Deadlines as Technology

Confession: I’ve never felt like a very productive person.

During the mobile app explosion, circa ~2009, I remember trying all kinds of different “productivity” apps that I thought were going to make me efficient and productive. Remember The Milk, Clear, Wunderlist, Things, all neat apps in their own right, but none of them really helped me overcome my human frailties.

In hindsight, what I was looking for was a productivity software pill I could take and it’d resolve all my problems. I know better now—I think.

But I still crave that productivity pill in other pieces of software: the best IDE that’ll make me productive; the best writing software (and workflow) that’ll make my life complete; they all claim it.

Then I heard Paul Ford, a professional writer for Wired and other publications, say something on The Aboard Podcast, Episode 3 that resonated. Referring to a moment when lots of folks online were looking for the perfect writing environment, he said the software tool, workflow, environment, whatever, it didn’t matter. You could do it with pen and paper if you want.

The only technology that you need is deadlines.

Ooff. Yup, that resonates. That’s been the best piece of technology for making me productive too.

It’s especially good advice if you’re making a personal website or blog.

Go ahead, use Wordpress. Use a static site generator. Custom roll your own solution. Serve it with a server on Prisma. Static host it on your own S3 bucket. Use an EC2 instance. Build and deploy and serve it however and wherever you want. Do it all with a raspberry pi (is that possible?). Feel free to make it as complicated or simple as you want.

But before you do, set a deadline. That’s the one piece of “technology” that’ll really help you ship. It’s a wonderful constraint. Here’s Rich (from the same podcast):

Deadlines are huge, but really what are deadlines? They’re opportunities to fail. That’s all they are. They’re actually opportunities to learn, to fail. Hopefully not fail catastrophically, but it’s an incredible data gathering moment.

Set a deadline, even if the one thing you learn when you fail to ship, is that you’re bad at estimating and meeting deadlines. That’s a chance to improve for the next one you set.

And best of all? There’s no yearly subscription. Deadlines are free.