Earlier quoted context omitted.
You’re creating a false dilemma. It’s entirely possible to be a disciplined programmer and use good tools. And, yes, a teacher should care more about the skills than the tools, but Uncle Bob is actively against the tools, claiming that they impede learning the skills. Which is no more true than claiming that automatic transmissions or anti-spin in modern race cars impedes learning how to race.
I don't think he's actively against those tools. I think he's actively against claims that those tools actually solve the problems developers deal with, instead of uncovering the true behavior that lies beneath those problems.
And by the way, noone is making the argument that tools solve all the problems developers deal with. But to say that actually, they solve none of them, is foolish. Optionals, to take one example of something Uncle Bob is against, prevents a large proportion of what is probably the most common runtime error, namely dereferencing a null pointer. And yes, Uncle Bob is right that it comes at the small expense, which is having to think more carefully up front about your data and your abstractions, and there is no doubt he is right that some programmers will feel constrained and will find and use whatever mechanisms exist to bypass the safety that this feature offers. But in much the same way, there are also some people who feel constrained by seat belts, hard hats, helmets, dust masks etc. and choose not to wear them, yet you don’t find many people who would argue that this makes them pointless and generally a bad idea.