Paolo Belcastro

Cynical Optimist

ship30for30

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  • How I went from publishing once a year to once a week and finally built a daily posting habit

    Estimated reading time: 2 minutes

    Writing has always been part of my professional life.

    I am not new to writing.

    Besides my blogging adventures, I worked at Automattic for the past 11 years. Automattic is a fully distributed company with a deeply ingrained love for transparency and a communication culture. Over these 11 years, I published more than 15,000 posts and comments on our internal sites, as well as about 250,000 slack messages. That’s about 4 million words.

    For reference, Lord of the Rings counts about 578,000 words.

    I decided to make writing also part of my personal life.

    Two years ago, the world changed.

    The pandemic, local lockdowns, and travel limitations have made it harder and harder to see other people in person. As a result, the tools of everyday life have become more and more similar to the ones we use for work. None of my friends or family had heard of Zoom before 2020, and now it has become a common verb.

    Writing has become more critical than ever in all contexts.

    The secret to succeeding: Community+Consistency

    I decided to dedicate myself seriously to learning in public.

    I took two cohort-based courses, Write of Passage, and Ship30 for 30. I learned many things from those teachers, but the two most important lessons were not techniques or recipes; they were revelations:

    • Community gives strength, courage, and feedback. It has become a crucial part of my process. Not being alone has helped me keep going on days I felt less like writing. It has shown me it was ok to open up. It has provided me with great feedback to improve my writing.
    • Consistency is a secret in broad daylight. In writing like anything else, showing up every day and doing the work relentlessly, gathering feedback, improving, and repeating is a system that can’t fail and yet is so hard to implement alone.

  • A Twitter thread about 1-1 meetings.

    Today I published this as I am playing with the format, but in the near future, I’ll most likely develop all points in that thread as essays here.

  • This is the simplest and most effective framework to help Product Managers triage large numbers of ideas

    Estimated reading time: 2 minutes

    The 2×2 Matrix, an unsung hero.

    Imagine a long list of ideas, limited time, and people.

    Consider two uncorrelated dimensions across which you can compare these ideas. Pick what makes more sense to you. I generally use Effort and Impact. Rate each idea on each dimension with only two options: high & low. You’ll find the exercise surprisingly quick and easy.

    Soon you’ll have sorted your long list of ideas into four buckets:

    • Low effort / High impact → Low hanging fruit
    • High effort / High Impact → Important ideas
    • Low effort / Low impact → Nice to have
    • High effort / Low impact → Trash

    Comparing vs. Measuring

    It’s quick and easy because humans are good at comparing things.

    Give two objects to someone, then ask them which one is heavier, and they’ll answer without hesitation, even with a small difference. However, ask them how heavy each object is precisely, and most people won’t answer correctly.

    Our brain is not very good at measuring things.

    Complex frameworks don’t work at scale.

    Forget RICE, BRICE, and all the others to triage long lists.

    Measuring requires time and effort. It is not sustainable to do so for a large number of ideas. If done quickly, it only becomes a hand-wavy exercise to cover one’s ass in case things go wrong.

    Don’t run away from responsibilities.

    The 2×2 Matrix can save your life too.

    Another popular 2×2 Matrix is the Eisenhower Method.

    It uses Urgency as one axis and Importance as the other. You then rate each task on your to-do list as urgent or not, important or not.

    As a result, you’ll get these four buckets:

    • Urgent / Important → Do it yourself, now.
    • Not urgent / Important → Schedule it for later.
    • Urgent / Not important → Delegate.
    • Not Urgent / Not Important → Don’t do it.

    There are many other examples. The 2×2 Matrix is a life-saver!

  • Is remote work hereditary? A short story of my distributed life

    Estimated reading time: 2 minutes

    1984 was the year that changed my life.

    My Dad started transcribing music in Braille.

    The library he worked for is in Zurich, but we couldn’t move to Switzerland despite his rare skillset. He had to read and write music both in Braille and print. The work was manual and only needed a small Braille typewriter.

    He started working from home.

    Transcriptions were highly fragile, so he traveled to Switzerland once per month to deliver them personally. So we moved to the east of France, which made it more manageable. Once there, he taught my Mom, and for many years, they worked together remotely.

    I grew up stranger to the notion that you had to go to an office or a factory each day to work.

