At the end of my work day today, I dropped from a Zoom call, ending the process of unofficially handing off the responsibility for coaching, helping, and advocating for the members of the team I lead at work to one of their peers, who will be stepping in for me over the summer while I take my (overdue) sabbatical.

(She’ll be officially taking over leadership of the team when I sign off for the summer in a couple of weeks, and the team is in great hands.)

What remains at this point is the intangible stuff that you need to do to put things in a good place while you’ll be out for an extended amount of time: locating the “hidden work” you do every day, every week, every month, shining lights on those things, and asking for folks to step up and perpetuate things you have set in motion.

It’s a very different process than the one I went through almost seven years ago when I took my first sabbatical, and I wasn’t yet in a position of hierarchical leadership.

It was remarked during one of these calls today that I have spent more time preparing to leave for three months and come back than most people spend preparing places for their leaving permanently. I suppose that’s just natural, given that I am returning to work after my sabbatical break, and will step back into a position of being accountable for at least some of the things I have set aside while I’m out.

But I also think that—and this is one of the reasons I very much like the benefit of the sabbatical every five years—it’s a very good thing to remove specific pieces from the board every so often. It gives them a chance to recharge, relax, and refresh; to reevaluate their values and goals and then come back with renewed purpose.

It also gives the team a chance to find out what that person has been doing that’s not necessarily been obvious the entire time. Every one of us has things we pick up and run with at work that we just do, and we don’t necessarily crow about it or otherwise draw attention to that fact. It’s good to remove that presence from the equation for a bit, to see where the “missing information” is at.

What’s trapped in my brain that others could use in their day-to-day? What do I need to write out or explain for others that I’ve taken for granted? What approaches and thinking have I brought to the table that will now be missing?

The first time sabbatical came up, I was super-hesitant to take it, because I didn’t fully understand the proper questions to ask. Instead, I was asking things like “what if they find they don’t need me, and I come back and they say ‘dude; you weren’t needed around here, sorry!’” It turns out that’s not the right way to look at it, but instead see it as an opportunity to get some rest while the team looks at things from a slightly different angle for a while. Again: it’s healthy for both groups of people.

So mid-May begins another adventure: a huge benefit that I’m happy to receive from my employer.

It’s going to be a busy next couple of weeks, but I’m looking forward to unmooring myself from those things and taking some time to drift over the summer, spending extra time with my wife and children.

At work, I have taken it upon myself to try and spearhead various initiatives within our Customer Success team that act to push forward how we work and what we work on, as iteratively as possible, taking into account various feedback channels and measurements, and involving anyone who is interested either in reporting something that could use optimization or helping to optimize something that needs help.

We use a threaded discussion system called P2 to do most of our asynchronous communication at work, as we are a globally-distributed company. I have teammates around the world, and we need to collaborate and work with each other “overnight” (which is a relative term, as is, say “summer,” or even “Thursday”).

For each P2, we have a small sidebar image, tagline, and site icon that’s generally chosen by the person who starts that P2. Here’s what I chose for the Quality project P2:

The sidebar from the P2 in question, including a still image from the movie "Tron: Legacy," and the logo of Garlond Ironworks from Final Fantasy XIV. More details are below in the post text.

I felt like sharing why I went with these things, because I don’t ever choose anything for no reason, though I am known for occasionally doing so out of whimsy.

The sidebar header is a moment from Tron: Legacy, as the film heads into its climactic scene, and the main characters are on the run. Flynn explicitly takes a moment to stop, head to the deck of the solar sailer, close his eyes, and find calm.

As he leaves to do so, he says:

“The old man’s gonna knock on the sky; listen to the sound.”

“Knock on the sky; listen to the sound” is apparently a somewhat old Zen saying. Sometimes, calming your mind and opening it to what is around you is the way to find inspiration, insight, or guidance that might be in front of you. It’s challenging to do this when you are running from thing to thing, or very frustrated, or distracted—but that’s maybe when you need to do it the most.

The site icon is the logo of Garlond Ironworks, a group of scientists who study various ways to use machines in the world of Final Fantasy XIV. The motto of Garlond Ironworks is:

“Freedom through technology.”

They intentionally do not study or manufacture anything that can be used for tyranny’s gain. It is a gathering of intelligent people who wish to utilize and study technology for purposes of lifting up all people.

