Great article. I have to agree that there are advantages to specialising in not specialising. Independence and personal freedom not the least of them. I've also lived my life on the basis that I should cast my attention over as wide a variety of subjects as possible. I follow this philosophy in action as well as thought, seeking to gain as wide a variety of life experiences as possible (having lymphoma, birth of my son, 10 month honeymoon literally around the world, emmigration, throwing lumps of hardened lava into molten lava and the agonies of working as a pumpkin picker in 40C heat are a few of my more treasured experiences).
That said I'll play devils advocate and take issue with a few things you've said or quoted.
First off I don't really agree that being a generalist is necessarily the way to go in terms of employment prospects in the future. It seems to me better paid jobs are increasingly about becoming "an expert" in ever more specialised fields. This trend can only accelerate with greater automation. Unless various systems change radically the future for the generalist could be tough "employment" wise.
Really though my main issue is about life being a game and money being the scorecard. I personally have never set out to have accumulating money as a goal, rather I prefer to change your equation. I would far sooner reduce the proportion of my life I must devote to aquiring money and free up more time for doing what I wish, exploring more of life. To me personally I believe it is infinitely more important to judge me by the number of people at my funeral, my family and friends, than by what I leave in my bank account.
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We have been raised to hate money but this is not the case. Whether we like it or not, it is what it is and we have to master the art.