If you spend any time on the internet, then you will inevitably run into the people who spend far too much time contemplating how they organize information and tasks. An entire industry has formed around something we seemingly did better at before personal computers. Digital tools can improve our productivity and it’s not by using any of the latest developments.
People often surmise that my personal productivity system must be complex and rely on nerdy tools. An interesting consequence of the values I hold is that my system is neither complex nor reliant on any dedicated productivity tool. Certainly, I’ve tried plenty of applications from Evernote to Joplin, Todoist, Notion, Obsidian, Logseq, org-mode, org-roam, denote, and intricately organized bullet journals, but in the end I have continued to use something far simpler.
First, what design goals strongly influence my decisions on how I take notes, synthesize information, and perform task management?
- I value simplicity
- I prioritize integrating information into established sources of truth, rather than merely keeping separate notes and logs
- I want to maintain complete ownership of my data
- I want to use formats that are robust and will endure over time
- I embrace tool constraints
- I place information where I will use it, not record where I found it.
Whenever I stray from these values, I end up trying some other shiny system and eventually conclude that the alternatives aren’t sufficiently better to warrant a compromise on these principles.
So what do I use? A few calendars and a small collection of large word processor documents (ODT files) that I edit in LibreOffice. My system would work well using Microsoft Word documents and Outlook, or Google Docs and Google Calendar, or any other feature complete stack of word processing and calendar. It pretty much doesn’t matter.
Knowledge Management and Role Formation
Here’s a simple example of the structure that I use:
/
├── resources/
│ ├── 2024-italy-vacation/
│ ├── cloned-repo/
│ ├── example.pdf
│ ├── something.odt
│ └── webpage-snapshot.html
├── role1.odt
├── role2.odt
└── role3.odt
I avoid nesting, whenever possible, and except for Git repositories, there is almost never a deeper level of hierarchy.
Starting at the strategic level, each word processor file (ODT in this case, but again, choose what you want) represents a role I fulfill in my life. These roles include the various capacities I serve, such as my job, “business owner”, “homeowner,” and “son and brother.” These are sources of truth. Each document contains all the information I need to fulfill that role at that time. It may be a map of where I’ve been and where I’m going, information organized into domains or areas of responsibility, a library of links with some information stored about each one, or anything else. They change a lot and that’s ok. It’s motivating when I see a mess on the page, a reflection of sloppy or incomplete thoughts, and by taking the time to clean up some part of the document I am simultaneously refining my thinking.
Because one of my values is durability, I take snapshots of web pages, save the content, and store it in the resources folder and link within one or more role files. Git repositories and the like also go in there. And I link it all in one or more role documents. This single resource folder serves as the central repository. If I need to find something I find it either through a) the appropriate role document that links to it b) resources folder sorted by modified time or c) my desktop search application. I also have a script that can scan all role documents for links and isolate files no longer linked for the occasional cleaning of cruft—this likely isn’t necessary for most people, admittedly.
These documents are crucial for me. I dump a lot of annotated links, developing thoughts, and rework it all to progress thinking into well-formed thought and systems. The structure within role documents is likely the most individual, non-transferable aspect what I do. I work to make it useful for me. I cut that which is no longer useful at any time and let the document history/versions save old details if ever needed. My goal is to always develop out a clear understanding of who I am when I embody that role and what I need across time to fulfill it. These documents are places where information is continually worked like clay. And, like clay, I sometimes need to add more material, or add some water, take a knife to it, spin it faster or slower, or stop and observe the piece. What’s consistent is that my hands are always dirty after.
The folder structure should be as flat as possible. I don’t nest things. I don’t like to link into any subfolders within resources. I only link to documents and folders that are at the top level. There are, of course, rare exceptions.
Separating Work from Personal
For many, this file structure requires one necessary deviation, which I also follow. I don’t want company proprietary information mixed with my personal items. I don’t even want to mix personal files and company information on the same computers. To accommodate this, I simply use the same structure on my work computers and my personal computers and separate my work role(s) and personal roles entirely.
In my personal documents, I maintain a role for professional development, separate from the role I am actively fulfilling at my company. There is some manual transfer of information, as I actively seek to grow as a leader, I bring that new information over to the role I am fulfilling at my current job as well. Again, like working with clay, it’s supposed to be messy.
Task Management
Notably, so far, there is no task management in sight in these role documents. There is some higher-level planning for efforts I want to take in the context of how I want to evolve in the role. Once the efforts have some shape and it’s time to work on them, they migrate onto the calendar, where all effort and task management occurs. There are no to-do lists anywhere in the role documents.
In doing this, I find that three primary calendars are generally sufficient:
- a work shared calendar
- a work private execution calendar
- a personal calendar
Work Shared Calendar
The work shared calendar is the one I use to arrange meetings with others at my job. I used to over clutter this with execution tasks, marked private, but found for my roles that approach was too unfriendly for colleagues trying to schedule with me. They could never find a time to meet when they required it. Instead, now I keep it uncluttered. This calendar only has my meetings with colleagues and, when things are getting too busy, work blocks to protect focus time.
