What exactly is it that Mr. Taleb proposes we do? Even starting one's own business means inflicting the state of being a domesticated dog upon others which seems even less laudable than being a domesticated dog oneself.
In real life, of course, the wolf just eats the dog because it's a dog eat dog world, and trading your next meal for ideological purity isn't something wolves do, it's a privilege afforded to dogs who sometimes like to imagine themselves as wolves.
Wolves eat livestock, not being trained otherwise. Wolves are rare in a lot of places where they used to be numerous, coincidence?
The wolf like an entrepreneur is still a slave to survival just with higher stakes. You may think that you don’t have a boss, but you still have clients/customers in the end. Freedom (Financial independence) is gained once you can collect rents, investment income, or delegate responsibilities - but someone else is now your ‘slave’ in those cases.
The company man in the tropical paradise was a strange example. The company gives him a better life than he would have otherwise had and let’s him live like a king - so he supports the company. Is there any treatment of employees possible that Taleb would think is a fair shake? Perhaps because the title is “skin in the game” he thinks they must make their income through company stock?
And in exchange I get to not really care about complicated things I do not enjoy other than whether it indicates I need to go find an owner with more dog food, I practically get to use many of those hours at work as I please, and at least as a professional, I can carve out hours as required for other things.
The answer (as usual) is 'it depends'.
The trend for employers is that they want unreasonable loyalty and/or employees as interchangable parts and the power to rearrange them at a whim.
Not all employers are like this, although many of them are.
I have to wonder whether posting of this 3 year old article is just an attempt at exploiting the long tail of his book sales?
Except that wolves are pack animals who work for the good of their pack, which isn't freedom. Solitary wolves exist but it's because they're trying to create their own pack.