Now, I don’t remotely pretend to view the work I do on supporting customers or improving internal things as being relevant to that ethical quandary specifically, but it does serve to remind me of two things: that ingenuity can come from a variety of sources and from all sorts of people, and that we have a choice regarding whether to further technology to good or evil ends. (The former is definitely why I chose to use it in this specific context.)

The desktop wallpaper for Final Fantasy XIV patch 4.2, "Rise of a New Sun," with artwork depicting the members of Garlond Ironworks.

I’ll have a more detailed post on the assembly of this thing once I have the final parts put together, but I’ve sourced myself the bits necessary for a ten-key-less mechanical keyboard (otherwise known as a TKL keyboard).

The keycaps showed up today:

And along with them, one hundred Cherry MX Blue switches:

I’ve been using mechanical keyboards for a while now, starting with a Model M I scrounged from the campus IT department I then used through college and grad school, then a Unicomp reproduction hard-wired to Dvorak (which was not a great idea), then most recently a Logitech Orion using their Romer-G custom switches, and a Corsair K70 mk.2 that uses MX Browns.

I have liked both the Romer-G and the MX Brown switches, but I’ve been wanted to go to something with a defined click again for a while. The K70 can be ordered with MX Blues, but there was a lot of appeal to finding myself a “standard” keyboard that can take various keycaps and be reconfigured at will.

The plate/board I’ll be using is the Drop CTRL, which I ordered without switches or keys so I could just use my own. I ended up not saving anything more than about $20 doing it this way, but in the end, I’ll have caps I wanted, the switches I wanted, and a keyboard that doesn’t require soldering work to swap out switches down the line if I want to test another brand or line.

The CTRL is the only part that hasn’t yet arrived. I’m hoping it’s here before the end of the week.

I get about a half-dozen emails a year via my contact form asking me this question or asking related questions, like how to craft a resume, or what it’s like to work at Automattic. I thought I’d jot something down so I can just send a link the next time this happens, as my advice hasn’t changed much over time. :)

I’ve been here for seven years as of this writing, so I thought I’d share what I tell people who ask me this question (in a slightly expanded format). I’m not involved in hiring. This is not “official” advice of any kind. It’s just what I say to people, made public and repeatable.

First things first:

I love working at Automattic. You might not.

I will extol the virtues of my job whenever you ask me about it. It’s the best place I’ve worked, and I have found it to be very rewarding.

Not everyone will feel this way. The amount of freedom we have to get or not get our jobs done is unlike anything else out there. It can be very isolating and lonely to not see your team in person more than two to three times per year. I think even those of us who have embraced what we do struggle with this from time to time, and for some it can be significant.

But if you are willing to engage without having to be asked to do so, love working with people who are intelligent and come from all walks of life, and are down with being challenged often, you’ll probably fit in well.

So, how to get a job here? Let’s talk.

Read through our open positions and see if something is right for you.

You can find Automattic’s open positions here. Take a look and see if you spot something you’d enjoy doing and think you can do well. Read the job description and requirements to make sure you understand them and know how you would theoretically fit in the role.

Now, take a strong, focused look at the part of the job listing that talks about how to apply. This is going to be very important. :)

Follow the instructions regarding how to apply. Read them twice.

There are some things you will see in every job listing regarding how to apply. Take note of them and follow them. They are not there at random. Basically:

  • Make a resume/CV/whatever you want to call it. Prioritize and emphasize experience and skills that would directly impact the job role, but don’t ignore even side things that make you unique.
  • Attach it to an email sent to the address provided in the job description. The email is your cover letter. Introduce yourself. Be concise. This is your first impression, and it’s text-only. (As we are largely a text-communication-driven company, you should get used to this idea.) Make sure you include anything that’s specifically requested in the job description call for applications.
  • Double-check your spelling and grammar. Fix anything you need to fix.
  • Check it again.
  • Once more.
  • Send and wait. :)

You might get a trial; you might not. But putting yourself out there is the first step.

(Oh, and if you don’t know about how our hiring works with the trial process, where you perform contract work to see how that goes, you should probably read about that.)

