I don't think you even understand what socialism is, and seem to think that it's just "central planning." If you're going to talk about socialism like you did, I think it's important to specify which socialism you're referring to.
In Chomsky's case, given his ideological sympathies, I don't think the kind of "socialism" he desires would have any issue if someone chose "to work for [themselves] in one form or another." Here are some references that might help with understanding where he's coming from:
https://en.wikipedia.org/wiki/Noam_Chomsky:
> Ideologically, [Chomsky] aligns with anarcho-syndicalism and libertarian socialism.
https://en.wikipedia.org/wiki/Libertarian_socialism
> Libertarian socialism (also known as socialist libertarianism)[1] is a group of anti-authoritarian[2] political philosophies inside the socialist movement that rejects the conception of socialism as centralized state ownership and control of the economy.[3] Libertarian socialism is close to and overlaps with left-libertarianism[4][5] and criticizes wage labour relationships within the workplace,[6] instead emphasizing workers' self-management of the workplace[7] and decentralized structures of political organization.[8][9][10]
https://en.wikipedia.org/wiki/Anarcho-syndicalism
> Syndicalists consider their economic theories a strategy for facilitating worker self-activity and as an alternative co-operative economic system with democratic values and production centered on meeting human needs.
> The basic principles of anarcho-syndicalism are solidarity, direct action (action undertaken without the intervention of third parties such as politicians, bureaucrats and arbitrators) and direct democracy, or workers' self-management. The end goal of syndicalism is to abolish the wage system, regarding it as wage slavery.
I grew up in the USSR. How could I possibly understand what socialism is? Especially the fictional varieties. Mordor has a wiki page too, right?
I don't doubt you have a very good understanding of the Soviet type, due to your experience there. However, your original comment seemed to present a false binary choice between Western capitalism and that Soviet-style centrally-planned socialism. It's clear that Chomsky opposes both the former and the latter, so brining up the latter seems like a bit of a straw man in the context of this video and its subject.