    In 1994, I discovered the web.

    The distributed gene took its toll.

    After studying in Paris, I went back to the east of France, working from home half of the week, traveling to the city the other half. The following years saw me moving a few times, including to New York and back to Paris, where I had an office and started going there more.

    Deep inside, I knew this had to change.

    By 2004, I had gained my freedom.

    Everyone I needed to do my job now lived far away from me.

    With a family of my own, I moved to Switzerland. To raise children in the countryside, and maybe as an act of small revenge for the fact that my parents couldn’t do it.

    I was living there when I joined Automattic.

    Back to the present.

    I live now in Vienna.

    Automattic is an entirely distributed company. I lead 89 people spread across 5 continents, 37 countries, and covering 17 time zones. Distributed, or remote, work has suddenly become common. We all know why.

    It may be comforting to realize that some have decades of practice already.

  • A single, short book made my back pain disappear—a summary

    I mentioned yesterday how I got rid of excruciating back pain by reading Healing Back Pain, The Mind-Body Connection by John E. Sarno, MD.

    Mine is just a minimal summary and in no way replaces reading the entire book. The key to removing the pain lies in understanding why it is there, and the path to that is short already, 200 pages only, so there are no shortcuts.

    Your mind is tricking you.

    Your brain is in the business of protecting you.

    At times, your brain believes there are thoughts it should distract you from having for some reason. A method at its disposal to divert your attention is causing some intense pain in your body. One could argue that this sounds like a terrible idea, but brains are in the business of ideas, so who are we to judge?

    Your brain achieves that by reducing the blood, your muscles can receive.

    It is a harmless condition with no consequences.

    It’s probably why your brain uses this subterfuge.

    A temporary constriction of blood vessels triggers intense pain but bears no consequences. The pain fades away as blood vessels return to their original state. It’s called Tension Myositis Syndrome. Understanding the process is enough to stop it.

    Once your brain can’t fool you anymore, it gives up.

    If you feel intense back pain, follow these steps.

    • First, see your doctor. Some pains have causes that you must treat.
    • If doctors can’t locate the cause and only offer scary options like strong medication, injections, or surgery, give the book a try first.
    • Read the book. It doesn’t recommend any treatment, diet, or particular practice. It is risk-free.
    • If the pain disappears, enjoy.

    Don’t forget to take care of whatever your brain was trying to hide from you, er else it’ll try again in the future.

    That’s my current focus.

  • I got rid of excruciating back pain by reading a short book that anyone experiencing it should read first

    Estimated reading time: 2 minutes

    It was the morning of December 7th, 2019.

    As my flight from Mumbai lands in Munich, I feel a sharp pain in my back. I immediately mentally blame the lack of comfort on this Lufthansa aircraft and sigh at the idea of having to cope with back pain until I get home in Vienna. At that point, the pain is present but bearable; I carry my backpack with caution.

    The following weeks will be a nightmare.

    A quest for a diagnosis

    The pain gets stronger, I have difficulty sitting, and laying in bed is torture.

    I sleep in 30 to 45 minutes chunks for close to two weeks. I moved to the living room, partially to allow my wife to sleep, partly because binge-watching Mr. Robot while pacing around the sofa is the only way I found to cope. Milk and cookies disappear every night from the kitchen.

    Of course, I see my doctor.

    Not surprisingly, we start tests and analysis.

    Blood work, MRI, stress tests, ultrasounds all show no damage, structural or chemical. I am given some meds for the pain. I don’t like the idea. It’s never a good sign when the Doc says to “ease in and out of your dosage progressively.”

    I am still in pain.

    An unexpected answer

    “I was in such much pain that I had to lie down on the floor, I read a book, and it went away forever,” – said my friend and coworker, Yvonne.

    I ask if I have first to wire all my savings to the author, but she promises that no, it’s legit, and I only need to read it: no diet, no medication, no strange exercise, or ceremonial dance.

    I went on Amazon and ordered “Healing back pain – The mind-body connection” by John Sarno, MD.

    I explain here how it works.

    Within days, the pain was gone and has never come back.

  • A (short) story of how I learned to speak three languages and lost my native one

    Estimated reading time: 2 minutes

    Yesterday, I had a sudden realization.

