How can I have the conversation with him about what he wants for his future?

He wants to do computer things as a carreer he said that in the past - (fair enough so far) but he's not applying for work cause he doesn't want to do a lot of the jobs, long term. I have previously told him that getting a first job is the hardest job to get.

If he doesn't take action soon and start actually looking for work and applying for work, I'm worried he will have too big a gap on his CV and then will never work, cause employers won't take on someone if the person has too big a gap on their CV

(resume in america, i think?)