Motivated by Big Ideas: Some SAO History

I have written some before about how I ended up specifically at Automattic, and what that process looked like for me. You can read that here.

I remember during my interview for the Happiness Engineer position (which was almost four years ago!), I told the interviewer that I wanted to work at Automattic because I was motivated by Big Ideas.

It wasn’t something I’d prepared – it sort of slipped out in the moment, the first thing that I thought of, a natural thing to bubble out of a moment of self-reflection. I’ve repeated it several times since, and I think about it a lot. I touched on this idea a little bit in one of my favorite of my own blog posts, Reformed Philosopher.

I studied philosophy as a young man, and even was a professional philosopher for a stint (a Google search for “Ouderkirk CCRI” turns up proof!) 

The process there went more like “Paying to study and talk about philosophy” to “Volunteer for AmeriCorps to live your philosophy” to “Have others pay you to talk about philosophy,” but each step of the way was motivated by different big ideas, different perspectives or insights.

The first, of course, is that philosophy, unlike statistics or biology or other more, shall we say tangible fields of study, rarely holds a correct answer. This means the focus becomes placed more on the process than in the result. The journey truly outweighs the destination. How you accomplish a goal can sometimes become bigger than the goal itself. These truths I find self-evident. They are in my bones in that way.

The second step, from school to community organizing, is outlined in more detail in the Reformed Philosopher piece. It’s a good one, I promise.

Moving from the community organizer piece to the professional philosopher is a little messier. I was in love, you see. I met the Doc, who at that time was not yet a Doc but a mere Graduate Student. The final piece of her studies was a practical year of clinical work – since she is much smarter than me, she was accepted into the program at Brown, in Providence, RI.

So, I moved with her. What idea is bigger than love, after all?

Rewinding a bit for some context; while I was in grad school myself for philosophy, I was also working at Starbucks and waiting tables. I was that kind of grad student! When we moved to Providence (the city which houses Brown University, the Rhode Island School of Design, Johnson and Wales, and of course, the Community College of Rhode Island), I cast a wide net; looking for waiting jobs, coffee shop jobs, teaching gigs, anything that might fit into my (even then) varied and disjointed resume.

I ended up slinging lattes and grading papers. It was not a bad existence! In time, I came to appreciate how high end coffee, what I still call progressive coffee, was both a force of deliciousness but also a force of economic good in the world. Progressive coffee was a non-coercive, delicious, delightful way to funnel the wealth of the West into some of the poorest areas on Earth.

This, this was a big idea. I worked in coffee for quite some time – I’d call it my first real career – I probably trained over one hundred baristas, for companies I worked with as well as for the Barista Guild of America. I was a regional barista competitor! I started a cafe professional community in Providence. I had a small but appreciative professional circle.

In retrospect, while what motivated me was the big idea, what really drove my success was the focus on process that my philosophy studies taught me. It wasn’t just the coffee – it was how the coffee was made, how we sold it, how we communicate with the customers, how we communicate with our space.

(You can see how these ideas manifest themselves in customer support for software products in this talk I gave with my a8cbff Daryl)

The focus on process combined with my experience teaching, helped me lead Seven Stars Bakery to be named the best cafe in Rhode Island. It was pretty cool! Even more cool was planting the seed of excitement about progressive coffee in the minds of tons of new coffee professionals – some of whom have gone on to outshine me in literally every way imaginable.

When the Doc got her first tenure track teaching job, and we moved to Saratoga Springs, where we still live, I was able to get a job opening cafes for a small regional chain – but it was clear that my values weren’t a great fit for their organization.

It was then that I discovered Automattic. Like many folks who end up working there, I had been a long-time WordPress user, but it had never occurred to me that I might work for the company behind – or even that there was a company behind It had never come up.

Of course Automattic immediately rang my bell. A company whose primary driver, whose raison d’etre is to ensure that every human being has a voice, is able to express themselves on the primary mechanism of communication of our time, The Internet?

It was an obvious fit. It was a great fit. I made it through the trial, and have been on board for over three years now. Customer Support, Customer Success, Customer whatever, these are terms that describe in a big way what I’ve been doing my whole life; taking a big idea, and applying it on the personal level.

Sometimes that means reading Plato. Sometimes that means knocking on doors all day. Sometimes that means creating a curriculum (maybe Logic, maybe Espresso). These days, it means leading a team of Happiness Engineers, who put the power of the web into new hands every hour of every day.

I lead a live chat and email support team at Automattic, and this is my entry for the Week 1 SupportDriven writing challenge: “History: Our history shapes us — what path led you to Support? Was it a planned career? Or did you happen upon it?”

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