How to Never Miss a Deadline, With Journalist Christopher Cox

Are you constantly adjusting your project timelines? Do you wait until the last minute to get started on something with a hard deadline? Well, stress no more because this week we’re bringing you a solution that will help you meet those deadlines every time.

Our guest on The Upgrade this week is journalist Christopher Cox, who as a former chief editor of Harper’s Magazine and former executive editor at GQ, knows a thing or two about managing deadlines. In his new book, The Deadline Effect: How to Work Like It’s the Last Minute — Before the Last Minute, Chris researched multiple organisations that are extremely successful at project management and meeting timelines to learn what the secret is to always meeting deadlines. And, fortunately for us, there are some consistent tips and tricks that seem to be effective.

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Highlights from this week’s episode

From the Christopher Cox interview

On what the Deadline Effect actually is:

It’s basically the tendency, especially in negotiations but really for anything, to wait to act to the very last minute. So the deadline effect is you have a long, drawn-out process or some sort of project or negotiation. You don’t make any progress toward it until the clock is really ticking down to zero. So that tendency is the deadline effect and it tends to have negative outcomes for everyone involved. And in this book, I talk about that a little bit. But then I also talk about, well, you know what if we took all the power of the deadline effect, you know, the sort of the ability of a deadline to force us to get things done, but tweak the timing a little bit, moved it so that we could use that deadline power, but earlier and when we had more time to get things right.

On why people shouldn’t fear shorter deadlines:

I was a magazine editor for 15 years, and it was my job to make writers file their copy on time. And I always thought that there was a tradeoff between enforcing a deadline on my writers and then letting them sort of take the time they needed to let creativity blossom, to do whatever you need to do to make a piece as good as possible. But in reading some of this research, I really concluded that creativity and sticking to a deadline are not at odds. In fact, like the sort of motivation of a deadline can create the space for creativity, it can be motivating to the kind of brilliant literary thoughts that you could have even if you were given all the time in the world. And in fact, if you give yourself too much time, you make yourself miserable. And that’s no way to sort of be your creative best person.

On why people should embrace more deadlines:

[I]f you’re beating yourself up because you procrastinate, know that you are absolutely not alone. In fact, 20 per cent of people call themselves chronic procrastinators, so they procrastinate on every single project they take on. In college, that number is even higher, it’s 50 per cent. So throw away the guilt about procrastinating and just think about what the fixes are. And basically, I think that rather than white-knuckling your way through a project by yourself, which is like, “I have to get this done, I don’t want to procrastinate,” you use a deadline as an external help to yourself, as a way to not rely on your own willpower, but rely on the power and focus that one will bring to you to get it done.

To hear more of Chris’s brilliant tips on how to meet your deadlines, we recommend listening to the full episode.

Episode Transcript