10 Lessons from 4 Years Working Remotely at Automattic

4 years ago today I started working full-time for Automattic.

Four years seems like a lifetime, but it’s a pretty short time in my work history, and it’s been the most life-changing job so far for me. I’ve had years where I spent 40+% of my year away from my home base (with only two weeks off), and I told you how I almost stopped myself from applying and sabotaging my own success. Working at Automattic and working in a distributed team has changed how I will look at work and being productive for the rest of my life.

I wanted to share some of my own reflections, lessons, and scenes of working for a startup with an entirely distributed team for the past four years, in no particular order. Some may say Automattic is no longer a startup, though we just raised more funding, but 4 years ago when there were only 50 of us, it definitely was, and we’ve grown together.

My work laptop proudly covered in WordPress stickers.
My work laptop proudly covered in WordPress stickers.

You are your own boss; aka set expectations, and meet them. Or get better at setting expectations.

At Automattic there’s a lot of responsibility pushed to individuals to get things done. We don’t have traditional managers, and team leads are responsible for their own output, too. No one’s checking you’re at your desk in the morning, so it’s up to you to show up and be ready to work. And you should know what you’re working on, too.

At the beginning you’re pretty much expected to decide what you’ll work on, and how fast, and off you go. You tell people what you’ll do, and you do it. It’s pretty simple.

Besides the fact that keeping someone in sight as a means of ensuring their productivity is immature and archaic, it’s also ineffective. If a person can deliver quality work, consistently, does it really matter where they are? Letting people deliver work when they say they will, by forging their own path & timing to get there, is ultimate sign of a company trusting its employees. Don’t you want to be trusted at work?

The wall of WordPress t-shirts at the Automattic lounge in SF.

Most meetings in the traditional business world are useless.

Meetings in the business world are often mistaken for “getting work done.” I know people who have had full-days of meetings to provide status updates a simple email would have sufficed for, and tales even of a team sitting on the phone together watching a single person work so they would be assured the project would be done on time. I had a phone call meeting recently that took a combined half hour of the participants’ time to find a good time for the meeting, and then the call lasted less than 5 minutes. And yes, we could have done it by email.

Status meetings are the worst use of collective time. Collective time should be used sparingly, to either help the group get to know each other and build camaraderie, or to arrive at a documentable or actionable decision (which I would argue decisions can still be done asynchronously). Instead of meetings, we publish our status updates every week for the whole team to see, where you say what you will do, and what you have done. Twice monthly, every team rolls the highlights of those updates up to the rest of the company, though any Automattician can visit any team’s internal site at any time to get a peek of what they’re working on.

So do you need a meeting? I think your question should be “do we need to make a decision?” or “what needs to get done?” and do what is necessary, and how, to make that happen, without forcing everyone to be in the same virtual space at the same time.

How we ‘meeting’ at Automattic – my WordPress sunglasses are sitting in the U.S. waiting for me.

You need a routine to start the day, wherever you are.

For the first few months I worked from home, I struggled to find a time when I should start working, especially since the majority of the company was in a different timezone. Having the flexibility to design my day also meant I didn’t have as many constraints or reasons to leave the house to catch the metro before it got crowded. I could work all day from home, in pajamas, never even leaving my house if I wasn’t careful.

Finally I got into a routine which always helps me get into work mode no matter where I find myself: I get up every morning, get dressed & presentable (brush teeth & hair!) and leave where I’m staying to get a coffee, ideally an espresso. My ‘commute’ is self-enforced and is as far as the nearest coffee shop. When I step back inside, I’m ready to work.

My little routine is multi-purpose: making sure I get completely ready and presentable every day (so I can be ready to go to lunch or join a friend at a moment’s notice), helping me to connect with my surroundings no matter where I’m traveling, and of course, I get to drink espresso (if you follow me on instagram you know I love it). When I’m traveling I even go as far as to Google map out my surroundings including my morning routine coffee stop.

