Support Driven Summit: a Career Peak and Pivot.

Last week I experienced a defining moment in my career: I was asked to speak at the Support Driven Summit in Los Angeles. It was a great time of being around “my people” and contributing to the community of folks in whose waters I have swam for more than a decade.

Support Driven is a true community: one that I wish I had invested more into over the past few years. It was a delight to take the stage and talk about the principles of technical support and customer service.

But it was also a turning point in my career.

I haven’t talked much about it online, but in December I started a dream role in a related-but-also-completely-different field.

That story starts years ago, though I didn’t know it. We were (in my role as a Director of Technical Support) in a meeting that had an ice-breaker question. The question was “if you were given a billion dollars, what would you do?”

As I listened to the answers from around the group, my mind was floating around searching for what my answer would be. If I didn’t have to work for a paycheck, what would I do with my time?

As I scanned my memories and life experiences, a theme emerged. Every time I’ve truly been passionate about anything in life, one thing has been true. Across diverse fields, in large contexts and small, one consistent low hum of excitement swells when I am teaching, or more specifically when I am watching someone learn or experience a breakthrough related to learning.

If I could bottle up and sell the emotion I experience when somebody who didn’t know something catches on and learns (and perhaps more fundamentally sees their own capacity for learning), I’d have that billion dollars several times over.

I like learning things, and going things. I truly light up when I get to see others learn things, and be a part of facilitating those “aha moments.”

So when the question got around to me, I said “I don’t know what I’d do, but it would be somewhere and somehow related to education.”

On December 1st I started as the Director of Technology for Colearn Academy, a K-12 online charter school. My whole job is to create, maintain, and extend the systems that cultivate a space where students can experience that intoxicating emotion of learning. I get to set up teachers to create space in students’ lives to get little glimpses of how fun it is to know things.

So why haven’t I changed my job title on LinkedIn, or talked much about my new role on the internet? Perhaps because I was still holding on to my past career. I’ve been defined vocationally as “The Support Guy” and have carefully cultivated myself into a thought leader on technical support and customer service. That wasn’t something I was ready to set aside.

In certain circles (especially in the WordPress software space) my name has become synonymous with “Support.” People will loop me into conversations any time someone has a “hot take” that’s related to customer experience or support. I love that.

The Support Driven Summit was a loud signal that I could, if I so chose, continue in that role of “thought leader” in technical support.

Not to brag, but I had the entire room hanging on every word of my presentation. These were not just folks that I looked up to any longer. This was a room of my peers.

• Heads of Support
• VPs of Community
• Chief Executive Officers

Folks in the room represented hundreds of millions of customers and users, gigantic teams of agents, and are currently leaders in companies you’ve heard of. And I was leading them.

But bubbling under all of it was that dream job. The one I already have. The one that would (maybe) make these Customer Support leaders think differently about me.

I’ve already been out of the corporate technical support game for long enough that, realistically, within just a few more months my experiences are just not going to be relevant to that room.

So you’ll see my posting more about education and I’ll be changing my job title on LinkedIn. The Support Driven Community (and the WordPress Community) will still be a part of me and my story, and I even hope to do some stuff with them in the future.

But it’s time for me to start swimming in the Education waters, and surrounding myself in that world. What a treat to be a newbie: I get to go and learn how to create these systems.