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  The Legal Mac

Outlining Options for Macs

January 2009

PCs no longer hold the lion's share of outlining and information-organizing tools. In this article by Stephen Chakwin, learn about the large variety of tools available for Mac users.

The Mac world is rich in dedicated outliners and other information-organizing applications. (In Mac lingo, the word application is used where PC users use the word program. There’s probably some esoteric explanation for the different usage, but I don’t know it.) There’s a detailed and interesting survey of them in a series of columns by Ted Goranson that you can find at http://www.atpm.com/Back/atpo.shtml. Ted lists capabilities, does comparisons between similar products, and explains some of the design philosophy underlying these differences. You will come away from these articles with new appreciation for things you can do with your computer. You will also want to get and learn all the applications that he writes about.

The first type of outliner I will discuss is what most people think of when they hear the term: a dedicated application that works in standard headline / subhead / subsubhead / note fashion. Most word processors have some similar function built into them, but a dedicated outliner is able to reorganize entries and move information around in a way that makes the outlining function of word processors seem clumsy.

There are two main uses I’ve found in my practice for this type of outliner.

What I call a “catching” outline is a way of capturing and organizing incoming information. Since outliners are so flexible, I am not committed to a particular hierarchy or structure of the information. (One of the subtle traps in understanding information is the tendency of the structure of how information is presented to us – or stored by us – to influence how we understand its meaning, even if the structure is random.) I can assign a tentative structure (or none at all, just creating a list) and then go back later and see what I really have in the outline.

The other is a “throwing” outline, one that I use to prepare for a situation in which I am going to be presenting or eliciting information: a witness examination, an argument, a lecture. I can create an overall shape for the event by building a sequence of topics (headlines) and then, within each of these, a subsidiary sequence of sub, subsub, or deeper components, anchored to notes if I need them. With this type of outliner, I can display only the headlines (and key them to presentation slides in PowerPoint or Keynote, Mac’s superior presentation application, or to trial or deposition exhibits, or to anything else I choose). I can reorder the headlines easily and rapidly and test different sequences for effectiveness. I can also focus in on any single headline by “hoisting” it so that it is the only thing on my screen. If you prepare your witness examinations in advance (almost always a good idea), this outlining function is a powerful tool.

There are two main dedicated outliners for Mac. One of them – the most commonly used – is Omni Outliner (http://www.omnigroup.com/applications/omnioutliner/). The Omni Group makes fine products, and they both work well and look good on the screen. Outliner is a mature product, as it’s up to Version 3.7 as I write this, with Version 4 on the horizon. It is full of features but is easy to learn on a basic level. There are also video tutorials on the Omni web site. The two missing features that are most asked-for – a zoom ability to make up for aging or tired eyes and small screens and cloning (the ability to insert a specific heading in more than one spot in an outline and have it change in all places to track modifications you make any one) are alleged to be on the way in Version 4.

The other main contender in this category is called Tao. (http://blue-beach-systems.com/Products/Software/TAO/). Tao has a few features that the Omni product does not – most notably cloning. It also has an extensive set of keyboard commands that I have found idiosyncratic. The appearance of Tao on the screen is spare and functional, and it looks more like a Windows program than a Mac application to some users.

The next type of outliner is well-represented on both platforms, though my own prejudice is that the Mac platform is a better host for it. This is the “mind-map” type outliner.

A mind map is a great tool for dealing with free-form ideas, brainstorming, and creative thinking in general. The great virtue of a mind-map is that, it imposes no structure on information that it contains. Any element of the outline can be looked at in relationship to any other(s). The outline can display not only the elements themselves (as can a normal heads and subheads outline) but also the connections among them and make distinctions in the connections themselves. A connector can be labeled to show that one element is the cause of another, the result of another, dependent on another, or even inconsistent with another. A mind map lets you see connections that might otherwise remain hidden and can stimulate you to come up with new ideas.

Of the many iterations of mind-mapping software available for Mac, The Brain (http://www.thebrain.com/) is a clear winner. It has a spectacular visual presentation, easy-to-use commands, and – best of all – comes in a free version that is more than adequate to use to learn whether mind mapping is for you. You can upgrade to other versions with more features for a fee.

The third and last category is one that, to the best of my knowledge, exists only for the Mac. It’s hard to know what to call it. For our purposes, I will call it a notebook.

This notebook looks like a pad of paper, complete with lines, margins, and – if you wish – even virtual holes on the left margin. It also has tabbed dividers, a table of contents, and an index. This familiar façade disguises a clever combination of outline and database. The table of contents is actually an outline. The entries in the table of contents are linked either to divider pages (which show as tabbed dividers in the display) or to pages that are, themselves, either outlines themselves or text documents.

The margin on the left side of the page, set off by a dividing line, is a space where tags and symbols can be placed. And, yes, the document you create can be searched by tags, so you can pull up all entries with a particular tag. The entries themselves can be text, graphics (including movies), sound clips, files, or shortcuts to files. There are also automatically generated indices of words (yes, every word is indexed), capitalized words, URLs, highlighting, keywords (a type of tag), stickers (another type of tag), To-Do items, attachments, discarded attachments, dates (creation, change, due), and super-find results.

The elements of the outlines – both in the table of contents and in the outlines on the outline pages – can be manipulated in most of the ways that a normal heads, subheads, etc. outliner can offer.

The power and flexibility of a notebook of this type should be obvious. It offers a way to store information in a place in which it cannot be lost. As someone who has written many notes on many legal pads and lost many an hour trying to find them, I can safely say that this is a major move forward.

Some of the uses for this product include organizing case information or for major projects such as appeals or major transactions. Some lawyers even use NoteBook as a virtual trial notebook, with scanned-in exhibits, witness outlines, legal authorities, all available and indexed. With the Mac’s split-displays function, it’s easy to drag an image from a NoteBook outline onto a separate screen attached to a projector.

There are two major products of this type. One is Circus Ponies NoteBook (the one that I use) and the other is AquaMinds NoteTaker. Both of these are fine products. There are some differences in the user interface and features between them and there are zealous users of both who can’t understand how anyone could use the alternative.

All of these products are available for download for trial periods. Circus Ponies requires you to get a free demo license, the others come with automatically expiring demo licenses.

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About the Author

Stephen D. Chakwin, Jr. is an attorney based in New York City who represents plaintiffs in personal injury and civil rights cases.

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