Tag Archive | Productivity

My System for Tracking Deep Work

Fragments from imaginary dialogues

Why do you track deep work?

Deep work is an essential component of my day. I no longer conceive of a day without deep work.

Tracking allows me to continuously optimize my work day. Deep work is actually an oscillation between work and rest. By tracking it, I can assess the quality of the oscillation at a glance.

What do you track?

You’re familiar with the Eisenhower Matrix:

Important / Urgent – Important deadlines and crises.
Important / Not Urgent – Long-term development.
Not Important / Urgent – Distractions with deadlines.
Not Important / Not Urgent – Frivolous distractions.

I track only what’s important.

How do you track it?

I have a system for it. I use math paper, a pencil, and a pen.

My system at a glance

A dot represents a pomodoro – half an hour of deep work. This is my deep-work unit.
A pencil dot represents a regular pomodoro.
A pen dot represents a high-leverage pomodoro – a pomodoro of doing the things that have the biggest impact on my life.
A circled dot represents the end of the work day – for me it’s usually around 6pm. It’s important to have a ‘shutdown complete’ ritual, as Cal Newport calls it, to close the work mental process [<link; short read]; otherwise, your mind may remain stuck in work mode.

Two separate dots represent pomodoros with a break in between. I take a 10 minute break after every pomodoro, in which I seek to move as much as possible.
Two joined dots represent pomodoros without a break in between. This is a situation I try to avoid. Whenever this happens is a sign I may have lost balance.

Four dots in a row represent a work-block. After a work-block, I take a longer break – 30+ minutes long. If a work-block exceeds four pomodoros, this is another sign I may have lost balance.
A new column indicates that I’ve taken a longer break.

That’s it. Simple and elegant.

Can you give an example?

A work day might look like this:

At the end of the day, I can tell how the day went at a glance.

11 pomodoros of deep work (5.5 hours) in total, of which 8 high-leverage pomodoros (4 hours).

I lost balance three times, two times by not taking a break between pomodoros (the joined dots), and once by exceeding four pomodoros in a row (the second column).

As an additional optimization, I started adding a small I (Input) or O (Output) next to each dot. I have a tendency to have too much input. The I and O symbols allow me to assess my input/output ratio at a glance at the end of the day.


The ideal break

Fragments from imaginary dialogues

“What does your ideal break look like, viewed as a checklist?”

“It has the following components:

Micro Meditation – One or more centering breaths; connecting with myself.
(Centering, Shine)

Moving Meditation – One or more movement snacks, as a means to actively recover energy.
(Active Recovery, Perpetual Motion Machine)

Reflection / Recall – Looking backwards, asking three questions:

  • What went well? (Celebration, Shine)
  • What needs work? (Understanding, Design/Optimization)
  • What will you do differently? (Design/Implementation)

(Learning Cycles)

Intention-Setting – Looking forwards, a brief preparation for the next work cycle (pomodoro); getting clear on what I want to accomplish.

Getting Inspired – Right before the next work cycle, reading a few random inspirational quotes.
(Gratitude, Shine)”

Carpe Diem

Fragments from imaginary dialogues

“What does carpe diem mean to you?”

“I like to express it in terms of density [link; short read].

For me, carpe diem means maximizing life-density.

Maximizing experiential-density.
Maximizing fun-density.
Maximizing creative-density.
Maximizing learning-density.
Maximizing movement-density.

It means ZERO wasted time, and maximizing productivity.

I love Ali Abdaal‘s [<link] definition of productivity:

Productivity = (Useful Output / Time) * FF

FF is what he calls the ‘Fun Factor’.

The goal is not to just be productive, but also to have fun in the process.

Carpe diem means creating a beautiful antifragile structure for the day. 

I’m constantly optimizing it.”

“What’s the latest optimization?”

“Viewed as a template [<link; medium read], I know I want the day to have three parts: beginning, middle, and end. The beginning and end – the AM and PM bookends, as someone called them – are fixed, because those are the parts you have most control over. The middle is variable.

My previous structure looked like this:

AM Bookend
Activation [
warming-up, preparing for the day]

Deep Work
Deep Work 1 [
Deep Work 2
Deep Work 3

PM Bookend
De-Activation [
warming-down, preparing for sleep]

The first deep-work-block is always dedicated to writing.
The second is always dedicated to learning.

This is my most important work. Since these are so important to me and I want to do them every single day, I asked myself:

What if I made them part of the AM bookend?

This is exactly what I did.

The optimized structure looks like this:

AM Bookend
Writing 1
Deliberate Learning 1

Deep Work
Deep Work 1 [
MIT (Most Important Thing)]
Deep Work 2
Deep Work 3

PM Bookend
Writing 2

Thus, even if ‘life happens’ and I can get no deep work done in a day, I always do my most important work.”

