I Used to Be Steve.

Confessions of a Reformed Corporate IT Guy

I have a confession to make. It’s not something I’m particularly proud of, but I believe in being honest with people. And since we’re going to be spending some time together here at Open Source Outlaw, I figure you deserve to know the truth. Before there was the Open Source Outlaw, before the Linux servers, before the self-hosted applications, and before I started questioning why everything in the world needed a monthly subscription, there was another version of me.

I used to be Steve. There. I said it. Now, for those of you who haven’t met Steve yet, allow me to introduce him. Steve is our resident corporate IT enthusiast. He’s the guy with the clipboard, the pocket protector, the Microsoft lanyard, and, for reasons nobody has ever adequately explained, a necktie with a polo shirt. Steve has never encountered a problem that couldn’t be solved with a vendor-approved, enterprise-grade, cloud-based solution. Preferably one with a recurring subscription, an implementation fee, and a mandatory onboarding webinar.

And the frightening part? Steve genuinely believes he’s helping. I know. Because once upon a time, so did I. In the Beginning, There Was the Vendor

I’ve spent a good portion of my professional life working in information technology. Real-world IT. The kind where people expect their computers to work, their email to arrive, their files to be available, and their systems to stay running whether it’s Monday morning or Christmas Eve. I’ve worked with enterprise systems, Microsoft products, servers, networking, security applications, and all the other things that make modern organizations function.

And let me tell you something. There are some absolutely incredible commercial products out there. Microsoft makes some excellent software. So do plenty of other companies. Large organizations have complicated needs, and sometimes a professionally supported enterprise solution is exactly what the situation requires. But somewhere along the way, something strange happened in the technology world. We started confusing buying a solution with solving a problem.

Need to manage files? Buy a platform. Need to collaborate? Buy another platform. Need to organize projects? Subscribe to a service. Need to monitor something? There’s a dashboard for that, and the dashboard has three pricing tiers. Before long, we weren’t necessarily asking what we needed to accomplish. We were asking which vendor had a product for it. And I was right there in the middle of it. I understood the terminology. I knew the products. I could discuss licensing, integrations, security, deployment, and vendor support with the best of them.

And if somebody asked why we were doing something a particular way, there was always a perfectly reasonable explanation. “It’s the industry standard.” “It’s the supported solution.” “It’s what everybody uses.” “It’s an enterprise best practice.”

Sound familiar? Somewhere, Steve is nodding so hard his Microsoft lanyard is swinging. The Most Dangerous Question in IT Here’s something I’ve learned over the years. One of the most dangerous questions you can ask in an IT department is also one of the simplest.

WHY? Why are we paying for this? Why are we using this particular application? Why does this simple task require an expensive platform? Why do we need another subscription?

And perhaps the most dangerous question of all: Could we do this ourselves? Now, don’t misunderstand me. There are plenty of perfectly good answers to those questions. Sometimes you pay for a commercial product because it saves time, provides essential support, meets regulatory requirements, or handles something you simply don’t have the resources to maintain yourself. Those are legitimate reasons. But “because that’s what we’ve always used” isn’t much of an answer.

Neither is “because everybody else is doing it.” And “because the vendor says we need it” should probably cause us to ask a few more questions. I gradually began realizing that I had spent a lot of time learning how to operate technology without always stopping to question why I was using that particular technology in the first place. That’s a pretty uncomfortable realization for somebody who’s spent years in IT. But it was also a turning point.

Then I Started Experimenting I wish I could tell you there was some dramatic moment when the clouds parted, a beam of sunlight hit my computer, and a penguin appeared on the screen announcing that I had been chosen to lead the open-source rebellion. That would make a fantastic story. But the truth is considerably less exciting. I started experimenting.

I tried Linux. I explored open-source applications. I began looking at things I could host on my own equipment. I discovered that there were entire communities of people building software because they wanted to solve problems, not because somebody in marketing had identified another opportunity for recurring revenue. And some of that software was really, really good. I discovered that I could run my own cloud storage with Nextcloud. I could manage my own photographs with Immich. I could organize and stream my own music with Navidrome. I could maintain my own movie and television libraries with Jellyfin.

