A Year with Redgate, A Lifetime with Oracle

I was caught off guard last week when the “Congratulations on your work anniversary!” messages started rolling in on LinkedIn. It had slipped my mind that it had already been a full year since I began contracting with Redgate back in May 2024. And, true to form, LinkedIn, always eager to simplify the complexities of tech careers and notified my entire network that I’d officially hit the one-year mark, although I hadn’t started full-time till the beginning of October.  It can almost feel like an identity crisis as you perform so many roles for different organizations –  thrilling and satisfying for me, but very confusing for everyone else you speak to.

In May, I was still serving as Director of Data and AI at Silk, and to be honest, I was doing what I do best – keeping busy. I’m the worst bored person on the planet, so I was filling up my schedule with about 10 hours a week of additional contracting work. Redgate was just one of the organizations I was supporting. I had no idea it would become more than just a side gig or that I’d find myself diving back into Oracle technology in the process.

My journey with Oracle started 30 years ago. Like many long-term relationships, it was a love-hate affair. When I was working desktop support at US West, nobody wanted to touch software that connected to a relational database. Whether it was Sybase, SQL Server, or Oracle—it was left to sit quietly in the “not it” zone. Naturally, as someone who thrives on a challenge, I picked up every one of those tickets.

With no formal training, I relied on curiosity and determination to solve what I could. That determination paid off – Oracle ended up sending a specialist in after I’d written a script to allow Windows 95 users to toggle between 16-bit and 32-bit Oracle apps by switching out the WIN.INI file. At the time, this was no small feat to do this with my ugly BAT scripts. After reviewing my solution, the Oracle consultant told my CIO that I should be made a DBA. Apparently, the industry was desperate for people with the kind of instincts I’d demonstrated.

I dove headfirst into certification classes (thank you, US West, for footing the bill), and the rest is multi-platform history.

Fast forward to now, Oracle has been the platform that’s supported me more than any other. I’ve logged almost equal years with Microsoft tech, but Oracle has consistently been where I’m asked to solve the deepest, most technical challenges. Other platforms, such as Sybase, DB2, Informix all live on in niche pockets, but the market demand just isn’t there anymore. And while I have plenty of love for PostgreSQL, MySQL, and even MongoDB, I’m not here to chase what’s trendy. I’ve never been one to fight over tech. I just want to do good work and learn along the way. If something cool lands on my desk, great. If not? I’m fine with that, too.

Oracle is… different. I joke that in the year 3020, someone will resurrect me and say, “Hey, we heard you know Oracle. We’ve got this issue, and we’d love your help.” That’s the kind of resilience this technology has.

People like to say that Oracle is made up of the “old gray beards”, and there’s some truth to that. But here’s what most don’t realize: as Oracle moves deeper into the cloud, it must continue to become a black box. Easier to consume, harder to explain. The customer doesn’t need to know how it works – they just need to know that it works. And Oracle, like AWS, Azure, and Google Cloud, follows the same playbook.

But that’s exactly why the gray beards will stay essential. We are the last generation that remembers Oracle before the cloud. Before the “C” versions. Back when the version numbers stood alone, and understanding Oracle meant knowing the why behind every internal mechanism. We didn’t just understand Oracle, we often had to rewire it, dissect it, and rearchitect it. That institutional knowledge is fading fast and in my conversations with my Microsoft friends, many feel that SQL Server is quickly going that direction as well.

During my years at Microsoft, I spent a lot of time learning Azure and seeing how the future of cloud platforms was being built. I missed when the shift occurred – from needing to know Oracle from the ground up, to being expected to know only the cloud services and orchestration tools that sit above it. It’s not that one approach is better than the other. They’re just different worlds. And it’s been fascinating stepping back into the broader community after a period of self-imposed isolation.

Coming back into Oracle and finding myself part of Redgate has been a full-circle moment. I didn’t expect it – but I’m deeply grateful for it. This past year reminded me why I fell in love with data in the first place. Not because it’s easy. Not because it’s flashy. But because it’s complex, powerful, and always evolving. And for people like me – who just want to solve problems and keep learning, that’s the best kind of career you could ask for.

I’ll get back to posting on technical stuff next week, but these last two posts were a nice break as I travel to a number of events to speak.  Thank you to the Oracle Analytics and Data Summit, The Powershell Global DevOps Summit, SQL Saturday Jacksonville, NWOUG, (Northwest Oracle User Group) Training Days and SQL Saturday Raleigh for having me at their events the last month.  I really enjoyed speaking with your groups and hanging out with friends on both the Microsoft and Oracle tech communities!  I’m home for a couple weeks before heading off for ODTUG KSCOPE, SQLBits and the Level Up Tech Conferences – Can’t wait to share some more focused talks on today’s risk to data with AI, DevOps with Data and Oracle for the SQL Server Professional.