My improved self-management system

Last week, I reached a breaking point with my workflow.

Sticky notes covering my desk. So many open browser windows that my computer was freezing. To-do lists and half-finished thoughts spread across texts to myself, voice notes, journal entries.

My operating system was outdated.

I couldn’t continue working that way.

So I spent the past few days doing research to come up with a better self-management system.

Questions I started with

• How can I get more done in less time?

• How can I make sure I’m working on the most important tasks?

• How can I stay organized so that I don’t have stickies on my desk and open windows on my computer?

• How can I reduce my stress related to work?

Methodologies/systems I researched

• Eisenhower Matrix

• Ivy Lee Method

• Getting Things Done

• Waterfall

• Agile

• Scrum

• Kanban

• Srumban

My process before

1. An idea pops into my head.

2. I decide to keep thinking about the idea, or forget about it.

3. If I keep thinking about it, will the idea get better, i.e., will it expand or get more clear? Do I have time to continue thinking about it right now? Most likely I just need to translate it from thought form to written word ASAP, and then return to what I was doing before the idea popped into my head.

4. Where do I write it down? In the past, I was all over the place … sticky notes, text messages to myself, journal entries. I’ve improved this so that everything will go into a “dump” tray. More on this below …

5. So far the item has gone from idea —> written word —> what’s next? The next step would be action. Is there anything to do about the idea? Is it a task? Is it a bigger project? Is it a content idea? Is it a product development idea? I have to decide (1) whether it’s actionable (2) should I action it?

6. How do I decide if I should action it? That depends on my goals. I need to have already done the higher-level work about my mission, goals, and vision to know what I’m trying to achieve and whether this action will help me get there.

7. Here is where my old process was breaking down … how do I decide what to action? How do I prioritize? And then how do I keep track of what I’m actioning?

8. Once I’m in action mode, how can I be more effective? How can I do more, better, faster? Without being stressed, burning out, etc.

My improved self-management system

1. EVERYTHING goes into a “dump” tray.

   1. Whenever a thought pops into my head, it immediately goes into one centralized “dump” tray.

   2. This idea was inspired by something I read about the Getting Things Done methodology that involves having a physical tray on your desk where you put sticky notes, pieces of paper, or anything else that comes up throughout the day (and then review it later).

2. Once per day, I review the “dump” tray and decide on do, schedule, delegate, or delete (Eisenhower Matrix).

   1. If I decide do and it takes less than two minutes, I do it right then and there during the review. I’ll need to have time blocked out for the review.

   2. If I decide do and it takes more than two minutes, it goes into a backlog (not scheduled or delegated yet).

   3. If I decide don’t, it gets deleted.

   4. The “dump” tray is empty by the end of the daily review.

3. Once per week, I review the backlog of items that I either need to schedule or delegate and I quantify each one in terms of impact and effort.

   1. High impact / low effort items are #1 priority and they get scheduled/delegated first.

   2. Low effort / low impact and high impact / high effort items are #2 priority and they get scheduled/delegated second.

   3. Low impact / high effort items stay in the backlog until they become higher impact or lower effort.

4. After a project is finished, the next top #1 priority item gets moved into the “doing” column of a “project” kanban board.

   1. Within each card on the “project” kanban board, there is a “task” kanban board.

   2. Projects and tasks:

      1. Tasks are the items that need to be completed in order to complete a project.

      2. Projects take more than 1 day but less than 4 weeks.

      3. Tasks take more than 2 minutes but less than 1 day.

   3. I will estimate “time to complete” for each project (in intervals of weeks) and each task (in intervals of 30 minutes). This will allow me to block out company roadmap by quarter and my calendar each day.

5. At the end of each day, I move no more than six tasks into the “doing” column of “my daily” kanban board (number of tasks I can do in a day depends on the summed “time to complete” for the tasks selected).

   1. The “project” and “task” kanban boards exist at the company level. “My” kanban board exists at the individual level. This will help me differentiate between what the company can achieve and what I can reasonably achieve in a day as an individual human being.

   2. The next morning, I focus on the first task in the “doing” column of “my daily” kanban board until it’s finished, then I move onto the second task, until all tasks are finished.

   3. If any tasks are unfinished at the end of the day, they move into the “doing” column for the next day. If tasks are unfinished, that means either (1) I didn’t accurately estimate the “time to complete” for one or more of the tasks (2) or I didn’t stay focused. Whenever this happens, I’ll reflect and improve.

   4. Repeat this process each day.

   5. This part is basically the Ivy Lee Method with a few of my own modifications.

How to set this up in Notion

• “Dump” tray

  • This will be the first column in the “project” kanban board.

  • Each dumped item will be a card.

  • Use the Notion mobile app on my phone to add cards when I’m on the go.

• Backlog

  • This will be the second column in the “project” kanban board.

  • Cards get dragged to this column from the “dump” column if they need to be scheduled or delegated.

