PMPM Execution -- Task Estimation

This is part of my PMPM series. For other posts related to magical project execution, see the main Execution post.

We've been looking at project execution. Specifically, all things that can keep you from doing what you need to do in order to meet your PMPM goals. While magical project management can give you a boost in terms of achievement, we still need to get the work done. One of the ways this goes sideways is in task estimation, which seems to be a failing of human nature.



Two hours, tops!

Let's say you get up on a Sunday morning and decide you want to clean the garage, which is a gigantic, epic mess. You can image your newly clean garage and picture being able to park your car in it, find all your tools and garden supplies when you need them, and have the space to work on various projects. Your mind jumps to the wonderful conclusion and you get started with great enthusiasm.

Fast forward to six PM. You're exhausted, you're filthy, you're hungry. Your kids are complaining because you've been ignoring them all day. And the garage? It's in worse shape than before! I think we've all experienced this -- thinking that something is doable when in fact it's a lot larger and more work than you expected.

But here's the opposite example. You're dreading cleaning up after dinner. Fair enough, as the kitchen looks like a bomb went off, due to a combination of a) not having emptied the dishwasher beforehand, so there dirty dishes are everywhere, b) your spouse's sudden enthusiasm for Thai cooking, which means new sauces and spices that don't have a home, and c) a elaborate multi-pot dinner -- delicious, but what a mess!

But it has to get done, even though it will take all night. So you throw yourself into the effort with vigor, going through your normal routine (store leftovers, put ingredients away, empty dishwasher, scrape plates and toss garbage, load dishwasher, hand wash the pots, clean the stove, wipe the counters, spot clean the floor, take out the trash). And within 20 minutes, everything is done. In fact, unloading the dishwasher only took like 5 of those minutes, so you really should just do it before the dinner rush starts.

Honestly, we do this all the time. We routinely overestimate small projects and underestimate large ones. There have been various reasons proposed for this propensity, but what's more important is how to deal with it, because it's actually a pretty big problem. Underestimating big tasks is demoralizing, while overestimating little ones tends to breed procrastination. The biggest risk is that the little tasks you are putting off become big tasks over time, so you leave them until they are too big to tackle.

Why we Underestimate Big Tasks
1. The big jobs are usually not really tasks at all, but projects in their own right.

The process of getting your garage in order actually includes a ton of smaller projects and tasks like:
  • Separating and tossing trash
  • Identifying stuff to donate and actually donating it (small sub-project)
  • Identifying stuff to sell and actually selling it (which is a sub-project with a bunch of tasks of its own)
  • Figuring out what goes where (categorize and prioritize)
  • Figuring out where stuff goes (buy storage -- another mini project)
  • Letting go of things that you're hanging on to (oh god, emotional work!)
  • Actually getting the space clean, which is hard without completely emptying it
Break that big project down before you start and you'll have a better time seeing it accurately.

2. The big jobs usually don't have a set routine.

If you clean the kitchen all the time, you know the steps and the order to get it done quick. You know that taking the trash out is the last step and that certain items have to be hand washed. You don't have to stop and think about it. You don't have to plan. You don't have to buy special supplies.

If you're looking at a project you don't have a routine for, maybe take a bit of time and make a plan. So, first we'll go through the garage and throw out all the garbage and recyclables, then...

3. The big jobs have been lingering a long time.

If you ever want to motivate yourself to clean up your house, watch an episode of hoarders... or come look at my garage. See several years ago, we were planning on putting a workshop in the garage. The idea was to pull out some shelving, put in a work surface, and organize all the tools around it. Sounds great right? Except that in the middle of things our household suffered a serious injury. Suddenly the garage was the least of our priorities, but because it was in pieces, with less storage and more stuff in it, it quickly spiraled out of control. The old saying "a stitch in time saving nine" is absolutely true. The trouble is that because there was a very long period of time where we weren't finishing the project, or neatening the garage, it got worse and worse. Only now have things been slowly coming back together, and it's taking a long time to dig through all the layers.

Go one layer or zone at a time. And cut yourself some slack. A problem three years in the making isn't going to get fixed in a weekend.

4. The big jobs are usually dense.

If you look around your kitchen, you can immediately see how much mess there is because the mess is usually in a single layer. But look into a closet... there's no way of immediately seeing how much there really is to deal with, so you tend to assume it's less than there is.

Take a closer look before you judge the effort. Dig into the back of that closet... still feel like it's a 5 minute job?

Why we Overestimate Small Projects
1. Because there are so many of them.

The problem is not that the kitchen takes 20 minutes. The problem is that the kitchen is only one of about 8 things you need to get done before bed tonight. If I look around my house right now, I don't see 5 minute tasks, I see a whole list of things to do today.

Combine related things, either by type (all the dusting) or by area (all kitchen-related items). It helps improve efficiency and makes it easier to focus.

2. Because you can see the full scope of the mess.

The messy kitchen is a great example of a completely visible problem. But because it's visible, it can look much more daunting than that innocent closet door.

Sometimes you have to organize before you can clean. Maybe you put all the dirty dishes by the sink and all the pots in the sink and all the recyclables into a bag by the door. Now things are less crazy and all over the place -- even if they still aren't clean.

2. Because routine maintenance is boring and there isn't a big payoff.

You see this on TV ads for home stores. The couple looks out at their dreary yard and go to the hardware store. Cue inspirational montage and suddenly their world is transformed! Sure, they spent thousands and put in weeks of work, but the payoff is equally huge. But wash the sticky casserole dish and no one cares. Basic maintenance is by its nature never ending and not that rewarding.


This video clip resonated incredibly strongly with me when I first saw the movie (one of my favorites, natch). Not that I think you need a man (or a devil for that matter) to fix things. It's the acknowledgement that the daily grind is what drags you down and keeps you from being your best self.

... Still, after enlightenment chop wood carry water, you know?

Try arranging it so that part of your basic maintenance is giving you something back. When I clean the kitchen, yes I get the satisfaction of a clean kitchen (which is nice, but you know, not earth shattering). But when I clean the house altar and lay out new offerings, that gives me -- and the whole house -- a real boost. This is one of the reasons I have a mini kitchen altar (just next to the stove) so I can tie that benefit to the daily chore -- thereby making it less of a chore. When we go through and neaten and dust the living room (the place we spend the most time together) it feels good to wrap it up with a nice cup of tea together. And while cleaning off my desk is not that exciting, doing a reading for someone there? That's great stuff.

The more I can integrate my magic into my life, the easier it is to get those endless little chores done.

Estimating Accurately
If you, like me, tend to overestimate the small stuff and underestimate the big stuff, the best way to mitigate that problem is to just keep it in mind when you estimate.

First, make sure you know how long things actually take. Doing the dishes still seems like a long chore, but I've made a point of timing myself so I know it doesn't take much time at all. Once you know your tendency to mis-estimate, you can adjust on the fly.

For example, you automatically divide your estimate by four (for the little things) or break the big thing down into four parts. I do this routinely for myself and others at work. One engineer's estimate gets automatically doubled while another's gets halved.

I can do that because I know them and know myself, so you have to build a baseline first.

Understand what things eat time: Transitions eat time. Anything involving the car. Doing two things at once. Distractions of all kinds.

It can take a long time to get better at estimating, but it's worth the work because it makes the work easier.

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