4 Reasons My To-Do List Sucks and Yours Might Too

As a project manager, I find it difficult to balance my time between project tasks, project management tasks, functional tasks, and supervisory tasks.  Until recently, I thought a to-do list was a silver bullet for my lagging productivity.  Surely if I just write down all my tasks and check them off as I complete them, I’ll start getting everything done – right?

Not so much. After trying all kinds of different applications, sticky notes, and iPhone apps, I finally realized something – my to-do list sucks.  Obviously a list of things to do isn’t going to help – it’s just a list of things!  A to-do list is like a siren that sings a sweet song promising productivity, but crashes your ship.

So, I am on a journey to build a better to-do list.  First, I need to articulate some specific reasons why a task list doesn’t work for me, and turn those into guiding principle statements.  Then I can use those guiding principles to help build a new to-do list system.

Problem 1: A to-do list is not decomposed.

I love Work Breakdown Structures (WBS).  One of my favorite things about a WBS is decomposing (breaking down) project tasks into Activities.  When I look at an Activity that’s part of a WBS, there is no cognitive friction, no interpretation necessary – I know immediately what I have to do to complete that Activity.

Starting out, my to-do list was not structured around decomposed activities.  Take, for example, this task item on my list:

Send print activity report to budget managers.

My first reaction to that task is “how do I get started on that item?”  My second thought is “that’s super overwhelming – I think I’ll work on something else instead.”

It took me about ten days of moving that task around to figure out – there’s too much cognitive work I have to do in order to start working on it.  I can’t glance at the task and immediately know how to begin completing that task.  I need to decompose that task into several tasks.

The next day, I decomposed it into this list of tasks:

  • Pull list of budget managers
  • Sort print activity reports into groups by division
  • Create Excel graph showing print activity over time
  • Write email template
  • Send email to each budget manager
  • Send email to each budget manager group

This list worked much better for me.  I looked at the first item on the list, and knew immediately what I had to do to complete that task.  And see those marked off items?  Apparently I had grandiose ideas of things that would be great to include, and I ended up discarding them.  I would never have recognized those gold-plating features, things I didn’t actually need to accomplish in order to complete the task, had I not first decomposed that task item.

Breaking down my task into smaller actions helped me complete the whole task.  I know exactly what I have to do to complete each activity, and each activity I complete gets me closer to completing the task.

 Guiding principle #1: To-do list items should be decomposed to the Activity level. 


Problem 2: A to-do list is not prioritized.

A list of tasks does not communicate priority or importance. If I have to scan through my list and prioritize items in my mind, I’m spending mental effort calculating and categorizing priority.  It’s also an opportunity for my brain to pick a different non-task activity that doesn’t require so much effort, like checking my email “just for a minute.”  It’s easier and requires less mental work to slip into social media check-ins than to recall and re-calculate the priority of a list of tasks.  To prevent these social media slips, I have to plant priority reminders in my to-do list.

When I think of priority, I think of two things: urgency and importance.  Urgent tasks are tied to a time by which they must be completed.  I like how Steve Mueller defines urgency:

Urgent responsibilities require immediate attention. These activities are often tightly linked to the accomplishment of someone else’s goal. Not dealing with these issues will cause immediate consequences.Steve Mueller, PlanetofSuccess.com

OK, so I know what urgency means, but how to I convey urgency in my to-do list?  Tim Ferris at tim.blog gives some great guidance – by asking a single question, I can use urgency to prioritize my to-do list.  What’s that one question?

If this were the only thing I accomplished today, would I be satisfied with my day?

Tim Ferris also explains why this is an important question:

If I have 10 important things to do in a day, it’s 100% certain nothing important will get done that day. On the other hand, I can usually handle 1 must-do item and block out my lesser behaviors for 2-3 hours a day.Tim Ferris, tim.blog

These two concepts of urgency work well together.  At a glance, I should be able to quickly determine:

  • The ONE thing that must get done today
  • The task items related to timed events

We focused on urgency – what about importance?  Importance is related to goals or value, and deserves it’s own guiding principle.

 Guiding Principle #2: To-do list items should convey prioritization. 


Problem 3: A to-do list is not aligned to what adds value.

There are lots of definitions of “value” out there.  When I think of a to-do list, I think of value as a combination of two questions – “What do I want to do?” and “What do I need to do?”  The intersection of want (intrinsic) and need (extrinsic) is a great motivator.  I feel true accomplishment when I both enjoy working on something, AND it provides value to the organization.

A to-do list doesn’t really communicate value.  A list of tasks is an emotionless record of transactions I must wade through to end my day.  There’s no difference on a list of tasks between “take out the garbage,” “empty the dishwasher,” and “take the million-dollar donor out to lunch.”  I’m neither excited by nor proud of completing any of those tasks. I need to remember the value those tasks bring to me or the organization.  Otherwise, I’m not motivated to complete any tasks on the list.

Remember when we talked about event boundary statements? That’s a great example of how a list of tasks can convey value.  The best event boundary statement will remind me of both the intrinsic and extrinsic values in my list of tasks:

When I complete the last performance evaluation, I will meet the organization’s deadline and I will learn two opportunities for improving our project management processes.

 Guiding Principle #3: To-do list items should align with intrinsic and/or extrinsic value statements. 


Problem 4: A to-do list is not structured for inertia.

If I’m following along, I can now glance at my task list and immediately know which task is most urgent, which task is most important, and what I need to do to complete each task.  I select a task, complete it, and strike it off the list.  What happens now?

If you’re like me and most people, you check e-mail “for just a minute,” handle several issues, look up and realize it’s time for lunch.  If you’re lucky, distractions happen when you complete a task item.  We all know the reality though – distractions happen all the time, and re-engaging in a task is tough after a distraction.  Why is it so hard to keep up inertia?

According to a research paper by Sophie Leroy and Aaron Schmidt, we suffer from something called “attention residue” when switching between tasks.  Keith Webb from KeithWebb.com translates the concept of attention residue this way:

I’ve noticed how I can’t jump from answering emails to doing thinking work. My mind stays with the emails. I replay the email and my response in my head. Or I start thinking about or planning the work that email triggered. The more emotional my response to the email, the longer my mind stays with it. Business professor Sophie Leroy from the University of Minnesota identified this as attention residue.Keith Webb, keithwebb.com

The concept of attention residue applies here too – when I complete a task, I’m not quite ready to let go of it.  Sometimes, I’ll continue to revise a message I’ve already sent after marking that task complete.  Other times, I’ll be somewhat fatigued and a little directionless immediately after completing a task.  Attention residue as a concept is bigger than a to-do list, but my task list can improve by taking attention residue into consideration.

By sequencing or grouping task items in a way that one logically flows to the next, I can ease the transition between tasks.  If it’s easier to move from one task to the next, I’m less likely to get lost or stuck when I complete a task.

 Guiding Principle #4: To-do list items should scaffold or flow from one to the next. 


What’s next?

There’s a pattern with the four problems outlined above. To boost productivity, I need to reduce the amount of thinking required to start and complete task items on my to-do list.  Just by glancing at the list, I need to be able to immediately start a task, remember why the task is important, and effortlessly move to the next task when I complete this one.

I have my guiding principles – now I can start building a better to-do list!  Next article in the series, I’ll build a to-do list based on these guiding principles.

Have any thoughts about to-do lists you’d like to share?  Did I miss any problems or guiding principles? Let us know in the comments below!

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