5 Steps for Workmonster Project Planning

(Charlie here:) Okay, so the fact that I’ve missed two weeks of columns and Sarah’s theoretically on sabbatical is probably an indication that we’re still struggling with the workmonster in our own ways. I really had about a week of burnout where neither words nor code were making a ton of sense. This may have been a fit of sort of sub-clinical depression, as well as just being tired; starting the “walk to work” thing I talk about in my other column today may have resolved that. Certainly my mood is still sort of ridiculously good.


But while I haven’t been getting lots of production done, I have been thinking and trying to get something coherent together in order to start getting more things done. Basically, to review what I’ve done so far, I

  1. Picked a steno pad to serve as my “inbox”. When I have something I need to do, it gets entered on the steno pad.
  2. I have a second “projects” steno pad which captures more extended thoughts on something that will take more than a few minutes to do. The official Getting Things Done rule is 2 minutes.
  3. Every so often, usually while I’m writing my morning pages (when I often capture a lot of things for the inbox anyway) I go through the inbox pad and put things onto a Today’s To-Dos list. Sometimes I just cross them off, having decided they’re not worth doing. And here’s a practice that seems to be working well: when I do something on the To Do list, I cross it off the inbox list. At the end of the day, I throw away the To Do list. If it hasn’t been done, it’s still in the inbox; if it’s still important, it’ll get back on a to-do list eventually.

So, then, we come to the “projects” pad. Some of them are “little projects” and never get off the pad — they just become some specific to-do items. Others are bigger, and it’s those that have been a problem for me historically. See, I have so many ideas of things I want to do, and some of them didn’t fit at all on a single steno pad page. (Not that I expected them to, the steno pad was just a stopgap.)


So this week, I set up a project file box, shown below. Each project gets a file folder of some sort. I started off with some colorful ones but I could never remember what the colors meant, so I went back to vanilla manilla. Stuff about that project goes into the folder. You’ll notice the divider, artistically crafted from the cardboard back of one of the writing pads I use. (Two or three a week usually. Staples should hire me to do commercials.) The ones behind the cardboard are things I’m officially not working on, the things in front are thing that officially are on my mind.

2014-02-15 12.52.41

Now we get to the good part: what do I do with those folders? Okay, this is now work in progress, but Getting Things Done has a description of “natural project planning” that rings true to me. It’s five steps.


Step One: How Will You Know You Succeeded?

Now, this is something I’ve preached in software engineering for years and years, and it is frankly astonishing to me how few people do this, and how much resistance you run into when you suggest it would be a good idea. There are two key things to know here:

  • can you say specifically how you will know you’re done?
  • can you say specifically why you want it?

This turns out to be deadly in software projects, because an awful lot of “big idea” people aren’t good at drawing the line. Projects that are a floor wax, and a dessert topping, and are going to sell to everyone from a fifth-grader for their first laptop and the biggest enterprise customers, and that will be so simple a child can use it and that will be a breakthrough such that no one has seen its like before, usually are a sign that you don’t know either what you want or why you want it.


Step Two: Get a Clear Picture of What You Want

This almost seems like I’m repeating the point about, but it’s not quite. Let’s think about one of my active projects, getting the collected first year of 13 Weeks columns into an ebook. Step one for me is “I think the ebook would be valuable to the people who’ve followed my columns and I’d like the columns to be easily available; I’ll be done when an ebook is up on Kindle.”

Clear picture:

  • Kindle ebook
  • Good cover
  • All the columns collected
  • Wrapping text at the beginning and end to explain what the purposes was
  • Available for purchase
  • Promotional plan in place


Step Three: Brainstorm

You can read about brainstorming in a zillion places. What it really is, is like doing improv as an actor. The two rules of improv really are:

  1. Never stop until time is up
  2. Never say “no”.

Until you have ideas, you can’t tell if you have any good ideas.

Step Four: Organize

Once you have brainstormed a bunch of ideas, now you can go through them and pick the good ones. Some before and after pictures — yeah, that’s good. The nude flex poses, those can wait for another year (at least). Collect some of the sources I’ve referred to, good. Wait until I’ve figured out a compartmental model of weight regulation, not so much.

Now sort them into some kind of plan. An outline, a bullet list. And here, I’ll tell you a secret that GTD doesn’t often emphasize: some of those results of the brainstorming will turn out to be projects too. Hopefully the “why” questions will be easier, but getting clear on when you’ll know you’re done, and what the precise outcome should be, for these subtasks will be a big help in any larger project.


Now, this can be taken too far. You could, hypothetically, break this down until you had an aggressively large number of things to do, each of which takes two minutes or less; taken to this extreme, you could then sit like a clockwork automaton and assembly-line through each trivial little task until you were done.

Of course, that only works if you both are sufficiently omniscient to figure out what all those 2 minute tasks are — and get them all correct! — and then able to will yourself into automaton-like mindless execution.

(Oddly, a lot of software engineering as taught really does assume you can do this. This leads to what I’ve called “let’s pretend” schedules.)

Step Five: Do the Next Thing

Look at that pile of stuff, and pick something you can do next. Refine the plan for a sub-project? Research something? (For a fiction project I’ve been researching the pre-Sanskrit proto-indo-european language and culture; this is fascinating stuff by the way.)

Now, look back at my project box. Most all of those folders behind the “backlog” card are things where I’ve done just Step One, or Steps One and Two. That’s how I know they’re backlog. In a lot of cases, they’re kind of in Step Three now — an idea will come to mind, I’ll scribble it on a piece of paper and put it into the folder. But I’m not actively looking at them, it’s just a place to put a note when something comes bubbling up from the fœtid swamp of my subconscious.


The ones in front of the card are getting worked on. Right now, I’ve got about a dozen folders in that section, which is still too high. But two weeks ago, it seemed like all those folders were on my mind.


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