It Feels Like Love is the Hardest Art to Learn*

Back in October of 2024, I joined about 120 of my former colleagues, or about 9% of the company, and departed Automattic. I joined the company nearly 11 years earlier in 2013. I don’t think it is a stretch to say making the decision to leave was one of the most difficult ones I had to make in my professional career.

If I’m honest, I was at a crossroads where I could settle for the status quo, or challenge myself to new growth. For those who know me, you’ll know I’m not one to take the easy route. After some time off, I’m now actively looking for my next opportunity.

Below you will find the farewell message I left at my time of departure and I’m wishing Automattic all the best.

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You started on 2013-10-14. Of the 1,877 other a12s, 102 (5.43%) started before and 1,775 (94.57%) after you.

What a cliché way to start a farewell post I must say but it helps tell our story. When I first joined Automattic I had just graduated with a second associate degree and a plan to continue pursuing higher education. I had been using WordPress for several years at the time and was watching Automattic from afar. It was a pipedream, a moonshot, a fantasy to work here, at the WordPress company. I applied and several months later, after a successful trial and a lengthy Matt chat, Automattic has been my professional home for the majority of my adult career.

Looking at things holistically I can truly say that I have been proud of the work I have done, that we have done, for my tenure of just shy of 11 years. From those early days on +storep2 where we were calling users (yes, on the phone) to renew their domains I was greeted by imposter syndrome an all too familiar phenomenon. 

I’ve learned so much and I feel I am both a better person and a better engineer after being surrounded by so many smart talented people for so long. I’ve learned everything from the very basics of supporting WordPress.com customers to how to lead the support organization of a newly acquired small hosting company during my time at Pressable; I honed those skills when communicating publicly with our passionate forum users while on Chiron; and most recently by supporting some of the highest traffic WordPress sites along with my peers at WordPress VIP. 

That’s enough about me. Automattic was never about me, it is arguably not even about WordPress, it has always been about making the web a better place. That is a mission that I still believe in. I’m not leaving out of a place of malice or bitterness, but out of a place of love and respect for the work we do. There are too many individuals who have been part of my journey to name so I’m not even going to attempt it. From everyone who has led me, sat beside me (both virtually or physically) in a meeting, at a conference or meetup, or even just been a friendly face around P2/Slack over the years. Know you will be missed and I’m always just a ping away. 

The two questions that I have found asking myself over and over again throughout the years and will be the ones I continue to ask myself in the future are:

• “Where can I make the most impact?”
• “Where do I see myself in 3-12 months?”

It was answering these questions in the past few days that guided my decision to leave after much deliberation and a few tears. If I were to leave you with this last bit of unsolicited advice it is, to be kind, and do what is right, even when that is hard.

*https://www.youtube.com/watch?v=-O9_ElPTfq4