You can do this by being a franchise owner too, or by being a real estate agent, or lots of other flexible careers, but he's not choosing those paths and exploring why will help him figure out what it is he is really after. He already has a comfortable life and could probably live frugally and then live off investment income in much less than 30 years if that was what his main motivation was, but I think ultimately even if he succeeded at that he would find that his original lack of meaning remained, just with more time in the day.