The response to yesterday’s post caught me quite off guard. I was a bit worried that the general response would be “well duh!”. Goes to show I wasn’t the only person struggling with getting from next-actions to actual actions.

I’m going to walk you through my process for managing my calendar. There are a couple of software specific tricks to it. I use iCal – the Mac’s built in calendar. I’m not sure what Bill packaged for my PC cousins, but I’m sure there are options available.

Let me state at the outset that this system works for me because my work CAN be planned ahead of time. Through experience, I know roughly how long certain tasks are going to take. Also, all my work is time-based. That is to say that when I write a proposal, I base my estimate on actual hours worked. Which is where we’ll start today’s journey.

I use a program called Omni Outliner to brainstorm a project’s requirements when coming up with an estimate. I simply make a list of every element I can imagine will be required to get from point a to point b. Then, I go back and put a time estimate in a column next to each item. It’s a quick and easy way for me to put a dollar value on even the most complex projects.

a screen shot of omni outliner in action

Now, this works for me because I have a pretty good idea how much time it’s going to take me to do each task. This comes from experience. It also comes from breaking each task down into small components.

One of the reasons I favor Omni Outliner is how simple it is to nest lists. I start by making top level tasks, then revisit the big items to break them down in a nested list. The number of levels I break something down into is a function of how complex the task is. See the example below from a recent print project.

At this point, I’ve got almost all the information I need to schedule my project. Omni Outliner and iCal play together pretty nicely. It’s possible to convert an Outliner list into an iCal to-do list, saving one the necessity to re-type each aspect of the project. (If you want to know how, just google “omni outliner to ical”)

Next, it’s a matter of creating a new calendar for each project. In iCal, it’s simply a matter of clicking a button, naming the calendar, and choosing a colour (to change the colour, make sure the info pane is open [button at the bottom right of the ical window], select the calendar you want in the calendar pane, then lick the colour next to the calendar’s name in the info pane, then choose ‘other’ to select from apple’s colour picker).

In iCal, I can simply drag a to-do item onto the calendar. Easy as pie.

This system does require a bit of maintenance. Moving items forward when they inevitably snag is a pain. I’ve gotten into the habit of simply scheduling blocks of time for a given project. Then, at the start of the week, I’ll refine the schedule to reflect specific tasks. Moving a large block of time is easy. Moving a whole bunch of little blocks is still easy, but it’s a real pain.

iCal can sync with any palm device or ipod, meaning I’ve always got my schedule with me. I do leave a fair bit of flexibility in each day though, and I think that’s key to the system’s success. For example, I rarely schedule more than 8 hours of work, yet I work more like 12 hours a day. This flex time means that I can still take care of the inevitable delays or emergencies that always come up.

This is my life schedule, not just my work schedule. If there’s something I really want to do, putting it on the schedule greatly increases the odds that it will happen.

If you’d like to see a larger view of my calendar, to get a better idea of exactly what I’m talking about, please click here.

I’ve actually written a bit about this before. If you’d like to see how my system has evolved, you can read an article I wrote at Almost Cool titled omniOutliner + iCal = my wicked work flow.

20 Comments on How I schedule actions and tasks

  1. Peter Parkes says:

    If there’s something I really want to do, putting it on the schedule greatly increases the odds that it will happen. – very true.

    I’m sure there are plenty of us who’ll groan in sympathy at the the hour allocated to ‘Test in IE’…

  2. Sacha Chua says:

    I’ve always preferred blocking time off for specific tasks on my calendar, and it’s great to hear that iCal has an intuitive interface for that. I’ve taken to making my own paper forms (letter-size weekly calendar + notes) to fit my way of planning. =)

  3. Erin says:

    I’m going to have to look at this in more detail this evening (scribble note on index card to remind me). Thanks for posting. I think it’s estimating the time something will take that I need to work on.

    By the way, I really like the to-do labelled “God only knows!”

  4. John Wurzelmann says:

    What you have done is not trivial.
    It would be nice to be able to replicate this in a Windows environment, or alternatively on the web. I have not found any PIM that does this well, and I am not interested in using project management software for scheduling my pesonal work. Thanks

  5. Stu Schaff says:

    Like Mr. Wurzelmann above me, I’m wondering if there’s a similar tool for Windows I could use. Can anyone point me in the right direction?