Work Private Execution Calendar
This calendar is where I plan out my intended focus work tasks. Everyone has their own balance but I like to have two days or so neatly figured out. Tasks don’t live in a task list, they are scheduled work to be completed. I accept something will get scheduled over and I’ll be dragging things around to accommodate. This is a feature, not a bug.
By working in this way, I am forcing myself to prioritize in the most palpable manner I know of. I am committing my time with a defined priority that I cannot avoid setting. Sometimes a task takes too long so I make another block for it. If it’s important I’ll fit it in sooner pushing other things around. Or sometimes I’ll say “I got to a great place I’ll come back to this in two weeks.” If I finish early, I may knock out some low-hanging fruit, pull in another task, or put it all down and go for a walk. If an emergency meeting gets scheduled, I know exactly what’s being pushed out in order for me to tend to the new matter at hand.
Personal Calendar
Most people are well-served by having a single personal calendar as a separate version of the work private execution calendar. It must be separate from work because, again, I don’t want my employer to own my personal calendar. This works best if I can add my personal calendar to my work calendar, or vice versa so I can see them all in once place. Keeping separate calendars also helps with disconnecting from work since I’m able to toggle the work calendars on and off.
No to-do lists?
The biggest unlock I keep coming back to for task management is to completely eschew to-do lists. Even to-do list applications that have scheduling features. I don’t want the ability to delude myself into having a growing list of items with increasing cognitive load every time I open it. “Someday I’ll get to this item down here.” No, I won’t. Nobody ever has.
I can’t emphasize this enough: a great to-do list application with excellent scheduling still will fail this test, unless it can automatically delete tasks after some number of days that are not scheduled.
Calendars are self-limiting. If it doesn’t fit, it doesn’t fit. If I’m not willing to make space for it, then I must say “no.” If it’s too far out for me to want to reserve space for a request, I can ask them to follow-up at a better time. It becomes almost impossible to over-commit by adding ideas and requests to ever-growing backlogs. And that’s what we need to avoid at all costs in task management, the backlogs.
Also, I cannot lie to myself about priorities. I know, see, and feel what is getting time and what isn’t. When I feel the urge to add an interrupting task in the afternoon, I learn about priorities I may not have even realized I had.
Try it. This is the most effective method I have found to reduce the stress of task management and align what I feel I need to do with the realities of my life. And, as a bonus, I don’t spend time downloading new apps, making accounts, connecting them on my devices. And I don’t spend any time looking through lists of things I don’t need to know about at that time and may never even get to working on.
Efforts / Projects
All efforts/projects also go on the calendar! For most efforts, all the information I need for execution is stored in the description field. As I’m working on a task, likely scheduled as a work block, I’ll generally be updating information in the description of the effort for continuity.
The efforts are either multi-day or recurring daily, scheduled all day. The reason to use a recurring item is that I can update “this and following” to keep a nice log to see how it evolved. The reasons to use a multi-day event is because the UX of most calendars makes it slightly nicer. Either works.
As I’m closing out my day, executing my shutdown procedures, I check the next few days and make sure I have enough work blocks scheduled that align with my ongoing efforts. One great constraint that is softly enforced by calendars is I can see clearly when I have too many efforts in progress and I’m not able to make space to work on each over the next couple of days. This doesn’t mean my work is too complex for a calendar, it means my work is too complex for me to get it all done effectively and need to reduce efforts in progress.
Inboxes
Without a to-do list one could rightfully say “well I sometimes can’t immediately add a task to a calendar and rearrange so it fits. And then I forget it!” For face-to-face meetings, I bring a notebook. I can’t stand screens getting between me and the people I am supposed to be interacting with. Otherwise, for work, I use my private Slack message with myself, and I set it to expire messages in seven days. For personal use, I use Signal similarly. It’s the best compromise I’ve found with enforced constraints and I can do this in tools I am already using as a bonus. I appreciate the flexibility to throw down tasks, ideas, notes, etc. and have it all disappear if I do nothing. It, again, forces explicit priority decisions. If I can’t even be bothered to migrate it off before it expires, then it clearly wasn’t important enough for me to pay more attention to.
Conclusions
I’ve had a lot of interest from colleagues and other people about my unique approach to how I get work done. This probably works well for me because I’m particularly orderly. It may fall apart entirely for others. I’ve been motivated to share these details since there is so much effort among various people and communities to overcomplicate these matters. It doesn’t need to be complicated and it doesn’t need all these tools! The easiest way to slow productivity is to start adopting a new tool that promises to be the last tool you will ever need only to peter out.
Even if this system doesn’t resonate with you, I’d recommend to everyone that:
- stop chasing shiny new applications
- ditch the to-do lists
- avoid complicated hierarchies of organizing information when search tools are so good
- have a place where you integrate information it into a cohesive view of yourself in that capacity, and spend a lot of time there
Continuing the Conversation
The conversation shouldn’t stop here. Every situation is unique and I value your experiences. I invite you to reach out to me directly, for feedback on this article or to start a dialogue on how we can transform your challenges into opportunities.