The 23 stages of the task management software lifecycle

  1. Totally on top of all pending tasks
  2. Moderate slippage of select tasks leads to mild anxiety
  3. Catastrophic failure to complete one or more mission-critical tasks leads to wholesale re-evaluation of career choice, self-worth and why are we even on this earth anyhow?
  4. Application of medication, coaching and/or psychotherapy scales existential crisis back to actionable item: adopt new task management system
  5. All tasks put on hold for 3-14 days while documenting software requirements and researching available options
  6. Software selection creates brief window for completion of most-urgent tasks
  7. Installation of software across all desktop and mobile devices
  8. Optional: acquisition of any additional hardware devices or accessories that are revealed to be vitally necessary [read: nifty] in light of new task management software choice
  9. Troubleshooting of cloud-based cross-device task synchronization
  10. Capture of top-of-mind tasks
  11. Blissful peace of knowing all crucial tasks are captured
  12. Hey! all this blissful peace helped me remember the 27 other tasks I keep forgetting about
  13. Contact high from daily experience of checking off task checkboxes
  14. Evangelization of preferred task management solution to foolish friends and colleagues with their hopelessly antiquated systems
  15. Significant financial and/or temporal investment in software, workflows or custom hacks on the Best. Task. Management. System. Ever.
  16. Religious daily capture and review of all current tasks
  17. Religious daily capture of all potential tasks
  18. Gosh there sure are a lot of tasks in there
  19. Minor failure of task completion due to task management software avoidance
  20. Capture of project or event-specific task list in a separate app or document, where it won’t get lost in that big, overwhelming, depressing list of tasks
  21. Important tasks captured in emails to self so that they won’t get lost in the morass of recorded tasks
  22. Realization that completion of task list will require 8,918 hours worth of work leads to total avoidance of task management application
  23. Moderate task slippage (repeat from step #2 above)

5 ways to make task management software work for you

I have a love-hate relationship with task management software. On the one hand, I’m kind of obsessed with it: trying out new task and project management tools is one of my favorite pastimes, and it’s hard for me to resist trying out each shiny new entry in the market. On the other hand, I’m a fairly resistant user: once the honeymoon wears off,  and my task management program is full of a huge list of tasks that I MUST DO TODAY, I find that list so daunting that I tend to avoid looking at it, and go back to keeping my list in my head.

Recently, however, I’ve returned to the task management fold. For the past month I’ve been using Things, a task management app that runs on both my Mac and my iPad (and would run on my iPhone too, if I paid another $9.99). I hate to jinx it, but this time, my task list feels different. Not because Things is the Holy Grail of Task Management I’ve been looking for — I used Things for a while last year, and ended up in the same old avoidance pattern once I accumulated a few dozen items on my to-do list — but because I’m using my task list in a new way. Here’s what seems to be working, and could also work for you:

  1. Minimize your list. In the past few years, I’ve followed the GTD religion of writing down every task that is in my head, so I can free up my brain power to cure cancer or crack the problem of nuclear fusion. But in this iteration, I’ve returned to a piece of wisdom I read many years ago: for right-brain people like me, task lists tend to be generative, inspiring so many ideas that we soon get overwhelmed. So this time out, I’m writing down only the absolutely crucial tasks that I don’t want to lose track of — not the “some day” or “shoulda coulda woulda” tasks that tend to clutter up my list.
  2. Use existing software. As usual, I began my return to task management with my beloved process of investigating new software options. But I caught myself, and decided to just use the same damn software I had already purchased last year. I took everything that was in my old Things list, and archived it, so I didn’t have to deal with that backlog.
  3. Use one device. Syncing is another obsession that typically gets me worn-out with my task management regime.  Even though I use two computers, an iPhone and an iPad, I’ve resisted the temptation to pour hours into figuring out the right Dropbox setup to keep my Things list in sync across all of them. I’m just using it on the single computer I use most of the time, and since I’m only trying to track my major tasks — and not every damn thing — that is working just fine.
  4. Go solo. As a social software addict, I’ve been an intermittent evangelist of tools like Basecamp and Manymoon, which let me share tasks with my team. But one of the reasons I am now afraid to look at my Manymoon list (oh yes, it’s still there) is because of all the tasks other people have recorded for me, and one of the reasons I avoid Basecamp is that I get distracted from my own tasks by looking at other people’s. With Things, I fly solo, and if someone needs to get a task onto my list, they simply tell me about it — and I decide whether and how to put it on my list.
  5. Check rarely. One trigger of to-do list resistance is the feeling that I’m being ruled by my task management software, rather than vice versa. So I look at Things relatively infrequently — once or twice a day, or sometimes not at all. The only reason to look is if I have a major item to add, if I’m trying to decide what to work on next, or if I’ve just completed something and need to check it off.   Looking at my task list when I don’t have any time free to actually work on it is simply a source of stress, and my daily glance is enough to ensure nothing drops off my radar.

