The second solution I turned to, and the one that I have been using and fine-tuning for the last eight months, was VoodooPad. Despite some unique drawbacks of its own, VoodooPad offers near-perfect synchronization, a daily log that far surpasses Together’s in usefulness, and the ability to append text to practically anything. The only downside is that VoodooPad is less flexible about what it can store (and how you can retrieve that info later) because everything is text-based whereas in Together you can toss whatever you want into your scratchpad, be it a PDF, image, bookmark, etc.

Components

To setup your own scratchpad using VoodooPad, you’ll need three things:

• VoodooPad 4.2+; the lite version just won’t cut the mustard, and as of 4.2 the Pro version is rather anachronistic
• LaunchBar, Quicksilver, FastScripts, or some other easy way to invoke Applescripts
• The Scratchpad Template (that’s a download link)

If you wish to synchronize your scratchpad between multiple computers, you’ll also need MobileMe or any other WebDAV-based server.

Installation instructions are included with the scratchpad template; the key thing to remember is that your scratchpad has to be open in VoodooPad and be the only document with the word “scratchpad” (case insensitive) somewhere in the document’s name or the Applescripts won’t work.

What it does

The scratchpad uses enriched plain text to accomplish its organizational goals. Similar to TaskPaper, all of the text you enter in the scratchpad is without formatting of any kind. However, thanks to VoodooPad’s automatic linking of terms associated with a document page the text is enriched with links that lead you to various useful, automatically generated pages. (It’s worth noting that VoodooPad does support rich text; the scratchpad defaults to plain text because plain text is more portable if you decide to change scratchpad solutions and is also easier to export for the web. You can definitely switch the scratchpad to rich text if you like, but it’s untested.)

The most basic idea for the scratchpad is the textual tag. A textual tag is nothing more than a VoodooPad link, but the page it links to is special: it automatically collects all of the lines in the document that contain the page’s title and displays them in a list. This is a handy way to gather data from across the document without needing to do any work on your part. For instance, I create a textual tag for every one of my clients, so that when I need to review all the daily log entries associated with them I just click the client name in a recent log entry and am instantly provided with every other log entry for that client. You could also use textual tags similar to the way TaskPaper does and organize tasks with them.

A handy way to automatically create textual tags is to use any word prefaced by an @ symbol when using the daily log or quick note Applescripts (for example, “@today”). These will automatically be converted to textual tags (if they don’t already exist) without any work on your part.

There are other special scratchpad pages, as well: any page (including auto-generated pages) can be designated an inbox, which allows you to append information to it using the quick note Applescript; you can create index pages for listing tag pages, logs, etc.; and composite pages gather the full contents of other pages and display them in a long list (useful if you want to view all of the daily logs for a given month, for instance).

These special pages are all created the same way: you just add a new page to the document like you normally would (typically by selecting some text and choosing Edit → Make Link), and then attach a special Voodoopad page tag to the page. A VoodooPad page tag, unlike a textual tag, is applied to an entire page using the VoodooPad palettes. You can feel free to use VoodooPad’s page tags however you wish as long as you only use reserved tags like “tag”, “inbox”, and “composite” to designate special scratchpad pages.

Once you’ve added one of the special page tags to a page, the auto-generation script will populate the page contents the next time you open it. There are also several meta keys you can use to customize what is displayed on a given page, the order of items, and so forth. Full documentation is available within the scratchpad itself.

How I use it

Unlike my Together scratchpad of yore with its handy shelf, I interact with my VoodooPad scratchpad almost exclusively through Applescripts invoked via LaunchBar. When I finish a task or have something else that I want to log as a timestamped note, I hit control-space to open LaunchBar, type “dl” (for Daily Log), hit space, type my log entry, and hit enter to save it. VoodooPad typically is running in the background, so the whole operation takes a few seconds at most.

If I find a link or something else I want to save, I copy it, invoke LaunchBar, type “QN” for Quick Note, hit space, and paste in the URL or type whatever note it is that I want to save. I then hit enter, choose from the list of inboxes that the Applescript provides me with, and when I’m on my personal computer I can then check those inboxes to see if there’s anything I need to process.

I rarely use the automatically generated textual tags (although I thought I would originally) because I much prefer the clean @-less textual tags that I create by hand (which additionally can include space characters and so forth).

Additional deliciousness

Though my main usage of my scratchpad has tended over time to focus a lot on daily logs and—to a lesser extent—noting URLs or things I want to think about/remember when not at work, you can easily use your scratchpad in more interesting ways. For instance, the web export system is setup to automatically generate a nice-looking version of the scratchpad, including well-formatted daily logs, with everything else formatted using Markdown if you want to share it with someone.

Setting up a TaskPaper-like task manager would not be particularly difficult, either, since you can specify tag pages to be inboxes as well as tags (useful if you want to track quick notes right alongside relevant daily log entries, for instance).

I’m sure folks will come up with their own unique usages, too; I’ve tried to keep things flexible and simple enough that it can appeal to numerous different workflows. The page auto-generation and web exporting is controlled by a pair of reasonably simple Python scripts and a page that controls the web export template, so those should be easy to modify or tweak if you so desire and are comfortable with Python.

Caveats and downsides

Overall, I’ve been extremely happy with my VoodooPad scratchpad. Certainly it isn’t as flexible as Together, but it’s also been far more stable. However, it is not without downsides:

• Because auto-generated pages are only refreshed when you open the page, things can quickly get out of date if you leave pages open. Currently the only way to update every page in the document is to do a web export.
• As your scratchpad grows larger, opening auto-generated pages will grow slower. Mine is eight months old with hundreds of pages and still moving pretty snappy, but the slowdown is inevitable thanks to the way that I have to parse through every page in order to autogenerate others.
• The Quick Note Applescript relies on your inbox index page being up-to-date; sadly there is no way to request all pages in a tag from VoodooPad via Applescript, so you’ll need to close and reopen your inbox index whenever you create a new inbox.
• The lack of easy-to-define smart pages or collections is also unfortunate, although I’ve found the meta-information based approach to work reasonably well for me.

Make it your own

I’m providing this template because I’ve found having a digital scratchpad that I can easily sync among multiple computers to be extremely handy. If you end up using it, I’d love to hear how you find it useful or limiting! I’ll definitely be updating the scripts and so forth as I continue to use and refine it myself, and I’ll share any significant improvements (updating will likely be a matter of copying and pasting a couple of pages into your personal scratchpad and maybe updating the Applescripts).

Good luck, and enjoy the scratchpad!

Resources for the scratchpad:

• VoodooPad
• The Scratchpad Template
• LaunchBar, Quicksilver, or FastScripts

For the past few weeks I have been investigating software that might serve me as a scratchpad. Although I have not yet developed the perfect solution, I would like to share my first, somewhat flawed solution using Together from Reinvented Software. Together gets almost everything exactly right, but falls short for me thanks to the buggy and error-prone synchronization of MobileMe. Despite the shortcomings of its synchronization, however, setting up a scratchpad in Together is extremely easy and for people who don’t rely on synchronization (or perhaps just have better luck with MobileMe sync services than I) Together is an excellent choice for a scratchpad.

Update Sept. 2009: at long last I’ve published part two of this series describing my VoodooPad-based solution. Check it out!

Parts of the goal

When I set out to build myself a scratchpad I had two things I wanted:

1. Easy storage, synchronization, and retrieval of info
2. A daily log

The first is well covered by Together’s built-in tools for capturing files and so forth, complemented by some simple tag-based organizing and a couple of smart folders.

