Tuesday, November 18, 2014

Is your task management strategy more Sisyphus or Tantalus?

The premise of WhatNext, my task management program/concept/philosophical exploration, reflects the Johnson quote:
When a man knows he is to be hanged in a fortnight, it concentrates his mind wonderfully.
Given that you have a specific, limited amount of time to do anything before death's warm embrace, which mundane, trivial, or unpleasant thing should you do in the next few minutes and hours of your flash of existence on Earth?

Okay, that's a bit morbid, but lighten up: this blog post is really about whether you approach tasks as Sisyphus, doomed to forever roll a rock up a hill only to have it roll back down, or as Tantalus:
... the gods punished him by placing him in the nether world in the midst of a lake, but rendering it impossible for him to drink when he was thirsty, the water always withdrawing when he stooped. Branches laden with fruit, moreover, hung over his head, but when he stretched out his hand to reach the fruit, the branches withdrew.
I think most people perform Tantalus-style task management.  Do you make lists of things to do?  How does that work?  You go through the list, checking things off, and if you have had a very successful and productive day, you've merely gotten yourself from "behind" back to zero.  That is, the best one can hope for is to not be at a negative.  This is a miserable way to exist.  This mentality is reified in the software development process called Scrum, with the Burndown chart:

In the burndown chart, when all of your work is done, you are at zero.  Congratulations?  You have nothing.  You think you are finished and that you have reached the fruit, but instead of eating the fruit you just start looking for more fruit; it is as if the fruit sprang away from you. In response, some Scrum people have come up with the Burnup chart, where you can see your progress accummulate, and what I use professionally now looks more like this:

On the bright side, you can see all of that lovely green of completed work accumulate.  The other colors represent various stages of work in progress, and the gray the maximum amount of work the teams thought they might achieve in one "Sprint", which is our standard work cycle of four weeks.  On the dark side, however, every 4 weeks we start over:

So while you get to go as far as 28 days before seeing all progress flushed away, eventually the chart does indeed reset to zero, and you are forced to confront the reality that you too are Sisyphus, pushing the rock up over and over again.  Even if you maintain a project burnup that shows cumulative progress over months and years, eventually your project will end, and you will have to find another rock to roll up another hill.

Addressing that is beyond the scope of today's post, although I do think there is something there that Whatnext can help with, not as software per se but as an experiment in a better conceptual framework for getting things done.  As homework for that, however, I want to read this book that Marc Maron kept pushing on his podcast, The Denial of Death.  So far I've read the introduction, and while I really liked it, I can't say that it gave me any immediate ideas for task management software.

To get back to the tangible: Now that I have a minimally working task list program in Whatnext, I want to add the first feature that starts moving it from the Tantalus or Sisyphus model of most task tracking concepts to a more positive model.  If that's not a burndown or burnup chart, what is it?  I want an immediate, positive, visible indicator of progress, so that whenever I complete a task, I can see something that shows that I have spent my time wisely.

A program called RescueTime offers one idea: a "Dashboard" that shows a quantitative moral verdict on your minutes:

In this chart, red is time wasted, and blue is time well spent.  More specifically, blue is "productive" time, and you can numerically judge the quality of my time today by the ratio between the two:

This thread of thought—I beg your pardon, as I started this sentence, RescueTime, as if it was reading what I type (and, given the state of privacy and how little companies respect it in 2014, it may well have been), flashed up this quote:
“The time you enjoy wasting is not wasted time.” — Bertrand Russell
Which is exactly where I was going with this idea.  Before you can judge productivity, you have to categorize all of the ways you can spend time, but even before that, you have to understand what you mean by productivity.  My numbers for today looked much worse just now until I told it that blogging counts "Writing", which is categorized as "Design & Composition", not News & Opinion; that makes it "Very Productive", not "Distracting". What is your product?  Actionable deliverables?  Pages of product?  Clicks?  Revenue?  Acts of kindness?  A sense of satisfaction?  The ability to die in peace and contentment?  What are you being distracted from?  Being productive, or acknowledging the Grim Reaper?  Why does she always have a clock?  I'm very exciting to get into these questions with Whatnext, but I have plenty of philosophical homework to tackle first.