I’ve fallen off the to-do list wagon far too many times to feel confident that I’ve finally cracked the task management nut. But I’ve been shocked at how much more productive I’ve been in the month that I’ve used my task list in this moderate, non-fetishistic way. And it’s that productivity payoff — rather than the joy of using geeky software — that could keep me on track and to-doing.

AFTER e-mail: 5 steps to moving task management out of your inbox

If  watching It’s a Wonderful Life for the 8th time was the highlight of your holiday season, you obviously missed my awe-inspiring but tragically neglected 10-part series on 7 days to Inbox Zero. The day after I posted my initial promise to blog my way to empty, I woke up with the horrible realization that I just committed to spending my holiday blogging about productivity tips while the rest of you slackers were eating cookies and drinking champagne. By day 3, Google Analytics told me that your cookies and champagne were keeping you too busy to even read my blog posts, let alone act on them. But by day 4, I remembered that blogging productivity tips is my idea of  holiday, so I won’t begrudge you your slacking off: my version of slacking off just happens to involve more screenshots.

As it turned out, while it took much less than 7 days to empty my inbox, the documentation process required more than 7. So I’m supplementing the series with additional posts that fill out the workflow: please let me know if there are elements of my methodology that you’d like unpacked or clarified.

Today, I’m going to get you underway on a system that will help you process all those actionable messages that are piling up in your inbox…but with no action. In my case, that includes a lot of Google Docs invitations.  I knew there had to be a better way of handling all the messages that tell me when someone has just shared a Google Doc with me. And there are a few problems with letting those messages go to my inbox:

  1. Document invitations arrive at a moment when I’m not ready to look at the document, and get forgotten by the time I am ready to look.
  2. My inbox isn’t the context in which I work on documents.
  3. Notifications add to the inbox clutter, pushing me further away from my goal of Inbox Zero.

Those are three good reasons that this pile of Google Docs invitations got dragged to my “workflow needed” folder. That’s the folder I recommend setting up to file any kind of e-mail you receive on a recurring basis (like task assignments) so you can find a better way of dealing with them. Here’s what I’m trying to clear out of my inbox by setting up a new workflow:

Gmail window displaying many invitations to Google Docs

Google Docs invitations sure do pile up!

With some experimentation, I got these nasty, nasty Google Docs invitations out of e-mail and into my documents folder, where they belong. I’ll document these in more detail over the next few days. Basically it boils down to five key steps that you can replicate to create better systems for dealing with any kind of e-mail that lands in your “workflow needed” folder.

  1. Assess: Look at how you currently handle the tasks or information that come in through this type of e-mail, and identify your preferred context for handling them. In this case, I realized that I often end up downloading Google Docs so that I can delve into them more deeply, so the most useful place for me to keep my Google Docs is with the rest of my documents: in my Dropbox documents folder. I’ll outline how I’ve used Syncplicity and Dropbox with Google Docs to get my files right into my computer’s Dropbox folder.
  2. Filter: Set up the Gmail labels and filters that get those messages out of your inbox and into a more sustainable workflow. I created a label called Box/Notifications/GoogleDocs as the destination label/folder for all my Google Docs invitations, and set up a filter that (with some tweaks) sends most of my Google Docs notifications directly to that label/folder without cluttering up my inbox. I’ll walk you through the filter fine-tuning process in detail.
  3. Trigger: Automatically place reminders where they’ll trigger you to complete them. I use Things as my primary task management system, so I thought it could be useful to file my incoming Google Docs invitations in Tasks so that I’d remember to review those documents in the context of the projects to which they are related. I’ll tell you how I used a pre-fab Applescript to do the job.
  4. Execute: Implement the additional tools you need to execute those tasks (or digest that information) in an efficient way when the time comes. While I like storing my Google Docs in my Dropbox folder so I have offline access, a permanent local copy, and the ability to edit more easily, if I just need quick access to a document it can be easier to look at it directly on the Google Docs site. Using Fluid (Prism works too) I’ve set up a single-instance browser for Google Docs that makes Google Docs feel just like an application on my computer, with its very own spot in my dock.
  5. Refine: Adjust your new system with refinements that make it work better for you. In my case, I had to tweak my folder structure for Syncplicity, my Gmail rules to filter, and my Things list of projects so that I’d have someplace to file Google Docs. For the purpose of this series I incorporated most of my tweaks into my instructions for how to set up your system initially, but you’ll continue to refine these for your own toolkit and purposes.