The second required a bit more custom work. The idea of keeping a daily log is one that I first discovered when Chris Bowler described his custom log file. Although his solution wasn’t really what I was looking for, the idea of keeping an easily updated, timestamped log of what I’ve done throughout the day grabbed my imagination. When I’m focused on a task, I rarely remember to switch to my time tracking software and enter details about what I’ve just completed, but adding a line of text to a daily log would be another matter since I could use my favorite tool LaunchBar to easily make a note without switching applications or getting out of the flow.

Setting up the scratchpad

To set up your scratchpad, you’ll first need to create a Together library for it (you could use your current library, of course, but you’ll have that much more data to sync). To add and manage libraries, choose Together → Library Manager. I named mine “Scratchpad”, but the name doesn’t really matter. If you’re going to be synching your library with MobileMe you may as well turn that on now.

You’ll have more luck with synching if you sync hourly (or less frequently). You can change how often MobileMe syncs in the System Preferences.

Aside from daily logs, whether your scratchpad is useful will rely on how you organize using groups and tags. Because I’m using two computers, one for work and one for personal use, what works for me is to start with two root level folders (I work for a company called Tierra Interactive; you could call the folder “Work” or the name of your employer just as easily):

As you can see in the screenshot, I’ve opened up the Group Info window (accessible by right-clicking a group and choosing Show Group Info or by choosing File → Show Group Info). One of the big reasons to have two root-level groups (aside from making it easy to focus in on those two areas) is that you can use them to automatically assign tags to any item that is added to that group using the Group Info window. This makes adding items to your library and being able to utilize intelligent smart groups much easier because you can either:

1. Add an item to the Personal folder when you import it to have it automatically show up in any smart groups targeting the “personal” tag.
2. Add it anywhere else, but manually assign the personal tag to make sure it shows up in smart groups targeting “personal”

This may seem redundant (in the first scenario, you’re effectively categorizing something “personal” twice), but consider the following: what if you find a link to a piece of software that you want to install on both your computers? If you found it at work, you may not have time to do it right then, so you’ll want to make sure it ends up in your work folder. However, you also want it in your personal action items. If you were relying solely on folder-based organization, you’d have to either duplicate the item or create an alias, both of which require more effort and thus make it less likely you’ll use the system at all.

Depending on how you use your scratchpad, having two folders (with tags available in case you decide to use smart groups in the future) may be enough. You could, if you desired, use the two folders to track items for work vs. personal, and once you’d dealt with an item either move it out of the folder and back into the library to archive it, or just delete it entirely. However, I wouldn’t be me if I didn’t suggest one further refinement: a simple system of tagging to make retrieving and acting on items even easier.

Taking action

When I was setting up my scratchpad, I realized that there are two basic types of items that I’m going to be storing:

1. Things I want to take action on
2. Things I want to remember

With this in mind, I decided to use a tagging system that allowed me to filter for action items and, if I needed, search for specific types of items using descriptive tags.

Although a simple “action” tag would work fine, I ended up using tags that look like this: “action: install”, “action: blog”, “action: evaluate”, etc. For some people, this may be needless complexity. For me, though, it provides a simple way to remind myself what I wanted to do with the item without needing to add a note or some other piece of metadata that would require something more than the Together shelf. Why did I bookmark that page? Oh, I wanted to blog about it.

Remember: the fewer tags you assign to an item, the more likely you’ll be able to maintain your tagging system. I generally only assign two or three tags to any given item: a descriptive tag or two and an optional action tag. (And Together automatically adds “personal” or “work”.)

For other items, I simply attach a descriptive tag to it: “password”, “big web client”, “idea”, etc. I’m not currently using any of these tags to filter my items, but simple descriptive tags will likely be useful down the road if I need to filter the increasing number of items in my scratchpad to, say, find all URLs pertaining to a specific client.

In order to be able to easily focus on my action items, I have two virtually identical smart views (only difference is filtering based on work vs. personal tags):

The first rule uses a feature of Together that I didn’t know about before I set out to create a scratchpad. In Together rules, you can use an asterisk as a wild-card, which came in real handy for my “action” tags. The other rules should be self-explanatory, although the label is new. The meaning a label assigns can usually be duplicated with a tag, but I often find labels useful for marking priority or status because they colorize items. I opted to archive items with a gray “Archived” label in order to visually separate out the items that I’ve acted on from the ones that await action when viewing either my folders or the root library group. An additional benefit of using a label to archive items is that I don’t have to lose information; if I deleted the “action” tag, then I would have to rely on memory to recall why I wanted that particular item in the scratchpad at all.

Once you’ve got your folders and smart groups set up, you’re ready to start using your scratchpad. However, if you want a daily log there’s a couple more steps.

Setting up a daily log

Personally, I prefer the idea of keeping a folder full of daily logs rather than just tossing everything into an ongoing text file (easier to append text files than parse them, if I need to switch down the road), so I wrote an Applescript that will look for a file named based on the current date, create it if it doesn’t exist, and then add a timestamped log entry. The Applescript actually doesn’t require Together, so if you feel like running a daily log without Together feel free to give it a look-see, as well.

Download Together Daily Log Applescripts

Whether you’re using Together or not, you’ll need to create the folder for the logs to live in before running the script. In the earlier screenshot of my folder structure you can see I have them living in “Tierra/Logs” in my Tierra library.

Once you’ve got the folders set up, open the Applescript in Script Editor (or the Quicksilver version, if you’re a Quicksilver user) and change the property declarations at the top of the file to point the script toward the right folder (see screenshot below). Once you’ve done that, save the script and you’re in business.

Assuming that you’re running Together, it should automatically import the log files when they are created (just make sure you have “Auto import files added to library folders” checked in the Import preferences). If automatic importing isn’t working, try relaunching Together and creating an empty text file using the Finder to kick-start Together (this worked for me, but if you’re having trouble please refer to the Together support).

Here’s my daily log workflow: I’m using LaunchBar and have it set to scan the scripts folder in my Library, so I put Daily Log.scpt here: ~/Library/Scripts/Applications/Together. To add an entry to the log, I invoke LaunchBar, type “dl”, hit space, type my log entry, and hit return. Easy, quick, and then a log of what I’ve been doing during the day is available when I need to fill out my timesheet.

I’ve been finding Together an excellent choice for a scratchpad that includes a daily log; hopefully you will find it just as convenient (or at least have found some food for thought in my approach to some simple tag-based organization).

Downsides

I’ve been using Together as my scratchpad for a couple of weeks, and overall have really loved it. As I mentioned above, MobileMe’s significant issues with keeping even a simple Together library in sync have convinced me that I need to look elsewhere for my perfect solution, but if the synching were consistent and painless I’d have no qualms using Together for the long haul.

That said, there are some potentially significant downsides to this system, particularly for people with an eye on their budgets. MobileMe is not a cheap service, and because it’s the only way to sync Together it’s definitely necessary for anyone who’s interested in a scratchpad they can access from multiple computers. For an optimal workflow with the daily log you’ll also need LaunchBar or Quicksilver, and although Quicksilver is free, LaunchBar is far superior in my experience (and has the additional benefit of not having been abandoned by its developer).

It’s worth mentioning, too, that a computerized scratchpad like the one I’ve outlined here is completely worthless for some folks. Unless you’re on your computer for most of the day, you’ll likely find a pad of paper and pen far more useful.

Other options

Although Together was one of my first picks for scratchpad software, I did investigate other options. Evernote as an idea was extremely appealing, but in execution the service only seems worth using if you’re on the road a lot and need to store info (particularly images) via your cell phone. The desktop Evernote program is simply too clunky for someone who is always at the computer like myself, particularly given the existence of several excellent file libraries.