The most productive month of my life

Fragments from imaginary dialogues

The most productive week of my life [<link; medium length] has turned into the most productive month of my life. 200+ hours of Deep Work. I haven’t been so focused on something since my hardcore gaming years. Seven hours per day on average every single day.”

“What’s your maximum number of hours per day?”

“Nine. I don’t want to do that many hours often. It was more of a stress test for the system. It handled beautifully. Before learning to optimize my Energy, I used to feel so tired at the end of the day. Now after nine hours of Deep Work I felt I could keep going and going.”

“Are you going to keep tracking your Deep Work now that the system is working smoothly?”

“I think I’ll keep doing it indefinitely. It’s become a kind of ritual. Plus I’ve started using it to also track Presence.”

“How are you tracking Presence with it?”

“Remember that I’m using dots to represent a half an hour time-block [<link; medium], and two joined dots represent one continuous hour. One day, an idea struck me:

What if I used the dots to also track Presence?

The goal is to Center myself – that is, breathe and connect with my BodyMind – at the beginning and/or end of every time-block. Whenever I succeed in doing this, I mark the dot with a pen over the default pencil.

Simple and elegant.”

The most productive week of my life

Fragments from imaginary dialogues

“How can you measure progress?”

“There are many metrics you can use. One of them is Productivity.

How productive are you in the things that matter most?

In my case for instance, this was the most productive week of my life. 

The deep-work hours can be seen in the bottom right

Granted, I’m between jobs, so I have more time to dedicate my work than I would otherwise. What’s important however is the persistent structures I have set in place, which will stay with me for the rest of my life. They’ve become part of who I am.”

“What’s your secret?”

“There is none.

I like to think of Productivity as a system. I’ve been optimizing it for a long time now, and I will continue to do so indefinitely. The system has four components:


I call the capacity to maintain Attention on ONE thing Deep-Focus. This essentially means the capacity to deal with distractions, both internal and external.
You can train to deal with internal distractions through Meditation.
As for external distractions, you can deal with them in two ways: eliminating distractions, and building resilience to them.

The heroic level here is being able to maintain Deep-Focus despite distractions.

The Energy system is one of the most important systems of your life. It’s an enabler, which impacts EVERY area of your life. The system has four components:


Energy management is the reason why I track my work/rest oscillation every day [<link; medium length].

Effectiveness means being productive in what matters. This is a matter of gaining clarity on what matters, prioritization, and sequencing [<link; short].

Efficiency measures your actual productive-output. Optimizing productive output with the goal of maximizing productive-density [<link; short] is what I’m focusing on at the moment.

Then there’s also wasted-time minimization. We might think of wasted time as dead time, to use Robert Greene’s vivid terminology, which he contrasts with alive time. Dead time has a hidden opportunity cost because it steals time away from alive time. Although you may not see it in the moment, dead time compounds, and over the course of a lifetime, it amounts to a LOT of time.

The heroic level here is eliminating wasted time entirely.”

“Don’t you take any days off?”


If you manage your energy properly, you don’t need to.
If you work on what’s most meaningful, why would you want to?”

Work Optimization 3

Fragment from imaginary dialogues

“What does your daily work schedule look like?”

“I start with 6 pomodoros of deep-work, then I take an hour break. That’s the first deep-work block of the day.”

“Why 6 and not, say, 5?”

“I was aiming for 8, but I got too tired at the end of it, which I took as a sign that I’d overextended.”

“I like to make a distinction between goals and meta-goals

A goal has to do with what you’re trying to get done.
A meta-goal has to do with how you’re trying to get it done.

A meta-goal for instance might be to maximize productivity (work-efficiency). 
Another one might be to maximize energy conservation (energy-efficiency). 
Another one, to maximize productivity AND energy conservation. (work/energy-efficiency)

These are an application of the Quality macro-principle.

It’s important to focus on the meta-goals, not just the goals.

The pomodoro creates structure. That’s the deep-work unit, the fundamental building-block. However any structures you build with the pomodoro should be flexible and aligned with your meta-goals.

It doesn’t matter how many pomodoros you do in a row. What’s important is to assess your energy level after each and every one of them. If the energy level is high, go straight into another one. If not, take a longer break, or a nap. 

The beautiful thing about having a structure like the pomodoro in place is that you can use it to assess your energy-level. Energy-level correlates with willpower and decision-making quality. It takes willpower to interrupt yourself from what you’re doing and to keep your procrastination-impulses in check. 

Treat any lapses in willpower as a red-flag. Slow down, and create space to ask yourself:

What’s the best decision?

On Beauty and Implementation

Fragments from imaginary dialogues

“One of the many facets of my Life-Art [<link; medium read] is trying to put an aesthetic touch on everything I do.”

“Does it serve a practical purpose?”

Every instance of Beauty can serve a practical purpose if you’re receptive to it.

But what I had in mind is something more particular.

Remember James Clear’s second rule of habit creation?”

