My Productivity System - Planning

  • Post by Maxime Cote
  • Jun 25, 2021

For the last 4-5 years, I’ve been refining and building my productivity over multiple iterations. I went from pretty often forgetting less urgent or less important tasks to surviving a whole week of people throwing critical and last-second stuff at me without dropping one. While that week was very unpleasant overall, it was a great stress test of my current system (and myself too at the same time) since this situation is one of the worst scenarios that is somewhat common. Over the last couple of months, in the various articles I wrote here, I ended up laying most of the foundation for my system. So now is the right time to see how it all came together in workflows and processes to create my current system.

General principles

Let’s start here since those decisions affect the system as a whole. My system is a combination of a lot of other system and ideas from (in no particular order): GTD by David Allen, Just in Time Project Management by Tiago Forte, Start Finishing by Charlie Gilkey, the C-O-D and Time Sector system from Carl Puelin and finally Deep Work and Time block planning from Cal Newport, to name the most impactful one. From those, I took the pieces that worked best for my use and my workflow to create those fundamental rules:

  • Plan the next day, the night before
  • No more than five projects at the same time frame
  • Keep an easy to reach/add to/write inbox
  • Be deliberate about your time and where you spend it
  • Know where things will be used next and put them there
  • Plan work projects the same way when possible as personal projects

As for the application I also chose to use, I went with Obsidian for this version of the system. There are many reasons for this, but the principal ones are; I’m already spending a lot of time in it because of note-taking; with the help of various plugins, it works very well as a deliberate system, and it’s all markdown files on my computer.

Building on top of those principles, there’s another significant difference with my system now. It’s split into two primaries “mode,” planning and executing. There are a couple of differences between the two, mainly the mindset I’m in and the tools and workflow related to them. Planning is where I plan, outline, and think about bigger picture elements, like projects, whereas executing is the more “traditional” productivity with weekly review, tasks, routine, and reminders. Because ultimately, planning feeds into executing, that’s where we will start in this article.

Planning Philosophy


Let’s start first with a definition of elements related to planning. That should help make sense of what will follow since some of the things I will talk about might not make sense otherwise. First off, at the top of the pile is “Mega-Project,” those are what most people usually call “Project.” In my case, it’s a collection of projects that will take at least a week to complete and can last up to a quarter. I often use Mega-projects as buckets for keeping track of their children, but they are still their own thing since they too have a goal, a start, and an end date. Next, we have “Projects,” which are one step below mega-projects in the hierarchy. Those are a collection of tasks that will require at least two days of work and can last up to a week; more than that, it becomes a mega-project. A project also has a start, an end date, and a goal, but it will get completed faster since it’s limited in time, and it will often (but not always) be part of a mega-project. Below a project are tasks, but then we get into the execution section in part two.


Why did I decide to split things into mega-projects and projects instead of longer or shorter projects? There are multiple reasons for this actually; one of them is the clarity of the definition. If I had a definition that says it’s anything above one day up to a quarter, that’s anything but precise. With a description like that, you have to stop and ask yourself all the time which “kind” of project is it.

Having an actual “split” and definition is also helpful for the various layering at the planning stage. I split my planning across multiple planes of time: Yearly, Quarterly, Monthly, Weekly, each feeding into the one below it. That means that I know if I’m planning for a quarter, I will deal with mega-projects of quarter length. I explained in more depth this layering and split in the 5 Projects Rules article.

Another reason for mega-project is because of my knowledge management system. Projects need to be short and fast-moving through the system as they are its lifeblood and make everything work. That speed and rapidity are also instrumental in gaining and keeping momentum and motivation in a long mega-project. Those quarter-long mega-projects will include tons of small projects that you complete on the way, so you don’t have to wait until three months out to have the joy of completion.

The final important reason for the creation of mega-project is that they make it easier to split things into smaller chunks and see scope creeping. If I see a project going over a week-long, I instantly know I need to stop and evaluate what happened. From there, I can decide to stop and create a new project to finish some parts, or I can choose to promote it to a mega-project and split it further.

Periodical Planning

Like my mega-projects are split into layers, as discussed above, so are my planning sessions. To keep things flexible and achievable, I review and plan periodically how mega-projects and projects go in the various planes of time. That’s why I have a yearly review, quarterly planning, monthly planning, weekly planning, and daily planning sessions. That mechanism is also part of the same five project rules idea I touched on earlier. This variety of planning over time is also one of the main reason why I can afford to be more deliberate, as I explained in more details in Automatic vs. Deliberate Productivity What’s Best for You

Those periodical planning sessions are also one of the best ways to keep going in the direction that I set myself in. One of the critical reasons for this is that it makes it easier to see the “lineage” of things and how this task or project moves forward that yearly goal I set. That “lineage” comes from each of the planes of time feed into the text below it. That “feeding” happens during those periodic planning. I will look at the “parent” mega-projects to create the current mega-project for this plane during each planning session.

