First, let’s set the stage. Understand that job search is rarely easy but in this “wait and see” environment it’s even more complicated. Job search can be a full time job itself, especially in this uncertain economy. Still, hiring is taking place with different rules and realities depending on one’s skill and flexibility. However, given your friend’s field, that could work to his advantage. Tell him to think about the questions below and see if he’s on the right track. It might be he just needs to “keep going” with a support team in place when the going gets rough.
To answer your specific question, sure, I can definitely talk with him and possibly expand career options and direction. First, have him answer these queries which I prepared below. They should determine whether a meeting makes sense or if he’s already on the right track . (1) Does he still want to do copyrighting? Why? If not, What type of work could he envision himself doing at this point? If he doesn’t know, that’s an area where I can introduce him to new ideas (2) Is he open to travel and/or relocation? (3) Has he surveyed full time writing options with organizations in southern CT? Is he interested more in full time or free lance, entrepreneurial lifestyle? It sounds like he wants Full Time at this point, yes? (5) Has he connected with established organizations and networks in southern CT? (6) Does he have a plan in place of how to go about job hunting in this geographic area and in his chosen field?
If he feels he’s doing all of the above in multiple career directions, then he may need to just keep on plugging; if, however, he thinks he’s at a standstill, perhaps a meeting would be beneficial.