Given that there is a greater incidence of telecommuting as well as educated, low cost labor around the world, would it be possible to hold 2, 5, 10 or more jobs and not work at any of them?
It would work like this…Find a job where you can work remotely nearly 100% of the time. Ideally the work would be fairly autonomous in nature - recieve assignment, complete assigment, submit assignment without excessive back and forth. As soon as you establish a job, you outsource it. Even if you have to pay 60% or more of your wage to the person actually doing your job, you are scalable. Once you outsource one, you apply for and get another one.
It would be a truly interesting experience to have 5 full time jobs, make 200% (after expenses but before taxes) of a normal salary, but only have to work in a supervisory capacity (to the extent your outsourcers were not as intelligent or detail oriented as you were).