A flat-style digital illustration of a developer in his office. Christmas tree on desk and a summer scene out the window.

Merry Christmas from The Cynical Dev.


As we head into the last working day of the year for many of us in New Zealand (at least in IT), today also happens to be my final day on my current contract.

That feels like a reasonable moment to pause and look back.

This year ended up being a bit of a study in how software delivery actually plays out in real organisations in the real world.

I started the year on a contract working on a long-running migration from some very old JBoss EAP and Java into something more modern. It was challenging work, often involving bridging incompatible versions and dealing with technology that had been doing its job quietly for a very long time. From a technical perspective, it was deeply satisfying. These weren’t glamorous problems, but they were real ones, and solving them felt worthwhile.

Later in the year, I moved into a new contract and spent the remainder of the year there. I took on more of a tech-lead role, helped reset estimates to something closer to reality, and focused on getting working software and prototypes in front of people. This was in an environment that made delivery harder than it needed to be, but despite that, we were able to demonstrate progress. The team valued that, and I’m proud of what we managed to do within the constraints we had.

Alongside client work, I also started a couple of things of my own.

I launched Private by Design, focused on privacy education for parents and schools. I wrote a number of posts and resources and made some great connections before deciding to pause it rather than spread myself too thin. That decision felt like the right one at the time.

I also started The Cynical Developer, which has been a genuine source of energy this year. It’s become a place to write, spot patterns, and test ideas that have been rattling around my head for a long time. Running the first Career Course Correction cohort was a particular highlight, both for the person involved and for the insights it gave me.

Community has been a big part of the year too. I spoke at a local AWS meetup, attended the Canterbury Tech Summit, and put myself forward as a nominee for a board position with Canterbury Tech. I’m especially grateful to Liz Foxwell-Canning, MInstD, for the encouragement to step up and give that a go.

Through writing, events, and side projects, I’ve also made a number of new connections and friends this year, a good reminder that this industry is still full of thoughtful, generous humans.

More recently, I had the chance to appear on the Tech Waka Podcast & Leadership Collective podcast, which was an absolute blast. I’m looking forward to being more involved in that space next year.

If there’s a theme to the year, it’s probably this: organisations still struggle mightily with software delivery. Agile remains widely adopted and poorly understood. A lot of effort goes in, and not nearly enough working software comes out. That’s something this year reinforced for me again and again.

As I head into the break, I’ll be doing something that’s surprisingly new for me after 20-odd years in the industry: taking time off without having the next role already lined up. There’s a bit of uncertainty in that, but there’s also optimism. I’m looking forward to a proper rest, and I have confidence in my ability to deliver value wherever I land next.

For now, I just want to wish everyone a restful end to the year. Merry Christmas, and I hope the new year brings a bit more clarity, and a bit more working software, for all of us.