Make every morning a deadline, and achieve more

I come from a world of project deadlines. Until two years ago, I swore by them.

When you're in business school, you're taught that every project needs a deadline to even have a chance of being successful.

But what I've learned in my time out here in the Valley is that the reality of the situation is much more nuanced than that. Deadlines often hinder the achievement of objectives much more than the help. I'm going to try to explain why.

In a nutshell, the issue revolves around the arbitrary nature of deadlines. None of us can predict the future, and so by setting a deadline out in the future, we've put an arbitrary stake an the ground indicating that a certain result has to be achieved by a specific date.

When you really dig into how you picked that date, you'll often find that you arrived at it through one of the following two methods:

• Estimation: You add up all the hours you think you and others will need to complete a series of tasks.
• Hail Mary: It needs to be done by this date, so no matter what, you have to get it done by then

These are both equally bad, for different reasons. Estimation will never account for all the true variables that will affect (and delay) the delivery date as the work plays out, and Hail Mary dates have no relation to the work being done.

But just throwing away deadlines is just as bad: Deadlines are used to track progress and focus goals. Without deadlines, people get lazy and unfocused, and they achieve less.

So what's the answer? Make every morning a deadline.

I've found that making every morning a deadline is the only way to successfully navigate these treacherous waters. Here's what I mean:

I use Pivotal Tracker (PT), an agile Scrum development management tool, to break projects up into a series of small units of work, typically consisting of two types: Features, and chores. (In this blog post I talk in detail about how exactly I use Pivotal).

Every morning, I prioritize what I need to get done by re-ordering the features & chores in PT, with the top priority items at the top. Then, I work on executing on those items for the day.

This means that every morning, I'm re-ordering my priority list, and setting a deadline to get that list done by the next morning.

Giving yourself a deadline every morning is different for two reasons:

• You're not setting a deadline far into the future.
• Even if you miss the deadline, you'll have been working on what was most important for that day

By always prioritizing the most important things at the top of your list, and then re-evaluating that list daily, you can ensure that you are always working on whatever is most important. This is a huge distinction to having a project deadline that's, say, 30 days away. By instead having 30 daily deadlines, in those 30 days you will have achieved more, because every day you will have been asking yourself, "what is the most important thing I need to be working on today to achieve my goal?"

This same approach works even better for projects with multiple people -- in fact, it was invented for development of software by teams of developers. It's known as an agile development process, because the steps needed to reach the goal are re-evaluated at stand-up meetings that are usually held daily.

If you don't think you can set a daily prioritization deadline with yourself because you can't break your work into daily chunks, then you've already identified part of the problem: You have to spend every day doing something. And if you can't identify what's most important to do today, then you need to break your work into smaller chunks.

So next time somebody says "We have to get XYZ project done by ABC date," I urge you instead to think about how to break XYZ project into as many small chunks of work as possible (known as "stories" in the agile development world), then prioritize them such that the most important stories get worked on first, and then re-evaluate that prioritization on a daily basis. Who knows, it may take less time than ABC date, or it may take more (and it doesn't really matter, because ABC was just an arbitrary date that someone chose from thin air, and it's only function was to introduce stress to the team). But one thing's for sure: Starting today, you'll be working on what's most important to get XYZ done.

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The morning sunrise picture above was taken in Pismo Beach, CA. It's actually a sunset, but it's the closest I had to a "fresh new morning" pic!