My approach is based on Gina Trapani’s system, which she describes in this Lifehacker post. Her system is based on a slightly more involved method by productivity expert Merlin Mann, described here. And I suspect that his system is based on David Allen’s GTD, probably the most popular general time management method right now.

The four folders

I use IMAP to access my email. I archive all of my emails on my main computer, which is being backed up regularly. I’ve created three folders on my mail server: FollowUp, Hold and Later. On my main computer, I have a folder called Archive.

Here is what these folders are for:

• FollowUp contains any emails that require an action on my part. Not necessarily a response – an action. If I need to reply to an email, it goes in here. If I get an email saying someone is following me on Twitter, and I need to decide if I am going to follow them back, that email goes in here. Even if I just need to read and think about an email, but don’t have the time to do so right away, it goes in here.
• Hold contains any emails that I need to have around for awhile, but do not require an action. Examples are shipping information emails and flight and hotel reservations. The nice thing about IMAP is that I can access these emails from anywhere, as long as I have an internet connection. I don’t have a lot of emails in here, but I wouldn’t know of a better place to put them if I didn’t have this folder.
• Later contains emails I want to read later. It’s that simple. It usually contains emails from mailing lists or links to articles I intend to read. There is a grey zone between FollowUp and Later. Later means you will read it later, but that is an action, so why isn’t it in FollowUp? If it’s not important, why isn’t it in Archive? My rule is: If the email requires an action, but I can afford to ignore it, I put it in Later. Otherwise, it goes in FollowUp.
• Archive contains all emails I have dealt with. Again, it’s that simple. I used to archive using a hierarchical set of folders, but I stopped doing that and now just put everything into one huge mailbox. It makes archiving that much easier – meaning I actually do it – and search is powerful enough these days that I can find any email I need. I haven’t missed my hierarchical folders at all, especially now that I’ve added some smart mailboxes.

The final folder in this system is the Inbox. And again, the rule is simple: keep it empty.

My old system

Before I explain how I use these folders, let me tell you about my old system. I had a pretty full inbox. If something needed following up, I would flag it. I added a smart mailbox showing me all flagged emails so I could quickly see them all. This seemed a reasonable approach to me, but it didn’t work. It didn’t give me clarity of mind. I would still look at my inbox and feel stressed over certain emails, whether they were flagged or not.

I think there are a few reasons for this. First, when I looked at my full inbox with flagged emails, there was a lot of information on the screen, a lot of emails that all required different things: reading, replying, processing. In my new system, all folders except Archive contain a very low number of emails, and most of them are basically a little list that I can work through email by email.

Second, it was not clear from looking at my inbox which emails I had processed – in the sense of determining what I needed to do with it – and which I hadn’t. To me, the key element of GTD and similar time management methods is the processing and classification of items. You separate the time management itself from the actual work. You sit down and process your unsorted, messy list of (as David Allen puts it so well) stuff and you classify it into containers corresponding to how you intend to treat each item. Then you actually deal with the items.

When you do this, it becomes incredibly clear what you need to do with each email. Everything becomes nice and crisp. If it’s in your inbox, you haven’t processed it yet. And that is something that became hard to see in my old system. Unread status just doesn’t do it: often you need to read an email to decide what to do with it. Setting the mail back to unread is cumbersome, and then you can’t tell which are the really unread emails, and which ones are read, but unprocessed ones. With my current system, it doesn’t matter if a mail is read or unread: if it’s in my inbox, it’s unprocessed.

How to use the folders

After setting up the folders, there are a couple of routines you need to follow on a regular basis. First of all, keep your inbox clean. The nice thing is that this requires almost no brain power. I do this on my iPhone in the subway. Just go through each email and move them to the right folder.

Second: check your FollowUp folder and, well, follow up. The FollowUp folder is like a to-do list (but only like: I use a different program to handle my main to-do list, as I don’t think email clients are the right tool for this). Effectively managing a to-do list is a topic that is beyond the scope of this article.

