How to scale your TODO lists ✅✅✅

October 23, 202010 min read

Why a simple TODO list is mostly never enough?

Most of us are conditioned by our academic experiences. How we execute things is still influenced by our initial years. I complete 14 years as a working professional this year, but sometimes I feel that it still doesn’t beat my 18 years of schooling and college life.

In academics, we are subject to time tables, plans, goals, and evaluations — all of which are decided and planned by someone else. Even when we start our careers at work, we look up to our seniors and managers to provide us with the next task. We keep executing short-term tasks and at the end of the year expect our employer or our manager to “remember” our contributions, “evaluate” our potential, and to “plan” for our future. It is so deeply ingrained within us that if we take out that teacher, the manager, or the parent away from the room, we suddenly feel a rush of freedom. What happens next is either of the following …

We try to claim that freedom by mostly doing things that we aren’t allowed to do — relaxing, slacking, enjoying our favorite recreation until we get a hangover or worse … yak shaving (erm … like me writing this article). Why does this happen? We are not used to freedom (and it is OK, apparently). We realize that we need constraints. We need an external force. We need a Boss as a Service (BaaS)!


We try to build our castles in the air. We layout plans for everything under the sun and most of us fail because we over-commit or we don’t recognize the irregularities of the real world. We don’t learn. We don’t correct ourselves or our plans. Pop psychology will tell us that we are afraid of being free or successful and hence we sabotage our own plans.

Some of us have figured out the above or are self-motivated, but then we tend to attract more work and more responsibilities as we grow and succeed. The game of life changes and it presents us with one of our fiercest nemesis — frequently switching contexts.

Let’s sift through the above to collect all the pieces of the puzzle

  1. We need goals
  2. We need timetables
  3. We need evaluations
  4. We need to know what the next step is
  5. We need BaaS
  6. We need to retrospect
  7. We need to focus
  8. We need a plan!

There is a lot of content out there that talks about these things. All filed in under the topic - Productivity. I intend to give you a map to traverse through the myriad of systems out there. This is my initial attempt. I will add more articles based on my conversations and the feedback I receive.

🎵 interlude music appears then fades away ...


~ ▪ ~ breathe ~ ▪ ~

So, what has all this got to do with TODO lists? I find myself being asked the question - Which TODO list application would I recommend? I do have preferences and, it all depends on what you are looking for. This post is not about that. This one tries to address the underlying condition and helps you to become aware of the stages you'll go through. It should also act as a history lesson based on my observation of people in the Productivity space.

Stage 1: Using a TODO list. This is baby steps. It will work for a weekend chore, a small project. Even a small event to be organized. Why one list doesn’t work? After we are grown-ups, we are never in a single context for a stretch. We need to be “responsible” and for many things too. Mostly, people use this to dig themselves out of a ditch. If you are doing this often then you need to rise higher and look at the pattern of your ditches. How closely spaced they are? How deep? What triggers them?

You can use any of the following Apps at this stage — Todoist, Remember The Milk or Microsoft To Do - there are many others out there. Device sync and auto data backup are bonus features. You can always use good old paper and pen if you fancy that.

Stage 2: Using multiple TODO lists. Now we are mentally hopping and moving our attention around. Most of us need an isolated space to think about one topic at a time. We can capture or execute items related to the topic that you are focused on. We wear different hats, but having only one on the head at a time would be lighter and more fashionable. You will end up having more than 15 lists — personal, family, health, finance, office projects, courses. I can go on. This is a better place to be in. As an improvement, we can add date tags and then look up deadlines or schedules (preferably the latter) in a calendar view. This works for most cases where you have a Boss, an external force, or a deadline guiding you. It fails to give you the next action by default. You will have to set time aside to initially DUMP all your items, SORT them into different lists, REVIEW them periodically to keep them fresh, relevant, and actionable.

You can choose from the same set of apps as those mentioned in Stage 1 for this one.

Stage 3: The only constant in Life is change. Some of your lists will become irrelevant, and more will appear to add to the clutter. These new lists, however, will not create themselves on their own. When in Stage 2, you will have a list, a special one. The one that protects all other lists. Some call it the INBOX, some MISCELLANEOUS and some call it CAPTURE. The job of this list is to capture the randomness in life and take it off your mind. The thoughts or tasks will remain safe there. If you don’t attend to it regularly, this list will become large and unwieldy.

