At the very end of the week (Sunday), I’ll celebrate 11 years at Automattic. I checked internally, and it turns out that 3.78% of existing Automatticians started before me, and 96.22% started after me. I’m trying to think back to how I felt 11 years ago, and I think back then I was probably more tired. I had 1-year-old twins and was new to not sleeping well at the scale I was then toying with (and am now used to). I was overjoyed to join A8c, of course, and probably a bit smug about it. Back in the early years at A8c travel was pretty difficult – it’s hard to solo-parent twins after all, so it was pretty rough on my husband. Contrasted to today, where travel is far easier (though I’m still a highly valued member of the family Ring and everyone misses me in an entirely satisfactory manner). I’ve said this before, but joining Automattic changed the entire trajectory of my life, and the lives of my family members. It was a risk to join Automattic (though it didn’t feel like a risk at the time, if I’m being honest, it felt like common sense), and I can see so clearly that it was a major turning point in my life. I don’t think there is any other scenario in life where an art and English major who never took a business course (until this past summer — it was time) ends up as a COO. It just doesn’t track. But at A8c, those things can and do happen. The person I was in 2012, though, wouldn’t have guessed that.

I’ve changed a lot in the 11 years of my tenure, some of it at a leisurely pace and some of it with astonishing rapidity. I’ve worked on Tumblr for the past 22 months, and I would suggest that the period of the most difficult and painful growth and change has been within that span exactly. Which is not a coincidence. Working on a social media platform is hard. Working on one with zero experience working on one is also hard. Just as hard is directing the work of people on a social media platform without experience working on one, if not harder. I’ve had extraordinary luck to be surrounded by smart and generous people who have spent countless hours explaining things, providing links for further reading, and giving clear and candid feedback. I’ve been immersed in the platform and drawn the ire and sympathy (and appreciation for my dog, cats, and guinea pigs) of the community in turns.

It’s been hard! I’ve aged! The past 3-4 months have been the most difficult of my entire career. We made the hard decision to change the size of Tumblr staff, though now I’m pretty excited to see how we function as a much smaller team, and what creative shenanigans we get up to. I truly think it’s an opportunity for us! But getting to this point has just hurt. My husband has advised that I try to harden a bit, so that the plights of every individual working on Tumblr doesn’t reside in my heart, but unfortunately and fortunately, that’s just not possible for me. I got some good advice, which was to think about myself in 5 or 10 years’ time, and to “look back” to today, and think about how I hope I lead the team. The hardest part of that is getting the tenses right, because I think you need to engage with the pluperfect, thinking of a future state then a past state that is actually your future state still. But I think you get the idea – it’s an opportunity to rise to the occasion and be the leader I want me to be, and that leader is one who is taking care of her team as best she can. I think I’m doing that, for the most part. I have gotten some things pretty wrong, but with the benefit of caring feedback have been able to apply lessons learned going forward. Bit by bit, we make progress.

Today I have a lot more silver in my hair than I did a year ago. I’ve had way more sleepless nights. I suspect I haven’t been quite as good of a parent as I’ve been in the past (I mean, I’m not a great parent, but I’m also not a bad one). I tore my fingernails down to the quick, got fake nails, then ripped the fake nails plus my regular nails underneath off. (I still have fingernails, but there are chunks missing, and it’s unpleasant.) My anxiety has been worse in some ways, but I haven’t needed an updated dose of Wellbutrin. It’s been physically, mentally, and emotionally difficult, in other words. But on the plus side (which is significant), I’ve developed new relationships that I value deeply, I’ve supported my team through some pretty tough times fairly well, and I’ve gotten better than ever at learning new things.

I don’t know what the next 11 years have in store. I won’t even hazard a guess – that feels to much like closing doors. I’m looking forward to the challenge.