Part 2 of 3: The Long Game
Part 1: The Short Bus and the Fairway
I need to tell you something about myself before this piece makes any sense: I’m not a natural joiner. I’m definitely not a natural follower.
In high school, my teachers pleaded with me to join something. A club, a group, a something so that I had belonging. It’s not so much that I’m a maverick who has to go his own way — it’s that I tend to enjoy exploration. I value my quiet time. I find pleasure in small groups. I’m good with silence. In a world that is full of FOMO, I’ve described myself as having FOBI. The Fear of Being Included.
I was raised this way, I think, by parents who did their own thing. My intention is not to judge those who enjoy inclusion but simply to draw the distinction that there are those of us putting ourselves out there for our own reasons. And those reasons might not be the ones you’d expect.
I hate labels on humans. Not for the reasons that they seek to provide comfort and inclusion — which many do — but for the fact that they limit. I myself am an introvert. A term for those who recharge in private. I renew myself with quiet, with time with my immediate family, or a simple round of golf. I don’t finish a long day and desire to join a dinner party. Socializing drains me.
But the label of introvert has become so strong in tech that everyone claims it because they’re antisocial and “that’s just how tech workers are.” The truth is more complicated than that. I’m an introvert who is social but needs his space and time apart. I love connecting with others. It’s why I’m on social media and at events.
Here’s the thing that took me years to understand: I cannot have the conversations and relationships that I have online in real life most of the time. My neighbors are construction workers, teachers, small business owners, and many other vocations. They don’t want to talk about the existential threat or benefit that AI and agentic coding is having on the work of a software developer. It’s not dinner party conversation. So the community I built online wasn’t a substitute for real life — it was an extension of it that I couldn’t get anywhere else.
Somewhere around the 15-year mark of my career, I started to really understand that people — myself included — and their experiences are not fungible. This is hard to wrap your mind around until you gain more perspective.
For me, leading teams opened my eyes to this concept. Home ownership did the same. No two tile installers are the same. If you’ve laid tile or paid someone to lay tile, you know what I’m talking about. The difference between a craftsman and someone who just shows up is visible in every grout line. That distinction exists in our industry too, and for a long time we pretended it didn’t.
It was in this period where I started paying attention to broader communities, social media influencers, and my personal brand. I began attending tech conferences, which broadened not only my mental capabilities but also my social ones. Yes, I’d lived in a number of places across the USA. Yes, I’d always had a diverse social group. The short bus and the fairway taught me that friendship knows no shape, size, or capability. But I hadn’t been exposed to people in my field who were truly global. Truly living and thriving and struggling in other parts of the world.
After I was several conferences in, I started to lean in. I was curious about getting involved in some of these communities. I had thoughts of writing and sharing on my own platform. Not for attention — but because I felt that all those years ago people had invested in me, and I wanted to do the same on a different scale. I’d run a blog for years, but it had leaned personal. Facebook sort of erased its purpose, but I kept the domain I’d purchased in the late ’90s. I made the decision to keep the format but change the content. I began writing technical articles with sample projects centered around my current passion and expertise in AWS.
I cautiously but excitedly tested the waters. I was consistently writing, speaking, and meeting people, but also giving my free time to advocating for things I was passionate about but had no control over their outcomes. Over time, I’d even argue I became a fan of what I was writing and speaking on. I enjoyed the dialogue, the debate, the sharing of ideas. One of the reasons I stepped out from behind the keyboard was to engage. The exchanging of ideas is something I’m always interested in doing.
I can remember several key conference conversations that had more impact on me than any session I ever attended. There was one at re:Invent where a developer from São Paulo described building serverless applications on infrastructure that cost him a quarter of what I was spending — and the constraints made his architecture better than mine. There was a hallway conversation in Nashville where someone ten years my junior challenged an assumption I’d held for a decade, and he was right. Those moments don’t happen in sessions. They happen in the spaces between.
As a technologist, I find it imperative that I’m constantly challenging the status quo. Reviewing what I understand. Validating or invalidating it against what I might disagree with or not understand.
Something started to change in me though. There wasn’t an event, a trigger, an epiphany. I slowly found myself retreating. Not backing up. But stepping aside. Venturing out on my own path again.
If I put my finger on why, it was everything at once. It was the cloud wars. It was Serverless vs. Kubernetes. It was AI and vibe coding. It was the clickbait. It was genuine noise being thrown into my feed. It was the gatekeeping of certain communities — because I wasn’t a systems engineer, or because I wasn’t involved heavily enough in open source, or because I didn’t fit into some other box that was required for entry. I’d been sharing my perspective as a CTO and practitioner for years, but that apparently wasn’t the right credential.
Back to the labels. Back to the tribes.
Knowledge is free. Anyone should be able to obtain it. And in the tech world, we often speak of being open, collaborative, and accepting. But what I started to discover was that tribes and lines actually existed. Constructs that I’d been staying away from throughout my career — and more importantly throughout my life — started appearing in spaces I didn’t expect. I began to notice behaviors that I expected on other platforms rendering themselves where I thought we were better than that.
I’m not so naive that I haven’t seen this play out before in deep, dark spaces on the internet. I’ve been around since BBS, Usenet, and IRC. But the acceleration into public spaces like LinkedIn, the degradation of X, the launch of BlueSky and the migration to that platform — it all happened to coincide with what was happening in my own world. It all just started to be too much.
The FOBI I’d carried my whole life started to feel less like a quirk and more like protection. The part of me that never wanted to join was watching the joiners tear each other apart over tools, platforms, and ideologies. And I thought: I stepped out from behind the keyboard to exchange ideas. Not to pick a side.
The last layer in this evolution was the work I did establishing a public brand and identity. I spent months documenting what I most closely aligned with and how I wanted to present myself to the world. “Uniquely genuine and resourceful technology creator” is not just a phrase that describes me — it’s a phrase I identify with. It became a filter. When the noise got loud, I could hold something up against that statement and ask: does this serve who I am? Does this fit?
More often than not, the answer started being no.
I’m not here for the transactional. I’m here for the detail. The experience. The relationships. And the current landscape feels very transactional. Very tribal. Very hostile. Maybe it’s time for me to get out and visit an event again, but conference attendance as a consultant and business owner is expensive and rarely a revenue producer. Perhaps the algorithms are stacked against me and the content I actually need — and the people I need to hear it from — are just buried behind some AI-curated feed.
Or perhaps the FOBI was right all along, and the real community was never the platform. It was always the hallway conversation.
Next: The steam drill arrived. Read Part 3: John Henry at the Keyboard →