Coffee is always part of my daily routine and a way for me to kick off the work day.
Coffee is always part of my daily routine and a way for me to kick off the work day.

You need to prioritize your health.

Health should be a priority no matter how or where you work, but it’s even more important when traditional work structures are stripped away like commute times, lunch hours, and even quitting time. When I lived in California I would go to the gym at 5am because I had to be at work between 7 & 8am. Working from home or elsewhere, I’m now the one who decides when working out (& eating healthy) is what I should be doing that day.

Having access to your kitchen can make things easier to eat healthier (or harder if you stock your pantry with junk food), and working from the road can make it harder. It took me several months to make sure I was making time for staying healthy. Once I started scheduling out the week with those healthy appointments on my calendar, I was able to make my work schedule adapt rather than the other way around.

Getting in a run on a team meetup in Miami.

It’s rather easy to see when people aren’t working, even when we don’t see each other physically.

This is the concern I hear first from anyone who is skeptical about having a distributed team. ‘Won’t someone slack off? Won’t someone just go to the beach everyday and not work?’ The reality is, sure, a distributed company will always have someone who isn’t working, like most normal companies.

But knowing when someone is working or not is even easier when you’re working remotely.

When you work with a distributed team, the only way you measure if they are working is on their output. Did they do what they said they would do? Where is the result of that work? Did they even say they would do anything, or have they gone dark? It’s frightening easy to notice when a distributed coworker checks out or becomes disinterested in what they’re doing…they stop communicating, they stop creating. There’s no output.

Their lack of output may not be as visible to the whole distributed company as it would be to a company which shares an office and sees that person come in late & leave early, but it’s very visible to the distributed team that person works with. And they don’t usually remain long, whether by choice or by invitation to leave.

The team meeting in Las Vegas and working on some new features.
The team meeting in Las Vegas and talking about new features and ideas.

Emoticons are really important when you can’t see facial cues, and the burden is on you to make sure people understand your brand of humor (or lack thereof).

When we were a smaller company, it was easier to know that X person has a dry sense of humor, and Y is easily offended, and Z is always cracking bad puns. As we get bigger, it’s harder to really know each other (though our Day 1 intro videos help), and through communication we have to make sure we’re extra sensitive about being understood. I think as a company we put the burden of being understood on the speaker, and in many cases that’s correct. If they are trying to solicit feedback and wonder why they don’t receive any or receive the opposite reaction of what they expected, they need to make sure they’re being understood. As a speaker you hope someone asks for clarification if there’s some confusion.

And if there’s conversation where you disagree, either wholly or partially, it’s important to convey that diplomatically and carefully, though many fallback on emoticons to lighten their words. πŸ™‚

One of the few times we meet in person & see live emoticons.
One of the few times we meet in-person & see live emoticons.

We’re distributed, but we’re still very highly and constantly connected.

If you imagine a company of 250+ people all working solo and lonely on their little slice of the company, you’d be wrong. We “go into the office” every day when we log into our various communication channels – we use a mixture of 170+ internal blogs split by team or project (on WordPress, naturally), and use IRC, Skype, and now Slack for other private or instantaneous conversations.

We can ping anyone in the company in seconds (faster than you can look up their phone extension in your company directory, I assure you) and in many cases, you can ping an entire team for feedback vs. just one person to get a faster answer. It’s a lovely mix of immediate and asynchronous communication which allows for us to be apart and connected at the same time.

Highly connected remotely and in-person, too.
Highly connected remotely and in-person, too.

The goal of working remotely is not to work alone. Hardly! You’ll still crave interactions, chatting, and just riffing on ideas.

It can be a lot harder to have casual conversations in a distributed environment, because of the timezone differences, and the fact that when we see each other online, a good assumption is we are all working. It’s hard to know when to have a casual chat to check in on how someone is doing, ask what they had for breakfast, to talk about an idea, to vent, or perhaps even get their opinion on something not work-related.

We’re getting better at creating and using our online watercoolers – we have something like 40+ internal blogs where people can share their interests in gaming, music, books, children, pets, fitness, and even beards. You have to admit, sharing the latest meme and animated gif is even easier if you’re all in front of a computer.