I also considered just using plain text files and making a daily log that could double as a scratchpad, a la Chris Bowler’s solution, but I wanted a simple organizational method (in this case using tags), which was not possible with plain text. Tossing URLs that I want to visit into my daily logs would just be throwing them into a black hole; I doubt I’d bother to take the time to review them when I switched computers.

Together’s competitors, Yojimbo and EagleFiler, were worth consideration, but neither could handle the workflow that I desired (EagleFiler because of its lack of any kind of easy-to-use synching, and Yojimbo because it doesn’t offer any good way to append text to a file/library item so far as I could tell). For people who want a scratchpad for a single computer, however, EagleFiler might be worth a second glance (particularly if you own it and don’t own Together).

Looking forward

As you may have figured out from my dissatisfaction with Together’s synching and the “part one” in the title, my quest for a scratchpad is not yet over. I’m currently in the early testing stages of an alternative solution using VoodooPad Pro 4 that has fantastic synching support but requires a bit more gruntwork on my part to get up and running. I’ll be sharing my second scratchpad solution once it’s finished, but in the meantime I hope that my work with Together will benefit some other folks who have been battling with the same mind-overflow issues that I’ve been facing.

Resources for the scratchpad:

• Together
• Download Daily Log Applescript
• LaunchBar or Quicksilver

This tells me my system was a good one. Aside from not needing to expand the tag cloud, most tasks I only need to assign 1-2 tags per task, and and tasks inherit one more based on which project I stick them into. My tag filter bar is clean, and small enough to be useful even in lists with lots of tasks. When I posted the list in the Things wiki I got some very positive feedback. But having used the list religiously for a couple months, I have realized something: about 80% of my tags are completely useless.

This is because, up until now, I haven’t brought myself to noticed the obvious:

Tags are only useful if you need to find something.

Of course, it’s hard to tell when you’re first starting to tag whether you’ll actually use those tags down the road to find items easier. That’s actually one of the benefits of tagging: whether or not you use them, they’re easy to add.

The tricky bit is striking a long-term balance: if you tag willy-nilly with the assumption that it’s better to have lots of tags that you might search for someday than to have a few that you’ll definitely search for, you’re very likely to stop tagging sooner rather than later. Tagging may takes very little time but it adds up, and feeling obligated to attach a bunch of tags that you know you’ll never use is a quick route to tagging disillusionment (oh, the horror!).

So what’s to be done? Something really simple: look backwards.

You won’t be able to do this until you’ve been using a tagging tool for a while and you certainly don’t need to do it often, but every once in a while when it comes time to tag something, take a quick break and consider the tags you were planning to use. Have you ever searched for them? Have you even searched for tags similar to them?

When I planned out my grand Things tagging system, I included a subset of tags that described the type of task. I’m a web designer most of the day, so these were tags like “markup”, “styling”, “coding”, “research”, etc. Although I’ve faithfully used these tags with every task I’ve entered, I have never once filtered my list of tasks for any of them.

If I hadn’t taken a moment to look backwards, I might never have noticed this and would have kept wasting my time tagging tasks with tags that aren’t actually relevant to the task’s completion.

Of course, this example isn’t useful in all situations. Particularly in public and collaborative tagging systems, using tags that you’ve never searched for and might never search for can help others. Sometimes it’s a good idea to tag descriptively without worrying about the utility of your tags. But especially if you find yourself using a piece of tagging software that you originally loved less and less often, take a look backwards and ponder whether some of your tagging habits are just cruft that’s weighing you down. When you begin to tag things out of habit and not because the tags are useful, it’s the beginning of the end.

There are some similar aspects to all GTD task managers, but I think one of the primary deciding factors whether or not a particular piece of software will work for you is how much structure you need or desire. With that in mind, here’s the GTD software for Mac OS X, ordered from most structured to least: Midnight Inbox, OmniFocus, iGTD, TaskPaper, iGTD 2 (early development), and Things (approaching public preview). If you’re like me and agonize over task managers, then this is a pretty daunting list (and if you count some of the less polished options, it’s nowhere near complete). However, with an eye to structure, I don’t think it is all that difficult to narrow the list down to a couple of applications that you should try.

Just what is “structure,” anyway?

Structure in a GTD app applies both to the metadata attached to tasks (do tasks have contexts attached? Tags? Priorities?) and to the workflow that the application’s interface encourages (are you encouraged to focus on projects, or focus on tasks that you need to do today?). Some applications give the user very specific information and a very specific workflow (the more structured apps), while others allow much more freedom (the less structured).

For some people, the highly structured apps will be the most appealing because the workflow and information attached to tasks makes perfect sense to them. For others (myself included), the less structured apps will be more inviting because they allow the user to craft a more personalized system (and are often less complex for users who don’t want to use the advanced features).

Figuring out whether you prefer more or less structured approaches to GTD is something everyone will have to do on their own. Odds are if a screencast or feature list for a given application makes you think, “Wow!” and start imagining what you could do with it, that’s the type of application for you.

But enough with generalities! Let’s take a look at the actual applications side-by-side.

Structure to live by: projects and contexts

Midnight Inbox ($35) is by far the most structured of the available apps, and it is also one of the few polished GTD apps available (and has been available for some time, unlike the still-in-development OmniFocus). Personally I think that using Midnight Inbox is like having David Allen standing behind you, twisting your arm, and shouting in your ear, “Do it my way!” That said, if a five-step, context-oriented task workflow makes sense to you and you’re willing to let the software know best and collect what it thinks you need to organize, then Midnight Inbox is worth a look. It’s certainly a polished-looking piece of software, and is one of the few GTD applications available as a stable, tested release.

Midnight Inbox’s biggest strength (which also happens to be its biggest failing) is that it can collect practically anything on your computer automatically (email messages, iCal to-dos, text documents in a specific folder, etc.) and encourage you to review them for actionable tasks. This can be really handy, but for myself I’d just end up frittering away all my time collecting, organizing, and reviewing tasks rather than completing them.

OmniFocus ($39.95 prerelease; $79.95 standard) is nowhere near as controlling as Midnight Inbox, but it is still highly structured around projects and contexts. Tasks have quite a lot of specific metadata attached to them, but are displayed in an easy-to-understand outline similar to OmniOutliner.

OmniFocus is another app where, for me, there’s a little too much complexity (bringing about a “I’m not getting any work done because I’m constantly playing with OmniFocus” type of workflow). In its defense, OmniFocus does provide an inviting interface to tempt you in, and with complexity comes great power. If working out of contexts and projects makes sense to you, then OmniFocus is probably your best option, if only because of Omni’s attention to detail, great interface design (overlooking, for the moment, their obsession with inspector windows), and dedicated support team.

An unfortunate result of OmniFocus being the only one of these apps that is produced by a larger company (compared to the individuals and small teams working on the other apps) is that its price will be less competitive when it finally goes release candidate. At the time of this writing, there’s a lot of pressure to just buy OmniFocus without really being able to experiment with the other options because the prerelease price is half what it will cost after January 8, 2008.

Then there’s iGTD (free). I have a love/hate relationship with iGTD. It has a lot of power, but terrible interface design. Balancing that out, it’s free, which is a pretty tempting price point. iGTD has a far worse learning curve than OmniFocus and is plagued by many of the same problems (as far as restricting you to contexts and projects). It additionally has a bad case of feature bloat which OmniFocus, while pretty overwhelming at first glance, has minimized.

If none of the other options look like they’ll provide the power you need to manage your tasks, then iGTD is very likely the perfect program for you. It integrates with just about everything (notably MailTags) and provides more metadata than you ever knew you needed. However, particularly given the brief glimpses we’ve had of iGTD 2, iGTD looks like it will be badly outclassed in the very near future.

