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.


Four years with Automattic

I think it’s safe to say that I’ve found my home. I’m surrounded by people who inspire me, keep me grounded, challenge me, and allow me to be myself. I’m at ease knowing that wherever I land in the world, there’s someone that I can call on.

Today I’ve reached four years with Automattic, which isn’t something that I ever thought that I’d be able to say. I’m still humbled by the opportunity to be here, and amazed by the life that it’s granted me. While work isn’t always sunshine and rainbows, it’s a part of me. Part of my identity. A part that I’m proud of.

I’ve seen a lot of personal growth over the years, which has brought me to leading an international team that spans from Los Angeles to Prague and every timezone in between. I helped to lead WordCamp US through two incredible years, and will continue to work with the new organizing team. I’ve been given countless opportunities to grow and expand myself, and I’m forever grateful.

I’ve seen more of the world than I ever thought possible. Since last March, I’ve been to Sevilla, San Antonio, Vienna, New York, Dublin, Vancouver, Orlando, Iceland, and Las Vegas. Since I started, I’ve traveled 154,967 miles to 43 cities in 13 countries. I’ve been away from home for 274 days. I’ve done everything from hike up an active volcano to riding a motorcycle to the Valley of Fire. Travel, like my work, opens me up in ways that I didn’t know existed and I’m incredibly excited to be able to make more memories.

I’ve built lifelong friendships and achieved lifelong goals with Automattic. And while I know that I will continue to grow and expand myself, I consider myself extremely lucky to have been able to experience all that I have.

In the next year I’d like to take my team to the next level and kill it, 100%. I’d like to grow more and be more open. I’d like to take a look at my weaknesses and make them stronger. I’d like to surprise myself more often, and share in the excitement of watching the company grow. I’d like to be a part of that growth.

Thanks for sticking with me, Automattic. I’m happy to have you along for the ride and I’m glad that we found each other.


The day the tables turned

Today is the best April Fools day that’s ever happened. I have a few things up my sleeve, as usual, but never in a million years would I have expected my coworkers to Rick Roll me. . . live.

Check out the video below:

I’m just so touched and honored, and I’ll be laughing my ass off for years to come.

Three years with Automattic

Today marks three years working with Automattic, and I still pinch myself every day. I’ve landed in a place where I can be myself, work hard, and constantly be inspired by those around me.

My coworkers hold me up, and hold me accountable. They push me and make me want to be better at everything that I do. I’ve surrounded myself with people who are smarter than me, and its paid off in dividends. Life at Automattic is about moving forward; and not just in the professional sense. I’ve grown so much in my three years here, that it’s sometimes hard to imagine who I was before. What a wonderful adventure this life is.

I’ve accomplished a lot over this past year – not without help – but I’m super-proud of what I have done, and am really excited to see what comes next.

I was the co-lead organizer of WordCamp US, which was just the most amazing experience. Philadelphia really shined, and it was an incredible feeling to be so woven into the fabric of the WordPress community. December 5th was even declared to be WordPress Day, which makes me incredibly proud. We’ll be back here again this year, and I’m really excited about what’s in store.

I traveled quite a bit since last March: New Orleans, Dallas, Sevilla (and other parts of Spain), Amsterdam, New York, Park City, Phoenix, London, Lisbon, Las Vegas, and I’m getting ready for a few more incredible memories. All told, I’ve traveled 112,800 miles since I’ve started. This includes 34 cities in 10 different countries. I’ve been away from home for 184 days.

I’ve become the lead of my own team, which is an amazing experience. Leading a distributed team takes time and practice, and the group that I work with is the best of the best. They make it incredibly easy on me, and I’m lucky to serve them as best I can. I’ve found myself with an incredible group of passionate and talented people, and I couldn’t be happier about it. I’d be lost without them.

After three years, my job has changed quite a bit. It has evolved with me, and is ever-changing. This works incredibly well, and I’ve never once felt bored or unappreciated.

