Change isn’t an event it’s a process

Reflections on leaving Medium

After nearly 5 years I’ve decided to leave Medium. It’s been an incredible personal and professional journey, and I’ll be forever grateful to Ev for the opportunities and challenges he’s given me.

It wasn’t an easy decision; I love the team and truly believe that the mission is more important than ever. While cynics joke about hot dogs, burritos, and self-help, I’ve found it rewarding and enlightening to see how people use the platform, and my worldview has forever been changed by the first-hand accounts of racism, misogyny, war, and much more.

But nothing lasts forever. Five years is a long time: I have a 2-year old daughter, and am a few years from 40. There are other lessons I need to learn and challenges that need to be sought. So as Medium embarks on the next phase of its journey, it felt like the right time for me to move on.

When looking back at my time at Medium, my experiences fall neatly into a few categories. So in typical Medium fashion, here are three earnest vignettes reflecting on my time here.

Act 1: Faith in craft

Despite what I accomplished at Google I always felt like an imposter. I was brought in as someone who specialized in JavaScript and building web applications, things that in 2005 Googlers didn’t consider “real engineering”. But I absorbed as much as I could, learned from those around me, and left as a pretty good engineer who could get shit done.

The first phase of my journey at Medium was learning to engineer outside of Google. Both discovering the landscape of tools and frameworks, but also taking a fresh look at the development practices I’d held as gospel. What changes when you build for thousands instead of millions, when your codebase is touched by 10 people instead of 300?

I came to believe that the velocity vs. quality dichotomy was harmful, and the question should better be phrased in terms of depth of implementation. To use an analogy (I can hear the eyes rolling at Medium HQ) of crossing a river. If you are just one person, you’ll bundle up your belongings, grab a sturdy walking stick, and wade through. If you are a group of ten, you’ll string up a guide rope. If you are an army battalion, you’re going to build a bridge. But whether you are stringing a single rope or building a bridge, you still do your best to tie a decent bowline.

Act 2: Manage like a gardener

I never wanted to be a manager. I think it stemmed from a cultural belief that blue-collar work is real and virtuous, while white-collar work is overhead and “selling out”. Of course software engineering isn’t true blue-collar (we have it way too easy) but we still talk of coding as the only “real work”. And for many engineers our industry hasn’t done a good job of explaining the value and expectations of a good leader, which reinforces this notion.

When I stepped in to lead engineering, we were a bunch of engineers shipping product. What we needed was an engineering organization. At first, I didn’t see myself as a manager, just someone responsible for solving problems. We had junior engineers who needed support, there was infrastructure that needed ownership, we needed to refine our hiring process, and as we broke into sub-teams we need to clarify roles and responsibilities.

Over time, as the team grew and problems emerged, we solved them one by one. I tried not to be too predictive, being careful to avoid bureaucracy, and listened to the team for what they needed.

More gardener than architect, I saw my job as creating an environment that allowed everyone to do their best work. It’s been the most rewarding work of my career and I’m proud of what we created.

Act 3: Post modern

Engineering was the biggest team, so we often needed things before other departments (e.g. feedback, professional development) or had the largest constraints (e.g. seating plans, team structures, internal comms). This led to close collaboration with functions and teams outside of product development, which was a fun change of pace.

I approached these organizational design questions with an engineering mindset: go to first principles, consider goals/non-goals, assess various options, and ask whether we are actually solving the right problem.

All too often people cargo-cult practices from their previous company. If you look at the big tech companies — Google, Amazon, Apple, Facebook — they all operate in different ways, sometimes subtly so. You can’t just pick and choose things out of Netflix’s culture deck and expect them to work perfectly for your org. You need to think about these issues in the context of the system, looking to the de facto culture that already exists, and paying attention to the constraints of your business.

When we started talking about moving off Holacracy, I jumped in feet first. I spent nights and weekends reading literature on organizational design, theories of human development, psychology, and group dynamics. I tried to understand the intent behind the core principles of Holacracy and of Medium, what was important to us and where were there gaps. The system we designed and rolled-out wasn’t perfect — and is still incomplete — but it didn’t get in the way of the work and paid more attention to the human elements of the workplace.

This phase taught me that there’s no one-true-solution to most of the problems we face when building teams and companies. We’re dealing with complex systems and solutions need to take into account the human participants: their aptitudes, preferences, values, and their interrelations. As in engineering, we need to design contextually appropriate solutions.


It’s a strange time in America. It feels weird to write this retrospective when so much of the country feels like it’s changing, and I should be looking outward not inward. But I wanted to say farewell amid the turbulence to an exceptional team who I’ve come to feel incredibly close to.

In my parting email, I recalled how I’ve had the privilege to bid farewell to a number of talented people over the years. Often they would approach the conversation guiltily, feeling like they were letting me down or abandoning the team. I’d tell them that this industry likes to spin a narrative that companies are families, and while that has some positive aspects, the negative side is that when you leave, it feels terrible. It feels like a divorce or a betrayal. But it shouldn’t be that way.

I prefer to think that we are all nomads in the wilderness; all on our own paths. Sometimes paths align, and we walk together for a while. We work together; help each other out. But we know it’s not forever. Ultimately we have different destinations, and at some stage, we will need to say goodbye.

When that time comes, it will be a sweet sorrow. We’ll reflect on the times we had together, but be joyous and hopeful for the paths that lie ahead.

So, this is my fork in the road. This is where we part ways and I continue my own journey. I’m not ready to share where I’m going yet, but I’m excited for the challenges that lay ahead.