How I fell into the rabbit hole: life and work at the distributed wonderland

In 2001, I was 21 years old and had just started freelancing. Like many of us, it fell into my lap: someone asked me to make their website and so it went.

When I started, I had no clue how to run my business. So I did what I thought was right: I copied everything other people in the market were doing.

I made a stamp, business cards, templates for my business stationery. I bought a paper pad and a nice pen to take notes. I remember once I spent four hours refining my hourly rate with a friend. I had a multi-tiered system according to how many hours of service were required and so on.

I used the stamp maybe once, I haven’t printed a single paper invoice since then and every single client was treated as an exception, so the hourly rate never applied, the way it was supposed to.

For a long time I thought it was just my inexperience. I had the feeling experienced entrepreneurs knew something I didn’t, that they did things better. I felt like an outsider, I wasn’t one of those people who seemed to know what they were doing.

I’ve spent enough time in this industry to confidently say that I was dead wrong. This industry is not divided between who knows nothing and who knows it all, between who has no clue and the business guru.

There are however, two types of people in this industry: people who admit they have no clue and liars.

People who are open to admit they are looking for something better and people who rely on tradition, comfort and old habits.

When I speak to people about Automattic and our culture, it’s easy to indulge and focus on the most peculiar details, the obvious ones, the ones that surprise people and make them go “wow”. It’s easy to catch people’s attention just by saying we don’t have meetings. Everybody hates meetings, right?

We are also widely known as a fully distributed company. Everybody works from home and just with that simple fact, I easily get two polarized reactions: it intrigues those who would love to kick their commute and we get the old fashioned “that would never work if you sold physical products”. That is probably true, but only partially. There are elements in our work culture that are much deeper and way stronger than sitting at home by ourselves.

In my experience, there are three major elements which have really struck me since my first day at Automattic. I see these three elements as so deeply rooted in the company’s DNA that many of the other characteristics we have are simply natural consequences of these.


Firstly, we’re over the traditional view of time. We don’t let it control our decisions, we don’t use it to track our efforts, we don’t let it control our behaviours.

We have people all over the globe, sometimes teams are fragmented across multiple continents. But we don’t care when people are online or for how long. We don’t ask people to track their hours, we don’t ask them to clock in and clock out. We let people take time off when they think it’s needed and we let them decide when and how long they should go on holidays.

In a few simple words we let people work as much as they want, whenever they want. The only thing we care about are the results of their efforts. If things get done or not.

We also dislike synchronous activities like phone calls or video chats. Our team hangouts are limited to maximum once per week, per team. All the remaining communication is completely asynchronous.

Let me walk you through my experience as I began to understand this. I applied at Automattic and when my application was reviewed, I was invited on Skype by the person handling my file. He wanted to know a little more about me and he said: “are you up for a Skype chat?” I replied “sure, let me know when and for how long so I can put it in my calendar”. He clarified the process: “I’m traveling to Costa Rica at the moment, I’ll drop my questions in here when I have a connection, and you answer when you have time”. The chat went on for 3 days.

It sounds exhausting, right? Well, no it’s not. As soon as you get rid of the traditional concept of time, you realize that when we are connected to the Internet with any one of our devices, we are part of an extended reality where the traditional approach to time does not make sense anymore.

We are used to doing things synchronously because we mimic the physical world. But when you get over that, that’s when your true potential blooms and you start feeling really efficient.

Right now, we don’t use Skype anymore and we’ve migrated most of our real-time communication to Slack. Now we are really free because Slack allows you to seamlessly switch devices and you can keep chats open with multiple people, channels and groups at the same time.


The second element that sets us apart is the complete self-management, which is expressed by a flat hierarchy and a rejection of the status quo. We are entitled to use any tool we find appropriate to complete our tasks. That means that we don’t struggle with legacy systems. How many companies force their employees to use a specific hardware, software and follow specific procedures? We don’t. We just want to make sure it all works quickly and efficiently, but we don’t use things just because they were there before us.