Third, occasionally check your Later and Hold folders. This should be lower priority. You should not be able to get into trouble over ignoring these folders for a while. You did put that flight on your calendar, right?

How to get started

So how do you get started with this? It’s easy. Set up the folders, and process your inbox. I had one full inbox and at least two ‘DMZ’ folders containing emails going back years when I started using this system. I blew through all of them, many hundreds of emails, in a few hours. Just process. Archive, FollowUp, Later, Archive, Archive, Hold, Archive. Don’t think about what the email is about or what work it entails: just put it in the right folder. It was very easy, and incredibly satisfying.

So that is how I’ve been managing my email. It works for me: I have had an empty inbox since the day I started using this system. Maybe it can work for you as well. I have not used this system under the toughest of conditions. When I was a producer at Rockstar Games, I would get an incredible amount of email. We had many automated emails: repository summaries, vacation requests, build process reports. Everyone was strongly encouraged to communicate using email, and to put a ton of people on cc. However, I think this system, perhaps extended, will be able to deal with that kind of pressure.

How do you manage your email?

I sent an email with my feedback to Bare Bones Software (obviously I feel a need to bother others with my opinions, but you already knew that since you are reading this blog).

Some time later (not that much later, I’m a bit behind on posting this), I got a very nice reply from Patrick Woolsey, Director of Technical Services at Bare Bones Software:

Thank you for contacting us. We appreciate your interest in Yojimbo, and I’ve attempted to provide comments about some of your remarks below.

Apple + I does not open the inspector. I can inspect items in Yojimbo. In other words, I can look at the fields and edit them. I am used to doing this using the Apple + I shortcut from other programs (Finder, iTunes). This doesn’t work in Yojimbo. I don’t know what Apple’s Human Interface Guidelines have to say about this, but I missed it.

Since unlike the Finder and iTunes, Yojimbo supports editing styled text (meaning that Command-I invokes Format -> Style -> Italic), it uses the de facto standard key equivalent of Command-Shift-I to bring up the Inspector instead.

Am I Moving to Trash or Deleting? The icon says one thing, the drop down menu says the other. Is there a difference? I am confused.

For items, the result is always a Move to Trash; collections (only, never their contents) are deleted directly

Tag Collections only use ‘and’ relationships between tags. You can make tag collections in Yojimbo, kind of like smart playlists in iTunes, only dumber. You can enter a number of tags, but the collection only selects items that have all of these tags (an ‘and’ relationship). You can’t have collections that select items that have any of the tags (an ‘or’ relationship).

That’s correct. We do plan to support user-definable smart collections in a future version, which will allow additional relationships. Tag collections however will remain in their current form, as we may add support for tag-by-dropping in some future version.

Tag entry shortcuts suck. I can’t think of a better way to put it. I had the following tags: ‘to_blog’ and ‘to_read’. When I am tagging an item, I start typing ‘to_’. As soon as I hit the underscore, Yojimbo selects the first tag that start with ‘to_’ even though I had several other tags that start with ‘to_’. This is about as annoying as it gets. I renamed all my tags to (the inferior) ‘blog_it’, ‘read_it’, etc. [...]

Yojimbo is using a standard system facility for tag item creation (as also used for e.g. address entry in Apple Mail).

If you have tags “to_blog” and “to_read”, upon typing “to_”, you will get a popup list of possible matches from which you can either select directly, or you may continue typing to further narrow.

[I followed up on this as there really was an issue with underscores. This was logged as a new bug report.]

Renaming tags is impossible. You just can’t do it in Yojimbo. Or at least I couldn’t find out how to do it in less than 30 seconds, which is the same thing. (Remember: I am not arrogant, I read Donald Norman’s book.)

There is no facility for renaming tags at present (other than via scripting); this will probably change in some future version. :)

Entering tags is counterintuitive. To me at least. Type ‘atag anothertag’ and you get ONE tag called ‘atag anothertag’, instead of two tags. You have to type ‘atag, anothertag’.

