It’s so hard to say goodbye to yesterday…

I posted this reflection on our internal blog on my 10 year work anniversary in August:

Back at the end of July 2011, I had just returned to Rochester, NY from WordCamp Boston, which had been more of an incidental happening while in Boston for other reasons, and was looking at Twitter for the first time in a while because that seemed to be the thing that all these WordPress people were doing – hashtagging and tweeting about things. At that moment, I was holed up in our bedroom while my husband had taken over our living room with 3 other doctoral music students, all of them studying feverishly for comprehensive exams before each of them headed off to a different state for their first professorship. In our case, we were headed to Wichita, Kansas, and because it was only a one-year position, it was time for something new to ground us. For me, I knew I needed to find one of those remote jobs I had started to hear about because my job as a mid-level PHP/MySQL web applications developer at the music conservatory where I had also previously been a student couldn’t really move with me.

I saw a retweet from Brad Williams (remember when retweets were a manual copy-paste where we would type RT @whoever at the beginning?) from a @jakemgold saying that he was looking to hire a full-time WordPress developer to work from anywhere. I didn’t know who Jake was, and only followed Brad because he had co-written a book I found helpful, but it seemed serendipitous in the way I have a tendency to believe in and follow. So I messaged Jake, set up a call for later that day, told the living room study group “I think I have a job interview later”, did the interview, and then told the same group “I… think I have a new job?” If you know anything about how involved the music academia hiring process is, you’ll know that I was not very popular with our friends that day.

So we moved to Kansas and on Monday, August 15, 2011 I started as a Web Engineer at 10up. As it so happened, I was the first full-time hire! I knew absolutely nothing about working at an agency, or what caching in WordPress was, or anything about Git besides that it was confusing (it is still frequently confusing, to be fair, but at least now I usually know what went wrong), or really much of anything that we take nearly for granted today. It was me, Jake, and a TechCrunch-focused contractor named Luke who some of you may still remember. In the literal decade since, we’ve grown to almost 300 people looking at revenue in the 8 figures, I’ve been through several title and role changes, grown two humans myself, and became one of 5 lead developers on that piece of software we were always building on top of, going from 13% to more than 42% market share, all with the steadfast support of Jake and 10up at large.

At this point, you probably have a feeling about where this is going: yes, it’s time. I have wrapped up my long tenure at 10up and will be taking on my next challenge in the new year, after a little breather.

Once upon a time, if you asked Jake Goldman who the dream “we made it” client would be, he would have said “The White House”. And wouldn’t you know it, just as I hit a fresh global-pandemic-enhanced round of “what am I even doing with my life” late in 2020, the opportunity to work on the actual White House site for the Biden-Harris Administration and bring my ideal vision for a visually-driven editing experience to life basically fell into our laps. We absolutely killed it – I am beyond pleased with the outcomes, and learned so much in the process. Yet despite all the things I know we can do from here for our clients and for each other in the WordPress development space, I have found myself ready to close this chapter of my working life. It’s the capstone I didn’t know I was looking for.

If I’m being fully honest with myself, I’ve been on the path to this decision for more than two years. Part of my success in WordPress as an open source project has been that I’m generally comfortable with living in the in-between before making a decision, while still disliking the indecision enough to make sure I keep moving toward an end point. And that’s what happened here – I wasn’t sure I wanted to stay but wasn’t ready to leave 10up yet either, for whatever reason. I even took a 3 month break, barely touched a computer, looked at other jobs, and came right back. Maybe I felt like I needed that one last hurrah, maybe I hadn’t fully accepted that I would be leaving a large group of people whose company I deeply value, maybe some spidey sense was telling me that I should just wait a bit longer because something was going to happen. In hindsight I see that a really big thing did happen – I returned from my sabbatical in March 2020, just in time to see the world grind to a halt, where the changes in home life were incredibly disruptive in a way that would not have gone well on top of a new job.

In one last showing of why it’s been so hard to imagine leaving my beloved coworkers, my teammates Jeff Paul, Darin Kotter, and Tung Du, with an outside assist from Mel Choyce, surprised me with a WordPress block plugin they had created in my honor: a fully functional Winamp player you can insert into your content. Mel even designed custom skins inspired by my keyboards and general aesthetics for somebody to implement someday soon. You better believe I cried when they showed me 😭 There’s nowhere better than 10up if you’re into WordPress, so you know I can’t leave without one last reminder that “10up is hiring” and it should be your top pick for this type of work. I mean, just look at these!

As for what this means for my work with WordPress, I honestly don’t know! I’m still me, the same thinker and holder of many years of knowledge and history, and whether my job sponsors me or not I am still able to contribute to WordPress. I do know that over the last few years I have not been nearly as active as I once was, and am happy to continue to background support the people who currently do the bulk of the work to be their best selves without focusing on whether my title of “lead developer” is still important or chasing some concept of legacy. I don’t think I want to work on WordPress itself full-time again, and I think that should be okay – I have ideas and wants, but no real drive to manifest them myself anymore. I feel very good about the current direction of the project (yes, especially the editor) and the wonderfully smart and kind people who work on it, and am thankful to have been a part of such a great community and project for such a long time. You definitely have not seen the last of me – after two years without, I’m ready to hang out with all of you at a WordCamp again, hopefully in the near future.

I am incredibly proud of everything I’ve accomplished at 10up and with WordPress, who I’ve become and who we’ve become, but I’m missing something. It’s an honor to be able to shape what WordPress developers do and how we think about things like the critical nature of open source and the intersection of UX and development, but I want to learn and to coach again, the way I did when I was still a musician. That’s not to say I couldn’t do that in my current surroundings, but my instinct is telling me that I need to explore this in the broader tech product space, and in a way that isn’t quite so publicly visible. I have signed an offer to be an engineering manager for a great team doing the kind of work I love, so I’ve got a pretty good sense of direction now and am deeply at peace with my decision to do something new, but I’ll leave that reveal for my first first-day in over a decade. 🙂

5 responses to “It’s so hard to say goodbye to yesterday…”

  1. Aram Zucker-Scharff Avatar

    Congrats, and what a run at 10up! I’m definitely looking forward to seeing what you do next!

  2. Joost de Valk Avatar

    Thanks for all you did so far for our community Helen. It truly is appreciated!

  3. Jesse Gardner Avatar

    Wow! You’ve done so much incredible work at 10up (I’m a bit of a fanboy), and you’ll certainly be missed. Congratulations on your new journey, though! Can’t wait to see where you end up.

  4. Jeffrey Paul Avatar

    Not gonna lie, definitely missing our regular syncs, but after all those past talks I know you’re on the right path. Very excited for where things are headed for you professionally, hoping we can still chat on the occasion, and cannot wait for post-pandemic in-person events to catch up in person soon. Best of luck my friend, you’ll be missed and continually celebrated… cheers!

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