Another successful 90 day challenge!

This time, my daily commitment was to do all my work items for the day before doing anything else.

I tried a “worst first” challenge first, and failed it. It’s a tricky one because it’s not very specific. What really counts as the “worst”? That needs to be defined. And what if something genuinely urgent is in your inbox when you wake up that morning? How can you be sure that it really is urgent, or if it’s just a good excuse to avoid doing the worst thing?

So after that attempt fell through, I re-grouped and wondered how I could lessen the confusion, and make it work for a 90 day, daily commitment.

I came up with the Work First Challenge.

My Beta Test

A week before starting this challenge on the 11th of November 2014, I was about to go to London to spend the week, with a lot of socialising planned. Not a great time to start a new challenge in earnest, so I treated it as a beta test, with the following rules:

  1. Make a list of work-related tasks every day.
  2. Complete that list before doing anything else on the computer, by 5pm.
  3. After 5pm you can do what you like, whether or not you completed the list.

Why The 5pm Cut-Off Point?

I learned from my very first 90 Day Challenge – The Assignment Challenge – that with something as strict as this there’s a danger of creating strong incentives to give yourself easy tasks, so as to ensure you don’t technically fail the overall challenge.

During The Assignment Challenge, where the rule was every day I had to complete my to-do list, I noticed that some days I would give myself a super-easy list, so that I was sure to complete it. The challenge was intended to make me a harder worker, and it certainly did that, but it didn’t change me as much as it could have, and that’s all down to this one factor – that I didn’t give myself an “out”, and was forced to give myself tasks I was sure to complete in order to not fail the 90 Day Challenge.

By letting myself off the hook at 5pm, I would have little reason not to push myself and give myself more to do each day than I could easily complete. The challenge did not require that I complete the list by the end of the day, but without the 5pm cut-off point, I would be forced to keep working all day, neglecting things like social messages. I knew I wasn’t prepared to do that.

The Kind of Leniency That Won’t Make You Soft

This understanding is counter-intuitive at first. Giving yourself a way out in order to maximise your drive to push yourself? Really?

The thing that makes it work is the specificity of the ‘get-out clause’. It’s at 5pm, and that’s it. This means no watching Game of Thrones while I eat my lunch, for example, which has the effect of ‘softening’ my attitude in the second half of the day.

It’s a specific leniency that doesn’t let you get out of the truly important stuff – doing the work. When you’re conducting your own 90 Day Challenges, think about how you can design in a specific way to let yourself off the hook of the unimportant (such as doing every little thing you write down to do), so that you’re kept more closely aligned with the important (such as pushing your limits and making faster progress towards your goals each day).

Another (stricter) example for The Work First Challenge would be to have specific hours of the day where you do whatever you like, perhaps 12–1pm, 5–6pm, and 8–9pm.

Isn’t it funny how, with all the open criticism of the 9–5 workday from my generation of self-directed internet workers, in the end we have to come back to similar principles in order to be productive? It makes me think of a child who rebels against Mummy and Daddy in his teens, and then comes round to appreciate their discipline in his twenties.


After the beta test I noticed a few cracks in the challenge structure, and made the following revisions and general notes:

  • You can do something that’s not tasked, so long as it’s small, and supports the goals of the tasks.
  • Before you open laptop, make sure you’ve added all you must to the task list.
  • Calendar appointments count as tasks.
  • When you first open up the laptop, close all apps apart from:
    • Calendar
    • iTunes
    • Evernote menubar Quick Note
  • The “30 Second Rule” – if you catch yourself just after clicking through to something unrelated to tasks, you can avoid failure by closing it immediately, or within 30 seconds.
    • This is essential because my work includes researching on the internet, reading articles, and sometimes engaging in a discussion on social media – temptation at every turn, and literally impossible to keep such perfect governance over your mind that you don’t ever lose awareness for a split second and click through to something irrelevant.

The Result: I’m More Productive, and Have a Better Attitude Towards My Laptop

The Work First Challenge was essentially The Assignment Challenge 2.0. It addressed more the “inner game” of work, and fixed my attitude when I sit down at my computer.

I’m starting to take the view that our computers and other devices should be seen as tools, not toys. When so much of our work requires that we sit staring into these screens, is it really such a good idea to spend our recreational time doing the same?

Maybe part of it was the school environment I grew up in. All day we looked at white-boards and paper books, and each other’s faces, with lots of walking around between classes and kicking a ball around as our lunches settled. So it makes sense that when I got home, I saw my laptop as something inherently fun. It wasn’t associated with my work at all back then, and was full of video games, my half-finished novel, and perhaps the beginnings of my obsession with productivity and digital organisation (in the form of my old OneNote journal). It’s fun to blame schools, and that’s not what I’m doing because A) I know they’re changing (since oi were a lad!!) to include more screens, and B) It’s not been the same for my friends in the traditional working world, who spend all day on the computer and let their home laptops collect dust, so, like everything in my world, it’s my resonsibility.

(Quick Tangent: Some people say computerising school is a bad thing – screens at school and screens at home. Sure, there’s a potential for that, and for many homes during the transition phase between the old ways and the new, this will be likely. However, I for one would rather my own future kids learn to associate iPads with algebra and historical dates than Clash of Clans and Skylanders. Then maybe they’ll want to play outside!)


The Work First Challenge certainly brought me a little closer towards re-training myself to viewing my digital devices as tools for work, not instruments for life.

I would recommend it to anyone who feels distracted in the middle of the day.

Featured Image Credit: Sean MacEntee on Flickr