Weaponizing hyperfocus: Becoming the first DevRel at Tailscale

Photo of Xe Iaso

Hello, world! I'm Xe, and I am the first Developer Advocate at Tailscale. I'm a prolific blogger, VTuber, and an avid technologist. I started working on Developer Relations (DevRel) at Tailscale in Spring 2022. Today I'm going to trace through the history of DevRel at Tailscale and how working on DevRel has transformed a part of me from being an impediment that I was at war with into a catalytic asset that makes my job easier.

landscape, fuji-san, pagodas, space needle
Image generated by Waifu Diffusion v1.3, prompt: landscape, fuji-san, pagodas, space needle

In Spring 2022, I sat down and started to take DevRel seriously at Tailscale. I had heard about the practice in the past, but I had never done it before. I knew that a lot of it was talking about a product to people and finding new and interesting ways to use it, but a lot of that seemed too vague to really have any solid place to start from. It's like walking into an empty room and having no idea where to start decorating.

At some level though, it felt right for me in a way that I have difficulty describing. It's the same feeling of it being right that I get from working in software in the first place. It felt like the type of rabbit-hole you could spend an entire career in. After talking it over with some peers, I found out that what I was doing was already a split between my normal job and DevRel. I was talking about Tailscale in places. I was figuring out new and interesting ways to use Tailscale. I was advocating for developers to build things on top of Tailscale. It was working too, so all I had to do was do more of it.

I got permission from my manager to get a 50/50 split between what I was doing (work on internal tooling that was not sparking joy) and this new experimental DevRel thing. I took the leap and I don't think I am ever going to look back.

In 2022 I published a lot of projects, tools, and ways to use Tailscale that still come up every so often. I made an nginx-auth tool for a blogpost and it comes up in sales calls every so often. I was originally going to make the GitOps for ACLs tool into something for a blogpost, but it ended up becoming a fully fledged product feature and something that is currently in use by developers all over the world. I managed to expense a scalped Steam Deck off of eBay and wrote up how I figured out how to install Tailscale on it.

One of the primary challenges in starting out with something new like this in an existing company is that you need to define what DevRel means. You need to have an idea that you can use as the main point of alignment so that you and the people following in your footsteps can all focus on different aspects of that same idea. When I was thinking out what DevRel could mean, one of the topics that kept coming back up was the idea of Tailscale being everywhere with you so you can get back home. This was the heart of the Steam Deck article, among other ones. One of the next ideas I worked under was the idea that Tailscale knows who you are, so apps can easily know who you are too.

This is the heart of how nearly every one of the Tailscale as an authentication factor tricks works. Tailscale already maintains a list of IP address to user mappings. In order to connect to a service on your tailnet, your machine has to have the right private key. This can let you construct an identity factor for authentication. nginx-auth and proxy-to-grafana build on top of this idea, and that becomes a fundamental building block for future work. In one of my own personal projects, I've been able to rip out over 150 lines of boring authentication code because it was handled for me with Tailscale.

I made a measurable impact with my work and it helped to spread the word about Tailscale and it's still paying dividends to this day. The Steam Deck article gets mentioned in sales calls. I cannot think of a better measure of success than that.

In late 2022 I hit a point where there was enough work to be done that I wasn't able to keep up with it. I was writing, hacking, and advocating nonstop and I really needed people to help me. This ended up with the DevRel team getting formed and my teammates have been a blessing, even before things have gotten up to full speed.

the avatar for Xe Iaso

At some point in 2022 I ended up coming up with the joke job title of "Archmage of Infrastructure" with the intent that I would give people a different answer every time they asked for it. For some reason or another, the Archmage title stuck and now I'm the first Archmage at Tailscale. My life is great.

In the process of doing this, I also had a unique opportunity to weaponize something that had previously been a horrible vice: my tendency to hyperfocus on things. This tendency has been my savior and my jailor for most of my professional career. The most horrible part about it is that I don't have control over what it focuses on. It's like an itch that you can't ignore because you feel absolutely compelled to scratch and not scratching it physically hurts or can be impossible. It's great when it focuses on something that is "good" to focus on (such as the project I was assigned to), but it was horrific when it focused on something that was "bad" to focus on (such as literally anything else but the project I was assigned to). This has both saved my ass and gotten me into trouble countless times. It's why I've had such a rocky career.

Working in DevRel has offered me a chance to be able to weaponize this hyperfocus to help meet the needs. I have a few projects going on at once that I peck at as reality demands. This gives me the ability to wield my hyperfocus to meet my needs rather than being happy when it meets the needs of my employer.

This gives me the freedom to focus when I can and to not focus when I can't. This is an unparalleled level of inclusivity I have never had at any company I have ever worked at and this should be the standard. The DevRel team has grown from a single person doing things on the side into a team and I want to use this opportunity to help create the kind of team that I want to work for. I want to help create a culture where things like hyperfocus are seen as assets instead of sometimes-useful impediments. I want the DevRel team to be a viral force of good, and I feel that one of the ways to start that process is to create the kind of team culture that shows their morals rather than just writing them on a sheet of paper and saying "hi these things exist, please believe us uwu". Actions speak louder than words. I feel that this should be DevRel at Tailscale and I am going to do my best to help make that happen.