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.

Once you have a clear idea the value that you offer the workplace, then focus on specific industries and their needs. You never know how an organization might be able to use your talents. Create a list of industries (or specific organizations)that interest you. Place them in priority order and investigate opportunities. I wish you well.

When you say “I told one company I felt the job was worth X,” there is mistake #1. One of the cardinal negotiating rules is to put off discussing salary until there is serious interest in you and a job offer has been made.
In essence, you set yourself up for the interviewer’s comment about being unrealistic. Remember, we’re working post Bernie Madoff, Enron, and thousands of individuals have taken pay cuts and are being laid off.
Employers are sensitive to and concerned about greed.

Start with these guidelines regarding salary:

1. Once you know the company name, do your homework. Find out entry level salaries in the industry (vault.com, hoovers.com, salaryexpert.com) or print media like National Business Employment Weekly which lists job openings around the country with attached salaries.

2. When you’re on the interview, focus your interest and enthusiasm solely on the job you’re applying for. Ask questions, be enthusiastic about the work you’d be doing.

3. Once the job offer is made, go to the higher end of the range (if you already bring significant value/skill to the job).

4. In the interview, listen for other skills, talents they need. If you possess them, discuss combining skill sets and bringing more value to the job. As that is communicated and proven, salary goes up. Sometimes there’s a “proving period” after which salary is reviewed and an increase given after a few weeks or months on the job. Good luck. Joyce