A Personal Observation on Mac OS X Outliners

This is my own personal take on outliners.

I post it here rather than rant inappropriately on a specific product’s mailing list. Reasoning about things in a way that they can be written about helps clarify my own strategizing, so there is a selfish reason for this summary. I was aghast to discover no comparative writing about Mac outliners anywhere on the web, save TidBits. TidBits is great in having Matt Neuberg who writes with helpful insights. But TidBits has a policy against comparing products, and Matt has his own slant.

Outlining is a strange paradigm when it comes to products. There are so many different modes and uses that any public discussion devolves into arbitrary dogma. Part of the problem is antecedents which have established certain assumptions about outlining: MORE, Word, InfoDepot, InControl, ACTA, all but Word denizens of the now obsolete MAC OS. Outlining is a way of structuring, displaying and navigating information. Nearly every outliner extended the basic outlining paradigm in ways to accommodate these functions and often outlining is an incidental component. Also, many uses of outlining are as part of a larger work flow, or are tightly bound to other uses.

Mac users are particularly sensitive to outliners because the Finder is an outliner. It expands the paradigm by using tags (labels), attribute columns (in list view), hierarchical columns (in column view) and aliases. The latter simply and powerfully extends the organizational paradigm beyond a simple tree structure. The new finder also provides for representatives outside the hierarchy in toolbars and the dock. An ideal outliner — at least one concerned with structuring and navigating elements in the machine — would be seamless with the finder in important ways. For example, many mail programs, bookmark managers, adobe reader, even iTunes provide something Finderlike, indeed many of these use folder icons even when there is no corresponding folder. We’ll revisit this later.

Attached to this page is a rather detailed outline of comparative outlining characteristics I created. It is in OmniOutliner format. You can download it here. Please correct it or advise on adding to it. It breaks the problem into components of how the outliner extends the basic paradigm and what the intended uses are.

Some Personal Observations Not In the Outline On Program Characteristics.

User interface is key. The central use for me is in structuring information. Outliners are where half of the real work gets done. The other half is in creating some item, usually a text document, that becomes part of the stuff to be structured. Good tools are comfortable. OmniOutliner wins this for me. It just seems clean and right.

Tailorability is key. I need to be able to able to adapt the tools to reflect the way I work, even new modes of working that I may develop. Tinderbox has very flexible methods for this, albeit unique to the program and hard to discover. OmniOutliner has superb AppleScript support and relatively clean XML export.

Extending the outlining paradigm is essential. I mean outlining by itself like MORE/Word is fine if you are bound to produce a book. I DO produce books and book-like published items that have a linear structure, but I need more structuring methods. OmniOutliner uses columns, something that exploits tabular organizational methods. They haven’t pushed this very far yet, but it is unique on OS X. Tinderbox’s key attraction is that it really isn’t an outliner at all, rather a deep-structure tool that allows outline navigation. And its outline extensions are powerful: any outline element can be an alias and/or collect elements based on scripts. Independent of the outline are powerful, adaptable structuring methods.

Dual outlining mode is very important to me. What do I mean? Word’s outliner is basically an outliner of section/chapter headers (limited in important ways). Each header has text associated with it. But what if you want a mini-outline of sorts in those few paragraphs? I do this ALL the time, using bullets and sub-bullets. Can’t use the outlining commands for this. And if you could, there would be no relationship between the outline within and the outline without. I actually spent many days writing such an outliner within Nisuswriter (alas, now dead).

Think about this a bit. KeyNote DOES do this in a very creative way. You can have an outline to organize your slide show with each slide an independent small outline. Or you can switch to “outline” view in which case the outline OF slides goes away to be replaced with the outline of what is IN the slides. Promoting a bullet makes a new slide! Different programs have different approaches and balances. OmniOutliner outlines topics with notes but not within the notes. Tinderbox is similarly constrained if you just stick to the outlining paradigm. Notetaker goes in the opposite direction. It has two outlines: one of notes (which it calls pages) and the other far more powerful of outlines within the pages. Unfortunately, there is no relationship between them: you cannot use the outlining commands in the “contents” outline and that outline can only have two levels. But Notetaker has a third level, a “library” view that cuts across all notebooks to provide direct access to the second level.

An ideal outliner would allow two levels, would be robust outliners at both levels, and would allow combining and shifting between levels. It would allow nesting so that an image of one could be contained in the other: so for instance a hotlinked table of contents could appear in the outline.

I have chosen a mix of products. Few of them work well together at present. Here’s what I chose and why. In this, cost and learning curve were irrelevant. It is foolish to spend several thousand dollars on hardware and quibble over a few hundred here and there on the stuff that really matters. But the maturity and vitality of the vendor and user base did count. A lot — that’s because when you buy into a product, you buy into a way of adjusting your thinking. In a very real sense, how we think is determined by our tools. And what tools we have are shaped by market forces, at least as they come to us and fight for survival.

Snippet Collection and Management

I do not have much use for this. Most of my information is generated by myself. But Notetaker certainly has the lead here (among outliners), and I will be purchasing it anyway as noted below. IdeaKeeper is what I bought and would have used on OS 9.

List Management

I do not use calendars and alarms. But I do have huge amounts of information to track listwise. Columns are VERY helpful for this, as is clean navigation. So I use OmniOutliner. Notetaker could serve and might for some of this.

Presentations

I create two kinds of products. One is based on words, the other — presentations — on graphics. Oddly, I want to have as non-linear structure as possible with the word-based stuff as noted in the next section. And I want the graphic stuff to be linearly organized in Keynote. My suite here is clearly OmniOutliner, KeyNote and Omnigraffle. Any pair has an intimate relationship: I outline the presentation, bullets and script in OO and import to KN. The KN is primarily charts done in OG. OO and OG can switch back and forth (with greater capability planned), so some graphics can be autogenerated and updated via OO. I can also have charts in KN that display the structure of the KN outline. All three nicely scriptable and XML-able. The weakness in this suite at present is in KN export to PDF. I am building Quickey macros to give me psuedo-outlines in OO notes.

Text-based Documents with Dynamic Structure

Folks, Tinderbox is worth the hassle if you want to break out of precomputer document paradigms. There is nothing remotely as capable for either structuring or publishing to web.

Text-based Documents with Established but Evolving Structure

Nothing beats the power of Filemaker. I use pseudo-outline (parent-child) layouts. Highly scriptable, multiple views, well-behaved XML

Graphics-based Documents with Dynamic Structure

I have not had a need for this, but may find one now that I have discovered Notetaker. I am immensely impressed by its web publishing capabilities. For example, see the Outliner Outline in OmniOutline imported to Notebook via opml and exported as a web notebook. Note: notes do not translate.

Graphics-based Documents with Established but Evolving Structure

Portfolio. Uses the finderlike, “explorer” view, but allows many parallel outlines based on applied attributes. Portfolio makes it easy to apply and access these attributes. Notetaker allows a single category which is also used as a datatyper for templating. Portfolio’s attributes are simply keywords, but any number can be assigned and complex searches can be structured.

I suppose I’ll have to finally bite the bullet and learn AppleScript, because the only way I’m going to get my dream environment is to tie all this together. One of these will probably end up being the master. If I had to guess, I’d guess the next generation of OO.