Here is the case of a woman in her 50s who has not worked for 10 years. She has an Ivy League education, with excellent foreign language and writing skills. She worked as a paralegal 25 years ago to see if she liked law before attending law school. She liked it and was accepted, but didn’t finish because the pressure got to her.
Six years ago, the woman got a paralegal certificate because she thought it would make her more marketable. Her friends tried to discourage her, but she did it anyway and she still hasn’t been able to get a job in the field. One friend told her to volunteer at an organization where she might move into a paid position, but she thinks many of those jobs are beneath her. Instead, she volunteered at a place she thought would improve her social status. Her family has always supported her and still gives her money for everything, but they complain openly to her and her friends about her not having a paying job. What they won’t do is to stop giving her money. Though she still talks about wanting a job, she has used every excuse imaginable for not applying for jobs she could realistically get.
Frustrated, her friends would like to know if there is anything they can say to open her eyes to what she needs to do to get a job.
The woman in question is either conflicted about being supported versus her desire to work, or she is doing exactly what she wants: to be supported as long as the money keeps coming. She may also have a serious problem affecting her ability to stay in jobs long term. Her friends think that she hides behind her Ivy League education, pretending to be too good for most jobs, but to the contrary, she may be deeply insecure and aware that she is unable to perform under pressure.
Volunteering allows her to meet those of a certain social status while giving her that feeling of accomplishment, which she may sorely need. It also allows her freedom from re-living the failure she probably felt from not completing law school. She might talk about wanting a paid job to appease friends, so she can appear “normal.” She is intelligent enough to know that getting a selective job with her work record is unrealistic. If her family cut off her finances, you would then see her survival skills, or lack of them, and what follows may not be good for anyone.
Many companies will not consider a candidate who has not worked in 10 years and has a sketchy work history. It would help a great deal to tell her the truth — that she is not likely to get a job that meets her requirements; that you will still be her friend and then change the subject. She may be relieved that you’ve stopped giving her sensible solutions to her job search.