On personal knowledge management; using tools to help prioritize, plan, and get work done

On personal knowledge management; using tools to help prioritize, plan, and get work done

Tags
Process
Published
March 13, 2024

Context

A question that I’m asked with some regularity is, how do I keep all of the projects and priorities I’m supporting in a given time frame in my head? My answer is that I don’t keep it in my head. In order to keep all the plates spinning, I rely on systems of organization so that I don’t have to rely on memory (because memory is fallible) and aide me in organizing information and tasks over the near, medium, and long terms.

In this post, I’ll dive into the systems I leverage to manager information and tasks, the tools I use to do so, and the principles/framework that guide the evolution of those systems over time.

I make no claims of being a productivity expert. In sharing, I hope readers will gleam ideas for iterating on their own systems.

Systems I trust

There exists a polarity between getting organized and getting things done.

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The right level of organization is that which costs a little bit of time up front and makes subsequent time more effective.

Too much time spent organizing eats into time that would be better spent actually getting things done. Too little organization, however, and commitments start to be missed, balls get dropped, etc.

So the aim is to be organized enough that I can trust my system.

The criteria for a trust worthy system is:

  • Important work and relevant context gets captured
  • Captured work gets done and context retrieved while still timely and relevant
  • Work and context that are neither timely nor relevant do not create distraction

I judge the success of the system by:

  • A sense of closing cognitive loops. I can put info into the system and let it go because I know I’ll be able to retrieve it when relevant
  • The absence of moments of, "oh 💩! I forgot about that!”
  • Low friction, lower overhead: I can get in, get up to date, and get going

I’ve outlined the principles and frameworks that have informed the development of my personal knowledge management system as well how my current system works in practice. Either section serves as a valid starting point and therefore can be read non-linearly.

My current system

Tools

At present I use Notion the basis for my personal knowledge management system. But I this setup should work about as well in other knowledge management tools like Obsidian or even Apple Notes now that it supports back linking. The requirements that a knowledge management tool needs to meet for me are:

  • Ability to create pages and checkboxes
  • Support for cross-lining/back-linking. I should be able to link to a page and the destination page should automatically link back to the origin
  • Toggle lists are huge plus, since they let you cut down on visual clutter without the overhead of having to create a proliferation of pages

Weekly planning

I start the week by making a page from my weekly template. The template contains a toggle list for Focus Areas and associated priority levels (more on that later), a toggle list for each of the week, and, optional a toggle list for Next Week. Days of the week are pre-populated with recurring activities.

Weekly Template Example
Focus Areas
P0
P1
P2
Monday
Checkin: Person I
Checkin: Person II
Meet: Planning
Tuesday
Wednesday
Thursday
Friday
Recap progress on prior
Grateful for
Next Week

I then scan through the last week’s page and migrate, either by moving, duplicating, or syncing or backlinking, any work that rolls over to the current page. This exercise presents an opportunity to explicitly think about what should and should not roll over. It’s the difference between dropping a ball, which is bad, vs. putting a ball down and walking away, which can be right thing to do. More on this in the section on Eisenhower Matrix. For instance, if I see that putting something off week over week, that’s a signal that I either need to drop it, delegate it, or be disciplined in setting up time to do it.

Once I’ve determined what ought to carry over from the previous week, I think through what should or needs to be the focus areas for the current week and the priority level of each. This system is relative to me and what I’m trying to accomplish. Meaning, for instance, that a task need not be P0 to anyone else in order to be P0 to me. This exercise supports clarity on saying the right yes’s and right no’s. Meaning that there is no expectation that the initial list is exhaustive and final. Having it in place allows me to weigh emergent commitments against existing ones.

Lastly, based on the focus areas and rollover items, I take a moment to distribute tasks throughout the days of the week. This exercise is an opportunity to set reasonable expectations with myself and others on what I might be able to accomplish. For instance, too many items stacked up on any one day (especially Mondays for me) should prompt the question of what is realistic, ambitious, and necessary to expect from yourself on a given day and is there’s a better sequence/distribution to accomplish my objectives? Too many tasks not related to the focus areas means I might be misstating my priorities or I need to get more ruthless/realistic about protecting them.

At the end of the present week or beginning of the next, I try to update the project pages that I've tagged in my Focus Areas.

Priority levels

  • P0 → Must do
    • Things that may have commitments/deadlines associated or block progress for others until completed. Important and urgent
  • P1 → Should do
  • P2 → Nice to do
    • If circumstances permit, get it done. This is often used for things that I’d like to get a head start on if circumstances permit, but it’s OK for now if I don’t. Important but not yet urgent. May escalate to a higher priority over time

Projects board

Goals of this system

  • Prioritization: Track and, when necessary, limit work in progress.
    • Accomplished by sorting project by focus level. If I see too many things in Active Support, that’s an indicator that I may need to revisit how I’m prioritizing and tighten up the criteria’s for how I’m labeling things as Urgent and Important. That reevaluation may lead to either delegation or reprioritization.
  • Knowledge management: Retain information about projects beyond tasks.
    • Things like links to documents, progress updates, anything that I might care about in the future.
    • In the simplest form, this is a place to put/link to notes that I want to live beyond the scope of the current week
  • Create mental “cold storage”
    • Cold storage is where I place opportunities that may yet be valuable but I don’t yet have capacity to explore. A place for idea brain dumps, as it were. The ultimate fate of these explorations is to end up either being explicitly dropped or later reprioritized rather than being implicitly dropped because I forgot about them.

