08.16.14

The Perfect To-Do List Manager

Posted in Hacking, Random thoughts, Technology trends at 5:11 pm by ducky

There are a huge number of to-do list managers (TDLMs) out in the world now, but none of them do what I want.  Apparently, it’s not just me: I just read an article which said that when students were asked what mobile apps they really wanted, 20% said they wanted “a comprehensive to-do + calendaring + life management app that helps them better organize their lives”.  TWENTY percent!

Is it really that hard?

I have strong opinions about what I want, and I don’t think it’s that hard, so I will describe my desires here in the hopes that somebody will make me the perfect TDLM.  (Some of the features you can see in a TDLM which I wrote for a class project.  Sometimes I think about writing my perfect TDLM, but I’m busy with other things.  I want it to exist, not to write it myself.)

The most important thing is that the TDLM should make you feel better about your tasks.  The biggest problem with TDLMs right now is that they make you feel guilty: the list grows and grows and grows because there are an infinite number of things it would be nice to do and only a finite amount of time.  This means that every time you open the TDLM, you feel overwhelmed by guilt at all the things you haven’t done yet.

1. Hide stuff you can’t work on right now because of blocking tasks.  Don’t show me “paint the bedroom” if I haven’t finished the task of “choose colour for bedroom”.  (This means you need UI for showing what tasks depend upon which other tasks, and I warn you that’s not as easy as you think.)

2. Hide stuff you won’t work on right now because you are busy with other things.  Don’t show me “paint the bedroom” if I have decided that I’m not going to start that project until I finish doing my taxes.  “Do taxes” is not truly a blocking task — it’s not like I am going to use the tax forms to apply the paint — but hide it anyway. (This means you need UI for showing what the sequencing of tasks is.)

3. Hide stuff you won’t work on right now because it is the wrong time of year.  Maybe you want a task of “buy new winter jacket”, but you want to wait until the end of winter to get take advantage of the sales on coats.  You should to be able to tell your TDLM to hide that task until March.  (Or until May, if you live in Manitoba.)  Or “rotate tires” is something which only needs to happen every six months.

Note that this implies connecting the TDLM to a calendar, at least minimally.

4. Allow recurring to-do list items.  I don’t want to have to make a new task for our wedding anniversary every year.  I want to set it once and forget it.  Usually people put things on their calendars for repeating events, but “Wedding Anniversary” goes on August 22ns and is not a task.  “Plan something for anniversary” is a recurring task but should be hidden until at about August 1st.

The TDLM should distinguish between recurring tasks which expire and those which do not.  Non-expiring tasks are ones like “pay phone bill”.  Even if you forget to pay it by the due date, you still need to deal with it.  On the other hand, “run 2km” is an expiring item: if you couldn’t do your 2km run on Monday, it probably does not mean that you should run 4km on Wednesday.

5. Make me feel super-good about finishing tasks.  A lot of TDLMs handle checking something as done by making it disappear.   This is the worst.  I’ve spent hours, weeks, or months looking at that dang task, and when I finally finish it, I want to savour the moment!  I want my TDLM to cheer, to have fireworks explode on the screen, and maybe even have the text of the task writhe in agony as it dies an ugly painful death.  I want there to be a display case in my TDLM of things that I have finished recently that I can look at with pride.  “Yeah”, I can think, “I am ***DONE*** with painting the bedroom!”  Maybe I don’t need full fireworks for a simple, one-step task which took 15 minutes, but if it was a 2000-step task which took 5 years (like getting a PhD or something like that), I want the TDLM to cheer for a full five minutes.

6. Let me see what I did. Sometimes, I feel like I didn’t get anything done, and it is reassuring to look at a list of the things that I actually did accomplish.  It might be nice to show it in a horizontal latest-first timeline form:

  • 4:47 pm Laundry
  • 3:13 pm Groceries
  • 12:11 pm Replace laptop display
  • (etc)

I would also like to be able to modify the task completion times.  “Oh, I actually finished replacing the laptop last night, I just didn’t feel like telling the TDLM because it was late and I was tired.”

7. Let me see what I am going to do.  People usually use calendars for this, but as I mentioned before, calendars are kind of the wrong tool.  I don’t really want to see “buy birthday present for Mom” in the same place as “Meet with boss, 10:30 AM”.  Plus, a strict time-base is makes zero sense if the dependencies are other tasks.