The ability to use phrases as tags is intended.

Tags that are not used keep hanging around.

This also is by intent, so that (using the autocompletion) you can reapply the same tags you’ve previously used, even though there may not be any instances at the moment.

There is no purge, you need to delete unusued tags by hand, and you cannot easily see if a tag is in use or not.

If you attempt to delete a tag that’s in use, Yojimbo will warn you. Beyond that, I expect that going forward, there will be additional tag management options though I can’t say at present what exact forms these might take.

Adding items is inconsistent. In Yojimbo, you can add items using several different methods. Sadly, each method works slightly differently:
*
* When you drop a link (a URL) on the drop dock, there is no feedback whatsoever, but the software creates a new item with the correct title and URL. You just have to go in later, find the item, and tag it, which is a) hard (see below) and b) bad workflow.

The intent of the drop dock (and indeed all of Yojimbo’s input mechanisms) is to make entering info as easy as possible, so that you’re more likely to do so. :)

As we haven’t yet been able to identify a sufficiently low-friction way to handle tagging on drop, this doesn’t happen. :)

* When you press F8 with a URL in the clipboard, Yojimbo creates an item with the correct title and URL, but you can’t enter tags (even though a dialog box pops up).

If you open the tag field by clicking the triangular control next to the Name field, you can indeed do so.

* When you drag a link on to the dock icon, Yojimbo creates a new item that does not have the correct title (it uses the URL instead), but you can enter tags.

For bookmarks, this is a limitation resulting from how the Dock handles dragged info; we have more control over actions performed through Yojimbo’s own Drop Dock.

I can’t make an ‘Untagged’ tag collection.

Please see View -> Smart Collections -> Untagged Items.

So, I missed some stuff, I fell on the wrong side of a few design trade-offs, and some features are planned for the future. This was kind of what I expected, but still, I was very pleased by the nice reply I got. Although I still don’t think Yojimbo is quite right for me, you might want to check it out.

Here is a list of 20 useful OS X tips by Chris Howard over at Apple Matters. I am not a hard-core Apple geek, but I am not a noob either – I didn’t know many of these, and some of them are quite handy.

9. To select a block of text, click the start position, then Shift-click the end position.

15. Option-click the minimize button minimizes all windows in the application – and makes for a really cool animation (hold the shift key too if you want to slow it down to see it more easily).

16. Option-click on a minimized window will restore all windows for that application.

20. When menus are selected, press the option key to reveal alternative functions. Eg In the File menu of Finder, the Get Info item becomes Show Inspector which is like a context sensitive info pane.

And here is one I found out through TextMate – I can’t believe this is OS X standard. Select a block of text, press Command-E, then Command-F (or just select Find in the Edit menu of an application that supports it). The block of text is now in the Find dialog. (I’d prefer it if all Find dialogs would just take my selection, but eh.) The TextMate manual claims Command-G does something related, but I couldn’t figure it out.

Well, here is something I never expected to write. I am going to review Yojimbo – not the movie by Kurosawa or the comic by Stan Sakai, but the Mac OS X information organizer from Bare Bones Software, makers of BBEdit.

Why? Because I can. And because I have something to say about it.

Here is what Bare Bones say about Yojimbo on their website:

Yojimbo makes keeping all the small (or even large) bits of information that pour in every day organized and accessible. It’s so simple, there is no learning curve. Yojimbo’s mechanism for collecting, storing and finding information is so natural and effortless, it will change your life—without changing the way you work.

I am interested in personal productivity, so I decided to try the demo. I used it for a while to handle the things I come across that I want to read, blog about or cook (in the case of recipes). This blog post is about the things that started to annoy me quite rapidly. Now, if the following list sounds unreasonable, don’t blame me. Blame The Design of Everyday Things by Donald Norman. Reading it was an immensely liberating experience for me. Now, whenever I have trouble using something, I don’t feel like an idiot, I just blame the designer. Sounds stupid? I am quite serious.

