Recently, I killed an entire week moving from Things (3) → Asana → Todoist → Things. I won’t go into the details but I had a realization: I need to jot down how I think about my current system of productivity.

Having this clearly laid out will convince future me that moving to another tool is unnecessary if I follow the existing one I have diligently. I also think it necessary to lay down tactical instructions, so that in my moments of weakness I have something easy to follow and prevent me from going on a futile productivity sojourn.

Challenges

This system works for me because it addresses specific challenges that I face in getting things done. It’s worth pointing out what my challenges are:

Trapped in burndown continuum

There are days I’m able to knock out tasks one after the other. I go weeks like a programmed robot knocking out tasks one after another as they percolate into my “Today” list. But I quickly burn out and am unable to go any further in this mode because I feel trapped in a continuum.

I need to see the bird’s eye-view. I need to know why I’m doing what I’m doing. What are the daily tasks in service of? Am I reaching the goals I set out for myself this month or year?

Single task hang up

There are days I start with 3 tasks to get done. I start working on one of the tasks but get absorbed into it that I forget about the other ones due for the same day. I barely finish the first task; and the others get pushed to tomorrow. Tomorrow comes and the story repeats.

Work expands to fill the time allotted for its completion.

- Cyril Northcote Parkinson

A sense of urgency and being conscious of time spent on a task is important.

Overwhelmed with tasks

There are days I open up my Today view and find 20 tasks to do – all moderately important and valuable to get done. I didn’t choose to do these tasks. The tasks chose me, engulfed me, invaded my Today view! So I abandon it all and do none of it 🙈.

I didn’t choose to do these tasks. The tasks chose me, engulfed me…

There are other days when I wake up and see the same set of tasks over and over again. Monday, Tuesday, Wednesday … Thursday rolls over, still 20 tasks left. Little progress made and it knocks the wind out of me.

What should I do next?

There are days I open up my todo app and I just don’t know what to do next. I had ideas for getting things done this year, this month, this week… but where do i start? Have I progressed on my goals at all or am I taking on tasks as they come rushing towards me again?

Strategy

We always overestimate the change that will occur in the next two years and underestimate the change that will occur in the next ten. Don’t let yourself be lulled into inaction.

- Bill Gates

This quote summarizes well the challenge I face with my productivity system and why it doesn’t work for me consistently: I focus on optimizing the daily/weekly but lose sight of the monthly/yearly.

Judicious use of due-dates

You should pick your tasks for the day. They should not come for you.

To achieve this, I need to be judicious when picking a due-date/deadline for a task. Picking a date in the future means my todo app will automatically throw that task into my “Today” list in the future. I tend to get zealous and pick dates for when I think I can get the task done but when that ordained day comes around, I’m usually not ready to take on that task.

Few tasks are so important so as to take up valuable future calendar real estate. Here’s a helpful heuristic:

• Will you lose money if this task isn’t done?
• Will it affect your health?
• Will you be backing out of a commitment?
• Will it affect somebody else’s health?

Unless the answer to any of the above is a yes, remove that due date. Tuck it gently back into the backlog. If it’s important enough, it’ll crop back up again.

Monthly logs

Things captures my daily and weekly views. This works.

I track yearly progress with my #new-year posts. This doesn’t work too well. The format itself is ok but compiling it all at the end of the year means I miss a whole bunch of intermediate progress.

The missing piece was tracking monthly progress. Having the monthly check ins along with the daily + yearly ones will help me get a better view into the bigger picture with the visibility to course correct when needed.

I’m planning to use my blog here to track my monthly progress. I even tweaked my theme to accommodate these special kind of posts¹.

Tactical Instructions

What does this system look like:

#new-year retrospective posts

At the start of the year:

• Track my progress against previous year’s goals.
  • Go through my monthly logs and track the highlights.
  • Evaluate the lowlights and what I can do better.
• List my goals for the next year.
  • Create projects (or tasks) in Things for each of these.
  • I should see these on my sidebar every time I open Things.
  • It is ok to not achieve all of them.

#monthly retrospective posts

At the end of every month:

• Jot down thoughts on how the month went.
  • Especially the unplanned highlights/lowlights.
• ✅ monthly goals that got done.
• 🙅 monthly goals that couldn’t get done.
• Pick goals for the next month.
  • Carry over previous month’s goals?
    • It’s ok to throw them into a “someday” bucket.
    • Carrying over a goal or task for a few months now? Think harder about throwing it to the “someday" list.
  • Need to make more progress on the yearly goals?

Things

It’s a gorgeous app with top shelf UX. Stick with it. Sure Todoist has better integrations, Asana allows multiple sub-projects but not valuable enough to shift tools.

If you think of an idea, put all the context in the task and toss it into the Inbox view immediately. Don’t waste time categorizing the task in the right project list or worrying how it fits in your monthly/yearly goals. Mind dump and move on.

The most effective todo system:

1. Every morning, write a list of the things that need to be done that day.
2. Do them.

At the start of the day:

• Clean your inbox
  • If you need to clarify, add more context and details to the task.
  • Don’t be tempted to get them done Today.
  • Find a proper home in a corresponding project.
• Pick the 3 things you need to get done today.
  • Why couldn’t you finish yesterday’s tasks?
  • Do they need to go to the Someday list?
  • Don’t add more tasks if you can’t finish the day with Today 0.
  • Are any tasks coming up that are due?

25mt timers

I wear an Apple watch and every time I embark on a task, I start a 25mt timer. This helps me timebox things. More importantly it gives me a sense of the time I’ve spent on a task. If i’ve completed four 25mt cycles, I need to start thinking about the other tasks.

I’ll let you know how this all turns out.

I’ll update this post with screenshots once I have this system up and going for a few months.