That particular phrase was meant to be directed against the idea of hipster-judgement associated with “coolness/not coolness” based on doing some particular thing. (Something I associate with hipsters.) My intent was to say I don’t care if you write your own software or use WordPress or write assembly code. My hope is that the choices you can/do make are based on the pursuit of happiness rather than some attempt to belong to some particular hipster-clique. I don’t think the people around Reclaim have that kind of vibe. You don’t have to do anything to belong unless you want to do something to belong.
No question all this requires investments of time/energy/money etc.
I can’t speak to how that works for other people. I don’t know if/how my own experience generalizes. I have no idea how it works for people who don’t speak English.
I spent ten or so years trying to learn this stuff with differing degrees of focus/commitment/time. I remain very unsatisfied (internally mostly but with some envy as well) with where I am now but having a place where I might try things has been key for progress.
I think it takes lots of time to learn to do some of this stuff yourself– if that is what you want to do. And there’s no end to it that I see. My own path has been crooked and wandering but that’s my own preference and one I can indulge.