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Also, using technologies I ended up hating and/or experiencing the limits/downsides of is what compelled me into new, wildly different ones.

I think stagnating is the danger, not learning the "wrong" things. The latter is an important part of gaining perspective.

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Having experienced so many platforms with 0% thought put into how does this work on more than one platform certainly gives me a huge appreciation of stacks that are built multiplatform from the start. I don't see myself jumping deep into any tightly-coupled-to-one-machine tools anymore for example.

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