Can’t stop endlessly rescheduling your tasks? Try these two habits in Todoist

Todoist screenshots from the Todoist.com website

One of the biggest challenges is figuring out how to handle tasks that you keep continually putting off. Here is my step-by-step process to preventing that vicious cycle!

P.S. I use Todoist for my task management, but this method can be used with any product or even pen and paper.

After noticing this phenomenon, I wanted to dig deeper into the “why” of “why am I not getting this little task done.”

So, I did an experiment with the bigger and littler tasks I’ve been putting off and ones that I’ve been continually rescheduling.

As I approached each task that had been put off more than three times, I asked this question of each: What’s keeping me from doing this task? Why do I keep reshuffling this?

An example board from my Todoist and the some of the tasks I needed to analyze.

After answering these questions, I was able to group these tasks into two groups.

1. You have tasks only described by the outcome, not the action.

For example, if you have been continually rescheduling a task such as Create Web Design Case Study for XYZ client — while this seemed at the time that it was fairly actionable, maybe it was never scoped out how long this might take or the necessary components of documenting the project, especially since these two projects were larger anyways. Next question to ask yourself: How can I ensure I get this done? What is the scoping necessary for completing this task?

To accomplish this, I would break this task up into several other subtasks in a specific section. IE:

1. Schedule time to scope the requirements of the case study. (easily actionable first step—just putting time on the calendar for myself)

2. Scope 5 deliverables/problem statements from the project. (creating small, manageable numbers that can be knocked out in one brainstorm session).

3. Schedule 45 minutes of time to write and follow my documentation template to expand on those problem statements.

4. Take one screenshot of each website page and make 1 mockup of a computer screen.

6. Screenshot client testimonial and upload to site.

7… Schedule time to type up problem statements and documentation design onto the website… Etcetera

Scheduling these multi-part tasks into actionable time blocks and tinier, numbered tasks (eg: write 5 deliverables) will help reduce productive friction.

You can implement this using a Kanban-style board (see above) or just use a list. Use whatever system gets the job done for you!

2. You have personal/habitual tasks that you keep procrastinating due to too much friction.

These are tasks involving things like calling to reschedule a doctor’s appointment, painstaking book typesetting, setting up & sending email newsletters, admin/marketing. Another example is long writing sessions without an outline of the content I’m hoping to produce. For this stuff, I wanted to compile and source how to delegate these tasks to a contractor or assistant.

If it can’t be delegated, instead of creating a task for a specific one, the task will be converted to “Schedule X block of time for X task”- so it gets put on the calendar.

Time-based tasks for tasks you have the most friction

Then, if the task doesn't get done by its deadline, I will create a follow-up task on the calendar a week after it’s due to schedule time for it again. If it gets rescheduled 2–3+ times, it needs to be delegated, deleted, or re-scoped. (AKA: ask this question: What’s keeping me from doing this task? Why do I keep reshuffling this?)

Here’s the fix: implement a daily review and weekly task review to better understand and troubleshoot why a rescheduled task isn’t getting done. And if the task is just not important, or can be taken off YOUR plate— delete or delegate.

In Todoist, I set my task to be accomplished “weekly” on Sunday evenings. Choose whatever date and time work best for you.

A secondary exercise for you is to look for patterns in your current task lists of what’s not getting done, and see if they fall into either of those buckets or if you have other categories that they might be put into. Then, go down your list breaking the task down more, scheduling time for those tasks to be done, and implementing those times into Google Calendar using your Todoist/Google Calendar integration if you have one.

Once you figure out a good system, you can re-document those tasks however way you choose to time block. I personally use the formula: “if XYZ task is rescheduled 3x+ > then do XYZ.”

So there. Here are those two habits that will make your tasks be more actionable and more attainable:

1. Create a scheduled review process for each task that has been put off more than three times. Ask this question of each: What’s keeping me from doing this task? Why do I keep reshuffling this?

2. Describe larger projects/tasks by highly detailed and actionable sub-tasks. If those sub-tasks are not being completed, create tasks to SCHEDULE time to complete them with a follow-up task in case it is not completed.

How do you currently deal with the annoying little tasks? I’d love to hear your process.