    You know, one of those moments when an idea that has been true but somehow invisible to you all along comes to light, and you can’t unsee it?

    I do not have a “native” language anymore.

    First, there was Italian

    I was born in Italy, and for the first 14 years of my life, that’s the only language I spoke.

    Like everyone else in middle school, I studied a foreign tongue, French in my case, but I didn’t make much progress at that age like most people. Add into the mix two summers where I spent one month in the french part of Switzerland with my parents, and I could make sense of written French, not much more.

    That’s when I still had a mother tongue, Italian.

    Then French took over.

    I was 14 when I moved to France with my parents.

    The first year was quite intense. A deep dive, if you will, as I resumed school in a foreign language in a town where no one I knew besides my parents spoke Italian. I learned, eventually. My French improved year after year, and I reached a point where I was more comfortable speaking it than Italian.

    After all, I spent 28 years in French-speaking countries.

    Meanwhile, English snook up on me.

    English, like French years prior, didn’t stick in school.

    I started working online, building websites, hiring people from India to Thailand, to South America, doing business with American companies, and finally joining one 11 years ago. I went from using English a few hours per day to making it the primary language I speak, read, and write each day.

    To this day, I have more than 32,000 hours of English practice.

    I don’t complain. I enjoy speaking each of these three languages.

    But I had this realization that neither feels like my “native” one anymore.

  • New day, new format

    As we reached week 4 of 🚢 Ship 30 for 30, we started talking about Twitter threads.

    Years ago, I didn’t understand Twitter. Then I hated Twitter. I deleted my account.

    By meeting people whose intelligence I respect and love using Twitter, I realized I was simply using it wrong.

    Twitter is just a tool. Of course, I am quite sure its algorithms do not optimize for kindness and polite conversations, that’s not what generates more engagement.

    I get to choose who I follow, though, and so far it seems that I am on a good path.

    I find it extremely interesting to try and fit ideas in shorter form, so after Atomic Essays, tweets sound like a good exercise. I have set for myself a goal to become at the same time more concise and more clear with my writing.

    Tonight I experimented with a Twitter thread, here it is:

  • 5 Business books that deserve each minute you’ll spend reading them if you are a new manager

    Reading time: 2 minutes

    Popular wisdom says that most business books should be blog posts, and most blog posts should be tweets.

    It is often excruciating, even when the idea at the core is brilliant, to see it hashed and re-hashed over 300 pages when 20 or 2 would have sufficed.

    Here are 5 books worth each page, illustrated by one saved highlight each.

    Managing Humans, by Michael Lopp

    My first piece of advice to all new managers is: “Schedule one-on-ones with direct reports, keep them on the same day and time, and never cancel them.”

    Radical Candor, by Kim Scott

    THERE’S A RUSSIAN anecdote about a guy who has to amputate his dog’s tail but loves him so much that he cuts it off an inch each day, rather than all at once.

    Radical Focus, by Christina Wodtke

    Once your team is checking to-do lists instead of watching metrics, you’ve institutionalized self-delusion.

    Never Split the Difference, by Chris Voss

    It all starts with the universally applicable premise that people want to be understood and accepted. Listening is the cheapest, yet most effective concession we can make to get there. By listening intensely, a negotiator demonstrates empathy and shows a sincere desire to better understand what the other side is experiencing.

    Indistractable, by Nir Eyal

    Think of all the ways people steal your time. The Roman Stoic philosopher Seneca wrote, “People are frugal in guarding their personal property; but as soon as it comes to squandering time, they are most wasteful of the one thing in which it is right to be stingy.” Though Seneca was writing more than two thousand years ago, his words are just as applicable today. Think of all the locks, security systems, and storage units we use to protect our property and how little we do to protect our time.

  • 3 Tips to improve time management and get more free time in return

    Estimated reading time: 2 minutes

    As far as I can remember, I heard the adage: “Time is Money.”

    I thought it meant I shouldn’t waste time, and before doing something myself, consider whether it was possible to have it done for a lower amount than what I could earn with that time. I thought that work was about time for money.

    Today, I understand much better the adage meaning.

    Treat your time as your money: budget and invest wisely.

    If you don’t use your time wisely, it’ll just vanish like money spent on objects that lose value instantly as you purchase them.

