Everyday Systems: Podcast : Episode 53

Timebox Lord

The worst piece of productivity advice I ever came across -- in a very popular book on productivity, possibly the most popular book on productivity -- went something like this: any time you think of an undone task that will take two minutes or less, just do it. The idea being that we are oppressed by lots of half-remembered small undone tasks that barely take more time to do than to identify. Getting them out of the way gives us a feeling of accomplishment and frees us up to focus on the big stuff.

And there’s something to this, if only on a psychological level. It sure is satisfying, getting little things done! “Todo lists are my salvation,” I’ve sometimes thought to myself, as I lift myself out of despondent inaction by crossing off tasks.

But at the end of the day, the two minute rule is terrible advice, and there are two reasons why.

First of all, the guy who came up with this must not have had kids. If you have kids, you know that you have an effectively infinite number of things you should probably do that take two minutes or less. On top of the other infinite number of things you should do that will take far longer. So the two minute rule is naive in that it misses the first ultimate truth in the field of productivity: the fact that there is infinite work. You can’t do it all. You can’t even list it all. It would take forever just to make that list. Even if you don’t have kids this is probably the case, but once you do, forget it. It’s hopeless.

Infinite work. This is the first law of productivity. The first axiom. The first self-evident truth that is the starting point in our quest for self task-mastery. You can not possibly get it all done. In some sense, the first step towards getting anything done is to give up now. To give up on doing it all.

The second reason the 2 minute rule is such profoundly bad advice, is that it also flouts the second law of productivity, which is “first things first.” Given that there is infinite work, and that it is impossible to do everything because we do not have infinite time, we have to figure out what is most important so we can at least get to that.

Now it is not easy or obvious, in many cases, what is most important. The only really obviously most important thing to do is to figure out the most important thing to do. That is our most important task. Our first task is to figure out the second task, then maybe, if there’s time, the third task, etc. The most important thing is to figure out the most important thing. The priority is prioritizing itself.

The two minute rule gets this exactly backwards: it says, do the little, easy stuff first. Then, afterwards, energized by many little victories, you can get to the big, important stuff. Psychologically, as I’ve mentioned, there is something to this. The problem is there will never be an afterwards. The little stuff will utterly consume you. “Todo lists are your salvation” but also, in some sense, “todo lists are your damnation.”

But the “two minute rule” does give us something! By the light of its terrible counterexample we can clearly see the two fundamental laws of productivity:

Infinite work

First things first

These two laws should be the starting point of all our thinking around productivity.

Note that they are not solutions in themselves. They are merely true statements of gigantic, seemingly insoluble problems. But you can’t start solving these problems until you recognize them. That’s why they are so important.

Now “First things first” may seem like a potential solution to “infinite work.”

But if you think about it, it introduces as big a problem as it solves. And the same kind of problem as infinite work.

The trouble with “first things first” as a solution to “infinite work,” is that like “infinite work,” it too can take forever.

Think about it. You need to identify what is most important. That is the most important thing. But if you take that question seriously enough, it is not at all easy to answer. It’s almost like saying “1. Find the meaning of Life…” Imagine a todo list like that. You’d never get to number 2.

Many people see this difficulty immediately, shrug their shoulders, and throw themselves back into smaller implementational goals. The ultimate goals may be murky or non-existent, the tasks may be pointless, but at least they are doable. At least we can feel productive.

Think about it. The most important thing. The meaning of life. You could meditate for 40 years in the desert and still not figure it out. You know this. So what to do? Do you search in vain for the point? Or do you give up and throw yourself into pointless activity? It seems you have to choose one of two impossible paths. Either fritter your life away with infinite, pointless tasks, or do nothing but ask “why?” forever. Or just, I guess, give up. Throw all the goals out the window.

My friends, this is a self-help podcast, I do not want to plunge you into existential despair.

So be ye comforted. I have a practical tool for you to help grapple with this perhaps surprisingly profound productivity dilemma.

It’s inspired by the old and ever-rebooted British sci-fi TV show, Dr. Who. I call it Timebox Lord.

Dr. Who, as you may recall, was a Time Lord. He could travel through time in his blue phone booth, the Tardis. (I love that they called it the tardis. It’s like whatever time he travelled to, he was always late.)

Don’t worry if you’re not a sci-fi geek. That’s all you need to know about Dr. Who for the purpose of this system. It also has a killer theme song which I highly recommend you look up on youtube or spotify and use for inspiration.

Timebox Lord is based on timeboxing.

Timeboxing (I did not make up this term) is an established technique for breaking up daunting large tasks into smaller tasks by the very simple mechanism of chunking them into short, timed intervals. You don’t have to figure out all the steps in advance or estimate how long it might take. Just say to yourself, “I’m going to wrestle with this task or problem, for some predetermined amount of time, say 25 minutes, no more, no less. I’m going to set a timer, and when I will work at this task until the timer goes off, and then, wherever I wind up, I will stop.”

