There are two ways software development and deployment can go: the easy way; and the hard way. When it's the easy way, code works, deployments are one-click (or one command), and unicorns dance through rainbows during each build. This way doesn't happen very often outside of tutorials and extremely small projects. No, all too often, it's the hard way.
The hard way is characterized by messiness. Maybe the code is sloppy. Maybe the code is great but the deployment process is manual and error prone. Maybe the code and deployment ideas are great but different environments are all hand built, and none quite the same way. Maybe everything's fine, but getting approval takes forever so releases are slow. Maybe the development process requires things that don't get done, so you're stuck waiting on a code review... for days. Either way, nothing ever goes as smoothly as we'd hope. To some degree, "hard" characterizes most software development shops I've seen.
(Tangential note: I'm a consulting engineering manager. I probably see a higher proportion of software shops doing things the hard way. If it's already easy then my services are generally not needed!)
Building software the hard way isn't fun. It's frustrating for engineering, most of whom know better but don't have a clear path (or don't have time) to get from current to easy. It's frustrating for management, who would like to see new features more quickly and more reliably. I know very few people who actually enjoy doing things the hard way.
So how do we break the cycle? How do we make it less hard? We fix it. But we do so slowly. The first mistake most people make when they realize that developing and delivering software has gotten hard is that they try to fix it. All of it. Right now. That's a recipe for failure. If they can't fix it all at once - and they can't - then they don't fix any of it.
The trick is to make small steps toward a fix. Management isn't going to approve stopping all new work for three to six months and completely rebuilding production just to make it easy. So we do things that management can approve. Remember, it's in management's interests to see this problem solved, too; they want to approve changes that will make things easier. They just have to balance those changes with meeting all the other obligations. Hence: baby steps.
Start with finding something small you can change. It doesn't have to solve the hardest thing. It doesn't have to address the biggest problem. It doesn't have to fix things all the way. Our only two criteria are: (1) we can do it; and (2) it makes things a little bit better. Then do that one small thing.
You can guess what comes next. Yup, do it again!
Doing things the hard way is an uncomfortable reality for many of us. We can make it easier, though. Think small, think doable, and eventually what's hard will get easy.