8. Let me import/modify/export task hierarchies.  Suppose you want to have a wedding.  (Mazel Tov!)  There are predictable things which you need to do: book a space for the wedding, a space for the reception, book an officiant, book a caterer, choose a menu, etc.   If, say, you want a wedding sort of like your friend Joanne’s, it would be nice if Joanne could email you the hierarchy of tasks that she did for her wedding, and you could just drop it in to your TDLM.  (Perhaps that way, you wouldn’t forget to rent a dance floor.)

But maybe you have some Greek heritage and Joanne does not, so you need to add “get a stefana” to your list.  You should be able to do that — and then export your new wedding task list for your brother when he gets married.  Even better, you ought to be able to upload it to a site which hosts lots of packaged tasks, maybe even a whole section on weddings (so your brother could pick and choose which wedding task list he likes best).

Needless to say, the exported task hierarchy should be in a form which lends itself well to version control and diffing.  🙂

9. Let me share my task list with other people.  I would like to be able to share my “home” task list with my husband, so that he could assign me tasks like “buy three kitchen sponges”.  Ideally, I’d think I’d like for there to be three task lists: his, mine, and ours.

My husband and I would probably set things up to both have read/write permission on all three — there are some things that only one of us can or should do.  I can imagine other couples might want to not have write permission on each other’s, only on the “ours” one.

10. Make it easy to discuss tasks.  This means assigning a simple ID and URL to the task.  If Jim and I are going to share tasks, we are going to discuss them.  It would be nice to be able to say, “Task #45” instead of “that one about the paintbrushes”.  It would also be nice to be able to email a link to him which will take him right to Task #45.

11. (Nice to have) Allow putting a time estimate on the task.  If you know that it takes you about two hours to get to your locker, change clothes, stretch, run 2km, stretch, shower, change clothes, and get back to your workplace, then it might be nice to put in an estimate for the “run 2km” task.

If you can put a time estimate on a task and adjust it later, the TDLM could keep track of estimated vs. actual, and start to help you adjust your estimates.  “For tasks which you estimate are going to be about 3hrs, you spend an average of 4.15 hrs.”

It would also be nice if the TDLM could help you make estimates based on similar tasks which you completed.  When entering an estimate for painting the living room, it would be nice if the TDLM mentioned, off to the side, how long it took you to paint the bathroom and the bedroom.  (It’s even okay if it also tells you how long it took you to paint the landscape or your fingernails; presumably you’d be smart enough to figure out which tasks were relevant.)

12. (Nice to have) Make the TDLM geo-aware.  It would be kind of nice to be able to hide tasks until I was at or near a particular location.  For example, if I am not in a big hurry to paint the bedroom, hide “buy paint” until I am actually at the paint store.

Something requested by the students in the article I mentioned earlier was being told to leave in order to make it to the next appointment.  “Doctor’s appointment at 3pm” is a calendar event, but “get to doctor’s office” is a task which needs to happen at a time which depends upon how long it takes to get to the doctor’s office from where you are.  That’s another way that geo-awareness could be useful.

13. (Maybe nice to have) Be able to mark urgency.  I am not actually certain how useful this is.  I have had TDLMs which allowed me to mark urgency, and I found that I almost never used it.  I think people will expect it, however.

14. (Nice to have, but difficult) Integrate with my applications.  Tasktop Technologies has a product called Tasktop Dev, which kept track of what you did in the source code editor (and some other applications, e.g. web browser and Microsoft Office) while you were working on a specific task.  (You had to tell it, “now I am working on task #47” so that it would know to start watching.)  Then, there was a record of what you worked on for that task.  That was useful if you needed to stop and restart the task (especially over a long period of time), or if you needed to go back a long time later and see what you had done.  (“What was the URL of that caterer with the really nice cheesecake?”)

In a work environment, it would be nice to integrate it with other task management systems (AKA “bug trackers”) like Jira or Asana or Bugzilla.

This is what I want.  If it persists in not existing, I might have to do it myself someday.

2 Comments »

  1. Peter said,

    January 21, 2016 at 8:44 pm

    Hello Kaitlin.

    The last time we corresponded I suggested and incorrectly expanded NRSVP (it should have been “ne repondez s’il vous plait”) and my error is STILL bouncing around the net.

    Sucker for punishment that I am, I thought I’d point out that what you are asking for is a cross between Cortana/Siri, a calendaring app and Microsoft Project.

    That’s … a big project.

  2. Ducky Sherwood said,

    October 23, 2016 at 3:23 pm

    Aha! Toodledo has task list sharing (#9!), and it is geo-aware (#12!).

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