And suddenly, I started looking at the technology in my life a little differently. Instead of asking which company I needed to pay, I started asking what I could build. Instead of wondering what features would be included in the next subscription tier, I started wondering what features I actually needed. And instead of automatically assuming that a commercial product was the better solution, I started comparing the alternatives. That’s when things got interesting.

The Tractor Doesn’t Have to Be Pretty Now, anybody who’s ever spent much time around me knows I have a philosophy about technology. Sometimes you don’t need the fanciest tractor on the lot. You need one that cranks up and plows. That’s it.

I don’t care if the dashboard has animated graphics. I don’t need a touchscreen that tells me the weather in seven different cities. I don’t need a subscription to unlock the headlights. I need the tractor to crank. And I need it to plow. The same principle applies to technology. If I need to store files, I want something that stores files reliably. If I need to listen to music, I want something that plays my music. If I need to create a church bulletin, I want something that lets me put words and pictures on a page and print it.

I don’t necessarily need a complete digital transformation strategy. I certainly don’t need a quarterly stakeholder engagement meeting. And Steve, for the love of everything good and decent, I DO NOT NEED ANOTHER DASHBOARD. Sometimes the simplest solution really is the best solution. But here’s where I have to be careful. Simple doesn’t always mean easy. A self-hosted application might be simple to use after you’ve spent hours getting it configured. An open-source alternative might be free to download but require time and effort to learn.

There’s a cost to everything, even when that cost isn’t measured in dollars. And that’s something the Outlaw has to remember just as much as Steve does. I’ve Broken Things. Lots of Things. Let me clear up another misconception before we go any further. If you’re expecting the Open Source Outlaw to be some sort of technological wizard who installs Linux, types three commands, and watches everything work perfectly the first time, you’re going to be terribly disappointed.

I’ve broken things. I’ve broken things that were working perfectly fine before I touched them. I’ve spent hours chasing problems that turned out to be one incorrect setting. I’ve rebuilt systems. I’ve stared at error messages that seemed to have been written in an ancient language. I’ve occasionally questioned every decision that led me to that particular moment. And yes, there have been times when paying somebody else to handle the problem would have been easier.

But here’s the difference. When something breaks on a system I control, I have an opportunity to understand what happened and fix it. I can examine the configuration. I can read the logs. I can restore a backup. I can rebuild the service. And every time I work through one of those problems, I learn something. Sometimes I learn a great deal. Sometimes I learn that I should have made a backup before I started.

That particular lesson seems to require occasional reinforcement. But the point is that I’m developing knowledge and skills that make me less dependent on somebody else. And to me, that has value. Steve Isn’t Always Wrong Now, here’s something that might surprise you.

I actually like Steve. I know. After everything I’ve said about the clipboard, the subscriptions, and that ridiculous tie, you probably weren’t expecting that. But Steve isn’t a bad guy. Steve wants things to work. He wants systems to be secure. He wants somebody to call when something breaks. He wants documentation, predictable support, and solutions that don’t disappear when the one person who understands them leaves the organization. Those are good things.

In fact, in a large organization, they’re often essential. And I still believe in them. The problem isn’t that Steve cares about those things. The problem is that Steve sometimes assumes the only way to accomplish them is to buy another product. And that’s where we part company. Because I’ve learned that commercial software isn’t automatically better simply because it costs money. Open-source software isn’t automatically better simply because it’s free. And putting something in the cloud doesn’t automatically make it more reliable, more secure, or more appropriate for the job.

Every solution has advantages and disadvantages. The trick is learning to evaluate those honestly. Sometimes the right answer is Microsoft 365. Sometimes the right answer is Nextcloud. Sometimes the right answer is a professionally managed service with a support contract.

And sometimes the right answer is an old computer running Linux in the corner of the room. The important thing is that we make the decision based on what actually works, not on what somebody is trying to sell us. The Day I Stopped Being Steve I can’t tell you the exact day I stopped thinking like Steve. There wasn’t a retirement ceremony. Nobody collected my clipboard. I didn’t turn in my corporate IT membership card.