I definitely thrive on and get energized from casual conversations and even cross-company conversations about work, and those I think are the hardest ones to orchestrate if we’re not at a meetup together. Personal and play conversations are getting easier to define and enjoy, but casual conversations on work topics can be just as hard, and sometimes it’s where great ideas come from.

It’s hard to choose just one day as my favorite day working for Automattic, but I would say most of the best days I have had at Automattic have been during our in-person company meet-ups. You might think that this means we should work together more often, but on the contrary I think because we’re a distributed company we enjoy our time together in-person that much more. (from my interview with Daily Tekk)

A team photo opportunity on one of our twice-yearly meetups.
A team photo opportunity on one of our twice-yearly meetups.

You need less of an ‘office’ than you think.

You need less gadgets and things to make a workspace than you’d think. A great internet connection. Headphones with a microphone. A Moleskine and pen. And charging cables (always be charging).

That’s about all I need for my office. 4 years later, I’ve worked on the beach sitting on a chaise lounge, on a terrace with a plastic chair & table, at picnic tables, on couches, at desks, in numerous hotels, in co-working locations, and even in bed.

And though we have the opportunity to trick out our home office through our home office allowance, I know these will be my staples, including multiple external drives for backup. The most important thing I constantly need to pack with my traveling office is concentration, and that’s something which is consistently needed, no matter your location.

My mobile office, in a tattoo parlor, moments before I got one.
My mobile office, in a tattoo parlor, moments before I got one.

Remember to take holidays…at least on one country’s schedule.

I’m American, but I’ve been living in Italy for 11 years. Since I travel so much, I’m bouncing around countries a bit and sometimes I lose track of which national holidays I should be taking and whose holidays are being celebrated. This year, I’ve already worked 5 weekend days at events & traveling to them, and when I started thinking about national holidays, I realized I had only taken one of the 7 Italian national holidays so far this year (New Year’s Day). Oops.

Luckily we have a flexible vacation policy, but sometimes those national holidays are there for a reason. A reminder to take a break. Take those national holidays, and some real vacation, too.

Visiting Tokyo for an event & happily working a weekend.
Visiting Tokyo for an event & happily working a weekend.

UPDATE: I’ve since written How to Get a Remote Job (and Pitfalls to Watch Out For) with a list of places to find remote jobs and some tips as well. 

Interested in learning more about working in a distributed company? Just apply to work with usΒ (yeah, we’re hiring).

98 replies »

    • Great article! I could relate to each of the suggestions. I would add that when you are working internationally as well as remotely, it helps to bookmark WorldClock so that you can quickly check what time of day it is for the person you are talking to. There is nothing so good for team building as understanding the specific demands of the time of day your colleague is experiencing. “Isn’t it time for your kids to come home from school?” goes a long way, even if it’s 5 AM your own time, as does “Thanks so much for getting up so very early to join this conference call.” Just knowing the time of day, across the world, is a simple way to build teams.

  1. After having read your bio I still find quite unbelievable that a woman with an Italian name, with an Italian surname and living in Milan is actually an US citizen…

  2. Nice article, Sara. We had met at a Femgineer event in SF, few weeks ago.
    It’s great that you have distributed team which works so well. It’s a win-win for everyone!

  3. Wonderful feedback! I’d been working remotely for years even before coming to Automattic, but I still find myself learning new ways to make myself both productive and healthy every day. Thanks for sharing your experiences!

  4. This is a good read! You’ve got a great collection of laptop stickers.

    ‘Most meetings in the traditional business world are useless.’


    I spent most of my previous jobs in meetings.

    • So many answers to that! 1) Our future’s so bright…we gotta wear shades! 2) we’re cool (?) πŸ™‚

      We got the glasses recently – they say WordPress on the side! They’re available in the WP swag store πŸ™‚

  5. Fantastic post, thanks for sharing it.

    I’m self employed since getting laid off from my job in August of last year. Getting laid off was one of the best things that ever happened to me.

