I know it’s been 3 years since we split up, but I wanted to reach out to say that I’m sorry for all of the pain I caused you.

You see, back in 2010, I was on top of the WordPress world. I had great clients, was making OK money, and was making a move away from a city that hated me (Miami) to a city that might hate me less (Providence.)

I gave up my clients and my money to pursue you. I switched from Qwerty to Dvorak for you. I even tried new things I knew I would hate to try and make things work between us. I gave you my best ideas about Jetpack, Reblogs, Followers & Likes, but once I had you, you weren’t what I expected you to be…

That was my fault, for putting you on a pedestal. I set expectations you weren’t setup to meet for me.

When you asked me to join you as part of your distributed workforce, I asked if I would have to wear pants. That quip echoed through the company culture enough where The Year Without Pants was the popular vote for a book where I’d only be mentioned a few small times amongst a team of top-tier Automatticians.

When you asked me to work on Jetpack, I wanted to work on WordPress.com Profiles. I still think user profiles are a live cavity that desperately needs filling to make WordPress.com more enjoyable, but you didn’t agree. I know now that that’s okay, but back then I was pretty deflated… lost… really just aimless for a while.

When you asked me to try out VIP, I was excited to try out anything new (because back then changing teams wasn’t really a thing) but we both knew I’d be miserable in ZenDesk all day, so it was really just a kind way to force a mutual decision, and that’s okay too.

Looking back at our time together, there are some things I’d do differently, and some things I wish I had the opportunity to see through. I joined you with an agenda, which wasn’t fair. I wanted a very specific role that I felt entitled to; that I had earned; that I proved my worth a hundred props over. I wanted a role where I could experiment and set trends and feel like I was trusted to make decisions and change you for the better.

I guess I was pretty terrible to you. I mean… I never talked bad about you, or put you down, or made you feel less-than. But I wasn’t giving you my full effort or attention, because I felt like the open-source WordPress.org community work was more rewarding than the WordPress.com for-profit work. I felt entitled to work on BuddyPress & bbPress the way Andy & Sam had before me. I felt like there were things I wanted to accomplish that I expected you to support me in, and when I didn’t get my way, I wasn’t happy about it.

I like to think that in 3 years time, I’ve learned a bit, changed a bit, maybe grown a bit, and spent a few minutes here & there deep-in-thought about our time together, trying to unwind it and learn everything I could from it. There’s good memories & bad, ups & downs, but my personal takeaway is that I wasn’t a very good employee, as far as employees go.

You gave me all of the things that, on paper, make a great career and environment. You gave me freedom and liberty to work at my own pace and learn — I mean really learn — how to work within a complex environment of systems, people, interests, wants & needs. I could have probably been happy with you for a very long time, and I think you would have been happy with me too, but I let my pride & vision of what I wanted for myself prevent that kind of relationship from ever really maturing.

So, Automattic, I’m sorry. I’m really proud of what you’ve become since I left. It’s exciting for me to watch you grow, knowing that deep in the commit logs & company lore are a few of my fingerprints. I’m really happy that you’re branching out with WooCommerce, Calypso, and all the other neat little secret stuff that no one is supposed to know about but everyone kinda sorta knows about. It’s great that you continue to employ hundreds of people, give great benefits, and try to treat everyone fairly.

I’m not sure if you’re the one that got away, but I hope that no matter what happens with this whole WordPress thing, we can always be excellent to each other going forward.

Thanks for the memories,

-JJJ ❤️

If you enjoyed Matt’s post about the original Super Mario Bros. check out this video about Super Metroid’s hidden tutorials. I had posted this years ago internally while working at Automattic in a thread about new-user experience, specifically in regards to how WordPress (both .org and .com) can learn a lot from video-game design.

I think this still holds true, both for new users and for how new features are rolled-out and introduced to users that have already achieved mastery with the platforms. Even if you don’t like or never played the Metroid series, this video may inspire you to do so.

In 2010 I took a job with the fine folks at Automattic. Having been contributing to WordPress, BuddyPress, and bbPress since 2007, working with the biggest company in the WordPress ecosystem seemed like the next logical step in my career. If you somehow haven’t heard of them, they’re a great company with open-source in it’s heart and transparency in it’s soul; there’s so much publicly available about Automattic that I’m comfortable bypassing the details completely.

In short, it’s an absolutely amazing company to work for, and if you’re still reading this, you should probably think about applying.

Fast forward to 2013. After a few lengthy conversations with the most influential people in my life at the time about career goals, experiences, and my personal bucket-list, I came to the conclusion it was time to move on from the job I once thought I didn’t deserve to the job I needed to have, to keep growing, to keep learning… somewhere I would be able to make a larger impact on a smaller group.

Welcome to 10up.

10up is a company you likely know less about juxtaposed to Automattic, but that doesn’t make them any less impressive. 10up and Automattic both rely heavily on the success of WordPress to create and craft wonderful online publishing experiences, sometimes even in a collaborative way where 10up clients are hosted on WordPress.com’s VIP network, where I did code review and deployments for almost 18 months. One of my favorite parts of working at 10up was, selfishly, getting to interact with my favorite old colleagues at Automattic from the other side of the fence. I (somewhat discretely) left 10up in July, but don’t let that discourage you from applying. They’re hugely into giving back to the WordPress project, and they have some of the coolest clients you could ever hope to have. Again; if you’re still reading, you are likely a good candidate to be a future 10upper.