Straddling the fence between the more structured and less structured apps is TaskPaper ($18.95 intro price). TaskPaper is by far the least complex GTD task manager available, and if all you need to do is jot down lists of tasks sorted by basic projects and tags, then TaskPaper is probably the perfect solution for you. TaskPaper doesn’t compete with the other GTD apps as much as it provides an interesting counterpoint in task management minimalism. It is extremely limited, but a perfect step up from plain text lists for some people. Unfortunately, its tagging is only really effective when used similar to OmniFocus/iGTD contexts

I’ve actually been using TaskPaper as my primary task manager for the last few weeks just to see if I could, and it’s been an interesting experience. On the one hand, using TaskPaper made me realize that I don’t need a really complicated solution. On the other, it turned out that some features from the other GTD apps are things that I want. I highly recommend using TaskPaper for anyone who has tried a number of GTD task managers without being able to pick one. It’s an experience that really helps clarify your needs.

Laid-back structure: focus and tags

As much as I wish it were otherwise, the two less structured GTD apps have not yet been released to the public.

Although there has yet been nothing except preview screenshots and short screencasts, iGTD 2 (forthcoming; free) is looking like a solid step in the right direction for iGTD. iGTD 2 looks like it will abandon the standard project/context framework supplied by the many other apps in favor of tags and “focus.” Focusing on tasks, a central component of both iGTD 2 and Things, is basically looking at tasks based on general shared characteristics (such as tasks that need to be done next versus tasks that need to be done today).

Not only is iGTD 2 much less structured than other available apps, but it looks like it will be pulling on some of the immense power of iGTD, but filtering it through an interface that is far, far superior. The tabs and saved workspaces in particular are a pretty ingenious approach to viewing complex assortments of tasks. I also think that its attempt to use natural language for its interface elements is bang on target, and may well help iGTD 2 to dip into the more casual task manager crowd that iGTD is currently alienating through its complexity.

And finally we get to Things (forthcoming; pricing as yet unannounced), the least structured of all the task managers. Like TaskPaper, one of Things’s goals is to simplify task management. However, unlike TaskPaper, Things still provides a lot of potential power through its versatile and intuitive tagging system. Things doesn’t yet provide feature parity with some of the more structured applications; what it provides instead is an elegant and easy-to-use system for sorting and accomplishing tasks that scales to the complexity the user wishes to have.

Things still has a definite structure, of course; it provides an interface that expects your workflow to include steps like collecting tasks, organizing tasks, and then completing tasks like most of the other GTD managers. Tagging (and Things’s intuitive tag filtering) is what allows more freedom in Things structure than within, for instance, OmniFocus’s strictly defined metadata.

Which solution?

If you know whether structure appeals to you or not, you should hopefully now have a better idea of which GTD apps are the most worth the time it takes to evaluate. Thinking about task managers in terms of how they structure tasks and workflow is a much different way to think about software than most people are used to (feature comparisons are much more standard), but I think it’s one of the most important things to think about for an application that is so intimately related to the actions that you take in your life.

Of course, features are important, too. The applications with the most features (and thus the most complexity) are probably iGTD and OmniFocus. Things and iGTD 2 are difficult to evaluate based on features because neither is feature complete yet. Midnight Inbox is fairly feature-rich but in an all-in-one-solution way, and TaskPaper almost doesn’t have features at all (in a good way).

The truth of the matter is that it still isn’t possible to compare OmniFocus vs. Things vs. iGTD or iGTD 2. Until we have at least a 1.0 release candidate for all of the main contenders, it will be very hard to compare features and performance, which is why I avoided trying to compare specific features of any of the applications.

Just looking at the software that’s publicly available, iGTD and OmniFocus are the best choices if you need a feature-rich application, and TaskPaper is the best stopgap for people with simpler needs. Depending on how many features Cultured Code is able to cram into its public preview version of Things, Things may also be able to serve some people before it is released.

Although I’m really looking forward to the less structured software (I do love my tags), if you prefer a structured solution to task management you may be able to find the perfect application without much more ado. Whatever your preferences, good luck! Finding the task manager that works for you can be a difficult and time-consuming process, so I hope that this general comparison has helped you slim down the options somewhat.

Tags for every situation

1. Tagging for productivity
2. File library vs. file system
3. File system tagging
4. Tagging files with file libraries

I know it’s hardly standard practice to publish things on major holidays, but I wanted to give my U.S. readers something to do while they’re recovering from eating too much turkey, and I can hardly think of a better distraction than an article that I’ve been meaning to write for months, continuing my series of tagging software recommendations. This time the topic is file libraries, and unlike file system tagging solutions, there’s a lot of good options out there.

To recap, a file library is an application that collects, searches, and browses your files outside of the standard Finder and Spotlight interface. File libraries contain some of the best examples of tagging interfaces currently available on the Mac, and thanks to the limitations Spotlight has with regards to tagging often provide streamlined and useful tagging for a variety of file types.

The main contenders

To my mind, there are currently three main contenders if you are looking for a tag-based file library: EagleFiler, Yojimbo, and Together.

EagleFiler ($40) is currently my file library of choice. EagleFiler stores your files in a Finder-friendly format very similar to iTunes (they’re on-disk in a folder of your choosing, but EagleFiler manages them). This (and the pseudo-hierarchical tagging) is perhaps the most attractive feature of EagleFiler. Getting files into EagleFiler is dead easy (usually a single keypress away) and EagleFiler natively supports PDFs, web archives, RTF documents, emails, chats, and more (you can always store unsupported documents in EagleFiler, as well; they just won’t have a preview and you’ll have to edit them in another program). Of particular note is EagleFiler’s support for archiving email; this is a cool feature in and of itself (and not available in the other two), but to make things even better EagleFiler supports MailTags.

EagleFiler’s pseudo-hierarchical tags are one of its main selling points for me. Particularly when it comes to tagging generic files, most programs only support tag clouds which are often little use for people who have a large number of tags. EagleFiler’s tags are not truly hierarchical unfortunately, because the program doesn’t recognize any relationship between parent and child tags, but just being able to sort tags into related groups makes browsing them much easier, and EagleFiler’s developer has mentioned that he may in the future beef up EagleFiler’s hierarchical tagging. EagleFiler’s tagging is complemented by standard-style folders (which are mirrored in the Finder) for those who are not comfortable with a flat, tagged library.

The major downside to EagleFiler is that users cannot create smart views or otherwise save their searches. However, browsing by tag and then using the reasonably powerful search bar are usually enough for me. EagleFiler is not a program to miss if you are looking for simple, powerful, tag-driven document organization.

Yojimbo ($39) is probably the simplest file library you’ll find, but is quite effective despite its simplicity. Yojimbo provides basic tagging and folder-based organization (called “collections” within the program), but does not have any sort of tag browser. Instead, you have to create pseudo-smart view “tag collections” to browse your tagged files. Yojimbo does not store your files in a Finder-friendly format, but in this case it’s a good thing.

Yojimbo’s strength lies not in expansive features or open storage (Yojimbo is, to be honest, pretty bare bones), but rather in the fact that it is phenomenally portable. If you need to access to disparate files and data (such as text documents, images, PDFs, web archives or bookmarks, serial numbers, or passwords) across multiple computers (Mac or PC), then Yojimbo is a solid home run. Not only does it provide synching via .Mac (cool in its own right, when you consider the range of data Yojimbo can handle), but Webjimbo ($29.95) provides a completely web-driven interface into your Yojimbo library from anywhere (including your iPhone).

I wouldn’t recommend Yojimbo for large file libraries or for general tag-based organization, but for keeping yourself connected to your data and files, Yojimbo is the single best solution that I know.