Having scoped review also makes it a lot less overwhelming and stressful. If I plan for a month, I only have to care about its parent quarter and its children’s weeks. There’s no need to think about how my days will look like, or worst, how the year is going. On the other hand, I know that I can adjust the planning during those following weekly reviews if things come up.

Planning System

It’s now time to dive deeper into the “technical” implementation of my system in Obsidian and how I can make it work in practice.


One of the core things in most productivity systems is an inbox. It needs to be a quick, painless, fast way to add thoughts, tasks, and other things that come to mind so they’re not forgotten and don’t create open loops. Since my system is in Obsidian and I always have it available somewhere, I made an “inbox” note. It’s an empty note ready for me to put anything in it, but there’s no template or anything, so it’s faster to add things. For the speed, especially relating to tasks, I’m using the “QuickAdd” plugin that creates a small popup to write tasks into at the push of a button and add them to the inbox note. On the mobile side, when I’m off from my computer, I created a simple version of that popup with Tasker on Android that appends tasks to the same note, which syncs back to my vault.

Kanban Boards

On the planning side, most of the planning happens with the help of the Kanban plugin. The kanban boards make it very easy to see the state of the mega-project and project across various times. I have a board for each time frame (quarter, month, week) with all my mega-projects laid down, dates, and related projects. Those quickly show me where I need to watch out for: do I have too many projects in the backlog? Do I have more than five projects active? Do I have too much review to do? Given that, I can adjust my planning and add or remove a project or add review sessions.


On the mega-project and project side of things, I have a simple template for them that capture just the minimum I need to start on them:


## Goals:

## Notes:

The project template will be very similar, mainly without the child element and with an added reference section for notes. There are probably many things “missing” you might expect, like customers, teammates/collaborator, contact, etc., and there are two reasons for this. First off, it comes from how I designed my system for the needs vs. the “would be nice.” When I sat down and thought about what I need (which I explained in more detail in How to architect your productivity system yourself ), I came up with that list that allows me to do everything I need.

The second reason is that a lot of this is already in our internal system for work, so I don’t need to duplicate things. The way I plan things for work, in general, is by copying. I take the task or project given, and I “copy” them in my system, where I can split/chunk/merge however I want. That way, I don’t impact others' planning systems with my definition of projects or my system. That’s very useful for projects, primarily since I can split them further to match my definition, whereas work projects are more traditional, long-lasting projects. Often I will have multiple mega-projects for a work project instead of “the one.” Then when I give a status update or need to fill in time, I merge that info back together.

Planning session

The other part of the system is my template for planning, which is the steps I follow to complete a session. Here is the actual template for a Quarter Planning as an example:

## Reflection on the past quarter

#### List of habits to work on:

### Reflection
*In another note normally but pasted here for readability*
## Reflection on the past quarter
### Past Quarter

- Best thing this quarter (3-5)
- What I learn (3-5)
- Things to change (3-5)

### Going forward
- What responsibility/projects inspire you from this year you want to tackle this quarter?
- What responsibilities/projects do you want to keep doing longer?
- What responsibilities/projects can you let go for now?


## Planning next quarter
### Yearly Goals
- ![[Annual Review 2020-2021#Grouping]]

### Mega-Projects:

### Coming Months: 

### Planning
- [ ] Next months calendar
- [ ] Update mega-projects 
- [ ] Create the mega-project list
- [ ] Look at the Yearly plan for missing areas
- [ ] Review [[0. 📫 Backlog]] for ideas
- [ ] Create the mega-projects
	- [ ] If needed add those to their corresponding months
- [ ] Schedule next quarterly planning

The template is, by design, pretty self-explanatory, I don’t want to have to try and remember what I meant when I sit down to do the work, but there are some things worth pointing out. First off, it’s split into two sections, reflection on the past month and then actual planning. Looking back at what just finished, what went well or not, and what’s left is a great way to help improve in the future. It helps see the pattern or possible issue and helps you plan more consistently in general, and get better at gauging the amount of work you can do.

From there, we get into the actual planning; I start down from the yearly goals into the mega-projects selected for this quarter and then each month. If I’m already sure I will work on a mega-project during month X, I will add it to that month’s planning. Then when I do that month planning, I already know I need to plan for that mega-project. If the mega-project needs to get done, but I’m unsure when exactly I will create and fill the template and then leave it in the backlog. Then in my monthly planning, I will see what’s left to do this quarter in the backlog and see if it fits.

Next up

That’s about it for planning; the same pattern repeats down to the month and week, though those are slightly different because we fall more into execution. The general idea of taking things from the parent to help inform the future stays the same down to the tasks, though. Next up, we’ll get into execution, where it’s a lot more doing the work once we planned it.