Am I overthinking my boyfriend’s going back to school?

r/

My boyfriend (M26) and I (F25) have been together for 7 years and are moving locations because he’s going to school for 2 years for the Heritage Carpentry and joinery program. He took architectural technology at Sheridan 2 years ago and has been looking for a job in the field for 1.5 years, but couldn’t find anything. He’s been working some freelance gigs here and there, but nothing permanent. He wants to take this program to better equip himself in carpentry, as he wants to learn the basics and later use those tools to become a carpenter.

My concerns are that his main reasoning for wanting to take the course in the first place was that he couldn’t find anything in the field. He was super picky at first with finding a job (as in not looking for server / retail jobs and only jobs in his field after graduating), he now knows that it was wrong and regrets being so selective in looking/applying.

I have a friend who also doesn’t think the program will amount to him finding something, as a lot of carpenters they know haven’t even heard of heritage carpentry.
My family also thinks it’s a waste to go back to school because they don’t believe in extra school when not necessary. My partner is a very hard worker, and I believe he will excel in the program, but I worry that he’s sometimes too idealistic and just assumes things will work out. I’m also a chronic over-thinker and worry that this program still might not result in a job.

Should I be worried that he’s going back to school without having a job for 1.5 years? Also, a question for carpenters, does this sound like something worth his time in pursuing? I’m not sure if I’m just being super paranoid or overwhelmed with the thought of not finding a job afterwards.

tl;dr: My boyfriend’s going back to school being without a job for 1.5 and I’m worried if he’s becoming a perpetual student and won’t find a job with the program