The only word that I have to express my feeling here is gratitude. I’m eternally grateful to Automattic and its people for helping to shape me. For being there for me, and pushing me to do my best work. I’m incredibly grateful to be a part of such a amazing group who makes me laugh, think, cry with empathy, and feel like I’m part of something big. I’ve said it before, and I’ll say it again. These are my people. I’m home; and I couldn’t be more grateful for where I’ve landed.


Two years with Automattic

Two years ago, today, I started the current adventure of my life. I found a work community that appreciates who I am and the work that I do. I found friends that hold me up, and push me to be better on a daily basis. I found home.

In the last year, I’ve seen quite a few changes in both my life and my work.

I now help to lead our Store Team, and do less user-centric support. I harmonize happiness for 35 incredibly talented, driven, and passionate people. These people keep me up at night thinking about all that is possible. They drive me to push harder and be the best that I can be. These are the people that make the world go round, and I’m so lucky to be of service to them.

I lost the person who understood me most. Automattic held me up and allowed me to take the time that I needed to process and move myself forward. I would be in a very different place if it weren’t for this support. I’m eternally grateful for those who stood by me, and made this life transition as smooth as it could have been.

I started walking. After years of sitting all day, Automattic purchased a tread-desk for me. I now walk about 6 miles each and every workday. I have more energy. More focus. More happiness. Walking every day fixes something that was broken for way too long.

I’ve started to give back more to the community. I became one of the organizers of the Philly WordPress Meetup, and of WordCamp Philly. I’m excited to give back, even a little bit, to the community that has given me so much in life. I’m excited to continue to learn.

I traveled quite a bit to meet my coworkers. Italy, Kauai, New York, New Orleans, Mexico, Charleston, and Park City. In the two years since I’ve been here, I’ve traveled close to 68,000 miles to 26 cities in 7 countries. What an incredible gift.

There are more words than I can possibly write about the gratitude that I feel towards the company that I call home. I have a true sense of community and ownership. I have a true sense of belonging, and I’m just as passionate as the day that I started. I’ve grown up at Automattic and have learned more about myself than I ever thought possible.

Thanks for the amazing two years. Here’s to many more laughs, ah-ha moments, forward movement, late nights, and making the web a better place. Here’s to the future.

WordCamp Philly

Yesterday I had the honor of speaking at WordCamp Philly. What an amazing event in an incredible community.

The whole place was alive and there was so much learning happening around every corner.

My presentation was WordPress for Non-profits: For when your Operations Manager is also your Webmaster. Here are the slides from that presentation:

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Scripting for Linkinus (IRC Client)

At work we use IRC to communicate. It’s an old technology, but it’s really awesome. I’ve come to think of IRC as my home base. It’s the place where I chat with my colleagues across the globe and get to enjoy their company. With distributed work, it’s the best way to feel connected with people.

Because it’s my home base, I’ve always wanted to make it mine. I’ve made a few tweaks here and there, but I realized quickly that the only way to truly customize it is to write a script.

A friend of mine at work loves burritos. Every Friday (I suppose, out of companionship,) we have what’s called Burrito Friday. That means that no matter where you are in the world, you eat a Burrito of some kind. I personally don’t have too many options for Burritos in Philly, so I’ve decided that Burrito Friday is a state of mind. That means that anything that I eat on Friday is a Burrito. My friend hates that.

He hates it so much that I just can’t stop giving him a hard time about it.

What’s the point of giving someone a hard time if you have to do it manually? So I wrote a script1 to do it for me. Now all that I have to do is type /burrito in Linkinus to give him a hard time.

