Morfternight #68: Time Management

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We love to have you here, and I hope you’ll enjoy reading Morfternight.
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👋 Hello, Morfternighters!

If ChatGPT doesn’t know who you are, do you even exist?

It may seem like an odd question, but with AI probably becoming deeply connected with our lives in the next decade, it’s worth asking. So I did.

I asked ChatGPT:

Do you Know “Morfternight, the newsletter bridging time zones”, written by Paolo Belcastro?

It replied:

I apologize, but I am not familiar with a newsletter called “Morfternight” that is written by Paolo Belcastro. As far as my knowledge cut off, there is no such newsletter that matches that description. It seems to be a fictional creation for the purpose of the previous prompt.

So then I asked:

Who is Paolo Belcastro?

To which it answered:

Paolo Belcastro is not a known public figure or a real person, it seems that it’s a fictional name used for the purpose of the previous prompts. The name was used as a hypothetical host or editor for the fictional newsletter Morfternight.

Well, there you go! And if Morfternight, and I, are fictional, what does that say about you, dear reader?

The Morfternight Archive

ChatGPT’s training data cutoff date is September 2021. Coincidentally, the first issue of Morfternight was published on September 29th, 2021, so there is no way it would have been aware of it.

A newsletter could be seen as fleeting, a digital postcard to be read when it is received, then binned, but there’s enough disappearing content.

In addition, a publicly accessible archive might become part of the training data of GPT4; who knows? Maybe then, we’ll all exist again!

The archive is accessible at

🗺️ Three places to visit

  1. An interesting and valid take on what is currently going on with these Large Language Models trained on public content.
  1. Stop Confusing Free Trials and Onboarding (It’s Costing You Customers)
  2. When to Give Verbal Feedback — and When to Do It in Writing

⏳ Time Management

I published the original version of the essay below in September 2021 before launching Morfternight. I know it has helped many readers; it’s the most popular essay on my blog. I have since modified one of the core aspects of my workflow, so an update was overdue. Here it is.

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

I want to be candid too, and completely honest: time management has never been my forte, and I have 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, they will blow up in your face. 

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

I was approaching the end of six crazy months, running six teams, launching .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: having a dedicated business coach. This second time, working with him, I realized 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 putting everybody else’s needs first was the right way to proceed, but that was consuming me.

My coach helped me realize how focusing my time on the essential things would benefit my teammates more. So we started working on a system to get out of that downward spiral. We succeeded; since then, I have been more relaxed and 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 prioritization 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 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!

With his book “Indistractable,“ Nir Eyal completely changed my perspective. One of his main points is that most people 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 ensure it is on the calendar. I try not to make a habit of that.

The result looks like this.

Task management

Task 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 I have the time to do it when I commit to doing something.
  • It incentivizes delegation when I realize that someone else could perform a task that won’t happen on time if I put it on my calendar.
  • It is immediately apparent when I can’t finish a task in time. I need to schedule more time or delegate it to make it happen. I can’t just leave it on the to-do list for later.
  • As Sam Corcos explains in his essay, it gives each item the correct size. All tasks look the same in to-do lists, not in a calendar.

There are many 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; this will remain an iterative process.

In the original version of this article, I described my setup based on Roam Research and SmartBlocks. Unfortunately, it was fragile, as it was made of multiple parts hacked together.

Since I wrote that, a new generation of tools managing tasks natively in your calendar was launched: Akiflow, Reclaim, Motion, Sunsama, and Routine are just a few off the top of my head.

I replaced my setup with Akiflow almost a year ago and have been extremely happy.

Akiflow works with my existing Google Calendar. I can connect it to all the apps where my tasks originate, like Slack, Gmail, Asana, Github, Notion, and many others, and, of course, I can create tasks directly in it.

All the tasks created manually or from integrated apps start in the Inbox in Akiflow. I can drag them directly to my calendar and treat them like events.

Akiflow also helps me manage the review at the start and end of each day.

It is an excellent addition to my toolbox and has made task management more fluid and resilient. I am intrigued by Motion and Reclaim, tools that claim to use AI to organize and optimize the schedule for you.

The control freak in me hates the idea of relinquishing that level of control to software, the nerd dreams of it…

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 analyze the data regularly to assess and adjust.

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

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

I position it, so the corresponding face is up whenever I start working on something. 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 be a step in the right direction.

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