I’ve worked for some of the largest publishers.

I’ve labored for some of the most successful brands.

I’ve done my share of work for creative agencies.

And after all this time, I’ve realized there’s one thing all of them have in common: hoo boy, none of them can finish a project on time.

It’s not that the people I worked with weren’t smart (they’re wizards). It’s not that I’m not diligent (though I do like naps). It’s not that the projects were bad ideas (some were!), or that the project manager didn’t know a Gantt Chart from a gardenia.

No. It’s more than that. In fact, I’ve never even heard of a project at any company, anywhere, that has gone precisely as planned.

There’s a reason for that.

In fact, there are two very powerful reasons for that:

  1. Cognitive bias
  2. Random chance

These two factors affect our lives and our work more than any others, and we consistently fail to plan for either, or both.

Cognitive Bias

When it comes to prepping for a project, most humans fall prey to the planning fallacy.

First proposed in 1979, the planning fallacy describes how most people’s prediction for how long a future task will take display an optimism bias. That is, we tend to underestimate how long a task will take.

We tend to do this even in the face of more general knowledge that would suggest otherwise (say, you know how long a similar task has taken before).

In a famous 1994 experiment, college honors students underestimated — by roughly 60% — how long it would take them to finish their thesis.

Everybody else does this, too: stockbrokers, engineers, people planning to go shopping, and  anybody who sits down at 6 p.m. on April 14 thinking it won’t take long to do their taxes (🙋‍♂️guilty!).

Of course, optimism bias only applies to tasks we, personally, do. When judging the tasks of others, we tend to take a more realistic view.

Unfortunately, other cognitive errors come into plat as well. Here are a few of the more common whoopsies everyone tends to make when scoping and executing projects:

  • Self-Serving Bias: The tendency to ascribe success to your own abilities and efforts, but ascribe failure to external factors.
  • Hindsight Bias: The common tendency for people to perceive events that have already occurred as having been more predictable than they actually were before the events took place. That is, we forget how terrifyingly mismanaged the previous project was.
  • Survivorship Bias: The logical error of concentrating on the people or things that made it past some selection process and overlooking those that did not, typically because of their lack of visibility. That is, we fail to account for the projects that failed, and why.
  • Coordination Neglect: Organizations often fail to organize effectively because individuals have lay theories about organizing that lead to complications.
  • Strategic Misrepresentation: In planning and budgeting, the tendency for those presenting projects for approval knowingly to understate costs and overstate benefits.
  • Continuous Partial Attention: As opposed to multitasking, CPA is “an automatic process motivated only by ‘a desire to be a live node on the network’ or by the willingness to connect and stay connected, scanning and optimizing opportunities, activities and contacts in an effort to not miss anything that is going on.”
  • Brook’s Law: Adding human resources to a late software project makes it later. Same for creative agencies.
  • Reality Distortion Field: Originally used to describe company co-founder Steve Jobs’s charisma and its effects on the developers working on the Macintosh project, this term has broadened and is today used to describe leaders or managers who demand the impossible without understanding timelines and dependencies.
  • Procrastination: You know what this is.
  • Idiocy: 🙃

Random Chance

Randomness, chance, and luck influence our work more than we realize, too.

The more complex our work becomes — across time, geography, personnel, and technology — the more opportunity there is for random events to occur, and for that randomness to not only be unfavorable but undetectable. And, because of hindsight and survivorship bias, we create reasons for prior success when in fact that success may have been random.

There is no way to prevent randomness. But you can prepare for it. You can build systems are resilient to — and even benefit from — randomness.

And that’s what we try to do when planning marketing systems. Create processes and assets that will weather the worst storms.

Fortune favors the prepared, as they say.

Oh, and however much time you’re allocating to that next task? Add about 60%.