I'll avoid the personability side of the question, but focusing on the "change" aspect: Let's not confuse "physical" tools - like a hammer, press, CAD program, or text editor - with "thought" tools - like a paradigm of programming, say, Functional or Object-oriented.

I'm still a rather young programmer (only about 6 years into my career). But I've found myself actually working in a reverse flow of technology, in terms of what tools I use on a daily basis to do my job. I'm primarily a Microsoft-stack web applications developer. I spend most of my day writing out c# and t-sql; often, using Visual Studio and MS Management Studio to interact with my code and the database. Those are the tools I used at the start of my career, when really getting the hang of basic programming.

As I've moved forward (career-wise), I now find myself using rather "older" tools for my day to day tasks. I hate to touch a Windows machine without Cygwin installed, as BASH is my primary interaction with the computer now. And I find myself generating code at a faster pace in VIM than I can in VS. As I've started using more Postgres databases, I've grown more comfortable with psql, and the terminal-based interaction with the db.

So the actual tools I'm using to generate my work are, in a sense, "old". I've found myself almost shunning new tools. Or at the very least, not embracing new tools _just_ for the sake of them being new. A new tool has to have some value aside from "newness."

Use of these "old" tools is not to say that my skills as a developer are lagging behind, however. The same even goes for the languages I've been using for personal projects. I find myself working out ideas more quickly in Common Lisp (how's that for old?) than I can in c#.

The point I'm trying to make is: don't focus on whether or not the person is using the newest tools to do the job. What's going to matter more is how well they understand the fundamentals of their discipline. Granted, I'm still young, but I feel like the craftspeople that really understand the core principles of their craft, and keep an eye on the horizons of their craft, are going to remain in demand (so long as the craft is needed). And if that craft is software development, it won't so much matter whether the coder is embracing Rails or not; what will matter is that s/he understands the new ideas that Rails might embody, and can incorporate those ideas into their daily flow.

Not necessarily. We don't know if what made him so incredibly productive sprung from those same qualities. In fact, refusing to learn new processes when the old ones still worked might have aided him in gaining expertise.

I know what you mean, but I would say no. This is getting a little philosophical, but bear with me. It's like saying, "what if Steve Jobs were a little more down to earth?" or "What if Nick Saban was just a little easier to get a long with?" It's tough to separate out what makes a man who he is. The same unreasonableness that made people not want to work with him is what saw his designs through to production unmolested by the compromises of what he would likely have deemed lesser minds (or "fucking idiots" as he'd have said).

Depends what he wanted out of life really. He may just have run into the point where having a little extra leverage would have been meaningless, or at least more bother than it was worth.