Together ($39; $14.95 upgrade from KIT) is a recently released massive upgrade to KIT (Leopard only, unfortunately). I was never a big fan of KIT. It was completely tag-based, which was cool in theory, but it was as simplistic as Yojimbo without really providing a compelling reason to use it. Together, on the other hand, is a whole new story. Together now permits hierarchical folder organization (mirrored in the Finder), smart groups, a tag-browser that mixes in other types of metadata in addition to tags, tab browsing, and a svelte widescreen-optimized interface that will be instantly familiar to anyone who has used iTunes.

Together provides an excellent merger of form and function. Its tagging is not as good as EagleFiler’s, but its tag-browser-on-steroids provides a kind of power that casual taggers who aren’t totally comfortable with giving up folders will find intuitive and useful. Its interface shares many similarities with Yojimbo in a really good way (particularly the quick import “shelf” that hangs out at the side of the screen) and is all around just a little more inviting than either EagleFiler or Yojimbo. Additionally, Together allows you to move, copy, or simply link to your files, which means that you can, presumably, use it as a searching and browsing front-end to your current file system without modifying your folder hierarchy. Like EagleFiler, Together also easily supports multiple libraries if you want or need to separate your files.

The pseudo-libraries

Although EagleFiler, Yojimbo, or Together is probably what you’re looking for if you’re looking for a file library, there are also a couple other pieces of quality software to consider. They aren’t quite file libraries in the traditional sense, but they aren’t quite file system tagging, either. The culprits: Nifty Box and Leap.

Nifty Box (€24.95) provides a tagging and searching interface for your files, but doesn’t collect or manage them in any way. Instead, adding a file to Nifty Box creates a link to that file. Additionally, tagging files in Nifty Box causes the tags to be added to the file’s Spotlight comments, allowing you to find your files via Spotlight as well as using Nifty Box’s quicker and more efficient tag database. Nifty Box doesn’t have any particularly standout features, but it is a solid possibility if you want something a little more involved than TagBot or Punkea but a little less managed than typical file libraries.

Leap (currently $34, bundled with Yep), currently in public beta, is another pseudo-file library but with slightly more ambitious aims than Nifty Box. Leap ties directly into Spotlight, thus requiring no “importing”. Tags applied in Leap are not attached to files in the Finder (although the developers plan to export tags to Spotlight comments), so if you want to tag or browse via tags you have to it from within the program. On the other hand, Leap has a complex tag browser similar to Togethers, allowing both folders and tags to be browsed as if they were tags. This makes migrating from a complex folder structure to Leap’s tags that much easier, and allows you to find a fair amount of usefulness from Leap without ever having to tag a file.

Leap is advertised as a Finder replacement, and although I don’t think it’s adequate to really replace the Finder, it’s an intriguing way to access your files, and may be a great solution if you don’t want them managed, but still want the lightning fast searching and tag browsing of a file library.

When I was your age, tags was called folders!

Although it pains me to admit it, there are a plethora of options for collecting files and other data that don’t involve tags at all.

DevonThink ($39.95 personal; $79.95 pro; $149.95 pro office) is a favorite for people who like real ultimate power (no, not that kind) when it comes to handling their files. DevonThink’s complexity and price point have always scared me off, but if you’re looking for something with a little more umph than the file libraries above, this may be the one.

Generalized data managers such as VoodooPad, Journler, or Circus Ponies Notebook are also popular places to collect files and data for some people, but I’ll take a dedicated file library any day.

Whatever you end up using, by choosing a tag-based file library to manage your documents, files, emails, and whatever else, you’ll be providing yourself with a searching and browsing experience that Spotlight, Leopard improvements notwithstanding, still can’t match. If you’ve ever wondered if there’s an easier way to store files than your documents folder, you have only to download a good file library to see the difference it can make.

Found the perfect tag-based file library and shocked that I didn’t include it in the list? Give me a shout and let me know the error of my ways! I always love hearing from readers, and any excuse to try a new piece of software is good thing.

Definitely a useful article to read if you use Spotlight much (for finding tagged files, for instance), although it doesn’t have anything to do with tagging specifically. (Thanks to Daring Fireball for the link.)

I’ve finally finished writing up my own list of 35 essential Mac apps, posted over on Beckism.com. There’s some overlap with Freelance Switch, and some of the really good stuff from Freelance Switch didn’t make it on because I personally don’t find it particularly essential, so you’ll probably want to check out both lists. Of course, it doesn’t have much to do with tagging (I haven’t needed tagging software for my freelance work, so there isn’t much tagging software on the list), but I figured you’d be interested nonetheless. Enjoy!

For visitors from 43 Folders exploring Tagamac for the first time, welcome! you might want to check out Tagging best practices (the site’s most popular article to date), Easy choices (a short counterpoint to some of the thoughts from the 43 Folders article and my previous “The what” article), or the software reviews. There is also a list of the most popular articles in the archives.

This tendency also translates into my advice on tagging. When I came up with the idea of “the what“, it was because I had sat down and tried to think of the most efficient way to tag. The article didn’t come from a system; the system came from the article. But mine is not the only way.

Arnaud Leene notes that “the what” is a very formal way to tag. He’s right; identifying “the what” is a step-by-step process focused on consciously crafting a consistent tagging system. It’s not fun. It’s not flashy. It’s plodding and onerous. When I myself take the time to sit down and identify the attributes that I’m tagging, I feel like some sort of robot. Hello-I-am-tag-o-tron, well-oiled-machine.

I have to admit, though, that not everyone in this world is addicted to logic or methodically moving from point A to point B. In fact, I suspect that most people turn to tagging because they find it easier than using single folders or categories. When you’re tagging, you can just toss any jumble of words on something in the hope that it’ll make finding things easier in the future. Choosing a tag isn’t a life-or-death, here-or-there choice. It’s naming a possibility.

No matter how much you take my advice on finding “the what” (or anything else) to heart, when you’re tagging things in everyday life you should always remember that tagging is about making easy choices. If you find yourself freaking out about what tag to assign to your photo of Aunt Sally, then you may as well not be tagging because you’ll be wasting as much energy and time as if you had thrown the photo in a random folder and then had to search for it later. If you think about “the what” more than you tag, then that system isn’t working for you.

Whether you lean more towards sober planning or random free-loving tag-fests, if you’re able to find the method that makes assigning tags to an item nothing more than several easy choices, you’ll be reaping the benefits of tagging in no time.

Tags for every situation

1. Tagging for productivity
2. File library vs. file system
3. File system tagging
4. Tagging files with file libraries

The fact is that people usually want to tag their files, but unfortunately file system tagging is still one of the most difficult and onerous tagging activities. Although there are a number of different tools now to choose from, if you want to use tags in your file system you will likely need to roll your own solution to some extent.

There are two main categories of file system tagging software: software intended to help you tag your files, and software that you can use to roll your own solution. Keep in mind that the focus of this series of articles is on helping you find software; coming up with a workflow will still be up to you (although I’ll be publishing some workflow advice down the road).

The main two

There are two programs whose entire point is file system tagging: TagBot and Punakea.

TagBot ($20) provides you with a floating palette of tags for drag and drop tagging and a Finder contextual menu. Although you can double click a tag in the palette to open a Smart Folder for that tag, TagBot is primarily useful for tagging (rather than browsing or searching). Tags are stored in Spotlight comments using the popular &tag format (tag name with a “&” prefix). Unfortunately, this means that you can only use single word tags (so get ready to replace those spaces!).

TagBot is not an all-in-one tool, but may be the perfect companion to your other tagging tools; it fits particularly well into Quicksilver tagging systems (more on this later). If you’re using TagBot alone, FileSpot would be an excellent complement, because it uses the same format for tags and picks up searching and browsing where TagBot leaves off (besides having loads of other cool features).

