All projects yield a pair of quantifiable results:

  1. Completion or not
  2. Time spent on the project

Projects are fundamentally forecasts. They are best guesses of future events leading to the hopeful completion of some goal. Like any forecast of future events, projects are subject to two broad sources of inaccuracy:

  1. Human error and bias
  2. External random events

If people were perfectly rational beings who incorporated all available information, including their own past mistakes, to plan projects, I would expect the distribution of time spent on projects to look something like this:

In other words, there would be equal numbers of projects completed ahead of and behind schedule. The actual completion time would mostly be a function of external random events beyond the project planner's control.

I think that on some subconscious level, we imagine the future success of a project in terms of a symmetric normal curve. We believe our best estimate of the completion time is really good—even when past experience looks more like this:

We don't really need any formal theory here. A little intuition is all it takes to see that the uncertainty of a project's completion time is a function of the number (and uncertainty) of all of the project's sub-projects.

Therefore, typical projects aren't just forecasts of the future, they're a series of nested forecasts of the future. As each sub-project's actual completion time comes in over its estimated completion time, the total project's completion time skews ever farther to the right.

When confronting our behavioral patterns in this way, it would seem like this should an easy problem to solve: we need to be more realistic with time estimates.

It's not that easy.

We are finally getting smart enough to know we're kinda dumb

Unfortunately, knowing that we should be better at estimating time and actually doing it are vastly different neurological notions. When it comes to accurately planning projects, we are swimming upstream against powerful psychological currents. Our brains weren't designed to map the future accurately beyond more than a few time steps.

These behavioral biases have been well documented under the so-called planning fallacy. Our minds evolved to have an overconfidence bias and hyperbolically discount the benefits and costs of far-off events. We're able to do a decent job of forecasting our immediate future, then we implicitly hope that only roses grow beyond our field of view. We block past experience from our mind, and repeat the same mistakes over and over and over again.

To be clear, I'm not talking about stupid people. Just people. These are fundamental features of the human mind. We are poorly adapted to do the kind of project planning that modern work requires. Our priorities dramatically and inconsistently change with time, and this is exacerbated by a modern world where all of our basic needs are met, leaving us to create and manage extremely abstract priorities to deliver products and services that are mostly exchanged in our minds.

Simply put, projects are complicated. Far more complicated than we give them credit for. We can't expedite human evolution, so let's bring projects back to us. Let's dumb them down for the emotionally handicapped creatures that we are.

One idea that makes sense to me: let's look at the characteristics of successfully completed projects and see if we can recreate those conditions for other projects. It's easier than it sounds.

First, care. Then, schedule.

Once upon a time, Merlin Mann said "First, care. . . Because, in the absence of caring, you'll never focus on anything more than your lack of focus."

No one can objectively argue against this caring principle. The catch: caring is entirely made of human emotion. At one extreme, caring is the arousal induced by productivity porn—you know it when you feel it, but you can't measure it. At least not like time. Caring is a very different substance than time, which in many ways is the antithesis of emotion. But both time and caring must be present to complete a project—any project.

In words:

  1. Projects are more likely to get done if there is time to do them
  2. Projects are more likely to get done if you care to do them
  3. Caring has a stronger effect than time

Further, time is independent of caring, but caring can be negatively correlated with time available. If time is a river, we're more likely to care to work harder when the precipice of a waterfall is in sight. In other words, deadlines.

Caring is a function of much more than time available. Any happy or sad stimulus that motivates you to do something is a source of caring—from the pleasure of reading your Twitter to the cold steel of a metaphorical corporate revolver against your temple as you write a TPS report.

An economist might call caring the "utility" of doing a project. It's the sense of satisfaction you get just from carrying the project out. Which is actually the secret. Projects are ostensibly about reaching future goals, but what we really experience in total are the emotions of each project's steps. That's where we spend all of our time anyway.

If you don't care about what you're doing, the amount of available time doesn't matter—much less any effort you spend on project planning, contextualizing, and pseudo-prioritizing project steps.

I bet most people could get incredible things done with only a notebook and a calendar. This is fundamentally the direction my personal project management systems have been heading in the past year, even though the notebook part isn't explainable in a few lines. Maybe I'll do that later, if I care to.