I’m not lying when I say that’s pretty much it. When you boil down the process of applying for a job here, it’s pretty simple. That said:

Here are some focuses/traits I believe in based on my time at Automattic.

Again, let me stress this is my opinion and not in any way “official.” Nothing I say here is even remotely a guarantee, and I don’t have anything to do with hiring (really, I don’t), but these are things I will usually recommend to someone when they ask me personally what they can focus on.

These are mostly things I really like to see or admire in people I work with. :)

Be open to criticism.

It’s totally possible you’ll be rejected for the job, either before or during the trial process. When this happens, you may receive some reasons why you were turned down. Or you’ll receive some constructive feedback during your trial. Be open to it. Embrace the idea that you don’t know everything, because believe me—as a full-time employee for many years now, I still realize this often.

Be dogged in adapting to and implementing that criticism.

I applied to Automattic three separate times over a year-and-a-half before I received a trial. I had to change focus mid-trial before I was hired based on feedback. Some of the best colleagues I have at Automattic went through a trial, received feedback and a rejection, and then trialed again later with success. If and when you receive feedback, take it to heart and then apply it. Or apply again. Or both. :)

Be willing to say up-front when you don’t know something and be open to learning.

I would rather work a million times over with someone who is willing to admit when they don’t know something or are stuck on something and ask for help than someone who tries to fake it. Admitting you need help is not a weakness. It is literally impossible for everyone to be an expert at everything.

Be willing to help others.

I’m big on leading by example. Everyone has gifts and strengths, and everyone is at a different level. Just as you should be willing to let others help you, be willing to share your knowledge and experience with others. Be kind and instructive. Don’t always offer to just take charge of things—though on occasion, that’s necessary—but aim to level up your (potential) team.

Be yourself.

Automattic contains the most diverse and interesting group of people alongside whom I have ever worked. It is an amazing collection of individuals from whom I have learned much and with whom I have enjoyed spending time during meetups. Embrace this and be willing to commit yourself to it as well. (BTW, if the real you is introverted, that’s totally OK. There are lots of us here. If you have to take a break, we understand.)

Have at least a passing familiarity with the Automattic suite of products.

How much of this depends greatly on the job for which you are applying. Some positions might not require a lot of PHP or familiarity with WordPress. Others will be based almost entirely around this. I think it’s a good rule of thumb to at least know the core business of Automattic and what we do before wanting to work here. :)

Embrace open source.

An open source ethos drives Automattic and is core to our identity. Know what that means. Past and ongoing contributions to open source projects, whether it’s code, testing, design, documentation, or whatever, will give you valuable experience in what it’s like to work with those types of projects and is a bonus.

(Again, this will somewhat depend on your desired job role.)

Get comfortable with text-only communication. And in learning how your writing tone can be interpreted.

To be honest, I still have trouble with this sometimes. Text communication is hard. Without vocal inflections, facial expressions, and other body language, it’s easy to read something and get the wrong impression.

It’s a skill to craft your text communication in a way that others will understand your tone and intention. Dedicate yourself to learning that skill. (Yes; sometimes this means using emoji. They are very, very helpful for establishing tone.)

This space reserved.

I’m sure there are things I’m not thinking of, but I have been writing this blog post for three days and I should probably just publish it. If you are a fellow Automattician and reading this, and I forgot something obvious, ping me and let me know. If you are a reader and you have additional questions, feel free to contact me. I’ll edit some things in to this post later if needed.

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. I will build our business sustainably through passionate and loyal customers. I will never pass up an opportunity to help out a colleague, and I’ll remember the days before I knew everything. I am more motivated by impact than money, and I know that Open Source is one of the most powerful ideas of our generation. I will communicate as much as possible, because it’s the oxygen of a distributed company. I am in a marathon, not a sprint, and no matter how far away the goal is, the only way to get there is by putting one foot in front of another every day. Given time, there is no problem that’s insurmountable.

If you have talked with me, my skepticism with regards to Avyd and what they are doing should not be much of a surprise at this point. (I hesitate to talk about it much because there are good people I respect who are doing business at and with Avyd and I am of course always worried about causing hurt.)

I need to say something about this, though.

Today, they are talking about the support they’ll offer as part of their service:

This reminded me of the job posting they’d put up a couple of weeks ago, about which I’d intended to say something more directly.

