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.

As I type this, I have just closed Slack on my main workstation, and I don’t plan on opening it up very often (if at all) for the next three months.

I previously mentioned the benefit at Automattic of the sabbatical every five years of employment, and I’m taking mine starting this weekend. I hope to be blogging a bit about what I’m doing with the time I’m gifted and other things while I am out.

I do have some rough goals for the time I’m out. I’d like to:

  • Take the family on a road trip at some point during the summer.
  • Get in an hour of guitar practice at least three days a week, to focus on just basic learning.
  • Up my CrossFit activity from the current 3 times a week to five times a week.
  • Get another one of my eternally half-baked plugins out there for others to start using.
  • Raise some money for Extra Life prior to my 24-hour marathon for the year, hopefully a good chunk of it. This means more streaming on Twitch!

If I get in even half of that, I’ll feel like I’ve done a good job. I want to use the time to spend it with my family and do more things with my children while they are out of school, but I also want to take the time to level up some skills and improve myself while I’m not in the daily routine.

It’s going to fun! If you want to follow along, following this blog is a pretty good way to do that, or following me on Twitter.

And subscribe to my channel on Twitch!


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.

Working at Automattic is pretty much the gig of a lifetime. It’s the future of work: you can build your schedule as needs dictate, you get to work from anywhere, you can take time off as you need to attend to various needs and life events (for instance: I take all family birthdays off and that’s not seen as bad, but a cool thing to do), and you get to work with the greatest people.

And with that schedule freedom, it’s often tempting to not take an extended vacation. The type of self-starter who is attracted to the open work culture we have defined tends to not want to take extended time off. When you can schedule a day here and there to take care of needs, why would you disconnect for a week or two weeks at a time?

(Yes, I know what I am about to say is the way I see things and not everyone works this way.)

Taking extended time away from the day-to-day is important.

For the last few weeks, I’ve been feeling ragged, distracted, almost out-of-it on some days. I wrangled a week where I had multiple projects converge on the same moment in time, and that week I worked several late nights and through meals during the day. I did this voluntarily—if anything, I always want to be dedicated to making sure the things I start are finished and are done right.

I even took a three-day weekend after doing this to give myself room to breathe, but in the end I had exhausted my body and mind and those things needed some extended time to think about other things and have other priorities.

I’m so fortunate to work at a company that gives me more freedom than I’ve ever had working anywhere else. The amount of time that I get to invest in being a husband and father as well as an Automattician is much greater than it would be just about anywhere else.

But for the next two weeks, I get to just be that husband. I get to focus on being Dad. ((Obligatory mention that I work somewhere I feel perfectly safe leaving for two weeks; I know my teammates will take care of things and I’ll have plenty to do when I get back.)) It’s refreshing and clears the mind so it can come back and attend to the daily routine with a renewed focus and energy, which is good for everyone.

I have plans: we’re going to drive around St. Louis a lot and work on our family project of seeing all of the Cakeway to the West locations. Two of my children are finalists in a LEGO competition that is being held by the Botanical Garden. I’m taking care of things here for a few days so Amanda can go to an educational conference she wants to attend. I’m going to sit around and watch as much of Evo as I can with my kids and feel really bad about my Street Fighter IV skills for a weekend.

Last night, I started off my yearly fundraising for Extra Life with a 12-hour game marathon (that ended up being just 9 hours) that raised the first $30 for the year. I went to bed tired and exhausted, and slept in a bit longer than I would have normally.

I opened my eyes this morning to see my two-year-old daughter’s face about two inches from mine as she was climbing onto my bed. She exclaimed, “Hi, Daddy!” and then proceeded to make herself comfortable and give me hugs. She doesn’t know I’m taking two weeks off to spend more time with her.

But it was the kickoff to two weeks of recharge, and what a way to start.

No matter where you work, take the time to take time. Spend time with your family. Spend time with some books or some movies. Go somewhere you haven’t; do something you’ve never done. Grab your pack and hike into the woods or the mountains for a few days to commune with nature. Take a week or more and just spend that time being the you that you are when you aren’t working.

You’ll come back better for having done it. :)