Hi Nelie
It's sounds a little like your son's questioning life in general and perhaps coming up with a lot of depressing answers, which leads me to wonder whether he's ever displayed a sage-like or philosophical nature. My 16yo son's a little like this. He's an incredibly sensitive kid in so many different ways. While his older sister's also incredibly sensitive in many amazing ways, it definitely feels more like a challenge when it comes to raising a sensitive boy.
With my own sensitive boy, he spent the first few years of primary school sitting outside on his own at lunch time, remaining sensitive to the need to not give up his true nature and simply go off and click with the kids he couldn't tolerate (those who loved swearing, the blokey-bloke boys who pick up this nature from their dads, the boys who spoke poorly of girls etc). He remained true to himself, which amazes me, at that age. While he was bullied to some degree through primary and the earlier years of secondary school, he was sensitive to the nature of a-hole behaviour. When being advised to 'Just hit 'em', he was also sensitive in remaining true to his pacifist self. He's sensitive to his imagination, how truly brilliant it can be and how potentially depressing it can be at times. To the best of my ability, I help him manage his imagination, triggering it to take different directions. He's sensitive to questioning life to the point where we have fascinating conversations about the nature of reality, with elements of quantum physics thrown in.
Sounds like your son's become highly sensitive to some shi**y aspects of life, aspects of life which are not natural: You work, you get home exhausted, you sleep, you get up, you work, you get home exhausted and so on. Somewhere amongst it all, you get paid for the soul destroying process. In speaking to people who have a different sense of reality - you work to raise funds for your natural self. You work hard to buy the mountain bike which puts you in touch with 'the adventurer' in you and the part of you that rides as they work out the stress in life. The riding is their daily or weekly 'workout'. Their recreational activities are a part of their constant re-creation (of self).
'Who am I? Why am I here? What's the point? How am I going to choose to not live that groundhog day lifestyle?' Could he gradually be waking up to who he doesn't want to be? That lifestyle is, without a doubt, depressing. Living in Melbourne lockdowns, I can feel it at times.