Nice post.
I think many low wages and middle class "regular jobs" will disappear in the forthcoming decade due to automation, robotics, machine learning and other techniques. For more and more fields, such kind of jobs will become commodities: rich will become richer. It is already a reality in many manufacturing fields.
I think the only way to not be too poor is being a kind of entrepreneur. The forthcoming problem will be to have funds to start: less wages for the same job (and less demand from the market), and on the other side more market pressure on VCs (less money and/or less deals), and finally to bootstrap and to generate enough money to get assets.
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