Punakea (free) also uses Spotlight comments, but approaches them very differently: Punakea tags are surrounded by a truly horrific bunch of gobbledy-gook. Although this makes finding tagged files with Spotlight more onerous, it also allows Punakea to offer much more advanced tagging (including multiple word tags). Punakea provides a drag-and-drop sidebar for tagging that conveniently stays out of sight when not in use, and has an excellent cumulative tag cloud for browsing tagged files.

Despite some shortcomings, Punakea is well worth trying out because it is the only software that comes close to being an all-in-one solution for file system tagging. You also can’t beat the price, although the software is still technically in beta and may be buggy.

To be honest, I’m pretty torn between Punakea and TagBot and have not settled on one to use myself. If you prefer a simple tagging solution to supplement your folders and Spotlight use, then TagBot is likely the best solution. If you’d like to try using tagging as your only way of organizing documents (or want a great tag browsing interface), then Punakea is the answer.

Roll yer own

Outside of TagBot and Punakea, Quicksilver (free) is your best solution for file system tagging (it’s possible to use Applescript and LaunchBar for tagging, as well, but Quicksilver has Spotlight comment editing integrated). Some people also like to use Default Folder X ($34.95) to throw tags into the Spotlight comments when they are saving files (further streamlining the process). You may also find Hazel ($21.95) useful for managing files, or even assigning tags automatically, although it will require some creativity on your part to come up with useful rules.

If you’d like an in-depth walkthrough on using Quicksilver and Default Folder X to tag files, try the Apple Blog’s series on using metadata in OS X. Unfortunately, the series doesn’t have any internal navigation, but you can link to all five articles in the series from Tagamac’s tagging resources article.

Of course, you could also eschew all that fancy schmancy software stuff, and just tag files using the Finder’s Get Info window.

Rolling your own file system tagging can be very rewarding; after all, you have complete control over every step of the workflow, so you can craft it to suit yourself. However, it also requires the most energy, thought, and training. If you’d like to roll your own system with the least amount of effort, then you’re likely best off with a combination of Quicksilver, TagBot, and possibly FileSpot. Definitely check out the Apple Blog’s series mentioned above; it’s required reading for Quicksilver-based file system tagging.

But wait, there’s more!

Okay, I kind of lied when I said there were only two applications dedicated to file system tagging. The thing is, there are only two obviously good options. There is a third sort-of-good option, and a slew of stuff that’s unequivocally bad.

The third option is a Java application called Nucle Browser (free) and its companion, the McNucle server. This is actually a very promising project, not least because of its cross-platform nature and ability to remotely access your tagged file system. Of course, I can count the number of decent Java apps that I’ve used on one hand (and wouldn’t be impaired in said counting even if I lost a few fingers), but there you go.

Although my initial experiences with Nucle Browser were very negative, the most recent beta is much more useable. Of course, the double application server/client setup is annoying, as is the occasional unresponsiveness, long launch time, and fact that they store your IP address on their server (which is how you connect the Nucle Browser to the McNucle server). If you can get over these shortcomings, though, it definitely has potential. I wouldn’t recommend Nucle Browser for most users, but if the feature-set sounds intriguing feel free to download it and give it a whirl.

Finally, if you’re really a glutton for punishment, you could try out DropLight, DeskLamp, Branding Iron, or any number of Applescripts. I wouldn’t recommend it, though. Most of this software is scraping the bottom of the barrel, and some of it has somehow managed to bury itself beneath the barrel entirely.

If you’re comfortable defining your own workflow using multiple pieces of software, then you will likely find file system tagging useful and rewarding. If, however, you aren’t interested in putting that much effort into your tagging system or only need to tag a subset of your documents, you may find a file library more to your taste. I’ll be covering file libraries next, so stay tuned, or, if you don’t want my advice, check out file libraries on the software page.

Know of a better way to tag your file system? Let me know! I love to hear from readers, and I’m always looking for new software and workflows to try out.

Tagging guidelines

1. Tagging best practices
2. A singular question
3. Replacing spaces
4. More to life than tags
5. The what

Creating a consistent tagging system is like baking a perfect pie crust: it makes you salivate to think about, but some days it just doesn’t work out. Fortunately, consistent tagging (unlike a perfect pie crust) isn’t affected by humidity; all you need is some careful attention to detail. And perhaps the most important detail to keep in mind while you are tagging is “the what”.

Quite simply, the what is just your answer to a two-part question: what item and what attributes? Despite the simplicity of the question, knowing the what is a vital part of creating a consistent tagging system. You can take or leave my SLS guidelines, but if you really want consistency you’re going to have to ask yourself about attributes.

What item?

The first part of the what is usually pretty obvious: are you tagging photos, email, journal entries, characters in your novel, or something else entirely?

Obvious as it may be, deciding what items you are tagging can still require some thought. Although you can generally delineate items based on their file format, there are some exceptions to think about. For instance, JPEGs, PNGs, and GIFs are all images while Word, Pages, and RTF documents are all text documents. When answering “what item?” you’ll need to decide what items to group under a larger heading and which to separate out on their own.

Keep in mind that if you are grouping items you’ll want to use only the most generic groups. Thinking of Pages and Word documents as essays is not useful, even if you only ever write essays in Word and Pages. You may in the future write something in Word that is not an essay, and then your whole way of thinking about tags will get fouled up. When you aren’t using items inside specific programs or individual file formats, use the most general categories of items that you can.

If you’re having some trouble thinking of what items you’re tagging, here’s a list of common ones to get you started:

• Photos (or images) — JPEGs, PNGs, TIFFs, etc.
• Text documents — Word, Pages, RTF, etc.
• Bookmarks (or web pages)
• PDFs
• Email
• Other program-specific items

Once you know what items you are tagging, you can figure out what attributes to tag.

What attributes?

Knowing what attributes you are tagging is the heart of the what, and the key to crafting a consistent tagging system. Basically, you want to identify what you think of when you think of a given type of item. You can do this by looking at items that you have tagged in the past to see trends in what kinds of tags you’re using or by brainstorming out a list of an item’s attributes (or for best results do both).

For example, perhaps you tag text documents based on their status (unfinished, first draft, revised, etc.), their genre (nonfiction, fiction, poetry, etc.), and their type of writing (essay, short story, fragment, etc.). If so, then status, genre, and type of writing are the attributes that you are tagging, and you should try to use them for all text documents (to the extent that it makes sense).

The attributes that you’ll use will differ based on the type of item, so you’ll have to come up with a unique list for each item type. Make sure not to use any attributes that are already available in the item’s metadata (after all, there’s more to life than tags).

Once you have your list of attributes for each type of item, you’ll need to decide which attributes on the list are worth tagging. After all, if you think of a text document’s subject but are never going to search for text documents based on subject then there’s no reason to use a subject tag.

At last, though, you should have an idea of what attributes you want to tag for any given type of item, and then all that’s left is to consistently tag based on those attributes. This will help you in two ways: first, you don’t have to waste time and energy when you’re tagging new items trying to figure out what tags to use because you’ll know which attributes you should tag. Second, you’ll know what kind of tags to search or browse for to find different kinds of items. And perhaps best of all, you’ll have a set of general guidelines based on your unique way of thinking about tagged items that will stay consistent over time.

There will of course be cases where you’ll not use an attribute for an item or will use another attribute, but in general knowing the what will allow you to keep your tags much more consistent than if you were just throwing tags on items based on your feelings and thoughts of the moment.