The listing is here, but I’m assuming that it will expire at some point, so I’ll put the pertinent bits below:


  • Customer Service Representatives are responsible for handling our Client’s highest level of service issues to ensure customer issues are resolved in an efficient and timely manner. Agents provide knowledge and expertise to all online customers to effectively resolve any service-related, while balancing both the needs of the customer and the business.
  • Use empathy with the customer; allow them to vent frustrations, while staying in control of the conversation and maintaining focus.
  • Must be able to multi task
  • Follow up with customers to ensure issue has been resolved
  • Will be answering customer support tickets, inbound calls, and support chats.

Successful Candidates will have:

  • Previous Customer Service experience
  • Proficient in typing and computer skills
  • Energetic and motivated personality
  • Gaming knowledge
  • Available to work nights and weekends as needed
  • Be fluent in English
  • Team player
  • High School Diploma or equivalent

What We Offer:

  • Unparalleled work environment
  • Unlimited growth from within
  • Paid training
  • Continued development beyond entry level
  • Travel opportunities
  • Career advancement into management

On its own, that’s mostly fine. It’s a lot of attention-splitting, and the bit about nights and weekends without specifically stating what that means is a little concerning.

And then you get to the stuff about “growth” from the support position. It’s so much of a focus that it’s literally half of the bullet points in the list of “What We Offer.” It’s a red flag, especially when you hit this part:

Job Type: Part-time

Salary: $10.00 /hour

I don’t suppose I need to state that this is in an office and not remote, because the job posting should lead you in that direction on its own.

This is troubling because it doesn’t see support as a worthwhile career in and of itself. I am growing to understand that my current employer is somewhat unique in this, but I want to see the idea and the respect for support professionals continue to grow.

User support has been my full-time, salaried and benefited career for the last six years. It supports my entire household. I have had different responsibilities and been on different teams, but through the whole thing, I have been well-appreciated and been given the ability to build my career on having pride in the fact that I make our customers’ and clients’ lives easier, and that the ability to do so in an exceptional way is deserving of being a full-time employee.

The wage and (lack of) benefits in this Avyd job posting is sadly reflective of how a lot of tech sees support. Support is a place where you go to wage slave until you earn yourself a place as a supervisor, when you make a bit more and maybe get full-time, and then after even more time you might end up in charge of support for something and possibly get a salary and benefits. Or you have the (often just a) pipe dream of learning another skill and changing job responsibilities, which is seen as a promotion simply because you aren’t doing support.

I’m proud to work somewhere that prides itself on seeing professional support as a career, helping people build that career by supporting them and helping them develop, and giving those people good compensation, good opportunities, and good resources with which they can make the services we provide amazing experiences for the customers who pay for them. We make all employees who don’t work in support do a rotation in support every year, and every new hire regardless of position does front-line support for the first three weeks.

User support and respect for the people who work it is foundational to the culture here, and I wouldn’t have it any other way. No matter your industry, I encourage you to consider making it just as important to your company as well.

And yes; we are hiring.

J Jennings Moss for the San Francisco Business Times:

Alignable, which is headquartered in Boston and has members across the country, started doing its SMB Trust Index at the beginning of last year but this is the first time the company has released its findings to the public. To do its analysis, Alignable relied on the Net Promoter Score approach companies use to gauge their own customer loyalty.


Most trusted: WordPress— The website creation tool had a NPS of 73 and the report determined that “WordPress proves ‘free’ doesn’t always mean ‘junk.'” Groves said he was surprised by how trusted WordPress was, which he attributed to its passionate following. “I knew it was a great platform, but I didn’t know that their following was that ravenous.”


(h/t Matt)

One of the problems I have historically had is either keeping focus on something too long or not enough. When I acquired a standing desk, I knew I would not want to either stand or sit all day long, as there is plenty of research now that says too much of either is bad for you, rather than one or the other being necessarily better.

I had spent a lot of time looking for a good timer to help me break up my day. After a lot of searching and trying out various options, I found AntiRSI (link opens in Mac App Store).

