Your Paper To-Do List Is Constraining You

Paper is flat. Not only does paper have a fixed width, but it has a fixed height too! What’s more? If you need more space to write or sketch, you need a whole new piece of paper! In today’s digital world, that’s quite constraining! And that’s a good thing. While digital productivity tools and on-line to-do lists get all the headlines, the research is clear that analog tools based on pen, paper, white boards, and the like, are more effective for many activities related to personal productivity. Much of that value comes from constraints.

The value of constraints

“I think frugality drives innovation, just like other constraints do. One of the only ways to get out of a tight box is to invent your way out.”–Jeff Bezos (Founder, Chairman, and CEO,

There’s a common misconception that the best way to be more productive is to have more time. It makes intuitive sense…if you have more time, you can get more done, right? Well, there are two problems with this. First, you don’t have more time – we all have 1,440 minutes in a day, 7 days in a week, and 365 days in a (non-leap) year. Second, getting more done does not necessarily equate to being more productive.

Constraints are paradoxically freeing. In limiting your options on certain dimensions, constraints let you focus more attention on those dimensions that you can influence, usually resulting in better results in those areas.

Furthermore, constraints save time. Give a choice of 500 different flavors of ice-cream, most people will take a significant amount of time deciding on which one to choose. Given a choice of 7 flavors, those same people will make a choice much quicker, and what’s amazing is that they’re likely to be more satisfied with their choice with less regret over the flavors they didn’t choose. Remove the choice altogether and just offer vanilla, and things get even simpler, letting the recipient focus on thinking about other things like toppings, or what they’ll do after dessert.

The value of paper as a constraint

Think back to high-school when you were given an assignment to write an essay. If your teacher told you to write on the topic of “Should the voting age be lowered to 15 years old?” what would your first question be? You’d have wanted to know how many pages (or words) were expected. In the absence of a page count (a paper constraint), some students would turn in a paragraph, while others would spend all available time to hand in a 100 page, meticulously researched report. A constraint of 10 pages lets you allocate an appropriate amount of time to each phase of the assignment.

Artists use a canvas as a constraint in painting. The edges of the canvass frame what the artist feels is important for people to see, and anything that doesn’t appear in the frame can be ignored by the artist. This constraint allows more effort to be spent on composition, symbolism, and the technical aspects of creating a masterpiece. A big challenge for artists working in 3d virtual reality is the lack of physical constraints that limit what needs to be built. Instead, artists must create their own constraints to manage the scope of these projects.

Constraining your to-do list with paper

An effective to-do list can serve 2 purposes: 1) it can remind you of all the things you need to get done – i.e., it can be a memory tool; or 2) it can prioritize the order in which you should get things done – i.e., it can be a productivity tool. Given how the human mind works, the truth is, a list can’t perfectly serve both of these purposes. Digital lists excel at #1. Keeping a running list of all the “open loops”, as David Allen calls them, is perfectly suited to a digital tool that lets you sort them, filter them, and group them. Further, there’s no limit to the number of items you can store digitally.

When it comes to prioritizing, digital tools support this too. But for most people, near term priorities are so fluid that digital tools become ineffective. Imagine everything in your life that needs to get done, irrespective of priority. All your work and personal items. Every call and email. Every bill to pay. Every item to buy. Things you need to follow-up on. Things you want to get more information about. Broken items. Chores and errands. Books to read. Friends to meet up with. We could keep going, but you get the point. We’re already into the hundreds of “to-dos”. Capturing all of these things digitally takes time, but it’s worthwhile given how easy it is now to add, remove, or edit items. Now prioritize them. Digital productivity tools typically allow you to assign priority to each item in some fashion, so this is straight-forward too.

But now let’s get down to brass tacks. It’s time to get things done. It’s Tuesday morning, and you’re planning your day. What do you do? The easy answer is to start with your top priority item on your digital list then work your way down from there. The problem is, you last updated the prioritization two Fridays ago, two of the top five items on your list can only be done “on the go” (okay, that’s 2 problems)!

Neither of these problems is insurmountable, of course, even with digital tools, but hear me out. Take a sheet of paper – any size will do – and fold it until it can fit into the palm of your hand (3″ wide by 4″ tall is a good size). Now quickly scan your entire Master To-Do List and identify the ONE thing that you would, above ALL else, want to get done today. Take into account the obvious: importance and urgency. If today’s the deadline for renewing your license plate sticker, that may be your #1 priority today, but if you’re flying out for a family vacation in 4 hours and you still haven’t arranged your transportation to the airport, your license plate sticker may fall down the list! But also consider other factors: Context (if you’re at work, can you action that item there?), Time (will you be able to dedicate enough time to complete the item?), Energy (do you have the mental or physical energy to complete the item today?). Once you’ve identified this top priority item, write it on your piece of paper with a big, empty check-box in front of it. Now go through the same exercise to identify 2-3 more items that you want to get done if (and only if) you complete #1. The temptation will be to cram as much as you can onto your page. Resist. If you have trouble containing your list, then fold the page one more time or write in bigger letters. The goal here is to use the constraint of space on the page to limit the number of actions you’re going to focus on today. I like to call this my Daily Focus To-Do List.

Daily Paper To Do List

Now, with your Daily Focus List in-hand, go about your day. Keep your list front and center, directing your time and energy towards completing your top priority item first, and then moving on to complete as many of the secondary items as you’re able. If you’re like most people, you won’t complete all the items, but that’s okay! If you’ve completed your #1 priority, you’ve had a more productive day than 99% of people. If, by chance, you happen to complete ALL the items on your Daily Focus List, rejoice! You now have the luxury of either a) going back to your Master List and picking the next 2-3 items you want to focus on and adding them to the back-side of your page, or b) taking the rest of the day off, safe in the knowledge that you’ve had a fully productive day.


Paper lists aren’t sexy, but they’re a simple, highly effective way to maintain focus in a world of unending demands. Using a paper list recognizes that our we can never complete every item on our Master To-Do List…and that if we did, it’s likely a sign that we’ve either set the bar too low, or we don’t really have a full grasp of the “open loops” in our life. It equates productivity not with volume of boxes checked, but rather with the impact of the few boxes we do check, liberating us to enjoy the fruits of our efforts, and leaving us with the time and energy to both guiltlessly enjoy life, and ensure we have sustainable energy tomorrow to do it all over again.

Do you see value in constraints? How do you use them to your advantage?

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