10up, much like Automattic, is a distributed organization of talented individuals located all around the world, choosing to meet in the midst of the internet chaos to create amazing things together. (Their distributed work environments are so similar, I didn’t even need to change payroll providers when I made the change.) There are hundreds of employees now, all working from home offices, coffee houses, planes, trains, automobiles… anywhere internet access allows. I’m curious who will be the first to push code from space, or a submarine, or some kind of dirigible. The sky isn’t even the limit anymore when you work in a distributed environment; the limit is you.

For all of the clearly amazing perks, make no mistake, this style and environment is not for everyone. There is an enormous learning curve, and working alone for years at a time, collaborating with people you rarely (if ever) see in the physical universe around you, undoubtedly comes with associated costs that are not made obvious until you’re already (feeling) committed to the cause.

When I started at Automattic I already knew what it meant to communicate effectively online; I’ve been doing it since around 1994 through AOL chat rooms, IRC channels, and SourceForge. Still, I didn’t truly appreciate what 100+ people across 100+ internally networked sites (used for managing projects and initiatives) would look like. The fury of activity, the fomo, the persistent connection & constant availability; it’s a lifestyle change not just for you and your career, but your family, friends, pets, etc…

You start carrying your laptop with you to dinner, because if something under your umbrella gets wet, you’re responsible for wiping up the mess. You meticulously configure notifications on your several devices to only alert you to the things you can directly impact and control. You stay up later, wake up later, pull a few all nighters; it’s exhilarating and rewarding and incredibly easy to slide into and painfully difficult to come out of. Maybe you get paired up with someone with different work habits than you, or are asked to work on a project you’re not passionate about. It’s not all WordPress all the time; it’s a job, where someone is paying you to do whatever needs doing, even if it’s not what you signed up for originally.

Yes… you’re changing the world, usually for the better. You go Spiderman on the world at the expense of going Peter Parker on your life. You sacrifice things (or relationships) you love for a perceivably greater good. This isn’t unique to a distributed work environment, but I think it is easier to identify someone starting to lose it when they show up to the office wearing a latex suit flinging imaginary spider-webs at the ceiling VS reading between written updates because you haven’t physically seen them in 6 months.

I guess what I’m saying is, when you work without seeing your colleagues on the regular, it’s incredibly easy for extremely unhealthy habits to go completely unnoticed (or be unintentionally encouraged) for extended periods of time. In a physical office, you pick up on body language, subtle cues, inflection, cadence, and you can smell when someone had a rough night at the pub and maybe shouldn’t be pushing code to 60 million sites. When that closeness doesn’t exist, you learn to be hypersensitive to written tone changes, fluctuations in the frequency of communicating, and increases or decreases in all areas of output, otherwise you’ll never notice someone’s physical or mental health decline. I know this isn’t unique to distributed working environments (it kinda sounds like college) but it is much easier to fly under the radar for longer periods of time before anyone notices.

At the risk of derailing myself, I think working from home for extended periods of time and not going at least a little crazy makes you evolutionarily superior. I’m convinced our primitive minds aren’t quite wired correctly (yet) to work from isolated pods for 8 hours a day, sometimes 7 days per week, for the rest of our lives, even if we get to decide when and where and how to do it. Maybe we’ll find that balance someday, and the future of work may be a division of physical and virtual labor, but this transitional period we’re in right now (where the first of us are figuring it out) sometimes feels like a dark and lonely place.

Succeeding within a distributed workforce requires a very specific set of interpersonal skills (Luca talks more about them here.) You need to be empathetic and supportive, but can’t be sensitive to criticism. You need to be confident, but not arrogant, because that bleeds through the virtual folds quite profusely. Communication is, perhaps ironically, more important than output (technically, it IS output) because no one knows what you’re doing unless you tell them you’re doing it. Communicate early, clearly, constantly, and follow-up on your follow-ups. You need to find a pattern in the chaos, and either lead people through it or risk being absorbed by it.

To be honest, even after 2 decades of online collaboration and leadership, I’m not sure how particularly great I am at it compared to the people I’ve seen actually be great, but that hasn’t stopped me yet from experimenting and learning and growing. I do stay in touch with a fair few of my Automattic and 10up family members, but companies, even distributed ones, are purposely inclusive, so I also try not to encroach.

Speaking of companies, Flox is nearly shippable, and I’m putting energy on the side into an agency focusing on creating great community sites with BuddyPress & bbPress. If you have any leads, I will greatly appreciate you and them.

I’m leaving comments open for Q&A about working in distributed environments like Automattic’s & 10up’s. Please feel comfortable asking anything you’d like, and I promise I’ll answer to the best of my ability. If you work at Automattic or 10up, and have anything else to add, please feel free. <3

There’s no other way to say it; August 1st is my last day working at Automattic.

To my ex-Automatticians, thank you so much for the hospitality. You’re a great bunch, and I’m excited about what’s in the pipeline. It’s been an excellent almost-3 years, and it will only continue getting better.

To everyone else… don’t worry — I’m sticking around BuddyPress, bbPress, and Dotorg. I’ll still be speaking at WordCamps, teaching people about WordPress Development, and doing my best to influence positive thinking and change in the community where I’m able.

Anyone looking for the scoop, there isn’t one. No drama, no hard feelings, no ill-will — just time for me to double-down on what I’m most passionate about, and that’s BuddyPress, bbPress, Multi-network, and a few other ideas that have been floating around my imagination for a while.

Overall… I’ve learned some, loved some, lost some, and am extremely stoked about the future, which I’ll post more about in the coming days.

<3

Checkout this time-lapse video, taken by Alex Mills with his GoPro.

It was made using 9788 images that were taken over the course of 3 hours and 24 minutes, before the battery died. The full-quality 2592×1944 pixel images totaled 16.6GB, and you can enjoy the video in that full quality size by choosing “Original” rather than 720p.