Four Ideas to Lower Your Stress With Smarter Deadlines

It’s fairly likely that no matter what kind of work you do, it involves a deadline of some sort. I mean, even a waitperson has deadlines. Theirs may be even more pressing than the deadlines imposed on those that work in the corporate world. Have you ever had to deal with a hungry person who isn’t getting their food on time? Personally, I’d take an angry boss over a hungry primate any day, even a human one. Clearly it’s no profound insight to observe that one of the more common sources of stress in the work world is deadlines. They can also be paralyzing at times, when being concerned about the deadline consumes more of your mind than actually performing the task at hand. So let’s take a moment to ponder deadlines, and constructive ways to deal with them.

First of all, let’s take some of the word’s mystical power away. Have you ever pondered the actual origin of the word? According to this Random House “Word of the Day” piece, there are two likely origins. One is a printing term from the early 20th century which means “a guideline on the bed of a printing press beyond which text will not print”. That sounds like a harmless enough concept, but it’s likely that the modern stress-inducing meaning has more to do with a passage in Lossing’s History of the Civil War which says “Seventeen feet from the inner stockade was the ‘dead-line’, over which no man could pass and live.” That sounds about right, doesn’t it?

But let’s get real for a minute. There are very few deadlines in ANY line of work which have that “over which no man could pass and live” level of importance attached to them. Sure, maybe if you’re working on the Manhattan Project and you don’t complete it in time, your entire nation will be at risk of being annexed by foreign empires. But even then, maybe the boss is lying to keep the pressure on. In any case, most of our deadlines have infinitely less import than that. If you work in high-pressure environments where thousands of people are depending on your ability to meet a deadline, the little ideas below aren’t meant for you; hopefully your process already has sophisticated methods for managing tasks and output.

But in less high-pressure environments, especially if you’re self-employed, your relationship with deadlines can be one of the most important parts of your work. Here are five friendly reminders on how to work with them:

Incremental Deadlines

This should be a no-brainer, but a surprising number of people I’ve consulted with don’t put this simple idea to work. It’s (ahem) dead simple. Say you’re writing a book, or building your website, for instance. Instead of having some epic deadline for when the entire project is going to be done, reverse-engineer it a bit, and chunk out specific smaller tasks that build up to the whole. Far too often, we set some arbitrary deadline with a vague intuitive sense of what is reasonable. CHUNK IT OUT.


Maybe you think this works for you, but it’s likely that work you cram into the last week, day, or even hour is in fact shoddier than you convince yourself it is. Chunking it out also helps avoid this tendency. The stress you create in yourself when cramming is going to shorten your life. Why do it?

When is it REALLY due?

In our book, one of Nick’s chapters addresses something that has helped me dozens of times in the last year alone. He asks the question “what are all the bad things that will result from not doing this?” Quite often we – especially us workaholic, self-directed types – ascribe do-or-die importance to meeting a deadline, when in fact the results of not meeting it are nearly nil. Even with externally imposed deadlines, the people we work with are just as relieved to bump a deadline back if it means creating better work. CHILL OUT.

In time? Or in the pocket?

You may have heard the term “trim or miss” in relation to deadlines. This is another simple decision tool that’s very helpful. We’d all like to be perfect all the time, but no-one – anywhere – ever is.  There’s an old “hacker’s way” principle that has been put to use by companies from Apple to Facebook. It’s “done is better than perfect”. The fact is that this isn’t ALWAYS true, but sometimes the ability to intelligently decide which is more important – timeliness or perfection – can make a world of difference in terms of how you treat a deadline.

For the record, using the tips I presented here, I finished this post two days early!


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