Farewell, Automattic

In hindsight, making my title “Release Candidate” when I joined the company seven years ago may have been a mistake.

All the “worst” things that have happened to me in life have turned out to be gifts I had no idea I needed until long after I received them.

The last one of these gifts was in July 2023, when my wife collapsed in our driveway from internal bleeding after an IVF procedure. Ninety minutes later she was in the OR having a lifesaving operation, and I was given 2 1/2 hours (an eternity) to wonder if it would be successful. There is an irreplaceable gift of perspective to be given a window into fully considering what your life would look like if your spouse died today, and then be able to walk away from that window and resume your life. For me, it shattered any illusion that I can make the world safe for the people I love; the only thing I can offer is that whatever happens, we’ll do it together. It’s that knowledge that gives me the greatest sense of peace as I start this new chapter.

Publishing over Perfection

Interest over time

There’s a cycle I’ve noticed in publishing my own thoughts.

Initial interest starts pretty high (otherwise why write about it?)

This rises steadily as I wrap my hands around the idea, feeling it’s edges. Gathering adjacent thoughts and ideas. Building a holistic view that explains in explicit terms of what I instrinsically feel is true.

Once I draft these thoughts, the loop feels complete. I’ve understood the topic, and communicated it. Of course there is much deeper I can go, but I’ve reached a natural milestone. In seeing my demonstration of understanding, the concept no longer holds power over my interest, which drops close to 0.

Leading as a Belayer

In rock climbing, a belayer is a partner who stays on the ground holding the safety rope attached to the climber’s harness. It’s a simple metaphor, but one that I’ve found a lot of mileage in lately.

Rock climbing belayer (Photo by Allan Mas on Pexels.com)

There are 3 main things I draw from this metaphor:

  1. It’s the climber’s journey
  2. The role & responsibilities of leading
  3. It’s a supporting role

It’s the climber’s journey

They’re doing the work

It’s up to the climber to choose whether they want to climb and initiate the process. Something my professional coach asked me that was really illuminating is “what do you want from your career at this stage of your life?”. I like that framing because it highlights the temporal nature of the answer. It’s ok to go through times where your career takes a backseat to other things in your life – and it’s equally ok if you want to challenge yourself and invest more heavily in your career. The important part is that the climber you are leading identifies this for themselves. Your role as a belayer is to provide support for whatever they choose.

Making Failure OK

A few months ago I overheard my colleague Andrew Spittle say something that stuck with me:

I primarily think of risk tolerance as a question of, “When something bad has happened how quickly do we know about it and fix it?” and not one of, “How few bad things happen?” It can be a subtle difference but if we start with the latter framing it’s going to lead us to make less optimal decisions.

The 80/20 Rule of Webcam Quality

Desk Front

One topic I’ve been monitoring during the pandemic is the availability of tools for producing better webcam quality. With so many more people suddenly logging onto Zoom to spend time with family and conduct their work, I’ve been waiting for capitalism to step in and offer better options.

Despite some interesting kickstarters, I haven’t seen what I’m looking for yet. Something elegant, affordable, and portable. That doesn’t mean there aren’t options.

Fighting Complexity Bias

Why is this so complicated?

Why is this so complicated?

The easiest time to identify unnecessary complexity is when you’re an outsider. Before you’ve grown used to the way things have always been done. It’s the hidden value of not knowing. Your judgment isn’t clouded by knowledge. All you have is reasoning.

That’s when you’re in the mindset to ask the right questions. The high-level ones. Why is it like this?

A Reason To Write

I recently signed up for a writing course, and shared with a few friends that I was thinking of writing online.

“Huh, that’s interesting. What are you going to write about?”

I’ve gotten some version of that response from everyone I’ve mentioned it to, and it’s a good question. Finding the answer is what held me back for 9 months from when I decided it was something I should pursue to taking the first steps.