But it’s not just a matter of tools, it’s a complete shift in the management mindset. Team Leads have the role of organizing work more than controlling productivity, they are responsible for keeping things together and making sure everything flows smoothly.


The third core principle is total transparency. Only a few HR-related topics are considered private. The whole production, product, and experience-related knowledge is publicly spread across the entire organization. Decisions are always linked to their context and all the pieces of information are quickly accessible to everyone. If a new member joins the team, they can easily access everything that happened before and can quickly get up to speed. If a team member is leaving, he doesn’t need to hand over his knowledge: it was poured into the internal documentation every single day.

We also lowered the cost of failure in order to make failure affordable and frequent. We disconnect errors from disciplinary consequences: it is not about the single mistake but how we make sure we don’t repeat it. This, within a context of full transparency, means people feel encouraged to document their mistakes and the learnings are shared with the whole organization.

I’m sure you realize that all of these principles: a new approach to time, self-management and total transparency are extremely long term investments.

If you suddenly implement these in a traditional environment you are going to face confusion, in the best case, or most probably total chaos. These principles need to be there from the very beginning and they are the result of much trial and error, fine tuning and negotiation.

Strict hiring

You are probably thinking that this environment is not for everybody. You’re right, our hiring process is very strict and requires dedicated, passionate and culturally like-minded candidates. Are they easy to find? No, they are not. But being distributed removes the limits of geography and allows us to access a much wider market of talent. We refuse more people than we accept and we make sure we hire only the best who meet our standards.

That makes it hard to grow in terms of headcount but gives us a formidable privilege. Every time a new person joins the company we know for sure they went through a strict process, so they immediately have our trust.

How many times have you required a new coworker to prove themselves to you before earning your trust? If you only hire the best people and you keep your standards high, then you only have A-listers.


But you are probably asking yourself if there are a few thing you can do right now to improve your company.

I cannot tell you what to do, but I can tell you, in hindsight, what I would do differently if I had to do it all over again.

Let me ask you something: don’t you get mad when your coworker is constantly on Facebook or answering text messages? I used to freak out, until I realized that I was the problem. I shouldn’t care what people have on their screens and how they organize their day. The only thing that matters is the output. Don’t let your cultural bias get in the way, keep your judgment to yourself.

I do my best to ignore what people do, when they do it and how they do it. My coworkers, my leads, my subordinates. I make sure goals are well defined, properly communicated and correctly understood. Then I make sure things happen without getting stressed about the minor details.

I understand it’s easier in a distributed environment, but regardless, let go of personal judgment, it will get in the way.

The second big change I experienced was a shift in my relationship with my mistakes. I learned how to forgive others but mostly how to forgive myself. I know I will make mistakes and I will fix them or someone will help me. Asking for help was one of the most difficult things to learn. Make sure your ego is not limiting your true potential.

Third key learning: say no. Don’t be afraid to have high standards. Make sure you surround yourself only with top players. If you cannot tell who’s the fool in the room, it’s probably you. But if you feel like the most intelligent person in the room, you should move to another room.

When I joined Automattic I decided to go all in and clear any other projects from my plate. It was hard but I know it was one of the best choices I ever made. Make sure you say no to difficult clients. Make sure you say no to candidates who are not meeting your standards. Make sure you don’t accept things that don’t feel right. We tend to think we should adapt, but adapting and conceding are very different things.

Take one thing you don’t like in your company, something you have the power to change and commit the next three months to that.

Profits come and go, but good work, good art and good people stay. Take pride in what you do, make the world a better place.

