Time Management

Reading time: 9 minutes

Time management is the process of planning and exercising conscious control of time spent on specific activities, especially to increase effectiveness, efficiency, and productivity. It involves a juggling act of various demands upon a person relating to work, social life, family, hobbies, personal interests, and commitments with the finiteness of time. (Source)

I want to share the system that dramatically increased my well-being and productivity over the past two years.

I want to be candid too, and completely honest: time management has never been my forte, and as long as I can remember, I tried to fit too much in each given day. As a result, I would inevitably fall into the trap of long nights and even longer weekends.

It is why I feel confident in sharing my system: it was not innate for me, I had to build it piece by piece, and this means that if I could do it, so can you!

History has a way of repeating itself. 

You get alerts, but unless you notice them and take them into account, it’s going to blow up in your face. 

My first time was in 2017. I realised that I was reaching a breaking point. The only reason I was able to push through it was that Automattic, the company I work for, offers a three-month sabbatical leave every five years. An incredible perk.

I was getting to the end of six crazy months. Running six teams, having just launched .blog, a new top-level domain name, and leading WordCamp Europe in Paris, France. 

My sabbatical started on June 19, 2017. And that’s what saved me.

The downside is that I didn’t immediately see the red flag.

The second time was two years after that, in 2019.

Once more, a company perk saved me, which is having a dedicated business coach. This second time, working with him, I realised that my interpretation of the “servant leadership” principle was flawed.

Being constantly available any day of the week, at all times, was not serving them well. 

I thought that putting everybody else’s needs first was the right way to proceed, but that was consuming me.

My coach helped me realise how focusing my time on the essential things would benefit my teammates more. That’s when we started working on a system to get out of that downward spiral. We succeeded, and since then, I have been more relaxed and more productive than ever.

I documented the beginning of this journey in Personal Scalability. Still, in case you don’t have time to read it, the main takeaways of the initial experiment were:

  • Build a solid and consistent routine, giving space to work but also personal time, family time, introspection, and last but not least, sleep.
  • Use scarcity as a prioritisation tool: artificially limiting my availability for meeting as a forcing factor of selection.

The initial routine evolved and, incidentally, allowed me to live relatively unscathed through a global pandemic, as I documented in System Resilience.

My current system comprises three phases:


Timeblocking is the practice of allocating a specific slot in your calendar to each thing you need to do. We all do it naturally for any event involving other participants, but that is rarer for any task performed alone.

To be sincere, I always looked at people using the technique with a mix of curiosity and suspicion. You know, as one looks at people doing a week-long juice cleanse: I know it must be good, but wow, that is not for me!

It’s Nir Eyal, with his book “Indistractable“, who completely changed my perspective. One of his main points is how most human beings start their day without a clear idea of how they will use their time, although no one can have any extra. In contrast, most people know how important it is to manage money, even though it is possible to earn more.

Timeblocking, in the end, is about budgeting time. So here’s how to proceed:

  1. Block non-negotiable time slots. These include sleep time, personal time, and family time.
  2. Start adding work, beginning with the most important. In my case, it means 1-1 meetings with my direct reports, peers, and leads. After that come team synchronous work sessions and a few recurring meetings.
  3. Reserve several hours for focused work, alone and without distractions.
  4. Make sure to include lunch breaks and small breathing buffers between calls.
  5. Leave a few slots available during the workday for impromptu conversations, exceptions, and other inevitable interruptions.
  6. Leave the weekends entirely open. But, whenever I need to get something specific done on the weekend, I’ll make sure it is on the calendar. I just try not to make a habit of that.

The result looks like this.

Tasks & Notes

Task and Notes management is where my practice has shifted the most over the years, transitioning from individual contributor to leader responsible for 66 people across 14 teams. 

I recently found the last missing puzzle piece in this article, An Exact Breakdown of How One CEO Spent His First Two Years.

The most substantial improvement in my ability to manage my time came from using my calendar as my to-do list (and subsequently killing my to-do list). Killing my to-do list has also had the unintended consequence of substantially reducing my personal stress and anxiety — it’s been one of my biggest mental health wins of all time. Sam Corcos

And so did I!

