In 2014, Matt Mullenweg challenged the WordPress community to volunteer 5% of their time towards open-source and WordPress.org.

A few months later, I ran a successful fundraising compaign that allowed me to donate 6 months worth of time towards BuddyPress & bbPress.

For 2017, and hopefully with your help, I’m going to try something a little different that I’ve nicknamed: ūüíĮ‚ąě.

My goal is be a fully funded independent ambassador for WordPress & the surrounding initiatives, backed by many of the best companies who continue to push WordPress beyond its limits on a daily basis.

Practically speaking, I imagine this to work like a monthly retainer to work on WordPress core and Dotorg. Someone pays, say, $7500, and I get to say January 2017’s progress was brought to you by Pagely, February by GoDaddy, March by CrowdFavorite, April by Jetpack, May by WebDevStudios, June by GiveWP, and so on, forever.

(The structure is a bit TBD. Maybe it’s weekly rather than monthly, or quarterly, or something else entirely. Hopefully you get the idea.)

It’s like a podcast, but instead of airtime ad placement, it’s coretime leadership, contributor relations, and issue management.

Some of y’all who think this is somewhat unconventional may say ‚Äď Why not just be a full-time employee?

That may end up happening ‚Äď it may actually be the smarter move in the long run here ‚Äď but I think there’s high value in being an independent, nonpartisan thought leader that *wants* to help everyone¬†navigate the ins & outs of contributing to open-source, more specifically WordPress, et al. Since that’s where I’ve seen the most success, I’d like to put maximum effort into continuing that trend; if it’s not sustainable, then we learned something together and try something different.

This weekend at WordCamp US, I’ve had the pleasure of meeting with several folks who love the idea and are‚Ķ deeply‚Ķ interested in making this work however they can, up to and including growth beyond myself for other individuals who are able to provide more value as an independent voice.

If you’d like to help, please email me. If you have questions, concerns, criticisms, or feedback, please get in touch somehow.

Thanks for having an open mind, and for considering investing in the future of something that really, truly means a lot. To the folks who are already onboard, I’m so excited you are willing to¬†give this a try with me.

P.S. Have I mentioned how much better WordPress is on mobile? I wrote all of this from my iPhone without any issues, which is still so incredible to me. Great job, mobile team!

P.P.S. If you’re unfamiliar with why I think I can do this, I’ve contributed to every major WordPress release since 2.5, am a member of the security team, meta team, and have helped lead BuddyPress & bbPress since 2009. I love WordPress and want to help it continue to grow in whatever direction it needs to take. I’m going to do it anyways, and with your help we can do it together.

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 ‚̧ԳŹ

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.

When I was in third grade, my elementary school guidance counselor setup a meeting with my parents and I to talk about my behavior. I’ll spare you the details, but the gist is that “John has a high comprehension level and enormous potential but does not apply himself.” Whether or not that was or is actually true is debatable on some days and a ludicrous notion on others, but this interaction stuck with me, and possibly accidentally influenced¬†the rest of my life, up to this point at least.

I’ve made it around the sun 36 times¬†now, and¬†in the past 28 revolutions since being told that my ability to grok how the world works was a super human ability yet to be seen in reality, I’ve identified several commonalities that boil down to one inalienable truth:

You’re¬†difficult to work with.

I’ve been told this directly several times in my life, and twice recently, so let’s assume that it’s true.

  • I’m stubborn; I get that from my dad who is always right even after you have definitively proven him wrong with factual evidence to refute his theories. I’ve always found this endearing in a way; “prove that I’m wrong” was a fun challenge growing up and learning how the world worked, and I also actively try never to operate in that capacity towards others because as an adult, it’s hugely frustrating.
  • I’m observant; I get that from both of my parents who both were always living on the brink of poverty and needing to keep an inventory of every scrap, every opportunity, and every potential threat at what they had already accomplished or accumulated.
  • I’m passionate; I get this from my mom; her heart is bigger than her head, and her¬†head is growing increasingly fuzzy. I want to make sure that people and things are taken care of, and I actively put forth my best effort to ensure the most positiver outcome occurs.
  • I “think too much.” I’m not sure when exactly this started or if it’s always been this way, or what exactly influenced my brain to work this way, but learning is my addiction and being fluent enough in everything to be able to hold down a conversation is a way for me to dodge any social anxiety I might have.
  • I expect too much from people. I expect people to understand my perspective as much as I understand theirs. I expect people to be as patient with me as I am with them. I expect people to be polite, and communicative, and respectful. I expect people to be considerate, kind, and compassionate. I’m constantly disappointed when they aren’t any of these things.

(Edit: I should note here that I think my parents are both amazing individuals. They’re brilliant in their own unique ways. They are savants that sacrificed their opportunities so that I could have mine, and I love and appreciate them immensely.)

This last one is (in my self-diagnosed opinion) ultimately the issue that makes me difficult to work with. I try not to offer unsolicited advice, but I desperately want to be helpful so when someone does ask for my opinion I have a well thought-out perspective to offer. That requires an education, which requires research, and doing this at scale with all the cool shit in the world requires an ability to¬†comprehend something quickly and filter out anything that isn’t relevant.