What it does is very simple, and gets the job done. It’s designed to prevent repetitive stress injuries, so it schedules both very small (“micro”) and long (“work”) breaks based on intervals you create. When a break happens, an overlay pops up on your screen and tells you to get with the not-working:

Screen Shot 2016-02-15 at 09.05.55

Because I don’t have any true RSI issues, I don’t run it with the micro breaks, just the work breaks. It’s nice because it does a few things I really needed it to:

  • Detects when you naturally stop typing/mousing and go do something else. This will either freeze the countdown internally or will actually count as a break if you are away for enough time.
  • The overlay steals focus and forces me to pay attention (if I want it to).
  • I can postpone the break if I’m really in a flow and want to just push it back 15 minutes, which both is helpful and forces me to be more responsible with my time. It’s no one’s fault but mine if I work too long in a row.
  • You can drop it in as a menu bar item, which is an unobtrusive look at how much time you have until your next break:

Screen Shot 2016-02-15 at 14.37.58.png

I use it mostly as a long-form pomodoro timer. I will work on a single task for the whole space of a work session. When the time is up, I’ll use that as a cue to at least stand up and walk around for the eight minute break I have configured. I’ll see what my wife is up to, refresh my water, check on something with the house, or check in on the kids to get some hugs. Then, it’s back to the desk for another 50 minutes of work.

If you have any questions, drop them in the comments. In case you give it a spin and want to know what my settings are, here’s my Preferences pane.

Screen Shot 2016-02-15 at 14.32.19.png

The electrical work was finally completed on Saturday morning; I now have a second dedicated circuit as well as a cat6 dedicated run to the office. Once that stuff was in place, I was able to start moving things into the room proper and wiring everything up for the new environment.


The electrical work was done by Jeff Foutch at Loco Electro, and for the most part it was a very pleasant experience and the work was well-done. The finishing in the room itself is great and the basement work is top-notch. He very clearly understood the correct way to route cat6 so it didn’t run into EFI problems with the power run, and secured the cables the correct way.

However, the process of getting it installed was needlessly destructive to the walls. They tore up a fairly large section of wall in the garage before finding it was in the wrong place and then having to move two studs over and do it again. And because my home has what was to them an unusually large gap between floors, they ended up having to cut into the ceiling as well.

My poor garage:


And because of that same gap, they had to take a larger-than-I-would-like chunk out of the boys’ room as well, which because of the proximity to the baseboard, is going to be more problematic to repair than it should have been:


My final opinion on his work is that he is an amazing electrician and the right one for the job (he even came in under bid) but I’m going to have to pay out more than I thought I would to fix the cutting into my home, and I can’t even get started with any of that until the electrical is inspected later this week. I’m disappointed in that aspect of the project. I blame part of it on the ridiculous construction of my home, which is probably fodder for a whole other post.

I would hire this out but I’m not even sure how much that would cost. (Read that as I’m dreading how much it’s going to cost.)

After another few hours of finding the right cables and trying to wire things up proper, I at least have the room in a condition where I can work, but it’s going to be another half-week at least before I can stream from it just because I need to wait for some different cable lengths.

The shelf of consoles is put together, but I haven’t hooked most of them up to power yet, and I need to get some more ethernet cables to hook them up without insane amounts of coiled cable everywhere.

IMG_1144 2

You can see that I had to finally upgrade to a 16-port switch there under the shelf. Really, after a couple of days of trying to get everything wired together, it’s close enough that I can see light at the end of this tunnel.


(The PC is the big loser in the setup right now and the main reason I can’t stream yet.)

I even found a place for my 3DS and Vita charging cradles.

Now, I just need a longer power cable for the TV, one for the PC tower, and some various ethernet cables and USB runs. When I have everything together, I’ll try to remember to post about the connections and the various bits of hardware that come together to create my office environment.

I call this the “beta release” of the office because I can technically work out of it now but it’s not what I would call “complete.” Hoping for RC1 this weekend. :)

Previous office posts: 2.7, 2.5, hugs (2.0), 1.4, 1.3, 1.2, 1.1, 1.0, beta

For the last two-and-a-half years, my office has been a good friend and a nice space in which to get things done. For a while, I’ve had some bookshelves behind the desk, but last week Amanda and I moved those around to fit another shelf and instead put the couch behind my desk, which worked OK:


But after putting it there, I sat down on the couch and Amanda sat across the room, and we looked at the desk. We realized that it was now the most out-of-place thing in that room.

