Mail > File to Task…

Perhaps this is already obvious to everyone else who has inbox overload, but I just figured out what I hate about e-mail and task management: they work against each other. Even if you’re the sort of person who diligently creates to-do lists in applications such as Anxiety or Things, any incoming email about your to-do items has nowhere useful to go. You currently have the following options:

  1. Leave it in your inbox until it’s done. I believe this is the most common and works decently if your load is low. It breaks down big-time when you have hundreds of e-mails on the same subject though and negatively affects your ability to deal with the rest of your inbox as a result. Even when you complete a task under this strategy, you often have to sift through your inbox and delete many e-mails afterwards.
  2. File it in either a simple or complex folder arrangement. This does not work well for many people, including me, because if something is not in our inbox, we tend to forget about it. Filing is for long-term storage, not easy recall.
  3. Make use of the “flagging” function in your email app, and flag each incoming message that requires action. This is mainly an improvement upon method 1, but it doesn’t solve a lot of problems.

I’ve given a bunch of different workflows a shot but nothing seems to have struck a chord yet. In popping open Anxiety today for the first time in about a year, I was reminded of how much I like its simplicity. It’s an automatically synching list of tasks and nothing more. You click to add a task and then when you complete it, you click its checkbox and it goes away forever. There’s no tagging, no dragging, and no nagging. It’s basically a half step more advanced than electronic Stickie notes… which I love.

That got me thinking, however, of how a nice simple app like this could play a role in finding the holy grail of time management: a simple solution that both declutters and organizes your information workflow, helps you get things done, and doesn’t require you to learn much or add administrative tasks to your routine.

I may eventually mock this up and screencast it or something but I’m too lazy right now so here it is in a nutshell:

  1. You receive an email from a co-worker telling you that you are on the hook to provide a mockup for a new product. It is due in a week.
  2. You click once in Anxiety (or a similar app, or some similar function in your Mail app) to create a task. You call it “Create mockup for Product X” and it instantly shows up in your task list.
  3. Every subsequent mail that comes in about this subject is either deleted by you if it’s trivial or “filed to this task”. Filing a message to a task removes it from your inbox and places it in some sort of mail folder that is linked to the task you created in Anxiety, Things, or whatever app. The key is how it gets there. Dragging messages in mail applications requires too much precision and mouse movement, in direct opposition to Fitts’ Law. Dragging 100 messages a day to different mail folders is incredibly onerous, especially if you have a ton of mail folders. Instead, inside each message would be a few buttons representing recent tasks you’ve filed messages to. There would also be some intelligence built-in based on subject lines and senders. With one click, you could file the message to any of your open tasks.
  4. You send off various mockups over the next few days and every time you need to refer to an email you sent or received about the project, you could simply click on the task in the task list and a (smart?) folder would open in your mail application showing you all messages filed against this task.
  5. You send off your final mockup and check off the task as “done”. The task is removed from your list and the folder full of messages tucks into an archive somewhere, out of sight and out of mind.

To me, this is the ideal workflow of an e-mail/task management system, and I haven’t seen anyone do it yet. Microsoft, of all companies, actually tried something along these lines with “Projects” in Entourage, but the interface got in the way. I’d love to see someone tackle it but with a keener eye towards simpler, more natural interaction. I almost wonder if the entire thing could be done with and AppleScript.

Whoever finally solves the problem of inbox overload is going to make a lot of money. This would be a great first step.

28 comments on “Mail > File to Task…”. Leave your own?
  1. Gmail (and Google Aps) addresses this very well with the Archive and Labels features as well as the integrated Tasks application.

    I haven’t touched Outlook (or whatever email client) in 3 years, and never missed a bit of it.

  2. Mike D. says:

    Jean: Interesting, I’ll have to check it out. Unfortunately I never really warmed up to the Gmail web interface, although I know others love it. I still feel like I want e-mail as a dedicated application and not just a web app.

  3. Sean S says:

    I’m with you on this — and have found relative success with the latest version of Things and it’s Autofill function. Now, when I receive an email that requires action, I use the Quick Entry HUD with Autofill (control+option+space) to create a new To Do item with a link to the email.

    Of course, this workflow is still flawed since it (1) still requires you to file the message(s) in a folder system in order to achieve Inbox Zero, (2) doesn’t really work with multiple email messages well, and (3) isn’t drop-dead simple to learn and perform.

    I hope something like you’re describing is either possible with AppleScript, or really simple to implement in a light-weight app.

  4. AJ says:

    I definitely agree – whoever solves this and integrates it with mail will definitely make a lot of money.

    In the meantime though, I’ve solved this by 1) linking to the thread in GMail in the URL field, and 2) adding notes for any relevant emails/phone suggestions/ideas I have on my own afterwards/hours worked on this/etc.

    I use RememberTheMilk and since it syncs my notes to my phone and the web interface, I think it’s great. When I have a task that has a long thread linked to it or a lot of notes, I just print the task details on their own page or print the thread out when I’m working on that task so I have all those comments as a handy reference.

  5. Hans says:

    Looks like Anxiety is actually found at Hadn’t seen it before. I like the price.

    OmniFocus is another alternative, though more expensive than Anxiety and Things.

    (Editor’s note: Thanks… fixed the Anxiety URL!)

  6. masklinn says:

    > You click once in Anxiety (or a similar app, or some similar function in your Mail app) to create a task. You call it “Create mockup for Product X” and it instantly shows up in your task list.