“Make it attractive.”

“That one. The important question is,

How can you make it attractive?

One way is through the power of Beauty.

Make it beautiful.

Making something beautiful makes you more likely to engage in it.”

“Can you give an example?”

“Let’s take Deep Work, since we’ve talked about recently [<link; medium read].

In the context of Deep Work, my objective is
productivity maximization, and
perfect energy conservation.
To achieve this, how you optimize the work/rest oscillation is key.

We’ve talked before [<link; medium read] about the micro-oscillation and the macro-oscillation.

Micro-Oscillation unit: pomodoro – 25 minutes of deep-focus, 5-minute break
Macro-Oscillation unit: deep-work-block – 3 pomodoros, longer break

It looks great on paper, but I’d been struggling for a while with implementation.”

“What was the failure-point?

“The Macro-Oscillation.

Micro-Oscillation: I strictly respected the pomodoro. 
Macro-Oscillation: I often yielded to the temptation to do too many pomodoros in a row, which sapped my energy, which triggered a downward spiral of inefficiency and poor decision-making.”

“How did you solve this problem?”

When you struggle, it’s time to evolve a system.

I asked myself a macro-question:

What do you want the structure of your work-day to look like?

Then I sat down to answer it, in writing, with Simplicity and Beauty as guides.

The outcome is a pattern that looks like this:

30 30 30 15
30 30 30 30

“What am I looking at?”

“The bolded numbers represent pomodoros.
The un-bolded numbers represent breaks.

I do a deep-work-block, and take a 15 minute break.”

“Why 15 and not, say, 10?”

“It’s a littler aesthetic touch. 15 is 5 multiplied by 3.

Then I do another deep-work-block, and take a 30 minute break.

These form a cycle.

So if I were to extend it in time, it would look like this:

30 30 30 15
30 30 30 30
30 30 30 15
30 30 30 30

Or, more exactly, like this:

(25 + 5) (25 + 5) (25 + 5) 15
(25 + 5) (25 + 5) (25 + 5) 30
(25 + 5) (25 + 5) (25 + 5) 15
(25 + 5) (25 + 5) (25 + 5) 30

Four deep-work-blocks is 5 hours of deep-focused work, and 2.30 hours of rest in a beautifully balanced distribution.

Having this detailed aesthetic view has made implementing it a joy.”

Beautiful Systems: Deep Work

High-Quality Work Produced = (Time Spent) x (Intensity of Focus) (Cal Newport, Deep Work)

Fragments from imaginary dialogues

“Deep Work is a beautiful concept I know from Cal Newport. In his words,

Deep work is the ability to focus without distraction on a cognitively demanding task.

I’ve tweaked it however to suit my own purposes.

I refer to the ability to focus without distraction as ‘Deep Focus‘. 
And I like to think of ‘Deep Work’ as a system, whose function is to maximize daily productivity.”

Basically, to maximize productivity, you need to maximize the time spent in Deep Focus. However Deep Focus is energy intensive, so it’s not possible to maintain it for long periods of time.

To maintain Deep Focus, rest is essential.

This requires creating a beautiful oscillation, alternating between periods of Focus and rest. And the quality of rest is also important.”

“So we could say the quality of work depends on the quality of focus and the quality of rest.”

“Indeed. I call quality rest ‘Deep Rest‘.

Ideally, while resting, you want to disengage completely from the work. I prefer to move away from the computer, to give my eyes some rest as well.

The micro-unit of the system is the ‘pomodoro‘, 25 minutes of Deep Focus, followed by 5 minutes of Deep Rest. I like to think of this as the ‘micro-oscillation‘.”

“I thought you’d stopped using the pomodoro.”

“I had initially, because I lacked the Discipline to make it work. I’ve since realized the pomodoro is a beautiful opportunity to actually practice Discipline [<link; long].

The macro-unit of the system is what I call a ‘deep-work block‘: 2-3 pomodoros one after another, followed by a longer break. I like to think of this as the ‘macro-oscillation‘.”

“What does an ideal work day look like for you?”

“It starts in the morning, to capitalize on the very first hours of the day, when energy is at its peak, and has at least 3 deep-work blocks.

The beauty of the system is that it’s modular. It can expand or contract based on the available time.”

“What do you do during breaks?”

“Breaks are a design space [<link; medium]. I seek to fill it up beautifully. I play with movement, meditate, take a (cold) shower, go for a short walk, take a nap, etc.

As for the work itself, the content, it falls within three main systems, which every single day must contain:

Creating (writing, playing with ideas)
Learning (absorbing information, eg reading; reflecting/reviewing)
Optimizing/Organizing (eg systems optimization)

I arrange the deep-work blocks in the order of priority: the most important first.

There’s a beautiful directive I know from Brian Johnson:

Be creative before you’re reactive.

I’ve taken that to heart.

I always start the day with a deep-work block dedicated to writing.”