What to Do If Time Blocking Doesn't Work for You

Time blocking is preached up and down to be the way to manage your time, be most efficient, and focus deeply on the work that matters. Numerous productivity thinkers and influencers advocate and use this method, including Cal Newport, David Sparks, and more. Heck, even Ben Franklin used something of the sort to manage his days.

But what if time blocking doesn’t work for you? Are you left out in the middle of the work-world sea without a productivity paddle?

I don’t think so. Let’s explore why together.

My Experience with Time Blocking

I’ve tried time blocking numerous times. I’ve even made resources to help others block time more effectively for themselves.

Many times, my time boxing trials started with great effect — increased productivity, higher levels of focus, and all the promises that come with using such a system to manage your time. However, I kept running into issues. Instead of feeling the freedom and focus of having a plan, I felt stress. My mind became constantly aware of what time it was instead of getting lost in the work. I was worried about breaking the plan instead of doing my best.

At first, I thought I was doing time blocking wrong. So, since I think of productivity in an iterative fashion, I tried to fix the problem in many ways. Over the course of weeks and months, I tried:

• Using a dedicated journal.
• Treating it as a loose plan, not a hard line that must be followed.
• Scribbling blocks out and rewriting plans.
• Planning the night before.
• Planning the morning of.
• Leaving significant blocks of margin on the calendar.
• Packing the calendar full.

None of this fixed the issue. I did everything right, listened to all the experts, and still found myself failing with setting bounds on my time.

However, when I dug deeper, I realized the issue was not with how I was time blocking, but the issue was with me.

Let me be clear — nothing is wrong with me per se, but I realized time blocking does not line up with how my brain functions. Instead of enabling focused work, blocking time caused significant mental stress. Instead of empowering my productivity, it empowered worry in me.

Work with Time, Not Against It

Time blocking approaches time management from a place of scarcity. You only have 24 hours in a day — how are you going to precisely use them? For some people, this works well. The knowledge of time scarcity provides motivation to plan how a day should be most effectively used.

But if you’re anything like me, this lacking view of time is the exact reason time blocking causes you stress. Instead of seeing the possibility in a moment or day, you see limitation.

In literature, there are two common ways to write a novel.

1. Planning, where the plot and arc of characters is determined ahead of time, and the details filled while writing.
2. Plodding, where you start from a point, and the characters and plot develop as you go.

In the productivity world, high emphasis is put on planning – set goals, make lists, schedule time, have vision, and hustle to get from A to Z. Yet not all of us are natural planners. Some of us, like myself, like to plod from one thing to the next. This doesn’t mean you and I don’t have goals or a vision for where we’re going, but we’re focused more on the moment we’re in and what needs to happen next than we are defining what the rest of our day, week, month, or even year looks like.

I have a number of thoughts on what plodding productivity may look like that I hope to write about in the future, but in the tactical sense of managing time, I think this looks like finding a way to work with time, seeing time as a friend instead of a master, as opposed to working against a view of limited time.

My Answer: The Pomodoro Technique

The Pomodoro Technique has been around since the 1980s. In fact, it’s one of the first productivity tools I encountered over a decade ago when I first started digging into the field. But I wrote it off. When initially researching Francesco Cirillio’s approach and how people use it, it seemed geared more toward people who have difficulty focusing. That’s not something I’ve traditionally struggled with, so I figured it wasn’t for me.

When I was looking for a solution to my time blocking problem last year, I ran across the Pomodoro Technique again. This time, something clicked. This is a system for working with time. Instead of planning out every moment and having to adjust your plans as you fail to meet them, you set a timer and start working. The small habit you build by working in short chunks with a defined end point (and baked-in rest break) moves the needle forward instead of obsessing over what the day should look like or if you’re on track. It seemed like the perfect solution for me. I’ve given it a shot, and so far, it’s working well.

How to Use The Pomodoro Technique

So how do you use the Pomodoro Technique? It’s quite simple.

1. Pick a task that needs your direct focus.
2. Set a timer for 25 minutes.
3. Work on that one task until the timer goes off.
4. Set a timer for 5 minutes, walk away, and take a break.
5. Repeat four times.
6. After the fourth 25 minute timer goes off, take a longer 15 minute break.
7. Repeat the process from the beginning.

This is the simple formula, but any of these variables can be changed to meet your needs. Working deeply on something where a break after 25 minutes will interrupt you? Set the timer for 60 minutes instead. Need to take a longer break? Just set a longer timer.

Short-term, using pomodoros as a way to get work done can help you stay focused on the work at hand while at the same time providing needed rest breaks to let your mind process the information it just chewed on for a half hour.

The benefits get more interesting long-term. You’re using the actual amount of time a task takes to measure productivity versus how well you can forecast it. As a result, you get a better picture of how long certain kinds of tasks take over time. This helps your ability to realistically plan what you can do in a day. This is really the problem time blocking aims to solve, but the Pomodoro Technique does so without the added stress for us plodders.

Planning Using Pomodoros

The technique itself is quite simple and easy to understand. Once you have this mastered, you can start to loosely plan your day around pomodoros.

Here’s how I do it:

In a weekly paper planner, I have goal set for an ideal day that looks something like this:

A: Deep Work Set #1 --> 4 pomodoros
B: Deep Work Set #2 --> 4 pomodoros
C: Communications --> 1 pomodoro
D: Health --> 1 pomodoro
E: Hobby --> 2 pomodoros

This adds up to a total of 12 pomodoros, which is equivalent to about six hours of focused work. This doesn’t mean that I’m not working the rest of the day. However, these are the five areas that I’m aiming to intentionally spend time on in my day because they’re important to me.

Then, on each day of the weekly planner, I write out a plan:

A: Content strategy
B: Complete 2 course videos/work on task list
C: Communications sweep
D: Go for a run
E: Write blog post

Then I get to work. Once I complete a pomodoro, I make a tally mark next to the task on that day. If a task is done before the end of the pomodoro, I move on to the next one in the list.

A note about customizing those variables I mentioned earlier: Sets A & B are both focused on deep work tasks, so instead of the normal 25 minute timer, I have it set for 60 minutes (which counts for 2 pomodoros by how I tally them).

Intentionally Invest Your Time

The reason I even care about time blocking or pomodoros at all is I want to intentionally invest the time I have. For me, time blocking has too much of a time-scarce view on the world, and that causes me stress. The Pomodoro Technique, however, is more liberating and helps me invest my time where I find it important while letting me still see the potential in the time ahead of me.

Of course, as with any productivity advice, this might not work for you. You’re a different person than I am with different needs and a different life experience. However, if you’ve experienced the stress of time blocking, I definitely recommend trying out The Pomodoro Technique for a week or two. You might find it helps you out.