Last week, I had the chance to speak at two very different events, and the contrast between them really stuck with me.

The first was all a traditional vendor conference-  enterprise-level, built around a well-established product with over 40 years of vendor-driven development. Think polished sponsor tables, polished shoes, and more than a few suits in the crowd. The second was a grassroots community event born from open-source tools and innovation driven almost entirely by the user base. Casual dress code, casual vibe, and deeper command line engagement vs. services and low-code solutions.

Both events charged about the same for admission, but that’s where most of the similarities ended.

You could see the difference the moment you walked into the keynote sessions, (which full admission – I was one of the keynotes and I feel my topic wouldn’t have gone over well at the grassroots event).  At the enterprise event, attendees wore jackets and skirts, chatting politely over breakfast while exchanging business cards and LinkedIn profiles. The community event? Hoodies, jeans, t-shirts, and the occasional sticker-covered laptop. Networking happened over WhatsApp and Bluesky, not business cards.

At the first event, I didn’t attend any sessions beyond my own. Most of the content focused on services and marketing focused products and features—great if you’re an executive, but not much for someone craving deep technical knowledge. The community event, on the other hand, packed in five highly technical sessions in one day (not counting the one I gave). Each session felt like a mini hackathon—practical, inspiring, and immediately useful.  Although my keynote was considered riveting for the event and well-received by the students who had attended, I hope the subsequent day keynotes balanced out from my “rebellious” view of AI to promote vendor products.

And that’s the difference. The enterprise event was clearly built for the people who sign the checks. Nothing wrong with that—sales teams love these environments, and I get it. If you're not pitching to the person with the budget authority, you're not making a sale. But for me, the community event was where I wanted to be. I learned something new. I left inspired. I regretted not attending the whole thing.

Here’s the thing: many organizations are leaning harder than ever into attracting that C-level audience. It makes sense. Demos get polished, messaging gets fine-tuned, and events become showcases more than learning spaces. But for those of us on the ground, actually doing the work, what we crave is connection—peer collaboration, shared insights, real technical depth.

I get bored easily – I’ve never shied away from my AuDHD self, recognizing the capabilities, as well as the shortcomings the mindset brings. Most enterprise events only hold my attention because of the people I meet, not the content. What keeps me coming back are the conversations, the hallway chats where we dig into what’s actually working, what’s not, and how we’re solving real-world problems.

When everything becomes about the sell, and I’ve been told many a time that WE’RE ALL IN SALES, we lose a big piece of what makes tech so exciting. That’s why community events, local meetups, and grassroots conferences matter so much. They're often the only spaces where deeply technical folks get to truly engage, especially since we’re usually last in line for training budgets and time off.

The truth is, most vendors don’t want us kicking the tires too hard. It’s safer to impress a VP with a shiny demo than to let a technologist dig in and ask the tough questions. But that’s what we do. We tinker. We test. We explore. That’s how we gain the confidence that a tool or service will actually make our jobs easier.  I’ve never been one to be able to stand behind a feature or product I didn’t truly find value in or value.

And that’s what I love about grassroots events—they still make space for that kind of curiosity. They remind me why I got into tech in the first place.  I will always be part of both types of events, but I have to recognize my excitement, my renewed energy and investment when attending a deep technical conference.

Have a great week,

DBAKevlar out.