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I don't know, so this is a genuine question: How much language/tool advocacy does DHH do?

Plenty - I mean, the guy wrote his own tools, and he's not shy about promoting them. I wouldn't call him a zealot, but he's manifestly picky about tools.

Not that there's any contradiction here. It is true that your skill transcends any particular tool, but it is also true that skilled people often become quite picky about tools. I doubt that Eddie Van Halen owns only one guitar.

The mistake is not caring about the tools, or taking trouble to find - or build - the tool that suits you. The mistake is attributing too much power to the tool and not enough to the user.

There are two kinds of seekers of good instruments. One kind pushes him/herself so hard that they run up against the limitations of their instruments and so are driven to find better ones. Another kind doesn't push themselves so hard, but gravitates towards the advantages of better a better instrument even though they still have even more scope for improving their own playing through technique.

I think this also extends to software tools.

Good tools also give you room to grow into them, so you can concentrate on learning without having to worry too much about housekeeping or maintenance tasks.

As a personal example, I became a better photographer when I bought a good (but used) Nikon, because I know it's built to take some abuse (people photograph wars with these) so I happily take photos in wild places and never worry that it's going to get damaged.

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