    I’d argue that it is even more crucial to care about time because it is finite when, at least in theory, you can always make more money.

    On the other hand, managed and invested intentionally, time like money will generate interests, in the shape of more free time.

    Allow me to share three steps to achieve that.

    #1. Never trade time for money.

    What I mean by that is to avoid work that doesn’t generate any additional value for you than being paid an hourly wage.

    The bare minimum is to make sure that you will get the opportunity to learn new skills and be trained to progress towards a higher compensation.

    #2. Budget your time like your money.

    Budgeting guarantees two things. The first is that each unit of time has a purpose and only a single one. The second is that such purpose is the most valuable opportunity for that unit.

    #3. Invest your time for higher returns.

    Last but not least, try as much as possible to invest your time in activities that will later generate income without requiring more time.

    If, like me, you didn’t realize that earlier, don’t worry, it’s ok. What matters is, from now on, to treat your time like your most valuable resource.

  • The unexpected way I learned about leading a distributed team

    Estimated reading time: 2 minutes

    I have been leading distributed teams for Automattic since 2011

    Not my first rodeo.

    In 2004 I started a side hustle.

    Every evening, I led a team, also distributed internationally.

    Like we do at Automattic:

    • We would interact mostly online and meet in person a few times a year.
    • We tackled complex challenges by leveraging our cross-functional skills.
    • We often executed tasks separately but regularly handled mid-size projects in small teams of five and occasionally larger ones in groups of 10 to 25.

    Like at Automattic, we had multiple communication channels.

    • A website for asynchronous communication.
    • Text-based chat for real-time communication.
    • Audio if the situation warranted an increased bandwidth.

    We had a lot to do.

    You may have heard of some of our achievements:

    • Clean up the trash in Gruul’s Lair to sell better.
    • Move Illidan to a nursing home, and transform the Black Temple into a timeshare.
    • Convince Kael’thas to give up the penthouse.
    • Get rid of the Lich King, and convert the Icecrown Citadel into a 5-star resort.

    If you are not familiar with these names, these are a few of the 10 or 25 men raids that my World of Warcraft guild and I beat over the few years I was a guild officer and raid leader.

    It was my closest experience leading a distributed team before joining Automattic.

    I learned that the most direct path to a result often isn’t the shortest.

    Specifically, people are much more efficient when they do something they enjoy. In a game such as WoW, this is crucial as people play to enjoy the game, and nothing is stopping them from leaving if they don’t. The need to pay rent changes the equation in a professional setup.

    The reality, though, is that money is a weak incentive.

    Curiosity, learning, agency, recognition, and ownership are essential to building strong and lasting teams and successful guilds and raids.

  • 2 Tips Radically Improving Communication Within Teams Distributed Across Time Zones

    Estimated reading time: 2 minutes

    I started leading distributed teams in 1998.

    I have seen many different teams, some within a country, others across continents. Distance is not the determining factor; the spread across time zones is. It is a powerful tool to make progress around the clock or guarantee 24/7 coverage without asking people to work at night.

    It is the most challenging when there is little overlap between work hours.

    1. Introduce asynchronous communication.

    Which tools you use doesn’t matter.

    You can convert almost any communication tool to work asynchronously. What matters is changing expectations and accepting that your messages won’t get an immediate answer because they often don’t need one. These adjustments, by the way, are beneficial to all teams, not only distributed ones.

    You need to remove interruptions.

    Establish that, by default, messages don’t need an immediate reply.

    This simple change will allow people to ignore them while focusing on their current task, then give replying their full attention when the time is right. Unfortunately, developers know too well how powerful it is to focus and how costly interruptions are. The same is true for people in all roles.

    Removing interruptions will skyrocket your team’s productivity.

    2. Trust and empower your team.

    You need to remove communication bottlenecks.

    Do you like feeling useful? Do you think that you need to take part in every decision? Every process? Do you fear being replaceable? Guess what, in a distributed setup, if you channel all communication through a single individual, failure is just around the corner.

    It’s not just about being a bottleneck anymore.

    It will completely obliterate your team’s ability to make any progress.

    Unless you are ready to work 24/7, many decisions will occur while you sleep. Define clear areas of responsibility, enable direct communication channels between teammates, and trust your team to make the right decisions.

    These two simple tips will change everything.