Pomodoro/Timeboxing on Multiple Projects

I accidentally besieged Laralyn McWilliams w my thoughts on pomodoro technique / timeboxing on twitter earlier today before realizing probably a blog post would be a better way to do this. So here is that blog post!

I have been working independently (self-supervising?) for maybe 8-ish years now, and one of the most popular suggestions for how to help yourself have a bit more discipline is Pomodoro Technique, sometimes called "timeboxing".

The rough idea is you close your web browser, your email, your phone notifications, your twitter, your facebook, and for ~50 minutes at a time, you focus solely on the next task on your to-do list. At the end of the 50 minutes, you can stand up, stretch, check some emails, but then 10 minutes later you go back in the zone and knock some more items off the list.

It's a really easy way to be really "productive" or whatever, but there are some catches or things in my experience that have helped me make better use of it. Like a lot of things, it's not some magical silver bullet, just a nice tool to have lying around. Some stuff I've noticed over the years:

I need to have a good to-do list done already. What is a "good" to-do list? It means I already know how to accomplish every item on it. Each thing on the list (whether that list is in my head or on paper or in an app) does not require strategizing about how best to approach it... I know exactly what needs to be done, I just need to do it. Timeboxing is perfect for this scenario.

I don't need any special equipment - any dumb timer will do. I use my dumb iPhone's timer, but I could use an egg timer or a complicated series of hourglasses or whatever I want really. The only thing that matters is that I can set it and forget it.

Ok actually, that said, probably the most crucial piece of equipment for timeboxing is really comfortable headphones. I have been using a pair of AKG K240s and they're pretty amazing - very lightweight, no pressure on my oversized ears. Depending on your like skull shape (mine is enormous apparently?? awkward) i think there are lots of cheaper alternatives. They really do help me shut out the outside world and focus on the task at hand though.

Timeboxing does not work if you have weird nebulous brainstormy tasks for the day. Maybe this is just a personal hangup or a weird issue for me, but I've found that going to a coffee shop and just talking out the issue with a fellow designer has a way bigger impact on this sort of task than something like timeboxing. If your to-do list for the day includes tasks like "have an epiphany about how to defrag our over-complicated inventory system", I would not have super-high expectations for timeboxing working on that.

If I'm timeboxing I need to take a long break after 4-6 hours. When timeboxing really works, it is extremely intense. Without constant breaks for snacks, social media, email, etc, I can get so much work done, but I also seem to drain my creative batteries a lot faster. Timeboxing 10-12 hour days is a really good way to get ulcers or find yourself in the fetal position shivering!

And Oh Yea - if I am working on multiple projects, I find it massively helpful to work on the least fun ones first. Do the contract work before lunch, the passion project after, for example. I find it very easy to upshift, and very hard to downshift. There's a tradeoff here - if your brain works best in the morning, sometimes you need to commit that good morning brain-time to the passion project, and that's ok. For me it is important to acknowledge that I probably won't manage to switch off to contract work if I start on the fun stuff though.

Ok that's it! Hope this is helpful. Timeboxing is flippin' great, but just keep an open mind about your own work habits, and I encourage you to think of it as just one tool in your belt. Good luck!