E18 - Attention to Time: [The Planning Fallacy]

Why planning fails and to-do lists get longer.

Hi everyone,

My name is Lemmy and this is my story of how I became The Attention Master.

If your (personal or professional) to-do list is getting longer instead of shorter, Episode 18 is for you. Let’s dive in!

Here is what you are going to learn today:

  • Why to-do lists have little value.

  • Why timeboxing sucks.

  • The two mistakes you make when planning your day and tasks.

  • Actionable tips for getting things done.

Have you ever closed your laptop on a Friday and found your to-do list getting longer, not shorter?

Don't worry, you're not lazy. It has happened to all of us. Here's why:

1. Why to-do lists are distractions

Oh! My to-do list says it’s time to rearrange my desktop icons into color-coded, alphabetized folders!? OK! I guess I’ll do that real quick before I start writing that report I’ve been putting off.

- Nir Eyal, Israeli-born American author, lecturer, and investor

(Disclaimer: The following paragraph is excerpted from an article by Nir Eyal, a noted productivity author. See the full article here)

To-do lists are supposed to keep us on task. They don’t. Rather, running your life using a to-do list leads to more distraction, not less.

When I used a to-do list to run my day, I’d start the morning ticking off tasks, thinking I was on point. I didn’t realize I was letting my to-do list lead me towards distractions that were preventing me from reaching my goals.

For instance, even when I knew I had a big project looming and needed to spend the morning working on it to meet my deadline, glancing at my to-do list gave me permission to escape into doing something (anything) else.

To-do lists allow us to get distracted by the easy or urgent tasks at the expense of the important work.

We run faster and faster in the name of getting things done, without realizing we’re headed in the wrong direction.

When we realize we didn’t allocate the necessary time to work on the most important tasks, we justify it by telling ourselves, “there isn’t enough time left anyway,” and with a few clicks, we make the hard work disappear by pushing it off to the next day or the next.

2. What Nir Eyal suggests instead

What Nir suggests instead is another time management concept called timeboxing.

In a nutshell: Instead of writing down your tasks on a list, you schedule them into your calendar.

Sounds great in theory, but it fails in practice.

Meetings get postponed, your kids need an unexpected pickup, and your dog gets sick. Life hits you multiple times a day, and each time you have to rearrange your time-boxed calendar. It's super annoying.

But even if nothing happens, your timeboxing efforts will fail because of 2 major estimation errors we make:

  1. The Planning Fallacy

  2. The Time Availability Fallacy

3. The Planning Fallacy

The planning fallacy is a phenomenon in which predictions about how much time will be needed to complete a future task show an optimism bias and underestimate the time needed. This phenomenon sometimes occurs regardless of the individual's knowledge that past tasks of a similar nature have taken longer to complete than generally planned.

In a 1994 study, 37 undergraduate psychology students were asked to estimate how long it would take to complete their senior thesis:

  • The average estimate was 33.9 days.

  • They also estimated how long it would take "if everything went as well as it possibly could" (average 27.4 days),

  • and "if everything went as poorly as it possibly could" (average 48.6 days).

  • The average actual completion time was 55.5 days,

  • with about 30% of the students completing their thesis in the amount of time they predicted.

On average, the task took 1.63 times as long as estimated.

Simple math applied: Whatever you write on your to-do list on Monday, the best-case scenario is that you get 61% of it done.

So you lose 39% before you even start.

A terrible feeling, right?

And it gets worse because of...

4. The Time Availability Fallacy

8 hours of work. 8 hours of sleep. And 8 hours of "free time," right?

At least that's what many people think, so it's no wonder they get depressed when they look at their screen time and realize they haven't done anything useful with their free time and are falling behind on business goals.

But the truth is different.

We think we have more time than we do.

There are many activities that take a lot of time out of our day:

  • At work: Commuting, smoking & coffee breaks, small talk with colleagues, ...

  • Eating and drinking: People 15 and older in the United States spent an average of 85 minutes per day

  • Toilet visits: 4-10 per day at 3-5 minutes = 15 - 50 minutes

  • Food preparation: The average modern adult spends one hour per day cooking and preparing food (2020)

  • Grocery shopping

  • Cleaning

  • Showering

  • Morning & bedtime routines

  • The list goes on...

It just adds up. Therefore, the actual "free time" you have left after work for activities may be 2-3 hours instead of 8.

The same goes for work. According to various studies, the time for effective work is about 50% of your total working hours. The remaining time is lost to the factors mentioned above, administrative work and meetings.

Simple math applied: You may plan 30-35 hours of tasks, but in reality you only have 20 hours.

So you overestimate the time available by 1.5 - 1.8, both in your free time and in your working time.

5. The Protocol to take ACTION

  1. Stop beating yourself up. You are not a loser. You are just as bad at estimating as anyone else.

  2. Track your time meticulously for 1-2 weeks. Write down every single thing you do, when you did it and how long it took. This will tell you exactly how much time you actually have at hand to allocate. If you are too lazy to do this, start with 2 hours of free time for your evening and 50% of your total work week.

  3. Use the Eisenhower Matrix to prioritize your tasks, estimate the time needed for each of them and multiply it by 1.63. If you are unsure, ask your manager what you should work on first.

  4. Timeboxing 2.0: Start with the highest priority task and block time for it in your calendar. One task at a time. Ignore everything else.

  5. When you are finished, note how much you actually worked on each task to compare the number with your estimate. Over time, you will find your own "estimation error coefficient" that you can apply to future planning.

  6. Most importantly, change your mindset: Completing 1 important task a day is better than working on 10 but getting nothing done.

This knowledge comes at 0 cost

If you learned something,
be generous and share it with friends or family.

See ya next week


  • To-do lists allow us to be distracted by the easy or urgent tasks at the expense of the important work.

  • Time-boxing is impractical because life disrupts your plans every day.

  • Tasks take 1.63 times longer than expected.

  • Available time is 1.5 to 1.8 times less than expected.

  • Focus on 1 task at a time.

  • Prioritize with your manager and team members. Use the Eisenhower Matrix for discussion.


We know that mastering your attention is extremely difficult. It's not going to happen in a day. That's why we've created Lemio, an app designed to be your personal buddy on the journey.

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