Author: Luca Sartoni – Copy editor: Andrea Zoellner






20 responses to “How I fell into the rabbit hole: life and work at the distributed wonderland”

  1. […] This article is available in the original version in English: How I fell into the rabbit hole: life and work at the distributed wonderland […]

  2. […] Luca Sartoni writes How I fell into the rabbit hole: life and work at the distributed wonderland. […]

  3. […] Luca Sartoni writes How I fell into the rabbit hole: life and work at the distributed wonderland. […]

  4. […] within a distributed workforce requires a very specific set of interpersonal skills (Luca talks more about them here.) You need to be empathetic and supportive, but can’t be sensitive to criticism. You need to be […]

  5. David Guzman Avatar
    David Guzman

    Luca Sartoni,
    I read your post and I liked it! See, I work 2 jobs. The first one, I work at a restaurant at a resort in San Diego, California for 17years. And the other job, I work as a freelancer and do some contact jobs when ever I get a project. See, I got my certificate of achievement as a web designer 10years ago, and I would like pursue web work as full time job, but as you stated early in your blog post, I have “no clue” how to run my own business and there are moments I have no idea what I’m doing!

    I’m very familiar with the word Press platform been using word press for the past 5years, and I have some knowledge on PHP scripting and MySql, but not advance level. See, I like word press A LOT, and it’s a great tool for users and potential web clients in any industry to utilize it!

    About 10 months ago a friend of mine started a web design/dev business (, and she wanted me to help her out. She handles the business aspect of it, and I do the grunt work, but we’re not getting right type of clients, if you know what I mean. I want to help these potential clients how to use the word press system and how it will benefit them, but I have no idea how to do it! What do you suggest?

    David Guzman

  6. jdrch Avatar

    This is the best work environment I’ve ever read of. The only drawback, I guess, is that the people you hire have to be absolute ninjas, because (traditional) mentoring is difficult to impossible.

  7. kOoLiNuS Avatar

    Reblogged this on /home/kOoLiNuS and commented:
    GREAT stuff, Luca. Thanks for sharing with us…

  8. Fabio Avatar

    Really interesting, bravo!
    The most important thing that such a distributed environment can teach, is a really transdisciplinary way of thinking about any project/issue/research. Keep your mind open as it is, and don’t tie yourself into any specific discipline. You could find “new lands and new skies”!

  9. John Saddington (@saddington) Avatar


    “The only thing that matters is the output. Don’t let your cultural bias get in the way, keep your judgment to yourself.”

    Love that.

  10. markandphil Avatar

    Great overview on being in a distributed team. One question, you mentioned that you use “internal documentation”. What does this look like? Is it a wiki? Or some kind of WordPress frankensteined intranet?

    1. Luca Sartoni Avatar

      We use P2 (a special theme for WordPress) and Slack. Everything is public (internally) and everything is searchable.

      1. David Guzman Avatar

        That is an awesome system that have!

  11. Adam Avatar

    A simple yet brilliant post.

  12. […] Evita le riunioni inutili: come abbiamo letto in questo articolo di Luca Sartoni, si può fare a meno delle riunioni, soprattutto di quelle […]

  13. […] who lives in Vienna like me, we often cowork, he wrote recently a very good post about how we work at Automattic. All the other people named are my teammates, sorry for the ones I haven’t mentioned here,I […]

  14. stefanvetter Avatar

    Great article. Love your conclusion!

  15. Stephen R Avatar

    “But if you feel like the most intelligent person in the room, you should move to another room.”

    I’m in Mensa. I’m not saying that to brag, but to put the following in perspective: A while back somebody on the Mensa forum said something very similar to what you said. I loved it then, and I still love it. Her version was, “If you’re the smartest person in the room, you’re in the wrong room.” 🙂

  16. Wayne Curry Avatar

    I think you would be very interested in Holacracy. Our company is using it with great results.

  17. Claudiu C. Avatar

    Thank you for this great post.
    I really love the culture of Automattic ever since I read A year without pants, and would love the chance to work there someday.
    I’ve applied a couple of times, but I wasn’t lucky enough to get a reply, so I will keep trying.

    Keep up the good work.

  18. […] September 2014 I published “How I fell into the rabbit hole: life and work at the distributed wonderland“. It’s an in-depth first-hand experience about working at Automattic. Check it […]

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