Amusing read from way back - guy outsourced his own job and watched cat videos.

https://www.npr.org/sections/thetwo-way/2013/01/16/169528579...

That has been tried and if (when) found out will get you worse than fired. Data entry and administrative paper-shuffling often involve highly sensitive data (e.g. medical) and you can put the whole company in jeopardy if you outsource this to mturk or similar parties outside the org.

Although I agree in principle that a lot of these jobs could greatly benefit from automation (or even just OCR and scanner).

If you have these skills, why not go to a big insurance company or a medical research organization, show off your AI and offer to "digitize" their workflow across the board? Could make big bucks off of that.