It had to go.

So the question became where to move the desk and my office space. We have a fourth bedroom that is not normally in use except as a library for all of our books. (We have many.) There was also a bed in that room as it is normally where my parents stay when they are visiting—or any other guest with us.

Amanda simply said, “Sofa bed.”

And the furniture moving began.

And then the furniture purchasing.

Less than a week later, my coworkers have been very generous and patient with me as I have been without the comforts of my desk and standard work environment, because the room I normally work in looks like this right now:


(Actually, there is even less in there now. The wall hangings to the left are down and there is new furniture in the room. It is no longer my office.)

The room that will become my new office is in this state right now:


I haven’t moved my desk in yet, because there is still a whole lot that needs doing in that room before I can do that. The list, in order of what gets done when:

  • An electrician needs to come out and install a dedicated circuit for my PC, laptop, and screens. I’ve probably been putting too much stuff on the one in my current office, so I thought I would just cut to it and have a new one put in this time.
  • The same electrician is going to run a Cat 6 line in that room because it will be both my work and my stream room, and I am not doing either on wifi because wifi sucks.
  • The room is getting painted. My best friend has for some reason volunteered to do this with me. I hope he is still my friend after we are done.
  • It needs some lighting. I am already looking at ceiling fixtures, and I need to come up with some kind of solution for streaming/video calls that is not behind me.
  • Then we move in the desk and the gear. I’m taking the opportunity to do things like install a cable tray on my existing desk and get a better ethernet switch for the room as well.
  • Wall hangings are totally happening.

Sadly, the electrical work is probably not going to happen for a couple of weeks, so I’m nomadic within my own home for a while. At the very least, I have created a cozy nook in my bedroom using one of the chairs we moved out of the lower level of the house.


I’ll be working out of this space for the near future as I wait for the work to be done on my new office. I’m really stoked for the new space, so I’m happy to put up with some inconvenience to get there.

And—oh yeah—we managed to throw out a ton of stuff, which is pretty cathartic, even if it is very sad at the same time because it feels like we are saying good-bye to the “parents of tiny humans” phase of our lives as our youngest will be turning four soon.


Previous office posts: hugs (2.0), 1.4, 1.3, 1.2, 1.1, 1.0, beta

I had meant to write this much earlier in the day, but it’s been so busy that I’m just now sitting down to hammer it out.

Today was the sixth anniversary of my start date at Automattic. It’s hard for me to think that so much time has gone by and to consider all the things I have learned, accomplished, and even gracefully failed at (and learned from!) as an Automattician.

At six years, that means I’ve been around longer than a huge part of the company as it stands now. From the time I joined to now, the company is now almost 10x the size, which I could not have imagined when I started. And we keep finding amazing people to work with, who we can hire because we don’t make them move anywhere. :)

I’m constantly grateful for the opportunity I have to work with colleagues who are as thoughful, intelligent, patient, kind, and supportive as my friends at Automattic. And I get to work with an open source ethos and a dedication to improving the ability for people everywhere to have a voice. It’s humbling and sometimes even intimidating.

Think about all the things in my life I likely would not have had I not been doing this for the last six years:

  • Learn so much more about code and about how things just work, even though IMO I still have so much more to go and am nowhere near where I want to be
  • Gain the ability to leave a job and path I ultimately found much less fulfilling and satisfying to work and learn from and alongside fantastic people
  • And do it while now getting to spend more time with my wife and children than I could have otherwise, simply by eliminating my commute
  • Travel to places I never thought I’d see or experience
  • Help countless people with their WordPress sites so they can get on with making content and not worry about the technical bits
  • Be constantly challenged by new problems and questions that push me to my limits and nudge me to develop new skills and proficiencies
  • Help coordinate the migration of an entire platform (Live Spaces!) of sites over to
  • Launch some of the biggest websites on the planet with some of the coolest partners around
  • Re-discover my love of Doctor Who
  • Learn there are other smart people out there who think pro wrestling is rad
  • Overall, worry a lot less and just have fun with what I do, how I balance that with the rest of my life, and who I am

There are probably other things I am forgetting, but I have only five minutes left to publish this post. :)

I really do love what I do. Maybe you’d like to join me? We’re hiring.