Here is my litany of complaints about Yojimbo in no particular order:

Apple + I does not open the inspector. I can inspect items in Yojimbo. In other words, I can look at the fields and edit them. I am used to doing this using the Apple + I shortcut from other programs (Finder, iTunes). This doesn’t work in Yojimbo. I don’t know what Apple’s Human Interface Guidelines have to say about this, but I missed it.

Am I Moving to Trash or Deleting? The icon says one thing, the drop down menu says the other. Is there a difference? I am confused.

Tag Collections only use ‘and’ relationships between tags. You can make tag collections in Yojimbo, kind of like smart playlists in iTunes, only dumber. You can enter a number of tags, but the collection only selects items that have all of these tags (an ‘and’ relationship). You can’t have collections that select items that have any of the tags (an ‘or’ relationship).

Tag entry shortcuts suck. I can’t think of a better way to put it. I had the following tags: ‘to_blog’ and ‘to_read’. When I am tagging an item, I start typing ‘to_’. As soon as I hit the underscore, Yojimbo selects the first tag that start with ‘to_’ even though I had several other tags that start with ‘to_’. This is about as annoying as it gets. I renamed all my tags to (the inferior) ‘blog_it’, ‘read_it’, etc. Or, rather, I wanted to rename my tags, except:

Renaming tags is impossible. You just can’t do it in Yojimbo. Or at least I couldn’t find out how to do it in less than 30 seconds, which is the same thing. (Remember: I am not arrogant, I read Donald Norman’s book.)

Entering tags is counterintuitive. To me at least. Type ‘atag anothertag’ and you get ONE tag called ‘atag anothertag’, instead of two tags. You have to type ‘atag, anothertag’. To add insult to injury:

Tags that are not used keep hanging around.
There is no purge, you need to delete unusued tags by hand, and you cannot easily see if a tag is in use or not.

Adding items is inconsistent. In Yojimbo, you can add items using several different methods. Sadly, each method works slightly differently:

• When you drop a link (a URL) on the drop dock, there is no feedback whatsoever, but the software creates a new item with the correct title and URL. You just have to go in later, find the item, and tag it, which is a) hard (see below) and b) bad workflow.
• When you press F8 with a URL in the clipboard, Yojimbo creates an item with the correct title and URL, but you can’t enter tags (even though a dialog box pops up).
• When you drag a link on to the dock icon, Yojimbo creates a new item that does not have the correct title (it uses the URL instead), but you can enter tags.

Each method does something different. You have to choose the lesser evil (the drop dock in my case).

I can’t make an ‘Untagged’ tag collection. This personally drives me nuts in a lot of tag- or collection-based software – the worst offender is OS X’s Address Book. If I want to do a GTD-like ‘throw into inbox, process later’ process, I need to be able to see what I haven’t processed yet. Only I can’t, because I can’t make a smart collection that checks for the absence of a tag, or the absence of all tags. Note that I don’t really want to process later, but I am forced to because I can’t easily enter tags for a new item (see above). I can’t implement the workflow I want using Yojimbo.

So there it is. I didn’t do full-fledged hyper-analytical testing, but I did try each thing a couple of times to make sure I wasn’t mistaken. As far as I can tell the natural thing I expected to happen, didn’t, every time.

I am still slightly puzzled about why I wrote all this. I think if over 75% of the items on this list hadn’t occurred to me in about 15 minutes, I never would have written it down.

Although I can get pretty passionate about software usability, I intend no disrespect towards the developers of Yojimbo or their ancestors. In fact, I am going to try and send them this in the hope that it is of some help (that is, if I can find some way of doing so short of signing up for their mailing list). Good feedback can be hard to get, and this post at least beats saying ‘Yojimbo sucks’ or just quietly looking for another piece of software.

Having said that, I am going to look for another information organizer.

Updated: Melodie Neal wrote a 6-part series of blog posts about her quest for a better information management tool. You can read it here. Her needs are slightly different from mine, but it was still a very good read.