Whenever I take on a task, I evaluate how much time I need to perform it and add it to my calendar instead of writing it on a to-do list. The immediate benefits are almost unbelievable.

  • It removes lots of stress from the process, as I know that I have the time to do it when I commit to doing something.
  • It incentivises delegation when I realise that someone else could perform a task that won’t happen on time if I have to put it on my calendar.
  • It is immediately apparent when I can’t finish a task in the allotted time. I need to either schedule more time or delegate it to make it happen. I can’t just leave it on the to-do list for later.
  • It gives each item, as Sam Corcos explains in his essay, the correct size. In to-do lists, all tasks look the same, not in a calendar.

There is an abundance of apps, frameworks, and philosophies about managing tasks and getting stuff done. I have tried many myself, and I am sure I will try more in the future; after all, this will remain an iterative process.

These are my primary requirements for the system:

  • I need it to guarantee that I never become a bottleneck. My job is to accelerate my teammates, not slow them down.
  • I need obvious alerts whenever I take too much on my plate and need to delegate tasks for them to happen in a timely fashion.
  • I need to quickly take and find notes related to any conversation as I shift between contexts frequently.

I started using Roam Research to take notes almost one year ago. Roam has seriously improved my ability to create and surface connections across people, teams, and projects.

The daily notes system in Roam is a step forward in tying discrete notes to specific events on my calendar. However, something was still missing as I managed my to-do list in apps like Asana or Things. Such tools are ephemeral by nature (completed tasks tend to disappear) and poorly connected to calendars. 

I added a calendar RoamJS plugin to Roam. A SmartBlocks template then allows me each morning to import the content of my calendars as a list of tasks in my daily note.

With a couple of clicks, I can generate something like this in my Roam daily note:

This last touch brings two very welcome improvements. First, it creates for each item on my calendar a to-do item in Roam. Thus, I can indent notes just under it and check it when done (or see when it’s not). Second, it also automatically creates links to the respective pages for recurring tasks, people, or events that have their page in Roam.

Monitoring, Feedback, and Weekly Review

I am a product person. I love to build things, teams, and systems.

We live at an incredible time, where it is possible to build iteratively instead of delivering the final version from the get-go. An iterative process, though, can’t function without proper instrumentation. Therefore, one must collect metrics about how the system works and analyse the data regularly to assess and adjust.

I track what I genuinely do with an app and a tracking device called Timeular.

The device is a sort of plastic octahedron connected to my laptop via Bluetooth. It has eight faces, and each one corresponds to a type of focus.

Whenever I start working on something, I position it, so the corresponding face is up. If I switch between tasks, I turn the new side up. When I stop working, I put it to rest on its base.

I do not track what I do in my family or personal time. Still, tracking work time is enough to verify that I dedicate those slots to my family or me.

The result is something like this:

Each Monday, as the first thing of the week, I perform a weekly review. 

  • I check the Timeular data for the previous week against the calendar for the same period to identify any discrepancies and understand why they happened. 
  • I check the distribution across the focus areas to ensure I am not neglecting some.
  • I then check the upcoming week to ensure that I have no conflicts and that all the most important things are on the calendar.
  • I try to remove anything I can by delegating tasks or not attending non-essential meetings.

A final word

I understand how taking in this all at once might seem overwhelming. However, I got there over two years.

I also know that you may be using other tools and not interested in switching or adopting new ones. I am pretty sure, though, that you have a calendar.

Suppose you are looking to reduce your stress levels and improve your productivity.

In that case, I engage you to start there and place all the events in your life that are predictable and recurring, blocking the time they take.

Even if you do just that, the increased visibility into the remaining available time will already be a step in the right direction.

I am also more than happy to answer specific questions in the comments below or on Twitter.

