Dear Automattic,

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 ❤️