So, big news: I’m off to a new job at Datadog, working on their CoScreen screen sharing tool 😎. I’m gonna be working remotely from Vancouver, which will be interesting because I’ll be dogfooding CoScreen as I work on it.

It’ll be good to work on native software again. It feels like the vast majority of jobs today operate at a level of abstraction where the OS doesn’t matter much; when you’re writing REST services it’s rare that you actually interact with the OS itself, right? CoScreen is very different in that it’s native software that needs to do lots of interaction with the OS to provide a great UX. Which is exciting and fun and cool, at least until I get bogged down in the details of GDI or whatever 😅.

I handed in my notice; my last day at work is next Wednesday. My employer for the last 2 years has been excellent to me, but I’ve been itching to try something new.

I don’t have a new job lined up yet; I’m planning to use this time partially as a sabbatical, and partially to see what’s out there on the job market. A “serendipity break” during which I will actively explore different possible paths.

One of my plans is to explore the intersection of native apps and web UI; I’ve done some promising experiments with that and it would be a good excuse to overhaul ReiTunes. I’d also like to build some new tools for working with the best database. Here we go!

I’m taking a self-funded sabbatical after 8 years of working full-time. It feels like the right thing to do at this stage of my career.

I’ve had an unusually stable career for a software developer. When I graduated from university in 2011 I interviewed at a few places, including a mid-sized investment firm. I didn’t know anything about finance and the… rustic state of their website was a little concerning, but the people seemed great. So I took the job, and told myself I’d stick around for 2 or 3 years.

8 years later I was still at the same company. Orbis offers a lot of different opportunities; I wrangled big financial data systems, ran a small team, got my hands dirty building a modern web stack, and worked in London and Cape Town. It was a blast, and I’d highly recommend Orbis as an employer.

Still, after 8 years, it’s time to try something new. I miss the open-ended learning that’s so common in school, and I want to explore my technical interests with no regard for immediate relevance to my day job. Gianfranco Chicco’s description of a “serendipity break” really resonated with me:

In the note I sent out to my friends and network I mentioned that I’d be undertaking a Serendipity Break, which wasn’t a nice way to say that I wasn’t going to work for a few months but that I wanted to actively explore different possible paths.

In the book The Craftsman, sociologist Richard Sennett describes how “skill builds by moving irregularly, and sometimes by taking detours”, which is akin to keeping the Serendipity Engine in perpetual motion to encourage the strengthening of current skills and allowing the development of new ones.

Leaving a great job at a great company was a little scary, but I think it’s necessary for my long-term growth. Reading about Joel Spolsky’s sabbaticals helped a lot; it’s reassuring to see successful developers following similar paths.

My last day at Orbis was July 27th, and since then I’ve been trying all kinds of things. I’ve been diving into database internals, rewriting this website, and even learning Lisp/Scheme. I’m not exactly sure where my interests will take me next, but I’m looking forward to finding out.