The beauty of timeboxing is that it makes it easier to dive into a big, complex problem you don’t fully understand yet, and might otherwise keep putting off. Many problems fall into this category. They are messy, they are overwhelming, you don’t know how much time they will take and you are afraid you won’t have it. You just need to start. Timeboxing is a great technique because it reassures you that no matter how big and messy and time consuming it might wind up being, you will sacrifice no more than a small, predetermined number of minutes to it. It helps you get started on tasks you are afraid of and overwhelmed by and keep putting off. And just as important: It also helps you focus during that time because you know that time is a limited commodity. When the timer goes off, you have to stop. That artificial pressure helps you focus.

Sometimes the problem that seemed overwhelming is actually, once you start wrestling with it, quite doable. Great. Timeboxing helps you start that wrestling and get it done. This happens a lot. Other times it really is a gigantic mess and maybe not worth the gigantic effort it will take. Also good. Timeboxing helps you recognize that and you can cut your losses and move on to something else after only a small investment of time.

Timeboxing simultaneously diminishes the long term anxiety about a problem by not allowing you to see more than some small number of minutes ahead, blinkering you, like a frightened horse, and increases, helpfully, a short term pressure to focus. So it reduces one kind of pressure (a bad kind), and adds another (a good kind).

It also makes it easier to plan your day. You can block it out on the calendar. If you see that you have more time boxes than actual time, well, you’ve got to move something to tomorrow.

Another name for timeboxing is the pomodoro technique, literally tomato technique, in Italian, because the timer the guy who invented it used was shaped like a tomato.

Traditionally, the pomodoro interval was 25 minutes. With a five minute break before the next timebox of effort to rest and cleanse your mental palate. So with those breaks, 2 per hour. Each interval was called a pomodoro, so two pomodoros per hour.

But I find that even very short timeboxes can be helpful.

I prefer multiples of 7. 14 is my absolute favorite. If you do shovelglove with a 14 minute timer you’ve been doing exactly this. 21 minutes is about a high as I go for a single timebox.

Now you may be wondering, clearly timeboxing is good for getting a jump on (and limiting) “infinite work.” But how does it help with “first things?” How does it help with prioritizing in the deep or even in the shallow sense of the word?

The answer is what separates the Timebox Lords from the mere timeboxers.

It works in a surprisingly simple and elegant way: you timebox not only your tasks, your “infinite work,” but also the time you spend thinking about those tasks and how to prioritize them, the time you spend contemplating “first things,” asking yourself, what is the most important thing, not for humanity in general, though that may have something to do with it, but for me, right now, today? Thinking that through, with a physical notebook in hand, on a regular if not daily basis, for a set amount of time until the timer goes off: a “first things” timebox.

This ensures a kind of balance between the hopeless task of infinite work, and the hopeless task of “first things.” You have to do both. You can never finish either. Timebox Lord is a way to engage with both ends of this paradox of opposite impossible requirements in a way that is both practically and soulfully balanced and sound. It will not solve all your problems, but it may help put you in right relationship with them.

I have both open ended “first things” timebox sessions, when I have no specific idea what I’m going to think about and wrestle with beyond the question “what is most important, for me, today,” and specific brainstorming sessions, when I set myself some specific problem or prompt to wrestle with, usually a problem that’s been bugging me for a while. I try to do an open ending “first things” session every weekday morning, for 14 minutes, literally (almost) first thing, before I do anything else. I find this helps ground me for the day. Either way, with open ended sessions or specific brainstorms, I use a timer and a physical notebook, not a computer. Computers, those distraction machines, are the enemies of “first things” thinking. In the notebook, I just write the entries in chronological order, one after another with the date on top.

I’ve spoken before about my system of using index cards for task management. A new index card every day, with the day’s task written on it. I still do this, big time. And it works great with Timebox Lord. After I list a timeboxed task, I put a number behind it representing the number of minutes I will spend on it, then draw a little square around that number to literally, or graphically, make it a time box.

Some timeboxes are repeating routines. For example, I timebox the amount of time I spend making my first pass at the index card every day. I write YC 7 on the card (for yellow card 7, my index cards are yellow). Since, as I mentioned, I write my timeboxes on this card, I literally timebox my timeboxing.

Finally, here’s another dimension of timebox lord: Timebox both the things you want or need to do and the things you’d like to do less of but can’t quite resist. The good, the bad and the ugly. This way you reduce what you can’t eliminate. You keep it in bounds. Say reading news sites. Or social media. Blessed is the soul that never compulsively reloads the New York Times or scrolls their facebook feed to the edge of infinity, but for most of us, it’s gonna happen, and it might as well happen on our terms, in a nice, tidy, limited timebox.

By Reinhard Engels