Finding the what

There’s no one correct way to find the what. Some people may want to sit down before they start tagging at all and deliberately map out a list of attributes for each type of item they will tag. If you do this, you’ll likely have a very consistent and well thought out tagging system. However, you could also just keep the what in mind while you’re tagging and observe what attributes you tend to use. It’ll be sloppier, but you’ll still end up with a more consistent tagging system than you would otherwise.

One last thing to remember is that the what will change over time. New software will come out and you’ll think of new ways to organize items or begin to think about tagged items differently. Even if you take the deliberate road and create a list of attributes to tag, you’ll need to be flexible. Putting some effort into figuring out the what early on will certainly be worthwhile, but there is ultimately no fighting the vicissitudes of time and the human brain.

Tagging guidelines

1. Tagging best practices
2. A singular question
3. Replacing spaces
4. More to life than tags
5. The what

I’ve said it before and I’ll say it again: tags are an extremely flexible way to organize the mad rush of information that is your computer. As you no doubt have picked up (from the existence of this blog, if nothing else), I have a bit of a love affair with tags.

However, while tag-love is a special and beautiful thing, if you are going to create a really great tagging system one of the most important things you have to know is when not to tag.

Remembering that there’s more to life than tags is sometimes difficult, particularly if you’ve just discovered tags and had that little “ah-ha!” moment when you realized that folders are not the only way (if you haven’t had this moment, take it from me: it’s a good one). Many converts to tagging, in their zeal to jump into a new system of organization, forget a simple fact: tags are the least effective metadata you have available to use.

This is because most metadata comes in key / value pairs. The key is what the information is (for example, the date a document was created), and the value is the information specific to the item (for example, I have a text document on my computer that was created on Dec. 17, 2005). Key / value metadata is really useful, because you can search a specific key based on a specific value, so you know exactly what kind of items you should find. Custom searches can be targeted very effectively using key / value metadata.

Tags, unlike most metadata, are just a value. Unless you get tricky with your tagging, a tag contains no information about what it represents. If I tag a photo “paris” it could be the city or the celebrity, and until I’ve looked at each of the photos that my search turns up I won’t know.

Because searching through key / value metadata is far more effective than searching through tags, you need to make sure you know what kinds of metadata are already attached to the items you are tagging. Unless you’ve made a conscious effort not to duplicate information from key / value metadata in your tags, you may well discover that tagging and finding items is more of a head-ache than it’s worth.

There are several ways you can find out what metadata is attached to an item before you begin tagging. The Finder’s Get Info window is an excellent place to discover the basic, automatic information that gets attached to every file on your computer. You can also choose File→New Smart Folder in the Finder to see some of the information that you can easily search. Third party Spotlight extenders like FileSpot can help even more in this regard. In iPhoto, you can find the large amount of information automatically attached to photographs by selecting a photograph and choosing Photos→Get Info or hitting command-I. Most other programs that include tags have some sort of key / value metadata attached to items, as well. You just have to find it. (The shortcut command-I is fairly prevalent for getting such info; if you’re at a loss, just try it to see what happens.)

Once you’ve figured out what metadata is already attached to a type of item, then when you’re tagging those items you should make a conscious effort not to duplicate that metadata.

Tags are amazing and flexible, but unless you know when not to tag they will make your life needlessly complicated.

Tags for every situation

1. Tagging for productivity
2. File library vs. file system
3. File system tagging
4. Tagging files with file libraries

I suppose I’ve put off talking about the actual tools you’ll use for tagging long enough. It’s time to do a run-down of the available tagging software with some advice from your’s truly on whether it’s worth using or not.

This series will focus on the different areas where you might be tagging: productivity (read: miscellaneous), file libraries and the file system, photos, bookmarks, and general writing. These articles will not contain specific workflow examples, however; I’m just pointing out the tools you can use. I’ll get to how best to actually use them later.

I’m starting with my miscellaneous category because it contains what is essentially the One True Tagging Tool on the Mac: MailTags.

MailTags is not a perfect example of tagging or browsing (some of its failings are that it has auto-completion on single emails only, a clumsy contextual menu for multiple emails, and only allows searches or saved searches to locate items). However, it is still quite possibly the most useful tagging implementation on the Mac. Other programs make a point of stating that they are compatible with MailTags. That’s how cool it is.

The reason MailTags is so useful is because it does more than just tagging. The tagging, if you use it carefully and thoughtfully, will make locating and filing emails a lot easier and simpler than the old folder system (hint: define some rules to apply tags, and do it early). MailTags also offers iCal integration, project management, and more, which is what makes it really stand out as a must-have app. This is perhaps a useful object lesson: you can do a lot of cool stuff with tags, but the best tagging software will implement tagging into a larger picture.

Next up is iGTD, the “getting things done” app from Bartek Bargiel. Although I’ve written an in-depth review of iGTD, the short version is that iGTD is a very powerful application that is overly complicated to use. Tagging in particular seems like a feature that is of limited usefulness, although the integration with MailTags is definitely a big plus.

If you do much coding, you might want to try out Code Collector Pro, an app that stores snippets of code and sports a number of fun features beyond tags, such as support for TextMate syntax coloring bundles. Tags and smart views are the main organization within the program, and work nicely. Although text expanding programs or TextMate snippets might serve you just as well, Code Collector Pro is definitely worth a look-see if you need a quick and easy way to track reusable snippets of code.

Finances in need of some tags to make sorting them out easier? Check out Cha-Ching. Although the program is nowhere near as powerful as many financial managers, it is a lot simpler and it has a nice tagging implementation with useful and simple smart folders. I’ve been using it for a month or two and been overall pretty happy with it. Then again, my needs are simple and I’m biased towards tags.

Should you enjoy using 37signal’s Backpack service you should definitely check out PackRat, a desktop client to the web-based Backpack. I am not a big Backpack fan, but it can definitely be a useful service, and PackRat brings it offline; always a nice addition to a sweet web 2.0 application.

Of course, this is hardly an exhaustive list of tagging programs that can help your productivity out, but most of the others can be more easily categorized. Next up I’ll be covering those favorites of tagging junkies: file libraries and file system tagging.

Tagging guidelines

1. Tagging best practices
2. A singular question
3. Replacing spaces
4. More to life than tags
5. The what

Sadly, not all tagging software is coded equal. Sometimes tags are thrown in as just one more bell or whistle, intended to plump up a feature-set without being particularly useful. Other times developers don’t understand tags themselves and end up implementing them in a way that is not as friendly as it should be. Sometimes supporting spaces in tags causes other problems (such is the case when trying to roll your own tagging system using Spotlight comments).

In any case, you may well run across a piece of tagging software that does not allow you to use spaces in your tags, which can be a major pain in the nether regions. What you do about it is really up to you (although of course I have some suggestions), but when you decide remember the tagging mantra: consistency, consistency, consistency. Pick something and stick with it.

Developers disallow spaces in tags for any number of reasons. Some, such as the difficulties with Spotlight comments, are totally legit and you just have to work around them. Others, such as the idea that tags should only ever be a single word, merely show that they don’t really understand tagging (sometimes it is impossible to use a single word; for instance, when I’m using Cha-Ching to file my financial expenses, I need to tag some of them “one crayon” so I know it’s a One Crayon business expense; thankfully, Cha-Ching is friendly about spaces). In these cases, file those feature requests!

Whatever the reasons, we’re living in the present and not some perfect world of the future, so your best option is to use some character to substitute for a space.

I highly recommend the underscore. Underscores have been a standard space replacement online for quite some time; it looks kind of like a space, it’s about the same size as a space, and it doesn’t really have any other practical usage now that typewriters are out of fashion.

