Mr Squiggle’s Guide To Project Management

Mr Squiggle
Mr Squiggle

I’ve been thinking about how you can manage to complete your own projects (stuff you set for yourself, not work projects), if you have very little attention span and/or like starting more than finishing. Like me! Also this works for anyone trying to do anything in their spare time outside of any combination of work/study/family.

Let’s take a cue from Mr Squiggle. He used to finish drawings all the time, even though he had the attention span of a flea. He should have been leaving half finished projects all over the place, but apparently not (in fact, he finished the projects of lazy Australian children!) How did he do it?

1: Miss Jane grabbed him by the foot when he tried to go on a spacewalk

2: His projects (drawings), while physically large, were tiny sized projects.

Now the Miss Jane approach can work, but we don’t always have Miss Jane available, or if we do, we don’t let her do her job. But tiny sized projects, that we can do.

Here’s my categorization of project sizes:

  • Tiny: from a couple of minutes up to four hours of dedicated attention.
  • Small: from four hours to 2 days of dedicated attention (ie: a full weekend)
  • Medium: More than 1 full weekend, up to 4 full weekends
  • Large: Anything bigger than Medium.

The way to achieve anything, Mr Squiggle style, is to attempt the smallest possible projects that you can. This will annoy perfectionists, but frankly we just don’t have that luxury.

Why the smallest projects? Because every time you put a project on pause, to continue later, you have put it on death row. Ask yourself how often you pick up projects like this after you drop them? I give mine maybe 50%. If you pause a project multiple times, well, the chances are pitiful.

Tiny projects are the best. No matter what your life circumstances, you will find once in a while that you have a chunk of Tiny project time available. If you manage to find time for one tiny project per week, you are miles ahead of where you could be. Awesome!

Small projects are more troublesome. It can be really hard to find an uninterrupted weekend. These can be good if you can get a day or two of leave, or an unexpected public holiday crops up. Don’t sacrifice these times to fixing the fence, grab them and do something cool (like making a flash game of someone fixing a fence!)

Sometimes your project wants to be small sized, it just wont fit into 4 hours. Then, if you can, break it into Tiny sized chunks (4 chunks works here). Why? Because there’s a trick; if you can finish an entire project (even a tiny one, which is one of several to achieve a small project goal), you’ll feel like you achieved something, and you’ll feel much more able to start a new project using the previous one as a building block, than you would have felt about picking up a paused project and continuing it. I think this is about motivation; finishing is a reward, not only in itself, but because it unshackles you. Every project is a set of shackles. Every completion is freedom. Every experience of the reward of freedom makes you want to come back for more.

(Tip: Remember to overplay your successes. Milk every possible psychological reward out of them. Why not?)

Breaking projects up isn’t a total get-out-of-jail-free card though. For a piece of a larger project to stand alone as a project of its own, it needs to be meaningful on its own, and it must stand on its own. Meaningful on its own means it must be useful in and of itself. You should be able to look at it or think about it and think “yes, I did that, rock”. Stands on its own means it shouldn’t require context; you shouldn’t need to keep notes on where you are up to. You should be able to describe what it is in a short sentence.

Medium projects are danger territory. 2 to 4 weekends, for a person with a busy schedule, is necessarily going to include big pauses between the weekends. The answer again is to break it up. I have an even better approach though, it’s like this:

1 – Break the medium project in small projects.

2 – Break the first small project into tiny projects if at all possible.

3 – *Throw away all the rest of the small projects*

Yes, that’s right, chuck ’em out. Forget you were ever going to do them. Don’t keep notes, or only the most scanty. The first small project should make sense on its own, as I said above, so that should be ok. Trust your future self to see the finished small project, see the same possibilities as you see now, and pick up with another small project to move things forward.

Gus the Snail
Gus the Snail

Large projects are the most problematic of all. The grand vision is so unlikely to go anywhere, and will demoralize you in the process, as you beat yourself up for your terrible lack of progress. The answer? Don’t try! Truly! Pick a smaller idea and run with that. Your future self will thank you.

What you can keep from a large project idea is the vision, maybe a sentence long, the high level idea you’d like to reach. That’s valuable. But keep it in your head, there’s no reason to write it down. If you can’t remember the vision, it was probably a crappy idea to begin with.

This approach means you can succeed, even though they are tiny successes. These successes, over time, will make you feel more confident in your ability to succeed in successive projects. Meanwhile, projects wont be a mental burden, they’ll be short and sweet and fun. Over the longer course, you can achieve large things from all these little pieces, in an incremental fashion, that leaves the future you the space to steer the course, and not be committed to what would otherwise be likely to be an increasingly inflexible and inappropriate plan as time wears on.

And of course, you can also afford to fail with tiny projects. So what, it’s only a few hours. That can roll of you like the proverbial water off the proverbial duck’s proverbial back (I assume in a proverbial rainstorm or some such). Being able to fail is essential to being able to try anything unsafe (which is most anything worthwhile).

Trust your future self! Keep it tiny! Keep it fun! Enjoy tiny successes, shrug off tiny failures.

Oh, and don’t watch the tv, it’s just a grumpy snail anyway 🙂

(ps: this blog post was a tiny project. I finished. How cool is that? Yeah)

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Mr Squiggle’s Guide To Project Management

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