Tag Archive | Tracking

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.

Tracking Presence

Fragments from imaginary dialogues

“To efficiently practice Presence, I find it useful to track it.”

“How do you track it?”

“I have a system for tracking Deep Work. At some point, I had the idea to use it to also track Presence.

I track Deep Work (DW) using a pencil.

1. A pencil-dot in the middle of a square represents 30 minutes of DW. (short DW block)
2. Two joined pencil-dots represent 1 continuous hour of DW. (long DW block)
3. If two pencil-dots are not joined, it means there’s a break in between.
4. If more than two pencil-dots are joined, it means I lost balance. (Feedback)

I track Presence using a pen.

5. A pen-dot on the line between two squares represents a 5 minute micro-meditation.
6. A pen-dot over a pencil-dot means I started the DW block with a Centering micro-meditation.”

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.”

Habit Optimization 3

Make your best performance your new baseline. (Josh Waitzkin)

Fragments from imaginary dialogues

“How can I optimize habit-tracking?”

“Marking a habit as done feels good. You can amplify this effect by also celebrating your small win. 

I like to do it by saying to myself ‘That’s like me!‘ I know this little mantra from Brian Johnson. When I say it, I also express Gratitude to Brian, and send him and his family Love. This amplifies the effect even more.

If marking a habit as done feels good, marking ALL of them at the end of day feels even better. I like to call this AD (All Done). You can use this to your advantage.”


“The main benefit of tracking a habit is that you can see its continuity. ‘I’ve been doing this for x days in a row.’ The longer the chain, the harder it becomes to break, and the more satisfying it feels. 

What’s even more powerful than seeing the continuity of a habit is seeing the continuity of your AD. 

AD is also a habit – a meta-habit. The habit of completing all your habits every day.”

“So the idea is:

Track your AD, not just your habits.


I like to do it in writing.

AD tracking

I write the calendar in pencil, and whenever I have an AD day, I write on top with a pen.

Seeing the continuity of your AD feels really good. I’m now working on making it my new baseline.”

“That’s a useful feature for a habit-tracking app. I mean, the AD visible as a separate row, whose continuity you can see at a glance. Once you complete all habits for a day, the AD becomes marked automatically.”

“I guess it is.”

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?”

On Magic and Habit-tracking

In any given moment we have two options: to step forward into growth or to step back into safety. (Abraham Maslow)

The small things are the big things.

Fragment from imaginary dialogues

“I love that quote by Abraham Maslow. Brian Johnson likes to think of it as +1 or -1, and has a beautiful metaphor for it: Destiny Math

Every +1 and -1 is a micro-decision, which most often escapes notice. It is the compounded effect of all those little moments that determines our Destiny. 

Which brings me to Magic the Gathering and habit-tracking.”

“What’s the connection?”

“As you know, I love Magic. I love playing it, and I love delving into the design aspect of it. I love it as an experience, and also because it connects me with and allows me to practice some important values/skills: Creativity, Focus, Adaptability, Patience, Persistence, Decision-Making, Strategic Thinking, dealing with uncertainty, among many others. 

The problem is, for me, it has addictive qualities. It’s immensely engaging, and once I get going, I find it very hard to stop. My solution for the past few years was to stop playing altogether. Until now.

In an instance of Inversion [<link; medium read], I’ve taken it as a challenge to conquer my addiction.”

“You’ve tried this in the past. What’s different this time?”

I now see it as a spiritual practice

Thinking of it as a bet, the potential benefit of success is huge. If I can conquer my most powerful addiction, what else is possible?

Also, in the past, I was relying only on willpower. Not smart, since willpower is unreliable. 

I now approach it strategically

Every playing session is a meditation

Every playing session is a deliberate practice. I start each session with a written plan of action, detailing what I’m focusing on during the session, and end it with a debriefing session, where I analyze what went well and what didn’t.”

“Can you give an example of a spiritual aspect of the practice?”

“I play an online version of the game called Magic the Gathering: Arena. I play against real people. The game has very few social features. The only way to communicate with the opponent during a game is through a small selection of preexisting emotes, like ‘Hello’, ‘Well Played’, or ‘Good Game’.

I’ve made it a habit to always say ‘Hello’ to my opponent. And when I do it, I take a moment to center myself, focusing on my Heart, and send them Love.

Which brings me to habit-tracking.

That’s another strategic tool. I added Magic to my habit-tracker app [<link]. Initially, I added it as a yes/no ‘having completed the habit’ kind of thing. But then I had an idea:

What if I used the +1/-1 system for this particular habit?

Whenever I do something well, I celebrate it and mark it as a +1.
Whenever I lose balance, I mark it as a -1.

The goal for the day is to end it on at least a certain specific positive tally, like at least +3.

I call it +1/-1 Tracking.”

“Do you use this system only with this habit?”

“I’m thinking of using it only with the most challenging habits, as it’s quite laborious.”

On Tracking and Celebration

Fragment from imaginary dialogues

Track only what’s worth tracking.

“What is worth tracking?”

“It’s more important to track what didn’t go well than what did. That’s where the gems (principles) are found.”

“Tracking what went well allows you to celebrate it at the end of the day. (retrospective celebration)”

It’s better practice to celebrate what went well immediately after. 

Better to spend the day in celebration by filling it with little celebrations throughout than having just one at the end of the day. Their effect compounds.

To make the initial principle more specific:

Track what doesn’t go well.
Imediately celebrate every little thing that does.