It happened gradually. One application at a time. One subscription reconsidered. One successful Linux installation. One self-hosted service that worked exactly the way I wanted.

One moment of realizing that I didn’t have to accept somebody else’s definition of how technology was supposed to work. And somewhere along the way, I started enjoying technology in a way I hadn’t enjoyed it in years. I wasn’t just maintaining systems anymore. I was experimenting. Building. Learning. Solving problems because I wanted to solve them. And occasionally sitting back in my chair, looking at something I’d just gotten working, and saying something that probably shouldn’t be repeated in a professional IT meeting.

Usually followed by a very enthusiastic: BOOOOOOM! There’s a certain satisfaction that comes from building something yourself. Not because it’s necessarily better than every commercial alternative. But because you understand it. You control it. And you know exactly why you chose it.

That feeling is difficult to put a price on. The Outlaw Still Has a Little Steve in Him Here’s the part where I have to be completely honest. I haven’t entirely escaped Steve. After spending years working with enterprise technology, I still appreciate good documentation. I still believe in backups. I still care about security, reliability, and making sure systems can be recovered when something goes wrong.

And every now and then, I catch myself thinking that maybe a particular problem really would be easier to solve with a commercial product. Sometimes I’m right. Sometimes I’m just having a Steve moment. But the difference now is that I stop and ask questions before reaching for the credit card. What am I actually trying to accomplish? What are my options? What will this cost over time? Can I move my data somewhere else if I need to? What happens if the company changes its policies or discontinues the product?

And perhaps most importantly, am I choosing this solution because it’s the best fit, or simply because it’s familiar? Those questions have changed the way I approach technology. And that’s what I hope to share here. Why I Started Open Source Outlaw I didn’t start Open Source Outlaw because I believe everybody should abandon commercial software.

I didn’t start it because I think Linux is the answer to every problem. And I certainly didn’t start it because I have everything figured out. Trust me. I don’t. I started it because I believe we’ve reached a point where too many people feel they have no choice when it comes to technology. They pay the subscription because that’s what everybody does. They store their files wherever the default settings send them. They accept new features they didn’t ask for and lose features they actually used. They assume that building something themselves would be too difficult.

And sometimes they’re right. Sometimes an alternative really is more trouble than it’s worth. But sometimes it isn’t. Sometimes there’s a free application that does exactly what they need. Sometimes an old computer can provide a service they’ve been paying for every month. Sometimes a little knowledge and a willingness to experiment can save money, improve privacy, and give people more control over their digital lives. And sometimes all it takes is somebody showing them how.

That’s what I want this place to be. A place where we share ideas, discover useful applications, work through problems, and occasionally laugh at the ridiculous things the technology industry expects us to accept. I’ll tell you what works. I’ll tell you what doesn’t. And when I make a spectacular mess of something, I’ll probably tell you about that, too.

Because there’s no sense pretending the tractor always cranks on the first try. A Final Word to Steve Steve, if you’re reading this, I want you to know something. I understand. I really do.

I know why you love the enterprise solutions. I know why you trust the vendor. I know why you believe the next subscription tier is going to solve all our problems. I used to believe some of those things myself. And I’m not asking you to throw away everything you’ve learned. I’m just asking you to consider the possibility that there’s another way. Put down the clipboard for a minute.

Take off that ridiculous tie. Come over here and look at what I’ve built. You might be surprised. And who knows? You might even enjoy it. But Steve?

Leave the subscription agreement in the car. Because the biggest lesson I’ve learned after all these years in technology is that we don’t have to choose between blindly trusting Big Tech and rejecting everything it produces. We can think for ourselves. We can ask questions. We can make informed decisions.

And we can choose the tools that work best for us. I didn’t stop being Steve because Steve was stupid. I stopped being Steve because I finally learned to ask WHY. And that’s how an old corporate IT guy became the Open Source Outlaw. Now, if you’ll excuse me, I’ve got a server to work on.

And somewhere out there, Steve is scheduling a meeting to discuss it. Breaking the rules of Big Tech, one subscription at a time. The Open Source Outlaw 🤠