Your AFTER system will not only help you plow through that “workflow needed” folder and clear out your inbox; it will also help you work more efficiently across the board. Stay tuned for more on each stage in this process.

Day 6: Stop using your e-mail inbox as a post-it

Welcome to 7 days to inbox zero, day 6. By now you should have cleared out at least 60% of your inbox — and accumulated a giant pile of messages in your three “systems needed” folders: “unsubscribe needed”, “filters needed” and “workflow needed”. You’ve had an introduction to Gmail filters as a tool for managing an unruly inbox, and hopefully you’ve started experimenting with filters that can catch less-than-unmissable e-mails. Today you’re going to plow through your “systems needed” folders, and set up the filters that will keep those emails out of your inbox for good.

Much of this involves creating systems that allow you to stop treating your inbox as a giant post-it note. You know the inbox-as-post-it problem: it’s when you leave stuff in your inbox after reading it, simply so that you don’t forget to respond to that message, or attend that meeting, or have that conversation with your colleague. It may seem like a smart idea: you look at your inbox every day, so leaving stuff there ensures you’ll see and remember it. Except that the inbox-as-post-it approach invariably leaves your inbox so full that you actually can’t count on seeing the stuff you’ve left there….let alone see and process the incoming messages that are now mixed in with all that reminder junk. In fact, you’re even less likely to deal with your incoming messages, because your inbox is such a drag to visit: it’s a nagging voice that shouts at you with the fifty things you’re trying not to forget, but haven’t placed in an actionable order. If you’ve got bring forward boxes, and a decent task management system, you won’t need to leave stuff in your inbox as a way of ensuring you don’t forget it.

But a good filtering system isn’t just about finding other places to file all your tasks, appointments and reminders. It’s about taking less on in the first place. After all, if your inbox is overflowing, it’s because you have less time available for e-mail than you have e-mail to process. All those messages represent tasks — even if it’s just the task of hitting “delete — that you have implicitly taken on, but can’t fulfill. And every time you look at your inbox, you get a reminder of the gap between what you’re trying to get done, and what you’re able to do. It’s a lousy feeling.

Instead, your inbox can be scaled to the amount of time and attention you want to devote to e-mail. But for that to work, you’ve got to get your mind around the idea of not seeing everything that you “should” see. Maybe you “should” keep up with five different e-mail lists in your field. Maybe you “should” read every message in those e-mail threads that get cced around the office to discuss whether the next retreat should run on a Monday-to-Tuesday or Thursday-to-Friday. Maybe you “should” know the second a task has been assigned to you by your project manager. But to read all those messages the moment they arrive — or to let them hit your inbox as if your intention is to read them immediately — is to forfeit any sense of control over where you commit your time and attention.

The filters you’ll set up today will reflect your priorities about what is most important to see and reply to in real time. And the more categorical you can be about what kinds of things can be set aside for you to view when you have time — the more e-mail you’re prepared to file in quasi-inboxes by writing rules and filters — the more time and attention you’ll have available for what you consciously and deliberately set as your priorities. It may feel uncomfortable at first, because we’re used to the tyranny of the inbox and the expectation that we’ll see whatever comes our way. But I encourage you to try filtering as much of your e-mail as possible…and then to spend the first few weeks of your system checking Gmail’s “All mail” box regularly, so that you can see anything that hasn’t made it into your inbox. That will help you see whether your new filters are excluding mail that should have hit your inbox, and to adjust your filters accordingly.

My next posts will walk you through the steps of creating your filters, covering:

  1. How to set up your Gmail labels
  2. How to process your “unsubscribe needed” folder
  3. How to process your “filters needed” folder and create your filters
  4. How to process your “workflow needed” folder