One of the great things about working at Automattic is the feeling that most of us are in it for the long haul.

When I was hired, I distinctly remember Matt telling me as part of that process that he chose to hire people he could see himself working with ten, twenty, maybe even more years down the line. I remember being somewhat surprised at that notion; at the time the longest I had been at a company was approaching four years.

I’ve been at Automattic for five years since this past January. There are a good number of people still at Automattic who have been there for around ten years. I’d venture a guess that for many of us, it is the longest we’ve been employed by a specific company.

It’s clear from how our work and internal policies are structured that this is indeed a focus at Automattic. Not only because of the fully-distributed, work-where-you-like and live-where-you-want nature of the company, but also because our perks have been structured for the long-term health of employees and their relationship with work.

Allow me to explain and tell you about an interesting new addition to those perks that will affect my year in a pretty significant way.

Time Off

Automattic approaches vacation and time off in a very freeform manner. If you need the time off, you coordinate with your team and team lead and you take it as you need it. We don’t have stored PTO hours. You can cut days short or long if you need to for various reasons and you’re encouraged to just do so when necessary and not feel guilty about it.

It’s enormously freeing in terms of making your work fit around your life and vice versa. If I need to schedule a doctor’s appointment or other commitment, I can generally feel free to do so and not have to worry overmuch about work scheduling. Often, I’ll just step away from the desk just for that appointment and then come back and continue working.

I tend to do a mixture of things. It lets me leave for an hour each workday and hit the gym, then just come back and pick things up. I take two weeks off each summer and two weeks off around Christmas every year to rest and take time with my family. And occasional three-day weekends are not unheard of and always welcome.

There is provision for extended leave, as well. If you need a broad bunch of time off for medical reasons or family care reasons, you can take that as you need and if you have been at Automattic for at least a year, it’s fully paid. It’s why I was able to take six weeks away from work after the birth of our most recent child to help her mother and focus on being a dad before returning to the job.

It’s an open and trusting time off setup that gives Automatticians the freedom to focus on their personal health and sanity as well as their family life so they can be more focused on work when we are working.


The other thing we have that’s really cool is that a milestone system is gradually taking shape as we have employees who have been around for longer and longer.

I wrote previously regarding the WordPress-branded laptops we gain access to at our four-year anniversary:

One of the perks of reaching your four-year anniversary is being given a MacBook (Air or Pro) model of your choice, with the WordPress logo customized onto the top cover.

At first, this was a one-time gift when you reached four years, which was really cool because when you hit your next laptop refresh cycle date, you got to keep it permanently. Now, we’ve updated that policy so that every time you have a new laptop coming after your four-year, you can order a new W laptop each time.

I get to keep up with new tech and still have my flashy WordPress laptop all the time. Love it.

The new perk option we have is a combination of a milestone and time off, and it kicks in at your five-year mark, which I just so happened to pass this year.

“Get Away, Renew, and Refresh”

A few weeks ago, the latest milestone was added. Rather than recount it on my own, I asked Lori (our HR lead) if I could post the text of our internal policy on it, and she graciously said I could, so here it is:

If you’ve worked for Automattic for more than 5 years, we encourage you to take a paid sabbatical of 2 – 3 months. Taking an extended leave allows you to break away from the usual routine and return to work refreshed. “What should I do on a sabbatical?” you may ask? You could use the time to fulfill a goal, build a skill, or do research. Or, simply rest and relax. The key is to get away, renew, and refresh.

There’s so much I love about this and how it’s worded. It’s not just that you have the option to take this time off, you are encouraged to do so. You can do whatever you want. And the goal is to take you out of the daily pattern of your work and give you time to restructure and refocus. Automatticians get to take this sabbatical once every five years.

If I want to travel, I can. If I want to just hang out with the kids and play video games, I can. If I want to volunteer and do some rad things to help people, I can do that, too. If I want to take the time to level up some skills, well that’s another perfectly acceptable option.

So when I step back into my role, I’ll bring fresh eyes and hopefully a leveled up skill or two—even if it’s non-technical—to add to my contributions to the team.

That doesn’t mean it’s 100% easy to take this time off—and I’ll discuss that in a future post—but after some discussions with my team leads, I’m definitely going to take that long break this summer to focus on things that aren’t work. I’m not sure what I’ll do yet.

But I know that the time will be well-spent, whether I focus on spending time with my family, learning guitar, going on a road trip, or leveling up my dev skills—or even all of those things. And when I return to my work, I’ll be re-energized for the next five years of working at Automattic.

Maybe you should think about getting started towards that five-year sabbatical, too. We’re hiring.

A couple of Sunday nights ago, I was crouched over my laptop in a rental house in New Orleans working feverishly to help launch Women’s Wear Daily on VIP. It was (and still is) a huge undertaking, and to get it in shape for a successful Monday morning launch, I realized pretty early on Sunday night that I was going to have to pull an all-nighter to get it done.

I did, it launched, got the thumbs-up from all the personalities involved, and I collapsed into bed at around 7:30 a.m. on Monday morning. I was in New Orleans for a team meetup, and spent the majority of the time I was there focused on making sure the pre-and-post-launch processes went as smoothly as possible.

It’s my job, and I take great pride in what I do.

That kind of “crunch” isn’t abnormal in today’s working culture. Long hours, little sleep, and work focus are common. We all know that fatigue and long work hours end up causing less productive work, but sometimes the tasks just need to get done and require sacrifice. What I described may sound like something you have experienced in your work life, and maybe all too recently or all too often.

What I haven’t said yet is why I’m happy to put in those kinds of hours at work when it’s needed. And that’s because I’m happy to work somewhere that respects my time and my life the rest of the time.

When the project was launched, several of my colleagues nudged me and made sure I knew that I should take some time off to make up for the sacrifice of that weekend (and the weeks leading up to it). I was only too happy to oblige, given that I’d already marked today and the two previous days as time off. But it’s notable to be somewhere that recognizes the extra work people put in and then not only allows, but encourages comping that time after the fact with time off to rest and recharge.

And I’ve had a great three days off with my family, spending extra time with them and not worrying about work projects, checking email, or doing anything more than housekeeping check-ins a couple of times over that period to make sure things I’m responsible for are still progressing.

It’s in the time between the days off that Automattic is really special, though. My time and my family are respected by my employer and my colleagues. We have an HR staff and teammates who understand the value of time away from work, even in the middle of the day. I’m very careful to guard my time during the work week. I try to be done for the day around dinner time to spend the evening with me family, I take an hour during the afternoon three times a week to go to the gym and work on my personal fitness level, and I spend my weekends not doing or thinking about work the vast majority of the time.

When my last child was born, I was able to take six weeks off to be a dad and help my wife with her recovery. I take at least two two-week vacations a year to do something fun with the family and not directly think about work stuff. I even take the days off leading into Evo weekend to just enjoy watching some high-level gameplay. If I need a day off, I take the day off.

And this all works because as a team we all know that when things get real, we’re all going to pitch in and do the work that needs to be done. We communicate clearly and often about when we’ll be around and what we’re responsible for. You may find this surprising, but when a company and an employee mutually respect each other’s time, it appears to lead to more dedicated work, less fatigue, and a happier balance.

I know this is something that’s rare—if not unique—and I’m super-appreciative that this job exists and that I’ve been welcomed into it. I’ve been doing this for over five years now and I don’t see myself doing anything else. I think more industries and companies should take a hard look at how we are doing things and think—really think—about changing the face of work for the better. And if what I’ve described sounds like something you’re interested in, maybe you could give our hiring page a quick glance.