Why to-do lists don’t work

When you’re working in a fast growing startup, there are really no fixed roles and responsibilities, and there’s always tons of stuff to get done. Landing pages to be created from scratch and optimised, sales collateral to be written, content strategy to be formulated, new features to be built and shipped out, partnerships to be finalised, A/B tests to be run, case studies to be built, ad campaigns to be managed. . well you get the point.

Amidst all this rush to get stuff done, it’s really easy to lose focus, get distracted and not get anything of real impact done. When we have too much to focus on, we tend to do procrastinate and do low effort-low impact work rather than focusing on the one or two high effort tasks that will create disproportionate impact.

Today, I want to share THE biggest productivity hack I’ve stumbled upon, in terms of overall impact and that which works like a charm for me. But first

Stop making To-do lists.

The most productive people I know don’t.

I know that sounds crazy but it’s true.

Most of us who use a to-do list take out a sheet of paper and write out all the stuff we want to do, say on a Monday or during a whole week. It looks something like this.

The thing about to-do lists is that while adding something to your to-do list takes virtually no time and effort, the same can’t be said for actually completing your to-dos. There is virtually no or a very low barrier to add items to your to-do list and that’s the primary failing of to-do lists.

To-do lists work very well to keep a track of all the things we need to get done and haven’t yet. That’s really it. They’re not really there to push us to get things done or be more productive.

To-do lists are extremely easy to make and that’s a bad thing.

And because it’s so simple to add things, these lists tend to grow and grow. Even worse they encourage our default to be “yes” instead of “no.”

Ideate and design a new landing page? I could do that. Oversee a new ad campaign? Yeah, I could squeeze that in too. A new blog post? Umm sure, count me in. And on and on it goes.

It’s no wonder we feel stressed and full of anxiety. We feel good adding more and more things to our lists but the longer the list, the more mental load and stress it subconsciously adds.

The fundamental flaw with to-do lists is that it assumes that we have unlimited time and hence encourages us to keep adding as many tasks as we want. We can only do our best work when we say no to a hundred things and just focus on the very few things that really matter. To-do lists take the focus away from making the hard choices we need to make to create an impact and let us hoard as many tasks as we want.

They encourage procrastination as there are always a bunch of things to do in your list but without any time-constraints attached to it. You literally have till eternity to check them off the list. Until you don’t.

The solution to a to-do list is actually pretty simple. You only have to make a couple of changes.

1. Break down each task into many minuscule tasks

A big reason why we postpone a task is because when we think, “have to run that marketing campaign” or “need to plan that trip,” those tasks actually contain so many sub-tasks that it creates a mental overload, so we’d rather take the path of least resistance and wait until Parkinson’s Law kicks in.

The only way to beat this is to break down the task into multiple micro-tasks.

If I were to “write a blog post,” here’s what it might look like:

  • come up with 5 ideas,
  • come up with 5 more ideas,
  • narrow down the list to 1–2 ideas,
  • basic research for idea 1,
  • basic research for idea 2,
  • pick most interesting/appropriate idea,
  • in-depth research on idea,
  • create outline of blog,
  • write first draft,
  • make edits,
  • etc, etc

If you were to take it one small step at a time, it’s not daunting at all. And with each sub-task completed, I know exactly how far along I am and how much of a task is left.

Come up with 5 ideas? Shoot, I could do that right now. Maybe, if I’m feeling good, I’ll even do 7!

Do basic research on an idea? Google it. Easy peasy!

And just like that, instead of feeling stressed out about a longish task, I’m already done with a few sub-tasks that take lesser time and effort to do and feeling good!

Anyone can do that.

Our tendency to procrastinate is directly proportional to the seeming enormity of the tasks we need to do. Dividing tasks into small sub-tasks that take lesser time and effort, and then doing them, makes the task seem easy and effortless.

This is exactly why Duolingo and Treehouse are so successful. Instead of thinking of it as “I’m going to learn how to code” and feeling intimidated by the task because you feel like you have to be immersed, get a tutor, take classes on it, or study 3 hours a day… you just spend 10–15 minutes… every day, taking it one lesson at a time.

The more sub-tasks I finish and check off the list, the more I feel good and productive, turning it into a virtuous cycle. This is unlike having the mental load of having a huge task unchecked in my to-do list.

Like I said, the biggest problem with a to-do list is that it assumes an infinite amount of time and encourages you to keep adding tasks to it. The ideal solution to this problem would force you to look at the very limited time you have and make the hard choices that come to define the work that you do.

Which brings us to the second change we need to make to our to-do list.

2. Schedule the to-dos

When you schedule things, you are forced to deal with the fact that there are only so many hours in a week. You’re forced to make choices rather than add something to a never ending to-do list that only becomes a source of anxiety. And you can’t just schedule important work and creative stuff. You need to schedule time for rest and recovery and mundane things like email.

Some of the most successful people on the planet schedule everything right from sleep to spending time with the family. Scheduling things forces you to prioritise and focus on the things that really matter and also creates a visual feedback mechanism for how you actually spend your time — something we’re blind to while aimlessly chasing to-dos.

Scheduling time also forces you to allot hard deadlines to all sub-tasks and hence lets you take advantage of Parkinson’s law which states that “work expands so as to fill the time available for its completion”.

I schedule work in 20–30 min bursts and also schedule breaks in between. This lets me work with deep focus in those bursts and come out with work I’m really proud of. This is actually similar to what Cal Newport teaches us in Deep Work and also to the world-renowned Pomodoro technique.

Being more productive isn’t always about doing more and more, it’s about being conscious about what you work on and how you spend your time; about putting your energy into the two or three things that really do matter in the end.