To use this yourself, open up your AppleScript Editor and create a new document with the code below. Save the file as burrito.scpt to /Users/USERNAME/Library/Application Support/Linkinus 2/Scripts

-- --------------------------------------
-- Burrito Friday
-- by Alx Block
-- Version 1.0
-- Description: Automatically insert sentances claming that anything is a Burrito
-- Usage: /burrito
-- Output: [burrito]
-- -------------------------------------

on linkinuscmd()
	set burrito_list to {"Everything is a beautiful Burrito", "My desk is a Burrito", "This pencil right here is a Burrito", "Today is Friday, so that means that your mom is a Burrito", "My MacBook Pro is a Burrito", "Only at Automattic can anything be a Burrito", "I'll admit that my trackpad is a Burrito", "This monitor right here is a Burrito", "The Bagel that I had this morning was a Burrito", "This baby monitor right here is a Burrito", "The salad that I'm eating is a Burrito", "This coffee is a Burrito", "I got you a Burrito", "I'm sorry, but you've never had a real Burrito", "I was eating an egg and all that I could think about was that it's a Burrito", "My kid. A Burrito!", "The sun is out, so it's a Burrito", "Have you ever had a frozen Burrito?", "There's no such thing as a Burrito. Only ZUUUUULL", "Burrito? Where we're going, we don't need Burritos", "My motorcylce is like a fancy Burrito", "I'm wearing a Burrito costume", "You're a real Burrito", "I hear that all of the Northeast is a Burrito", "Have you ever even had a real Burrito?", "This muffin is a Burrito", "Twitter is a Burrito", "Once a Burrito, always a Burrito", "My dog ate my Burrito", "I think IRC is also a Burrito"}
	set the list_count to the count of burrito_list
	set pick to random number from 1 to list_count
	set result to item pick of burrito_list as string
	return result
end linkinuscmd

The beautiful thing about this is that it’s super-simple. This is such a basic script, but it allows me to customize my home base in a way that’s meaningful to me. I’m excited to try more things and see what I can come up with next.

  1. The script that I’m using is actually a bit different because it mentions my friend by name. You can simply edit the code to add in the Nick of the person that you want to annoy the pants off of in front of each sentence. 

One year with Automattic

It’s hard not to be passionate about the work that I do. We’re making the web a better place by giving the world a voice. We’re pioneers in an ever-changing world. It’s a marathon and I’m just so proud to be on the team.

One year ago today I started a new adventure and haven’t looked back. I’m forever changed by the decision to move towards happiness. The truth is that the years working on my own were tough. I had a ton of fun and learned more than I ever thought possible, but there was a tipping point. For the last year of being a business owner, I spent more time running my business than I did doing the actual work. I love doing the work.

Working with Automattic fixes this for me. I feel like I own something; like I make a difference. I get to work as hard as I like to work and I don’t have to worry about how the insurance is going to get paid. At Automattic we’re trusted to be ourselves. We’re trusted to be the best. To be thoughtful, passionate, hard-working, quick on our feet, and to learn all that we can. We’re empowered to do what we think is right. We’re human. We’re making a difference.

I work with some of the most talented people in the world. I’m inspired every day to be better at what I do and I’m completely humbled by the company that I keep.

I’ve found my home. This is my element.

Every day working with users is like opening a present. It’s true that it isn’t work if you love what you do. I get paid to do the hobby that I’m most passionate about and I get to do it in style.

It would be an understatement to say that I’m looking forward to what the future brings. I’m beyond excited about where we’re going and how we’re getting there. I’m ecstatic to be a part of it. Thank you, Automattic, for putting your faith in me and allowing me to put my faith in you. We make a good team. 🙂

I’ve moved to

So this is my first post on It feels a little odd to admit that although I’ve been a WordPress user for at least 7 years, I’ve never tried my hand at using

The move here isn’t surprising to me. I’ve been supporting users for the better part of a year, and have been thinking for a while that I should give it a try. Curiously, it isn’t my proximity to the system that spurred the change, rather, it was because rocks and I felt like I was being left out of the cool kids club.

So this begins the grand experiment to use as a user for the first time. I’m hoping that it really helps me to empathize and connect to our users in a way that I haven’t previously done.