, DevonThink, CarbonFin Outliner, Tinderbox, and Roam. Should have kept an outline of outliners; feels like I'm forgetting something. 🤔

"I'm going to build an outliner that works!" must be a common developer thought for there to be so many competing products. Heck, I've even thought it a few times myself while working with ThinkTank. Heck again, Dave Winer himself seems unable to resist the siren's call. His repo for Concord was updated just last year; that marks 50 years of development on the matter by the same man.

(Oh! I just remembered CrossLine.)

Interestingly, Winer didn't conceive of the outliner as a writer's tool, but rather for software developers. Developers rejected it outright, but writers gravitated to it, much to his surprise. He developed ThinkTank with their needs in mind, though I think it is important to note that he himself was not a writer.

(Also Bear for macOS and Ultra Recall for Windows)

Some think outlining should happen early and first, to kickstart the writing process. One study published in 2023 concluded, "From the results, can be concluded that there is a significant effect of the Outline Technique on Students' Writing Skills in Coherent Paragraphs..in the 2022/2023 academic year."

Conversely, Peter Elbow, Distinguished Professor of English at the University of Massachusetts, abandoned outlining entirely.

"Somehow the words of the writing and the words of the outline were in different universes and they didn't fit together. So what I learned was I needed to skip this principle of getting things clear in mind ahead of time. I need to plunge in on my writing before I know what I'm really trying to say. I needed to make a mess."
Peter Elbow

This isn't even my final form

Winer's core functionality of "outlining" has been incorporated into any number of products, including venerable Microsoft Word back in v3.0 for DOS. In a way it has become "just the way we do things." That ubiquity definitely speaks to the lasting allure of the power of the outline.

There remains a subset of the population, however, who are convinced that outliners are but a baby step toward something greater. We don't need outliners, we need, like, super-outliners! Knowledge itself must be tamed and wrangled into submission.

(And Bike, how could I forget?)

PKM IYKYK

Personal knowledge managers are the evolution of the outliner into something greater, for which 17K weekly visitors to r/PKMS are clearly on the hunt. I had no idea this category of software attracted users so (I will choose my word carefully here) passionate(?) about finding the "right" or "best" PKM workflow. As a man who maintains a blog about productivity software pre-1995, I am certainly not one to judge another's passions.

(InfoQube has outlining as part of its package)

Even with the research I've done, I'm fuzzy where lie the boundaries between outliners, PKMs, mind mappers, "note takers" and so on. Is a word processor which contains an outliner fair game in the PKM world, or is that a withering insult to the genre? Did I just get myself added to a "PKM Morons" outline by asking that question?

(Don't forget good ole' Emacs org mode)

My initial plan was to sample the latest outliners, as suggested by the Reddit forums, and see what they offer compared to ThinkTank. I'm sorry to say, I gave up; there's just too many. Outside of very focused, simple outliners, most felt heavy and cognitively burdensome.

In fact, I've come out the other side of this research to believe that no idea processor can ever win, because the concept of "idea" is itself not a fixed thing. How we think drifts over time, sometimes subtly, sometimes not. Just when we believe we’ve captured the shape of our own mind, it slips through our fingers like mercury. Using software like this has felt a bit like trying to sculpt with quicksilver.

(VimOutliner, for the vim loyal)

Fiddler on the roof

I committed myself to giving ThinkTank a fair shake and organized this post with it before committing anything to the blog. I did find it useful for organizing my initial thoughts, but then I found I didn't really need the advanced tools. The high-level structuring that proved useful could have been done (and has been to date) in any word processor or blogging platform.

I can envision scenarios where the advanced tools would be useful. The book offers good examples, mostly centered around using ThinkTank like a Rolodex or light database. So use it more like a PKM than an idea processor?

(Also, The Guide)

The core concept, that my thoughts are so scattered that I'll transcribe them willy-nilly to rearrange later simply doesn't match the way I think. As I thought of new ideas, I added them into their appropriate tree position at that moment. When I was done, everything was naturally self-ordered as a result.

(Maybe Thymer will have released by the "thyme" you're reading this?)

Where the program really failed me, personally, was in feeling denied a flow-state. There is a mechanical feeling to its tools which was, to me, at odds with its stated goal. Menu actions get the job done at a level which does technically do what was asked, but whose aftermath tends to require no small amount of housekeeping to reorganize everything back into a tidy structure.

You have to really love moving things around, promoting and demoting, copying and cloning, and generally just fiddling about with your outline. I can imagine there are personality types who are deeply attracted to this kind of tinkering, but it didn't come naturally to me. Bullet dodged?

It takes two to love and ThinkTank is making a good effort, even if it fumbles on the UI. The onus is on me to extend equal love back, but I can't. Sorry, ThinkTank, it's not you, it's me.

(Also Reflect, Orca, SiYuan, acreom, anytype, Affine, Zettlr, Amplenote, RemNote, My Life Organized, Tana, Journal it!, Heptabase, Clibu, Joplin, and Craft)

Sharpening the Stone

Ways to improve the experience, notable deficiencies, workarounds, and notes about incorporating the software into modern workflows (if possible).

Emulator Improvements

DOSBox-X did a fantastic job for me right out of the gate. All I really did to enhance my user-experience was edit the dosbox-x.conf file with the line
mount e D:\Emulators\PC\thinktank This mounted ThinkTank upon program launch, ready to go.

I didn't encounter any reason to boost the "cycle speed" for the emulator during my work sessions. Probably my outlines were too simplistic to push the program in any significant way.

Troubleshooting

• Neither the application nor OS ever crashed. It was a stable, smooth, snappy experience start-to-finish.

Getting Your Data into the Real World

With DOSBox-X, saving data goes straight to the native OS file system. So there is no trouble getting data "out" of the emulator. The real trick is in getting the data into a format that is useful.

ThinkTank can save data via the port menu option, going straight to textfile. This gives three options: formatted, word processor, structured.

wordprocessor specifically means WordStar compatible, which ultimately means just a raw text file, each header on its own line, formatting removed.

formatted replaces all of the indentations with decimal numbering, such that you have headers numbered like 1, 2, 3, 3.1, 3.2, 3.3, 3.3.1, 3.3.2, and so on.

structured gives us, perhaps, the best shot at automating the format and massaging it into Markdown (for example). All indentations are replaced with text prefix markers

.HEAD 1 +  My Rig
.HEAD 2 +  DOSBox-X
.HEAD 3 -  Default configuration
.HEAD 3 -  TrueType text (it's just nice!)
.HEAD 3 -  2x scaling (so I don't have to squint)
.HEAD 2 -  ThinkTank v2.41NP

The format is rigid and consistent, meaning a find/replace routine should be able to swap those prefixes out for Markdown equivalents fairly easily. I took a stab at it in Python, though I'm not completely happy with the final result.

What's Lacking?

• For my tastes, it separates the outlining from the writing a little too discretely. I'd like to be able to slowly change an outline into a finished work, but that's pretty much out of the question with these tools.
  • A memory-resident version of ThinkTank called Ready! allowed a slightly stripped down version of the outliner to be called up with a hot key. It would be possible then to have the outliner and word processor running concurrently, which would mostly alleviate my concern, as it would be easy to jump between programs on-the-fly.
• Inconsistent terminology and keyboard usage can be frustrating to learn.
• Tools can be half-baked. Why just-and-only "ascending alphabetic" sort order?

Fossil Record