Preparing for Sabbatical – Five Years with Automattic

I hesitated this year on writing an annual post on my anniversary with Automattic. While it’s true that I love my work and continue to push myself forward, so much of my growth has been internal and making a post to mark a date in time felt somewhat trite.

For me it’s not about what I’ve accomplished while working here or where I’ve been. It has always been about where I’m going. I’ve had a few professional setbacks, but nothing that has kept my spark away, and I’m coming to realize now that my optimism about the future stems from a wonderful gift that I’ll be receiving one month from today.

Every five years at Automattic we get a 2-3 month sabbatical. Yup. Time to recharge, to breathe, to take a step back and take care of all of the things that we’ve put on hold for the past 5 years. I don’t know about you all, but I work hard. I work a lot. I put myself third in the order of my priorities, behind work and family, always.

I’m not saying that’s a good thing, but it is reality.

I’ve scheduled this break for the summer months, which means that I’ll have the summer off, just like a kid. I’ll be around for my family and get to take time for me.

Take time for me. Even writing those words scares me. What happens when all the work stops? What do I do if I’m bored? I won’t have a default work to go to, so how will I spend my time? Is too much time on my own something I can handle?

I started to think about this quite a bit over the last few months, and I’ve come to the realization that if I want to make this break count, I need to do it right. So I’ve been preparing. I’ve been thinking about the fact that I’ve spent the last few decades working myself to the bone. I’ve been thinking about how I eat and my lack of exercise. I’ve been thinking about my need to have an internet connection and a computer that’s always on. I’ve been thinking about how I spend money and what I give priority to in life. I’ve basically been preparing for an existential crisis, and hoping like hell that I can avoid it.

In the grand scheme of things it’s impossible to know how I’m going to react when the time comes, but I absolutely want to be sure that I’ve prepared myself as well as possible. Here are some of the things that I’ve done in anticipation of more free time than I think I’ve ever had:

  • Started a household project list, including the small things like fixing the wobble on the living room ceiling fan
  • Started a project wish-list, like finishing my smart lights project that currently works, but only if you really know how to use it
  • Trying to figure out what Yoga is and how it might fit into my life
  • Eating less and with more purpose. Not really to lose weight, but I’m really sick of feeling sick
  • Going to the doctor. I had a full blood-work panel and now eat fewer eggs. I’ve also had my ongoing appointments to solve an ear problem that I’ve had since I jumped out of a plane in 2008
  • Working on my motorcycle and getting the equipment that I need for long trips
  • Playing more games with my kids and keeping my phone in my pocket more

I don’t know if any of these things will help me with what I’m about to get into, but I do know that they’ve all been missing from my life. The idea of always waiting until I have time to do something now seems so silly, because if I’m always waiting nothing will ever get done.

If there’s one lesson that I hope I learn here it’s how to be true to myself in terms of what I’d like to do with my life. Happiness only exist in moments, it’s not a state of being, but with any luck I can push myself to have more of those moments in my daily life, beyond the sabbatical.

I’m approaching this break with the intention of getting healthy. Mentally healthy. Physically healthy. Emotionally healthy.

I’m so incredibly fortunate to have the opportunity to look into myself this way. I’m really, truly, thankful to Automattic for supporting me in this way and incredibly humbled to have have made it to a station in life where I can make it count.


11 thoughts on “Preparing for Sabbatical – Five Years with Automattic

  1. We only met once a few years ago at some WordPress Meetup, but your posts are always interesting to read. Hope you have writing penciled in to your sabbatical ToDo list! : )


  2. One thing I will say, post-sabbatical, is to not be hard on yourself if you don’t do all of these things, or if the sudden free and personal time paralyzes you at times and you find yourself sitting and staring and thinking for part of a day that you’d had set aside to “do something new.” That happened to me many times, and I let it happen. Because that quiet, empty time was time I didn’t know I needed, and I realized I’d grown accustomed to a very specific definition of “productive.” I did not do all of the things I wanted to do on my list, and sometimes when I ticked something off (“take an art class,” “learn basic tagalog phrases,” “go on a silent retreat”) I didn’t feel as satisfied as I thought I should feel, but as the three months passed, I slowly realized that for me, what became most valuable or insightful were those days when I found myself sitting at home and thinking, what should I do? what can I do? do I even want to do anything? and then choosing to do nothing. Because that was also totally okay. I was grateful to even be able to do that — to adjust, to reset, to just be.

    All that said, enjoy your time off 🙂 We are so incredibly lucky to have it.

    Liked by 5 people

  3. I’m in week two of sabbatical right now and I didn’t schedule in time for my body to say “oh, we’re resting? Cool! We’re really sick! Watch some tv and cough for a week” So maybe slot that in with mental/ physical health?

    Interestingly I’m also pursuing yoga on my sabbatical. I’ll be interested to chat with you about it.

    Liked by 1 person

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s