"Hi, my name is Troy, and I've been working full time since I was 13 years old. Well, except for the last year. I've been taking a break but..."
Ok, wait, that's not the best hook. Lets try that opening again:
"Hi, my name is Troy, and I’m recovering from the tech industry’s favorite drug: momentum."
Yeah, I suppose that's an odd way to open a job search update post, but after a lifetime on the clock that's what it feels like.
Diary of a Teenage Line Cook
"Hi, my name is Troy, and I’ve been on the clock since the eighth grade."
At 13 years old, I started my journey as a line cook in a mom-n-pop BBQ restaurant in St. Louis, Missouri. I worked long days flipping racks of ribs, ten at a time, as fast as I could. Somehow I ended up building violins for a living, then went to China to teach English, and then I was in Portland building scrappy startups with hundreds of blinking servers in racks, and then touring the world talking about writing, and basically it's just been one long unbroken line of employment since the BBQ shop.
"Hi, my name is Troy and I'm a recovering full time employee."
Back in 2014, I wrote a post called Developer to Documentarian. That piece was a manifesto. It had a defined destination: I was joining Twitter to launch a cultural revolution around documentation. I knew exactly where I was going, what I wanted to fix, and how I planned to scale it. It was highly mission-driven, built on the sheer inertia of wanting to shape the culture of an entire industry... NBD.
For the next twelve years, that’s exactly what I did. After cofounding the Write the Docs conferences/community, I spent ~7 years building out Twitter's engineering culture and internal infrastructure, and then went on to try to bring that same wisdom to other places. But the last few years have been objectively insane for us storied technologists. The advent of pervasive AI tooling is by far the biggest disruption I've seen to the tech industry, and not really in that "good disruption" kind of way. Like in a scary destructive sort of way. It's one of the reasons I stepped back last year, just to watch and wait and see what emerges after the dust settles.
"Hi, my name is Troy, and I finally closed all the tabs."
The other reason was family and personal health challenges. That 35-year sprint caught up with me. I needed a break. My body needed a break. Not just to rest, but to completely halt the momentum.
I haven't been completely idle for the past year, and I will talk more about that in future posts, but I have been very much moving at my own pace and being careful about who and what I prioritize.
There and Back Again or Something Something LoTR-ish?
When I first started thinking about this new chapter, and this post, I was riffing on the classic There and Back Again framing. But I'm no hobbit. I have no desire to return to a tidy, static Shire and settle down, and I’m definitely not ready to "head West" just yet either.
My arc aligns much closer to Gandalf/Olórin.
"Hi, my name is Troy, and I'm following my nose."
In the LoTR lore, Gandalf the Gray was a wanderer who walked among the different realms, listening, learning, and gathering context for a long time before he rallied up a band of halflings and misfits to save the world by proxy. After that he became Gandalf the White realizing all of his power directly, taking over the magic tower, and all that. In my case, I'm sort of doing that in the other direction. I’ve already done the high-impact, institutional "White Wizard" phase of scaling massive systems. At this point in my story, I feel more aligned with the wandering wizard, heading down the road without a specific destination in mind.
Strategy: Choosing the Journey Over the Destination
"Hi, my name is Troy, and I will arrive precisely when I mean to."
To be completely candid, my motivation to return to the traditional world of work has been zero. After helping my mom beat colon cancer, moving my developmentally disabled little sister into supportive housing with 24/7 care, getting my kid off to college in DC, and personally surviving a heart attack shortly thereafter, I have learned that stress no longer can have a place in my life. Like, medically, if I want to continue to live, I cannot return to the day-in, day-out stress of productivity-obsessed workplaces, nor am I attached to the standard capitalistic markers of a job hunt or career path.
Instead, I am looking for roles, products, and environments that spark genuine joy and motivation. I am approaching the job market detached from outcomes. I don't care if I get replies (although it's nice), engage in interview loops (but I'd love to talk to you), or receive handsome compensation offers (the money will take care of itself). My focus is entirely on the journey of finding what makes me want to build again.
"Hi, my name is Troy, and I don't want to build software just to sell software."
Tactically, I’m steering my "gandalfy powers" (all those strategies built from decades at the intersection of engineering culture and complex platforms) toward a distinct paradigm: Tech Enablement.
I want to walk into spaces that aren't suffering from too much technology, but are suffering from not enough. I want to explore verticals like climate science, sustainability, carbon management, manufacturing, and energy grid simulation. I want to help people who have data but don't know what to do with it, and help people who don't have data yet to build it, so that they can use all this fancy stuff we've been building in the tech industry. I want to be in places where software isn't just a commodity to be shipped for business' sake, but a high-leverage tool that enables non-software experts and scientists to scale their critical, real-world research.
Failing that, I am looking for tech companies that are doing something genuinely interesting, things that will bring my eyes into focus, not send them rolling into the back of my head like a scared armadillo. I won't know what it is until I see it, but when I do, I'll make note of it and try to articulate why.
Documenting the Path in the Open
"Hi, my name is Troy, and I’m open-sourcing my cover letters."
Because writing and community building are central to how I operate, I plan to treat this job search as an open research project on my blog.
The process will look like this: whenever I find a company or an active role that stands out to me, I’m going to write it up in a dedicated post and explain my thinking. I’ll break down why the problem they are solving excites me, how a software platform can step in to amplify their work, and what a healthy engineering culture might look like in that context. The blog posts will be my de facto cover letters.
This serves two crucial purposes:
- For me: By analyzing these roles out loud, the commonalities will naturally emerge. It will help bring into focus the exact shape of what I'm being drawn to. It will help me answer "what do I want to do with my life"?
- For future collaborators: When people from the companies I’m engaging with inevitably visit this blog to see who I am, they won't just find a static resume. They will find a detailed document of exactly why I think their mission matters and how I can fit into it.
So, if this is interesting to you, feel free to follow my lil bendy walk about through the mid-AI-apocalypse software industry landscape. Let's see what we find along the way.
"Hi, my name is Troy, and I’m leaving this tab open..."