In the meantime, reeling us back from the abyss of nothingness to the simpler hell of management-speak, let's think about Milestones.  Or, let's call them Thresholds.  At the moment, other than blogging, I have a dozen tasks I'm thinking about for Whatnext.  If I arrange them around what they enable me to accomplish, I have a list of new capabilities and achievements instead of a list of tasks to burn through and hide.
  1. "testing".  Instead of a big handful of testing tasks that I've been neglecting, I have the opportunity to save myself from regression bugs in the future.
  2. "Toggl integration".  Instead of a messy API integration that will require me to climb up several brand new learning curves while experiencing the frustrations unique to cross-product integration, I have the opportunity  stop copying and pasting time data between websites.
  3. "Integrating task tracking lists".  Instead of the headache of merging my task lists from four different tools (Redmine, Checkvist, draft emails, Google Spreadsheets), each of which does only a fraction of what I need it to do (which is why I'm working on Whatnext at all), I have the opportunity to .... enjoy freedom from worrying which different list I should be looking at?
  4. "Preparing for a closed Alpha".  Instead of trying to scurry around and fix a billion bugs and catch up on the deeply unfun "DevOps" tasks that I have skipped to date but which are required for a stable, reliable, and safe website, I have the opportunity to share my ideas with some friends.
  5. "implementing thresholds".  Instead of wrestling to articulate a fuzzy concept of a data model and then stab in the dark at how to implement it, all which a severely limited set of tools due to my inexperience at Django, I have the opportunity to simplify how I decide what to do next.
At its worst this is just putting a falsely happy spin on unpleasent or difficult things, but I do think there's a nugget in the concept of Thresholds that is useful and positive.  My idea is that each tag could have some specific milestones (which I'll call thresholds until I get an idea which is both better and actually good), and then all tasks with that tag can be sorted as either needed or not needed for a threshold.  What could make this different from less-that-helpful paper exercises like Gantt charts and rollups and the like is if I can design an interface that makes it simple, fast, and context-specific.  In particular, I think this has to be tied into the idea that there is no two-dimensional wall chart of activities and durations; there is only a one-dimensional list and everything is sequence.  There's only one of you at a time so you can only do one task at a time so all tasks must be sequential.

It might end up something like this:

0) You jot down a bunch of things you think you need to do, and they all jumble in with the dozens of other things you previously jotted down.
1) You pick a tag, i.e., a context, to focus on.  Just stuff for your job, or just household tasks.
2) Within that context, you define one or two outcomes, triumphs, accomplishments.  Things that probably have a lot of separate sub-tasks.  Not tasks, but conditions of success.  "I am ready for my trip next week."  "My home is clear of things that I don't need which can be recycled or donated."  "All of my homework for the rest of the year is completed by captive demon."  Probably you rank or date these somehow to indicate priority.
3) Based on the tags and maybe dates and such, you are able to look at a limited number of tasks, maybe one screen full, maybe that's about 20 or 30, and you move the tasks above and below the thresholds you just defined.  Based on this, the system helps stack-rank all of the tasks.  E.g., "gather all old newspapers into paper bags" is not necessary to get ready for that trip, so if the trip is more important than cleaning out the home, gathering the old newspapers just moved below all trip-related tasks.
4) See at all times in Whatnext some kind of indication of the most important threshold, how far away it is in time: "you have an estimated 2 hours of work to complete to reach this accomplishment and have this result", and what progress is being made: "at your current rate of progress on knitting tasks you will finish those 2 hours of work in 3 weeks".

Where this gets messy: what is the interaction of tasks across different categories and contexts?  How do you stack-rank incommensurable thresholds, such as "get promoted" versus "watch all the good movies"?  What about dependencies?  But all of those things probably belong to thresholds below the five I identified above.  And building a prototypical threshold feature in Whatnext (#5 above) will make it possible for me to figure out what to do next, so all I have to do is achieve threshold #5 in order to figure out that I should probably work on #5.

Meanwhile, she is waiting patiently for you:

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