    Not that it will help you much, but note something important: Anxiety doesn’t actually handle tasks, it just gets them from iCal’s todo system… and it just happens that Mail (at least 10.6’s) can create todos straight from a mail itself (select some text, right-click -> new to do). There’s also Things integration via the Services menu (new to-do with selection as title and new to-do with selection as note).

    You can even link the todo item to a mail from iCal’s task inspector by using the `message:` URI scheme: grab the Message-Id header from mail (that part’s a pain because you have to use the long headers, a bit of scripting would probably be a good idea) and paste it with the `message:` prefix in the “url” field of your task.

  7. MAS says:

    Your post reminded me that I set up an account on many moons ago. Because it was not integrated with my email application, I forgot about it and stopped using it. So true.

    @Jean – I’m going to give GMAIL Tasks a try. Thanks!

  8. I use Things and Apple Mail, and when I get an email that needs to find it’s way into a to-do, I use the aforementioned Things service, which launches a HUD window instantly with that text pasted in, and includes a direct link within the note to the original mail message. I didn’t know about the keyboard shortcut, I’ve been using the right-click menu to trigger this.

    Things can also do this for linking to files. So if a to-do item relates to a text file, for instance, I’ll just drag and drop that file into the to-do to create a link to it.

    I’ve been very happy with Things, after a long search for the right app, including trying to do custom things with OmniOutliner. I don’t use it to it’s full GTD™ potential, but I developed my own, similar flow.

  9. hendryk says:

    There is AppleScript. You can create task based on email title, author, content it can go to particular list in your task managment app (Things, The Hit List and others which are also using AS).

    Some of my tasks are created when new mail arrives, some are created based on the selected message.

    You can find example scripts in Things wiki or THL grouplist.
    There can be dock icon for creating task from selected message, there are mailtags extension for Mail, you can assing mouse button and so on…

  10. Baxter says:

    Brilliant. I hope the folks at Apple are listening and include the idea in a not-too-distant-future version of Mail.

  11. Patrick Shaw says:

    I use Outlook with the Getting Things Done plugin – and while I’m only decent at using the entire GTD philosophy – the plugin creates mini folders, keeps track of all of the email (you have to associate an email with a project) and has a terrific set of “I’m waiting for Joe to finish . . .” reminders. Keystroke friendly, too – although – if anyone knows the keyboard shortcut for clicking the drop-down arrow in Microsoft Outlook – that would be even better!

  12. hendryk says:

    Baxter, you can try
    Every mail can be a task, you can assing project, deadline…

  13. Brade says:

    I’ve been recently thinking about just this topic and have considered trying my hand at an app that combines email and task mgmt. The problem is that Mac Mail is nearly perfect so I’m not sure I’d use my own app unless it tied directly into mac mail. I am going to try this anxiety thingie though…

  14. hendryk says:

    Once again MailTags is plugin for Mac Mail so you have everything in one place.

  15. Peter Kaizer says:

    Actually I have found the best way to do this is with the Mail Act on plugin from the same folks who make Mail Tags:

  16. The best solution for me, Mike, was to set up a simple web-based CRM system — I’ve been using Highrise from 37Signals — then use their dropbox feature. Just forward an email to your dropbox email address or BCC the dropbox in an email you send, and a copy goes to your CRM system. In there, you can associate with people, tasks, projects, etc, and a lot of that is done automatically for you by the application. It’s been a big help to me in solving the inbox overload and filing problems you describe.

  17. Andrew Korf says:

    I am with you…. I would pay good money for desktop > mobile (iphone) > mail > browser > calendar integration for a smooth simple todo application.

    taskpaper, simplenote, instapaper are all examples of clean simple apps that rock – integration and better cross platform syncing and I’d be a loyal customer.

  18. I programmed outlook to at least allow me to pop messages easily to a folder. If this was easily extend-able it could be partway there. I wonder if a macro could be written to do this…

  19. “I wonder if a macro could be written to do…” what you are after…

  20. Steve O says:

    This looks cool… I instantly thought of your blog post when I saw this:

  21. Drew says:

    This sounds very Google Wave-ish…

  22. Jon Bell says:

    I use OmniFocus, which allows me to press a hotkey from any app to immediately file the selected text/item/url/mail/whatever into my OmniFocus’ inbox.

    As long as you make sure to check your inbox, and keep the todo as an accurate reflection of what you have to get done, this method is as frictionless as it gets.

  23. Have you seen HitList

    You can get it for free the next two days from the new Nano Bundle from MacHeist

  24. pardon, my mistake, still a cool app though. I got it from the last macheist.

  25. Mike D. says:

    Steve O: Thanks for reminding me about Daylite. I have a friend who swore by that several years ago. I’ll have to see if he’s still using it. At $189, they have probably priced themselves out of most people’s budgets, but if it really does do what I need, I’d pay that much.

    Brandon: Thanks, hadn’t seen HitList. Looks slick. They appear to still be in beta, but I’ll give it a shot. They seem to be thinking about the problem in a similar way as I am.

  26. Will says:

    If an email needs ‘action’, I just click reply and save and it sits in draft folder. This forms a defacto to do list.

    Why make it more complicated? Searching out a new magical ‘app’ wont get things don’t quicker – in fact its probably just another form of procrastination from doing what’s actualy on the to-do list

  27. Mike D. says:

    Will: Very, very interesting… and very low tech. I like it. I may have to try it.

  28. […] with everything from design tools, pitching for a job, social media etiquette, or how to just do email better. Many “online personalities” have built entire careers on talking about productivity […]

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