In reality, though, what’s happened numerous times is someone asks for my opinion, and I blow their question out of the water with several layers deeper worth of feedback than they were probably asking for. Here’s an example based on a real life experience:

  • “What do you think of this new soup we are trying out?”
  • “I like it, but I don’t think it matches the rest of the lunch offerings.”
  • “Oh, okay. But the soup is good though?”
  • “It’s not bad, but it’s heavy on the spices and thicker than I expected it to be. And I think if I came in for an iced-tea on a hot summer day, that I wouldn’t want to pair it with a cup of tomato soup.”
  • “I suppose. We have a few days worth of ingredients so we’ll see how it goes. Thanks.”

Now, me… I don’t find this interaction off-putting at all, but the chef definitely does, and the manager who worked hard to make the decision to order the ingredients and put together the pairings and design the menu and bring out the ladder and chalk and write the specials on the board and convince everyone this was the right thing to do, doesn’t want to hear this feedback.

This type of scenario carries over to my current career, where interactions are largely public, relationships are largely friendly, interactions are usually with individuals I’ve known in some capacity for several years, but I still manage to piss off despite a lifetime of preparation to try and avoid conflict and accomplish cool stuff with people.

My hunch is that they’re probably right, and that working with me is difficult. Ironically, I don’t think it’s because I’m stubborn like my dad, or over-observant, or passionate, or think too much, but because I’m so fluent and familiar with every aspect and angle of every problem that needs solving under my umbrella of influence, that I’ve already:

  • Deeply assessed the entire situation
  • Tested several theories about what’s wrong
  • Cross-checked the results of my conclusions
  • Considered the social implications of communicating my feedback
  • Formulated a response catered to being direct, polite, jovial, and light-hearted enough to convey humor in whatever flaw it is we’re diagnosing and repairing

Ironically, even with all of this preparation, and time, and knowledge, and consideration, I’m still difficult to work with. ¬†And they’re right, they must be, because it’s fairly consistent feedback spanning several years and groups of friends and relationships and what-not.

My conclusion is that, in one sense, I’m over-applying myself to compensate for a conversation that happened when I was 8 years old. I’ve become addicted to learning things and applying what I learn to prove to myself that I can. I learned how to build, tune, and race cars when I was a teenager. I learned how to write code and make video games. I learned about making wine, brewing coffee, working on the house, auto-cross, electrical, plumbing, accounting, hiring, firing, small engines, milling wood flooring, drywall, pressure washing, video production, mixing music, turntablism, art history, design, typography, security, microwave emitters, steam cleaning, public speaking, community service, whatever…

Basically, I unknowingly fueled the depression and¬†anxiety of primarily inattentive ADHD. I included a link, but you can just search the web for it if you care to learn. Basically, my brain is a hummingbird that never lands, and is constantly on high-alert trying to observe and absorb, and there is no off switch within reach. When it’s time to communicate to someone else what’s been rattling around in my head for however long, it’s already been too long and I’ve worked too far ahead. The effort it takes for me to slow down to bring everyone else up-to-my-speed, means me sacrificing my momentum just so that people can think I’m difficult to work with anyways.

This doesn’t happen very frequently, but when it does it’s painful… it hurts my head to stop thinking so I can write down everything I just learned, with the knowledge that the recipient isn’t going to consider all of the angles that I did, and I’m too anxious about being perceived negatively to concentrate on communicating the depths of my thoughts effectively.

If I wasn’t a cargo-shorts wearing pizza-eating white-dude that looks and acts pretty normal most of the time, and if it wasn’t something I felt I could control enough to navigate the world with relative ease, I’d call it¬†a disability. It’s like being blind, and having people tell you that you’re difficult to work with because you can’t see.

When you consider the perspective of a self-aware recipient, being told that you’re difficult to work with is not feedback, it’s a personal attack, it’s dismissive, and it’s insulting. Combine that feedback with your efforts being voluntary, and it starts to look like management¬†is actively sabotaging your experience.

It’s perpetually negatively self-fulfilling. If you tell someone they are a jerk, they’re going to get defensive which heightens their anxiety and excites them into acting like a jerk, and then you get to say they’re a jerk. It’s unfair, manipulative, and not indicative of true leadership ability or spirit.

What should happen in these cases, and what I actively put mucho effort to¬†convey in BuddyPress, bbPress, and other open-source endeavors, is an appreciation for everyone’s efforts and perspectives, particularly¬†if I initially disagree, because it’s important to me and the projects I represent that I fully understand all perspectives before I can rightfully come to any conclusion, and it’s important that the delivery of my conclusion be respectful of their time & feelings related to the matter.

So, fine… I’m difficult to work with. I’m probably difficult to work for, too. And difficult to be married to. And I’m confident Paul the dog thinks I’m a difficult puppy-master because I spent 2 hours drafting this all up instead of walking him around the block this afternoon. If you know me, or you think you want to, or you’re forced to interact with me somewhere for some reason, please try to give me the benefit of the doubt, and if you aren’t able to, expect for me to be pretty frustrated about it, because I’m trying my best and I expect you to do the same.

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