Other good options are the hyphen and the plus sign, but they are less desirable for two reasons: 1) they are more intrusive when it comes to reading the tag, and 2) they are sometimes used for more powerful searching. Of course, if the software developer disallowed spaces, then they may well not support AND/OR and NOT searching, but you never know what the future may hold.

Another option, of course, is to go wiki-style and use camel case (for example: “ShortStory”). I personally advise against this because it opens up an even nastier can of worms than normal in the lowercase/uppercase debate (do you capitalize the first word or not? What about for proper nouns?), but it is as always up to you.

If you are lucky, of course, the software will be friendly enough to substitute an underscore when you hit the spacebar (instead of completing the tag). But if not, go with the underscore anyway. It’s a winner.

I will try to get some software recommendations and reviews written in the near future, but it may be some time before I’m able to jump headfirst into real workflows. In the meantime, I’d like to offer some good resources elsewhere on the web that you can use to get your tagging system off the ground. Sadly, I haven’t been able to locate many good resources (which is a big reason I started Tagamac, actually), but at least there’s a few.

Probably your best bet when thinking about tagging is The Apple Blog’s wonderful, step-by-step overview of file system tagging using Quicksilver and Default Folder X. Here are the links to the complete five part series:

• Part One: Using Metadata Effectively
• Part Two: The Tools
• Part Three: Screencast
• Part Four: Answering Screencast Questions
• Part Five: Wrap Up

If you are interested in collaborative or public tagging (through services such as del.icio.us), then you may find Wired’s Tips from Top Taggers or TechSoup’s Thirteen Tips for Effective Tagging interesting.

I’ve found some other articles on tagging, but they tend to either focus on very limited tagging systems (such as those on a single website), or not provide much of use. If you know of any other great articles or websites that offer good tips on tagging, please let me know! I don’t want to leave anyone out in the cold while I’m working on my great crusade to create a full and complete tagging resource, but I certainly don’t have encyclopedic knowledge of everything that’s been written about tags.

Tagging guidelines

1. Tagging best practices
2. A singular question
3. Replacing spaces
4. More to life than tags
5. The what

Since I published my advice on tagging best practices, the most common question I’ve received has been something along the lines of “why the heck would you use singular tags?” Everyone agrees that consistency is the name of the game, and it’s hard to argue with succinctness. Some people disagree with using lowercase tags, but quite honestly it’s mainly personal preference (unless the program uses case-sensitive searching).

Whether or not to use singular tags, though, is a much more open question, and I’d like to lay out the reasons that I included a recommendation to stick to singular.

First I should mention that I don’t think every tag should be singular; whether or not you use singular tags is highly situational. For instance, if you have a photograph with a group of people in it, then tagging it “person” is utterly ridiculous. When I advise using singular tags, my hope is that people will try to stick to singular tags only when appropriate. If singular tags are the baseline, then searching for “people” as opposed to “person” means you get two different sets of items rather than one set of items that includes both. (Of course it can work the other way if you use plural tags as your baseline, too. Whatever makes the most sense to you is what matters.)

Second, a major assumption that I held going into the best practices article was that you are tagging items in a desktop program for personal usage. In this case, there is no question over what you will search for because you have complete control over all three parts of tagging. However, if you are tagging items so that other people will find them (the case in most online tagging), you will need to think about tags differently. Sticking to plural tags may actually benefit you more for online tagging, because people tend to think of tags online as categories. Neglecting to mention that my SLS guidelines are most appropriate for personal use was an oversight of mine; there are large differences between personal, public, and collaborative tagging.

Ideally, of course, your tagging software would permit creating synonyms for tags. Unfortunately, we don’t live in an ideal world, and this is pretty rare (might even be non-existent; off the top of my head I can’t think of any software that supports tag synonyms).

At base, whether you tag by default with singular or plural really relies on how you think about tags: are you tagging what an item is or what an item is one of? In the first case, you should use singular as much as you can. In the second, you should stick to plural. For example, I could tag this article “clarification” because I am clarifying an earlier argument. Or I could decide that my “clarification” tag is more like a category; it contains multiple items, each of which is a clarification. In that case, I would tag this post “clarifications”.

I personally prefer to use singular tags as my default because I think of tags as terms that describe a specific item. For me, a tag says, “This item is a [blank]“. I am not sorting items into categories; rather I am attaching descriptive terms to items. The wonderful thing about tags, though, is that if thinking about tags like this makes no sense to you, you don’t have to follow my advise.

I knew when I included both lowercase and singular into my little “SLS” scheme that they were mostly reliant on individual preference. The reason that I included them, however, is because both the capitalization and plurality of your tags are things you must consider when you are building a tagging system. I don’t care whether you tag things the way I do; what I care about is that you think about the issue before you start tagging inconsistently and causing a lot of pain for yourself.

I hope this has helped to clarify my standpoint on the plurality of tags! If you have any thoughts on the matter, I would love to hear from you!

Tagging guidelines

1. Tagging best practices
2. A singular question
3. Replacing spaces
4. More to life than tags
5. The what

In all honesty, best practices for tagging vary greatly depending on the type of tagging system and tag browser you are using. Additionally, because tags are so flexible, how you use them also relies a lot on what makes sense to you. There are still some things you should think about when you tag, though, and I think they’re important enough that I’m posting them now before I dive more in-depth into tags.

First off is tagging’s golden rule: be consistent. You can disregard every other piece of advice I give you, but consistency is the single thing you must strive for when tagging. Everything else is window dressing. That said, here are three things that I think almost every tag should be, regardless of what program or system you’re using: succinct, lowercase, and singular.

Succinct

Of the three, this is the one that is absolutely necessary. Tags must be short, simple, and memorable. Always pick a single word over a phrase. Pick a word that is the most descriptive you can think of, but is also one you will remember later. Never use a complicated word when a simple one will work.

A succinct tag is easier to remember when you are tagging later items or searching, quicker to comprehend when you’re scanning through tags, and improves your sex appeal.

Alright, so good tagging and sex appeal aren’t actually related; you get the point. Be succinct.

Lowercase

Keeping all of your tags lowercase is a really, really good idea, but you won’t be struck by lightning or anything if you capitalize them. The main reason to stick with lowercase is consistency. Not only are tags generally lowercase by convention (which means some programs may have difficulties with upper case letters in tags), but lowercase is a better default.

For one thing, if you keep all your tags lowercase, then it is impossible to have problems with a program mistakenly matching the case of a tag. For another, it is easier to maintain consistency if you always use lowercase letters. Capitalizing only proper nouns may work, but down the road you may change which words you capitalize or use capitalization inconsistently with some words. And hey, lowercase letters are just quicker to type.

You don’t have to keep everything lowercase, but I strongly recommend it (grammar-Nazi that I am, when I first started using tags I capitalized proper nouns; then I sat down and thought about it and realized I was being a bit silly).

Singular

Of my three best practice guidelines, this is the one that you’ll ignore the most. The reason that I include it at all is that you should only use plural tags when absolutely necessary. If you stick to singular words by default, then it reduces the questions you may have when searching your tags. “Did I tag that photo ‘people’ or ‘person’?” is a question that wastes your time and adds unnecessary difficulty to tagging.

By consciously making an effort to keep everything single, you will improve your ability to find exactly what you are looking for, which is what tags are all about. There are certainly times when you should use a plural tag; just make it count.

Consistency

At root having “SLS” tags is really all about consistency. By keeping your tags succinct, lowercase, and singular, you’ll be making it easier to search them and tag similar items consistently.

There is, however, a lot of variation in how to tag an item. Whether you use specific or general tags, more or fewer tags, and redundant or distinct tags has more to do with the software you are using than anything else. But that’s a topic for another time; for now, I hope you will find the idea of SLS tags useful!