  6. Peter says:

    Well there is the bazooka which is MS Project. I believe it integrates with MS Outlook as well.

    Not sure if your looking for free or commercial options though.

  7. If you want to learn how to estimate how long something takes, just estimate and see how far you are off. You’ll get better in time.

    On estimating, see “Painless Software Schedules” By Joel Spolsky. That’s aimed at programmers, but most of us could benefit from it. It’s easy and just uses Excel or any other spreadsheet program. See

    David Allen advocates to keep the calendar a sacred territory: only put appointments there that absolutely have to get done that day or not at all. If a meeting is rescheduled that’s fine, but that’s about the only excuse you have for changing something in your calendar.

    Having said that, David Allen probably has a pretty full agenda. On most days I have at most one appointment. That leaves a lot of room for idling, sleeping in, posting comments… ;-) In that case it may not be that bad to deviate from David’s ways and schedule some time for specific next actions, making them “now-actions” so to speak.

    What you are effectively doing then is making those now-actions a priority. Of course David Allen doesn’t like that and he may have a point there. On the other hand: if it works for you, why not?

  8. Peter Flaschner says:

    Mozilla Foundation has an interesting product called (get ready for it) Calendar. It’s free. But it’s also in the early stages of development.

  9. Erin says:

    Another pair of questions — do you delete the calendars from iCal when the project is completed? If so, do you create an archive in some fashion first?

  10. Peter Flaschner says:

    Hi Erin – yep, I delete the calendars when a project is closed. I don’t archive them. I do keep my original Outliner worksheet which has all the relevant time info though.

  11. steve says:

    Great tips and thanks for sharing your workflow… I’m definitely going to look into it… I have a few questions though…
    -do your color schemes and calander titles translate into your palm and palm desktop?

    -with your main project priority/status list in OO3, can you drag your individual estimated list to it or do you just open multiple files?

    I’m sure if I start digging through the program I’ll find more info… need to schedule time to do this!


  12. slackah says:

    Scheduling continues

    To-Done continues with yesterdays scheduling topic. Interesting stuff. Mad mad mad amount of tasks.

  13. Peter Flaschner says:

    Hi Steve,

    The colours don’t travel to the treo unfortunately…

    One very cool feature of Omni Outliner is the ability to grab the application icon at the top of an O.O. window and drag it into another O.O. document. This creates a link directly to that other document, allowing you to quickly access your files from one spot.

  14. Erin says:

    I was trying to decide if I could do this without the intermediate step of OmniOutliner — for example, by knowing that I index a certain type of text at 20 pages per hour, usually require three hours for editing, and need to figure for fifteen to thirty minutes for e-mail exchanges and file transmittal. I can just type those into iCal by hand. But then I’m stuck with what to do at the end of the project.

    I might have to try that 30 day free trial.

    Thanks for answering my questions!

  15. Carol says:

    I can’t seem to get my hands on the script to export OO to-dos to iCal – every link I find for it sends me to the OmniOutliner Extras page, but the Useful Scripts posted there doesn’t contain the iCal script! Any ideas out there?

  16. tuqqer says:

    Great site, great ideas. But I can’t see your images. They come across way too small on a 20″ LCD at 1600×1200. It’d be great if you linked each smaller image to the full size one. Your pics are a valuable part of each article.


  17. I have the same problem as Carol, I can’t find the Export to iCal script anywhere. Any help?

  18. For Windows users you will find that Microsoft Outlook can also help a lot.

    it integrates a nice calendar along with the mail and address book.

    you can also organize by colors and turn on the reminders for any task…

  19. dwayne says:

    I love the fact that you use calendars to store projects and not contexts. Soon I will unearth my plan to use GTD in Ical ONLY yes, ( sorry Kinkless..) and though I have a few ways of still attributing contexts to tasks.. I was wondering HOW exactly did you do it…

    dwayne neckles

  20. Dwayne says:

    Do the times for the tasks u have in OO.. come over to ical.. and whats the point of making sub groups in oo if the main subgroup and its children tasks come over as individual tasks anyway in ical?

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