Why do we so often fail to complete the tasks that matter most to us?

There are many reasons why our short-term actions often don’t align with our long-term goals and aspirations. 
To understand these reasons, let’s divide them into two categories: the barriers that influence us when we are engaged in advance planning, and the ones that occur in real time as we try to decide what we should do next. Please note that these barriers are not truly independent. They both share similarities.

Barriers related to advanced planning:

1. Visualizing the cost of time is hard
In some ways, time is like money. If you spend it on one thing, you won’t have it for something else. This phenomenon is a bit more obvious with money than with time. If you have $3 in your pocket and you buy a latte, you will not have enough left over to buy a bus ticket.
When it comes to time, however, the cost is less apparent. The problem with time is that the specific task we’re doing right now is concrete, yet all the other things we could do with that time are too general. Since the cost of time is far too general, we don’t think about it very carefully. Right now, demands seem incredibly clear, but what we’re giving up is unclear. A good planning system helps us think not only about what we’re getting, but what we’re giving up.

2. Big-block goals: it’s hard to break them into granular tasks
Big blocks (complex tasks that require multiple tasks to be completed) are difficult to capture in a simple to-do list, and you definitely can’t do this mentally. The unordered things we just write down continuously remind us about their existence, but they’re not always the correct priority at that time. “Build a new e-commerce website for the company” is not a simple or single task for a to-do list. Large tasks such as this aren’t in the same category as action items like “respond to an email from Bob,” “submit an expense report,” and “approve Tina’s vacation request”, which are more typical to-do list items. Also, they often go unrepresented, because it’s difficult to conceptualize and capture these big blocks unless we break down all the required smaller tasks contained within them to achieve the final result.

3. It’s difficult to say no
There are many reasons why’s it’s hard for us to say no. We want to be perceived by those around us as nice, helpful, and generous. If the requester has helped us in the past, it’s even more difficult for us to say no, as reciprocity is a powerful force. Also, we don’t want to feel guilty.
Unfortunately, our difficulty in saying no is one of the greatest enemies of productivity. This is true for two reasons. One is that we say yes to things we really shouldn’t agree to (low priority, non-value-added items). Second, even when we do say no, we often spend too much time and energy debating it because it’s such a difficult decision for us to refuse.

4. The “Planning Fallacy”: We underestimate how long things will take
First proposed by Daniel Kahneman and Amos Tversky, the planning fallacy refers to our optimism bias when estimating how long it will take to complete a future task. In other words, we often underestimate the time needed. This happens because when we think about a future task, we tend to imagine the most optimistic scenario (e.g., all traffic lights will be green, no one will call us and interrupt us, and our computer will not freeze). We don’t account for the possibility that things might go wrong or we might be interrupted.

5. We don’t create concrete plans for how we will do things
Part of the intention-action gap stems from the fact that when we think about what we want to achieve, we rarely spend enough time thinking about how we will achieve it. Social scientists call this “implementation intention”. Spending even just a moment thinking through details (“How will I do this? When? Where?”) has been shown to increase the probability of it getting done.

Benjamin Franklin, an early pioneer in productivity, started every day by writing down his plan for what he would get done that day. What we can think about is how to help people think through the details of how they will get their big blocks done. Writing your plan down proves to be highly effective, and significantly increases your chances of achieving your goals.

Barriers related to real time decisions:

1. We don’t use our productive time well
For most of us, our most productive time is in the morning. Unfortunately, many of us do not use this time wisely — for example, one of the first things we do when we arrive at work is check our email. That time would be better spent doing productive work that requires a higher cognitive capacity (thinking strategically, for example). Instead, we procrastinate on those more cognitively difficult tasks and work on them when we are more mentally tired or depleted. The more people think about their productive hours and do cognitively difficult work then, the better. An example of an effective and productive “first thing in the morning” activity would be to sit down, review your tasks, update them and prioritize your short-term tasks and big blocks.

2. We don’t see progress
Unlike small, unimportant tasks, the challenge with big blocks is that we rarely see any visible progress. Responding to 15 unimportant emails has a tangible output of 15 emails. What about thinking critically for an hour? There is often no tangible output, which makes us feel like we made no progress. The challenge here is to break down big blocks into smaller tasks/milestones so we can feel a sense of progress. Then mark the progress on each milestone in a visual, dashboard-like way, so you can see your progress and be encouraged by it. For example, let’s say the critical thinking you need to do is about your department’s next big project. It could be broken down into smaller milestones: come up with shortlist of ideas, create a pro/con grid for each idea, create a list of requirements and dependencies, etc. 
Indeed, thinking about ways to give people a sense of progress on big blocks is critically important, so they don’t feel like they’re working on permanently unresolved open items. 

William James aptly noted, “Nothing is so fatiguing as the eternal hanging on of an uncompleted task.” 
This dislike for items, which we have started and remain incomplete, is called the Zeigarnik Effect in psychology. This is also why we get so much pleasure from crossing out finished tasks.

3. We engage in structured procrastination
Structured procrastination is our ability to do nothing while feeling like we’re doing something. These include things like zeroing our inbox and cleaning our desktop from old files. These tasks give us the sense we’re achieving something, when in fact we’re not.

4. We underestimate the cost of task-switching
As we try to juggle multiple priorities, we are often tempted to multi-task. Unfortunately, multitasking is actually a myth; it’s more accurate to think of this as task-switching. Unfortunately, doing more than one thing at a time actually has a very negative effect on productivity — we take a while to adjust back to the original task. This negative effect is especially strong the more complex the task.

5. The longer the list becomes, the less powerful it is as a tool
With a long, overwhelming list of to-do items, the more tempting it becomes to tackle the small, easy things. Doing so will give us a quick win and an artificial sense of making major progress. A solution to that would be to pare down your to-do list to a few tasks that serve a big block (high priority), high-priority tasks for today, medium-priority tasks for today and high-priority tasks for tomorrow.