  • Any card dragged to this column needs to have these fields filled out:

    • Impact score

    • Effort score

    • Priority score (combo of impact and effort)

    • Time to complete (this is similar to effort score, might not need both)

    • Department (Sales, Marketing, Product, etc.)

    • Task or project?

    • Definition of done (DoD)

• “Project” kanban board

  • Columns on this board:

    • Dump

    • Backlog

    • Doing

    • Done

  • Cards stay on the “project” level if “time to complete” is more than 1 day but less than 4 weeks.

  • If a card has a “time to complete” of more than 2 minutes but less than 1 day, it may be moved to a kanban board within a “project” card.

• “Task” kanban board

  • Columns on this board:

    • Backlog

    • Doing

    • Done

  • This kanban board will be used to keep track of the tasks that fall under the umbrella of a larger project.

• “My daily” kanban board

  • Columns on this board:

    • Doing

    • Done

  • Cards on this board will not be the originals. They will be links to a card on a “task” board. This way, as I go about my daily work, any notes I log or other changes I make to the card will be automatically applied to the original card on the “task” board.

• “My daily” journal

  • One journal entry per day.

  • Each journal entry will contain “my daily” kanban board for that day.

  • Here’s why I want to do it this way instead of just having one “my daily” kanban board:

    • If I just have one “my daily” kanban board, the “done” column will fill up and become meaningless very quickly.

    • If I have a journal with “my daily” kanban board from each day, I’ll have snapshots of what I was doing each day. I can see if I didn’t finish some tasks in the “doing” column or I might want to go back and recall what I was working on on a given day.

Other guidelines

Definition of Done (DoD)

• Before beginning work on a project/task, define “done.”

• No project can take longer than 4 weeks.

• The DoD can be adjusted so that each project takes the same number of weeks.

• DoD is a concept that comes from agile (scrum).

Work-in-Progress (WIP) limits

• Three places where I need to establish WIP limits:

  • “Project” board - “doing” column

  • “Task” board - “doing” column

  • “My daily” board - “doing” column

• This is especially important for me as a solopreneur. There’s only so much I can get done.

• This is why I need to hire contractors, agencies, software, AI. This improved management system will help me identify where I need to hire.

• WIP is a concept that comes from kanban.

Notion “Views”

• Views in Notion allow you to view a database in different layouts (table, list, board, gallery, calendar, timeline).

• You can also group by property, filter, and sort.

• Examples of how I can use this:

  • Filter “project” kanban board by “department” property to see what projects a department is currently working on.

  • Sort by “date completed” to see what projects I’ve completed in the past month, quarter, year.

Why this new system is better

1. I don’t have to remember anything

“Your mind is for having ideas, not holding them.” — David Allen, creator of Getting Things Done

I think this is a big part of what causes me stress.

I allow ideas to hold space in my head. Why? I think it’s a worry that they won’t get done or I’ll forget them, which stems from the ideas not being immediately recorded and properly organized.

With this new system, I can be confident that the ideas are captured and they are where they need to be, so they no longer need to be in my head.

It’s like having a well-organized external brain that isn’t connected to my somatic experience. The ideas can progress along in the external brain without causing stress in my body.

2. Clear separation between work and life

Before, I had sticky notes and journals on my desk at home. The work was physically encroaching into my personal life.

The new system centralizes all my work stuff in one contained place on my computer in the Notion app.

Now, when I’m done with work for the day, I can close my laptop and put it inside a cabinet to establish a more clear line of work-life separation.

3. Prioritization

Before, I was kinda guessing what was important.

Or, I was working on whatever was easiest or what I felt like working on at the time.

The new system prioritizes projects/tasks that are high impact / low effort.

4. Scheduling

Before, the only events on my schedule were calls.

Now I can schedule blocks on my calendar based on the “time to complete” for each task on “my daily” kanban board.

What I borrowed from each methodology/system I researched

Getting Things Done

• A tray at the beginning of the process to capture everything (GTD calls it an “in-tray”).

• The general idea that not having a work system that’s external from one’s mind can cause stress, distraction, and decreased productivity.

Eisenhower Matrix

• Do, schedule, delegate, delete.

Ivy Lee Method

• You can only do six things per day.

• Do them one by one.

• Don’t multi-task.

• At the end of each day, decide what you’ll work on the next day.

Scrum

• Do strategic planning first to decide on your mission and goals. Then make sure the projects you’re working on are directly aligned toward achieving your mission/goals.

• Prioritize backlog in terms of effort and impact (on achieving your mission/goals).

• “Sprints” shouldn’t be longer than 4 weeks.

• Definition of Done (DoD).

Kanban

• Design of the board.

• Work-in-Progress (WIP) limits.

Conclusion

This is not meant to be “I figured it all out.”

I’m also aware that it’s possible to fall into an obsession with “productivity” that results in doing more designing and organizing than actually getting things done.

I did this research and wrote this out of necessity for myself.

My old way of working was broken.

I’m hoping this new system reduces my stress and allows me to get more done at work.

I’ll undoubtedly need to continue improving this system over time as I start using it and figuring out what’s going to work best.

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