Project fields

  • Priority Level
    • Same framework as used at the Weekly level, applied at the Project level
  • Focus Level
    • Active Support
      • Things I’m doing
    • Passive Support
      • Things I’m supporting other people in doing
    • Back Burner
  • Due date (optional)

Principles and frameworks

The Eisenhower Matrix

I was introduced to the Eisenhower Matrix by my then-manager back in 2016. It felt almost criminal that I’d lived my life up to that point without having come across such a powerful framework. You may scoff, but I’m not alone in that feeling. Invariably, I end up sharing the matrix as a tool with my mentees and reports and they usually have a similar reaction. This framework could easily be a topic unto itself.

Urgent
Not Urgent
Important
Do now
Schedule
Not Important
Delegate
Drop

Mapping to my system

  • Urgent → Important → Do now
    • This corresponds to the list items under the current day
  • Not Urgent → Important → Schedule
    • This corresponds to the list items I distribute throughout the week or flag for “next week”
  • Not Urgent → Important → Delegate
  • Not Urgent → Not Important → Drop
    • If I’m dropping something entirely, I may
      • Check the checkbox and a “won’t do”/“didn’t do” suffix if it’s a decision that might matter to others / later on
      • Just delete it if it’s truly of no further consequence
      • Add it to cold storage if I suspect that it might be relevant in the future. Someone timing is everything, so designation of importance is contextual and therefore subject to change.

Making the list is worth it

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There is intrinsic value in having a prioritized list of tasks, but the primary value comes from making the list.

The act of making a list, like writing in general, allows you to martial your cognitive resources into thinking through: what are you goals and what do you need to or want to do in order to accomplish them? If those things can’t be done at once, what is the right / a right sequence to do them.

A common pattern I encounter being tasked with Activity A, which I don’t mind or actively enjoy doing and is due in X days and Activity B, which I don’t particularly want to do and is due in Y days where Y < X. Without stopping to prioritize, I’m more susceptible to doing Activity A first with that rationale that I’m getting something valuable done. Which is true. But that incorrect sequence may needlessly put Activity B at risk of being late. The appropriate sequence can lead to both things getting done on time, and listing things out and labeling the priorities is one may to tease out that sequence.

Be guided by necessity or opportunity

Different approaches work for different people. If sticky notes or pen and paper are the best tools for you, keep on jamming.

The main point of calling out iterations I've made over time is that copying another person’s system wholesale may not provide utility consummate to the level of effort to set up and maintain. Start simple, add components as you discover the need or benefit and remove components if they don’t serve you well. The process that I followed a few years ago would likely not hold up well to the strain of the volume of information that I manage today, but I hesitate to say that I should have adopted my current earlier because I simply didn’t need it back then.

What I like about tools like Notion, besides the rich content formatting options like toggles and check boxes, is the ability to define ad hoc taxonomies. For example, the Projects page is something I didn’t have in 2020 → added in 2021 as part of my experiment with PARA → removed in 2022 → have found both a utility and an implementation that has been working for me in 2023.

And if I decide that I want to introduce the concept of “task” and tasks should be associated with a project, a due date, and mood score with predefined for how I feel about it, then I can add it. And if I change my mind, I can change the fields or remove the concept entirely. This allows users to find the ergonomic flow that works for them.

Iterations

This setup represents roughly 4 years of trial and error. A simple truth is that any system of organization needs to have low enough friction to be of actual use.

I’ve tried PARA. That ultimately proved to be too much overhead for creation and navigation for me, just using checkboxes and projects proved to be enough.

I’ve started daily templates before moving to weekly. That required too much duplication in order to have continuity on tasks that ran for more than a day.

I’ve tried just having a single page with a continuous list of todos/checkboxes. And honestly, that is enough when cohesion around the checkboxes is high (i.e. all related to a single project) and the scope or duration is limited. But it get’s too noisy for initiatives of non-trivial scope.

For a while, I used a weekly template without project references. Adding project pages provides two main benefits:

  • It lets me “tag” work with the relevant project which creates backlinks from the project to the tagged updates
  • The project page itself serves as a hub to store documents, key updates, and other metadata about project.

Recall > Retention

Remembering is good and important. But memory, unaided, is fallible. So I don’t go to great paints to remember things. Rather, I optimize for ways to recall important things.

It’s akin to the difference between memorizing coordinates and making and annotating a map. If you get bombarded with information, are exhausted, hungry, or otherwise under duress, you may forget those coordinates. But chances are high that you aren’t going to forget how to read the map under those same conditions.

A corollary here is that the less things you have to remember, the more likely it is that will be able to successful retain the things that you do have to remember.

Delegate to tools

Delegation enables scaling. Relying on tools is a highly effective form of delegation.

Wrap up

This system is how I set myself up for success week over week. After years of iteration, I have a system that allows me to start my days and weeks with

  • A sense of what I should continue to focus on
  • A sense of what should come into focus
  • A sense of what to accomplish each today to add up to overall success
  • The ability to track progress over time
  • A single source of truth where I can place information with trust that I can recall it when needed