foresee an increasingly automated future where most of humanity would become either jobless or underemployed by the middle of the century. While robots take over the production of consumer hardware, Big Data algorithms like the ones used by Google and IBM appear to be displacing even white collar tech workers. How long before the only ones left on the payroll are the few "rockstar" programmers and administrators needed to maintain the system? Besides politics and drug dealing, what jobs are really future-proof?
Think of the big picture. If the future you are describing really happens, with the vast majority of society scraping for an ever smaller piece of the pie, what would be the natural outcome? What skills would be in demand?
There would be a lot of big crime targetted at the very few, very rich and the corporations (giant concentrations of assets imply large scale criminal operations). There would be a lot of petty crime between the proletariate (mostly crimes of opportunity with a low profit margin, probably not much of a career there except maybe in racketeering). Maybe some shakedown operations not too far removed from mass copyright enforcement. There would be religious and ideological pontification, offering hope to hopeless people, whether substantive or illusory. There would be a lot of civil unrest, and a lot of mechanisms for suppressing that unrest (tough to say which side will have the upper hand at any moment, but both sides will have openings).
So: Information security, physical security, ideology / idolism / propaganda and counter-propaganda, sockpuppet armies and microtargetted mass messaging, law enforcement and thuggery, lickspittle to the wealthy, and influence management and peddling, off the top of my head.
Consider what postmodern feudalism might look like. That should be a reasonable picture, if what you suggest should come to pass.