    I’m working hard now to build my own little business but, I’ll be honest, it’s my absolute dream to work at either Automattic or Treehouse one day. Location independence is a priority for me and for the dreams that my family and I share, but doing work that matters is also huge for me.

    Not that I don’t I love the work that I am doing now, but working for Automattic would just be so… next level.

    I’ll be applying very soon. All the best, thanks for the post!

  6. Sara, great inspirational post on how to stay focused and set expectations. I’ve worked from home and remotely from time to time, but not as long as 4-years. I’m currently working remotely and like you, I do get up early, take a shower, get dressed and get my day started like I’m going to an office. I find it better to leave the house and work from cafe’s where there are things going on around you, instead of the quiet confines of home, where the silence can actually be distracting. Glad you’re over there in Italy. I’m hoping to get there in the next year or so to see the towns near Rome and Naples where my ancestors are from.

  7. Sara, I found this blog post from Matt’s site – http://ma.tt/ and can’t describe how happy I am to read it! I am currently in a process of interviewing people like you who successfully work from any location they wish and Automatic is one of the few companies doing it right πŸ™‚

    Would you do me the honor to me my guest for my upcoming podcast (called Barefoot Commute πŸ™‚ and spare few minuted of your time for audio interview please?

  8. Great read, and so many truths. πŸ™‚

    Out of all this I find the one I relate to most is emoticons, I use to get told I was an ass or sounded like one (and probably still do when I’m not in earshot) because I’d come across dry and abrupt in written text and maybe even in life too occasionally. Sometimes I even needed to apologise and then do the whole explanation on how words can so easily be misconstrued over the net because that wasn’t how I intended to represent myself. πŸ™‚

    As time went on I constantly tried to lighten that up and now find I probably go overkill on those emoticons. πŸ™‚ This then led to a tricky experience I had with a customer because he felt I was being insincere and maybe even taking the pee a little. I guess as as a kid I was socially awkward for many years and that maybe made it hard to gauge how others interpret my words and actions.

    Anyway, I digress but my point being that emoticons are great to convey how you really feel but can also worsen the situation if you don’t take a few moments to try and understand the tension or upset that may be present from anothers words.

    The one I totally suck at is the health one sadly, I eat a lot more salads and fruits these days as well as the naughty treats but I lack the exercise. Something that I must and will improve on.

    I suppose I should stop hogging your comments now. Have a great day and thanks for the read! πŸ™‚

  9. Great read really.

    Thanks for sharing your experience, i’ve always been and am looking for experiences as yours to utilize in my own remote career.

  10. Great story and nice pictures. Makes me wish I worked for a larger company or had a position working for a more progressive company!

  11. Some wonderful points about distributed (remote) work environments. I never thought about the routine thing to get you going. The entire “meausure by output” is a lovely idea. In a company where my supervisors are in meetings all day, I do wonder if that is where their time is best served.

  12. Great article! Totally agree about the meetings! I can’t work remotely at my present job, but have done a few projects remotely-including online education modules- and I think it would work for me! Ciao, Cristina

  13. Thank you for this great article.
    Nice to see a little bit into Auttomatic.
    That’s definitely a working method i like. πŸ™‚

  14. Lots of good learnings for us at Adblock Plus as well – also running (partially) remote, so very similar challenges and opportunities. BTW, we’re hiring, too

  15. Sara – You stated “Instead of meetings, we publish our status updates every week for the whole team to see, where you say what you will do, and what you have done.” I would like to ask where your team posts this? Is this where you use Slack?

  16. Sara – You mentioned “Instead of meetings, we publish our status updates every week for the whole team to see, where you say what you will do, and what you have done.” Is this where you and your team use Slack? We are wanting to do something like this with our team so I am curious. Excellent article!

  17. Just ended up here don’t know why and gotta say this is the most interesting piece of content I’ve read in the last months. I feel very identified, I work from home as my company doesn’t have offices in Hamburg, where I live, and just saw myself πŸ™‚

    Great post!