17 responses to “Time Management”

  1. […] the past five years, I wrote about Personal Scalability, System Resilience, Time Management, and my Second Brain. More recently, I have sent out an update to my Time Management post in […]

  2. […] started “Timeblocking,” allocating each period to an activity. It doesn’t mean you can’t have personal […]

  3. […] explained previously in Time Management how managing tasks in a calendar is beneficial because it forces us to face the inevitable truth […]

  4. […] I couldn't agree more. Defining one's priorities and investing time is the same as budgeting and investing money. If you want to use your money well, you define a budget that guarantees it'll go towards what is most important to you. […]

  5. Raphael Avatar

    Great – sent you an email! Talk soon, Raphael

  6. Paolo Belcastro Avatar

    Hi Raphael, I’ll have a chat about this subject with pleasure any time! 🙂

    All my contact information is in the footer, with a preference for email.

  7. Raphael Avatar

    Paolo – this is fantastic, thanks for sharing and congratulations on the progress you’ve made in evolving this system!

    Would love to chat deeper on two points you made re: (i) reviewing previous week’s actual vs planned schedule; (ii) checking distribution across your focus areas.

    Disclaimer – I am prototyping a solution that does exactly this system. It’s something that also made a profound impact and helped me get back some control over my work-life schedule. There is a tool & analytics component. Very interested in learning more about your needs and workflows!

    What’s the best way to get in touch?

  8. […] of a calendar-based scheduling system. If it’s not on my calendar, it doesn’t get done. Similar to Paolo’s experience, a calendar-first approach enables sizing up a task. On your to do list, every task looks the same. […]

  9. […] recently shared how I manage my time. The system I put in place has been highly effective in helping me perform at high levels without […]

  10. Anne Avatar

    Fascinant !
    J’ai envoyé ça à Alexis, une personne qui a un travail. Pour ma part, je vais commencer par ouvrir le calendrier de mon iPhone, et chronométrer le temps de repassage de chaque pièce de linge… and so on and so on… thinking…
    Tu me fais réfléchir trop car maintenant Pops dort encore on va être en retard pour l’école et je suis là à écrire un commentaire débile sous un article de haut vol… heureusement j’écris en français personne ne lira 😜

  11. Brett Harris Avatar
    Brett Harris

    I love this! So many good takeaways from this. I read this about a week ago and started the calendar tasks, and it is a total game-changer. I have added a “Pomodoro” style to my calendar tasks. I figure out how long they will be and break them into 30min increments, with a 5 min reminder for my next block, giving me a 5 min rest block. So if it takes 2 hours, I have 4, 30 min blocks for that task, breaking the last 5 min of each block. If all that makes sense.

    I ordered Timular today. I am looking to measure how my time compares to my needs. I like the personal time budget and actually use that for the gym, journaling, and dinner. I can’t thank you enough for posting this.

  12. Robert Felty Avatar

    Very interesting Paolo! I really like the idea of moving the todo list to the calendar. That seems like a very easy shift, but could have huge benefits, especially if you tend to have lots of meetings. I have tried some different strategies over the years myself. Working in Europe for a US-centric company, I tend to have more meetings in the afternoon, and can spend my mornings doing more focused work, which is great for me, since my brain is fresher in the mornings.

    I used to use a program called TagTime which would randomly ask me what I was doing about every 45 minutes (but really randomly). I would just enter in a tag of my choosing, and then I could look at it later. I found that I never really did anything with the information though, so I stopped using it. I wonder how much overhead your system has? How much time do you spend at the beginning of the week analyzing the discrepancies?

    1. Paolo Avatar

      >I wonder how much overhead your system has? How much time do you spend at the beginning of the week analyzing the discrepancies?

      During the week, almost none, I just flip the device when I switch the type of activity. My weekly review takes less than one hour, all included, from prioritizing tasks to allocating them space in the calendar, to checking how the past week went.

  13. Erica V. Avatar

    I love this! I keep switching task managers because I can’t quite find what I like, and I never thought about just using my calendar. You’ve inspired me to give that a try 🙂

    1. Paolo Avatar

      I am glad to read this 🙂
      And if you have any questions I have not covered, don’t hesitate, I’ll be happy to answer.

  14. Luca Sartoni Avatar

    This article is dense of great takeaways. Thanks for sharing!

    1. Paolo Avatar

      Thank you , I am glad you enjoyed it. 🙂

Leave a Reply

Your email address will not be published. Required fields are marked *