I think perhaps more people are attempting this path then back in the late 60s through 70s. However, as opposed to the mainstream vs counterculture, we have influencer culture mixed in, e.g. vanlife or travel bloggers.
It's sort of conceptually hard to be an independent thinker/doer, and also emulate others, even if emulating someone like Steve. For all those that drop out of the mainstream yet still let themselves be known via social media, probably even fewer probably drop out completely; I suspect there are still many. I hunt for obscure artists on Spotify/Youtube, and if I find a small concert, this sort of community still seems within reach.
Ultimately, it's the devices Steve had a hand in innovating that are obscuring aspects of the old school vibes of being off the grid in the present. However, perhaps our current variation of hippie vibes will feel event more quaint to those looking back from 2060 or so.
Right, but the van life people aren't aiming to build a billion dollar startup company.
I specifically mean that young people today - that are deliberately trying to be world-changing entrepreneurs, and claim deep inspiration from Jobs - don't typically wander India, take typography design courses, or go to Reed College. They aim for prestigious universities and prestigious accelerators/VC firms.
I think there is probably a lot of value in that young person doing something like Jobs (not the exact same thing), even if it's not optimized for the credentialized society. Maybe it puts you a few years behind your peers on the credentials track, but the experience will be worth it in terms of having a novel/well-rounded/expanded viewpoint.