  18. Just stumbled upon this… What a great post! I am only a few months into working remotely. It took a bit of an adjustment moving from an open, bustling office with my previous team to spending more time working remotely but now that I have found my groove and the right tools, I am really productive in a shorter amount of time and can work from just about anywhere with an Internet connection.

    The world of work is definitely changing! Thanks for the insight. I will definitely be sharing your post.

  19. Very interesting article, after discovering your work (which I find amazing), I immediately sent my CV Automattic … we hope to become colleagues: D (although I’m Italian)

  20. Might as well join the group of Italians making comments. Seriously, I’m preparing to publish an article about teleworking, and I had to go back to it and squeeze in a link to this blog post. Your point about morning routine is so on the money; that pajamas and bunny slippers stuff is waaaaaay off. More folks need to know that!

  21. It’s rather easy to see when people aren’t working, even when we don’t see each other physically.

    Couldn’t agree more with this! Output is what indeed matters.
    Thanks for the great write up.:)

  22. Hi, Sara. What a great article! I enjoyed every sentence of it. You managed to provide a very interesting insight of how Automatticians work. I agree that there are many risks that comes with distributed companies but in the long run, I’m sure it pays off – not only for employer but also for every employee. It’s amazing that you can do a job that you really love. I am hoping to work for Automattic one day as well. πŸ™‚

  23. This article is about a year old. And 4 years from that you started working at Automattic. This was such an insightful, genuine look into the lives of an employee; culture and beauty of remote work.

    I am currently a Community Manager for a very large company and thought about applying to Automattic – I think I might now. Thank you very much for this article Sara!

  24. Great tips! I’ve been working remotely for a few years but there is always something I feel I’m missing. You’ve given me some actionable things that I can employ to feel more connected with my team. And I need to step up my coffee game.

  25. This is really great article! I just apply for job even i have good standing company in my country. Will be great to join your team and write article after 4 years πŸ™‚

  26. Great read! I’ve been eyeing, and dreaming about, and working up a sweat, thinking about a job at Automattic. To me, it sounds like a dream. I love a work environment that invites creativity, innovation and hard work, and I love working from home. But to be completely honest, I’ve been too scared to. Do you have advice to help someone stick out? I was thinking about applying for the Human Resources Wrangler position. I have a diverse background in science (meteorology), IT (cyber through the national guard) and human resources (current position). Sometimes having this variety hasn’t been helpful for me. I think some people look at it as little experience in many positions, but nothing concentrated. How do I show that I can do all of these things well? How does one convince someone they’re a really hard worker without sounding desperate? Thanks for the post. I look forward to reading more. (Oh, and love the Texas stickers. I’m no native but I got here as quickly as I could).

  27. Absolutely love this write-up. All points are so true. While I’m not with Automattic (yet, applied just a few hours ago), I’ve been in a situation where the boss really cares about output and his staff’s general well-being and it was such a great place to work.

    The amount of freedom and lack of need to be in an office on fixed ours made our group super dynamic and efficient. Not to mention, with such a perk, all of us were more than happy to produce great work, any time, any day.

    Ask us to deliver something urgent in 24hrs over a holiday? No problem, no complaints as we never had to remember when a “holiday” should be coz we’re never stressed!

    Automattic has taken this to a corporate level and that’s just amazing. I hope I make the cut πŸ˜€

  28. Sara, whether a person works at Automattic or not, this is a great article for every freelancer!
    Thank you for putting up your experience generously.

  29. Great post! I love that Automattic linked to this blog post when I received my auto-response that my application to work there had been received. Great way to get people amped to work there!

  30. Fantastic post, Sara! I’ve applied with Automattic and I really hope I get a chance to show my worth! You guys sound like a great team to work with! πŸ™‚

  31. Good post Sara detailing the work and culture at Automattic. Sounds like a fun company to work with. I am interested to know how your profile has evolved over the years while working at Automattic.
    PS: I also look forward to explore my options at Automattic.

