Simultaneous classicism and futurism
In addition to building a "classical" syllabus that I read, I figure my audio diet should be of a different nature, one that's as modern as possible. I'm going with the Moonshots podcast, with Peter Diamandis. This group of guys are probably more anchored in the future than anyone else I've found. It feels adjacent to the All In podcast format, but less business-focused, and more centered on futurism. There is a certainty among them that we are in the singularity, accelerating to a techno-optimist future, which is antithetical to the Neo-Romantic essayists (it is rare to find an essayist who is both a humanist and a technologist).
I do have to be skeptical of their worldview, however, for they are schmoozing among the elites building this stuff, and so they're likely to have a rosy-eyed view on how this might all fare well for millionaires, without realistically focusing on or caring about how it effects the daily lives. They do seem to harbor a certain fetishism about technology and progress, and a boyish fascination with going to space and uploading our consciousness, for maybe the simple fact that it's a science fiction dream beyond our current life. There's a Faustian sin in summoning the future for future's sake.
They also very openly want to live enough to live forever; if they can survive another 15-years, they are rich enough to have access to anti-aging technology. The whole premise of technologically cheating death is also a philosophy that feels disconnected from our history. But I wonder if you could make the claim that Montaigne didn't have the luxury of philosophizing about life extension. If we make shape our philosophies to justify our situation, then is our whole canon on "the importance of dying" only stemming from pains and fears of a low-tech society? I guess, intuitively, from a child's perspective, the idea of not wanting to die is a natural one, and to embrace it is the wisdom of an adult, but I suppose we're nearing a flood of new cultural debates stemming from a new reality where the immortality choice isn't theoretical, but real, which changes the whole calculus.
So the point of listening to a group like this that is openly "transhumanist" is to model the future, hear them out, but then take it one step further, and truly consider the moral and ethical implications of where all this is heading.