Stage 3 players prune, sort or empty this list often by moving items to their respective lists. They are quick to realize if the new entry is a task or a set of tasks - a Project. You will notice that the number of words I use and the time required by you to maintain your lists increases from Stage 1 to Stage 3. You will need multiple review and planning sessions — daily (15-30 mins), weekly (1-2 hours) and monthly (4-6 hours) for this system to work. If you don’t, then this will leak into your execution time and you will end up with a stagnant system that has a completely reverse effect and paralyzes you. If you don't take care of it, then just like a house plant it will die and wilt.

What should you do when you get paralyzed or if you failed to maintain your system? Start at Stage 1 again. First, get yourself out of the ditch. Feel better, accomplish a few things, and slowly move towards the next stages. Make sure you do a retrospective to understand what works for you and what doesn't.

Stage 4: Looking over the shoulders of giants. You haven't given up. You are ready to scale up so you try to research. Learn more about successful people and how they conduct their business.

How so they plan their day? How do they manage their lists? Erm, what TODO list application do they use?

You won’t get exact answers. You will get an overview of their daily plan, their habits, and how they wish to spend their time. You will read more and it will then click to you that TIME is a hidden essential resource that keeps slipping away. You will learn about PRIORITIZATION, attending to BIG ROCKS first, the Eisenhower's Matrix. You will learn to DROP and DELEGATE. This will help you reduce your backlog and go through your items effectively. You will feel better and may even execute better.

Stage 5: Someone else's system. First a WARNING. This is a place that promises ultimate productivity. It is full of guide books, manuals, and self-help books. My advice would be to tread carefully. There are good options here but it is cluttered with derived ideas and clones and false promises. Even without that, it could be a rabbit hole that could lead you to hundreds of articles and YouTube videos. You will end up having to learn, try out, and filter options. If you are like me, you will enjoy this but it won't make you productive, at least immediately. It needs a lot of investment and you need to constantly update yourself. There are courses and workshops worth thousands of dollars out there claim to help you set up your system. I have no experience with them so I cannot give you my opinion.

People who need this option are people feel the need to do more and that could be a whole other discussion.

If you have worked yourself from Stage 1 to here, you might find a lot of similarities between your system and theirs. I have tried out some form of two popular systems and they are similar but with some key differences — Getting Things Done (GTD) by David Allen and The Bullet Journal Method (BuJo) by Ryder Carol. I hope to post more about these in the future. Besides these, I am also looking into the PARA Method and the series of productivity Apps and note-taking applications that keep evolving as we learn about the gaps in our understanding of how we remember, execute and organize ideas. I am going to attempt a GTD from scratch again. I will let you know how it goes.

From personal experience and from what the authors have themselves mentioned, it may take around 6-18 months to set your life right i.e. if you are in a mess and reach a place where your system works like clockwork.

If you are a person that attracts growth, the current will become normal. The rate of change will be higher and what’s coming up will need your thought and attention to manage it appropriately. You will repeatedly find yourself in Stage N-1 and looking for Stage N.

~ ▪ ~ breathe ~ ▪ ~

CONCLUSION: The goal of this article was to allow you to reflect upon where you are and how do you feel about your system or the need for it.

  • If you have don't have a system, start at STAGE 1 or STAGE 2 and attend to your immediate priorities first
  • If you have a system and it works for you. Good for you! Stick to it but keep reviewing and improving it incrementally
  • If you pick up a minor change or somebody else's system, understand the principles behind it and don't just follow the mechanics. Try out things and see if you are ready to invest. How easy it is to migrate data or pause execution.
  • Collaborate with people and don't be afraid to ask for help or reviews (not just tips and tricks). People are generally willing to share their experience to help others 🙂

Remember: No system will work on its own. No app will work on its own. You will end up creating your system. You can learn and share what you practice and why it works for you. Through collaboration, exchange of ideas, and careful gardening, your system will evolve to suit your needs.

For more fun posts like these, click here to see a list of all my posts