  32. Amazing artical! My New Years resolution is to start looking for a remote job that fits my schedule and my skill sets. Searching for a job can take a lot of time so I want to start training myself now for a remote type of environment. I am trying to communicate with my coworkers more through email and skype. What other ways can I prep for a remote life style without having a remote job?

    • Hi Carolyn! One exercise that might be helpful is doing a weekly update like we do internally. It looks back at what you did the previous week and then you lay out what you’ll be working on for this upcoming week. Short, bulleted-style lists. The key is to track how well you predict what you can accomplish and what you actually did, the following week. Pretending that those lists would actually be shared with your colleagues is a great way to start being accountable for your work transparently!

  33. I just applied and praying this is the “match” I have been waiting for. This blog post is so inspiring – how did I not know about Automattic sooner (she says kicking herself again and again)…. Wish me luck!

  34. really insightful article Sara! Automattic sounds like the place for me! This kind of career and lifestyle is exactly what I feel I have been looking for. Glad you hiring because I had just applied this morning!

  35. What a great article! This was so fun to read. Also congratulations on your little one πŸ™‚ that could be the “part 2” mentioned in the comments above andante you already wrote it but for us other remote working espresso-loving mom’s it would be a great read.

  36. wow. Great read. I already feel like i am part of the family, can’t wait to be in the family though. Haha.

    I enjoyed reading every line and learnt somethings too. That picture of you visiting Tokyo is beautiful.

    I agree with all your points on working from home, dare i say when i worked in traditional 9 to 5 companies, my life was not balanced as is now that i work from home.

    I resume by 9am in my home office, work till 1pm in the most comfortable outfit i find myself in which could be nothing. I take a break till 2pm, work some more, do a 22 (do22.co) when i feel i need to clear my thoughts or feel stressed and overwhelmed. Work till 5 or 6pm, go be with family, close up shop by 7pm and just enjoy my evening doing something new or fun.

  37. Very good read. I certainly gave me hope for finding a job like this.

    When you talked about meetings being a waste of time, I wanted to scream! I swear I have wasted the last year of my career in meetings talking about problems but doing nothing to resolve them. Totally useless I would come out of every meeting frustrated and sometimes missed other appointments because they would run over for no reason. 9 times out of 10 it all could have been handled with a 10 minute pow-wow and an email. I think this culture comes from staff continuing to do things “the old way” instead of utilizing the technology we invested in to make better use of our time.

  38. Very well written and informative article. I stumbled into remote work from here in Japan as a result of my venturings into e-commerce and which led (of course) to WordPress.

    Sounds like an amazing company. So amazing that I just applied for a position as a Happiness Engineer. What an amazing job title, no?

    Thank you for writing this. It really is a great article.

  39. Hello Sara!
    I got the link to your interesting post (along with a few more) as part of the first response that I received in my email from Automattic, right after I sent my application for the Happiness Engineer position.
    I must admit that my excitement keeps growing as I keep reading every one of those links. I think that this is a good idea from Automattic in order to keep us learning about this wonderful opportunity to work from anywhere in the world, just as the first phrase states in The Automattic Creed: “I will never stop learning. I won’t just work on things that are assigned to me. I know there’s no such thing as a status quo.”
    Thank you for sharing your wonderfull experience with Automattic! I will be glad to share my own experience with Automattic some day in the future… even better in the near future! πŸ˜‰

  40. Hi Sara!
    This is one great post. I can’t believe I have never come across before. I am at the crossroads in my career life. My kids are all nearly grown and I would love to be at home more to see them and my great supportive wife. I am fairly new to this field but what does that matter. 😁 Your post has just reinvigorated me to pursue this remote work. Your company looks like they really enjoy the work they do each day. I will look at their job oportunities. Steve

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Director of Product Marketing @ HubSpot. Early hire @ Automattic / WordPress.com. Founder World Nutella Day. MBA Alumni Advisory Board @ Santa Clara University.

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