I am familiar with the state of being on hold
you describe your son to be in. I have been in a similar disposition for the last 10 years of my life. Some differences apply. Although I have worked, it has been in the family business, and I have been living above the business in a space I helped renovate, so I haven't ever felt that I was making it on my own
Its not surprising that his friends are like this as well, as I myself used to only seek friendships with people who were similar to me, since for the most part I, and we, only sought to pass the time with various diversions.
I have been content all this time, comfortable. For a long time I equated contentedness with happiness. About two months ago I reached a point where I was no longer content. In fact, since this time I have been downright miserable. It was the effect of sympathy on the mind that unsettled me. By chance I ran into quite a few people I used to know, and two things happened.
One, I was reminded of many things that I had forgotten about myself from the time that they had been my friends. Including all the things that I used to want out of life, things which I hadn't thought of in years, yet which I found I still wanted once having been reminded.
Two, I received a great displeasure by sympathizing with the disapproval that others felt when they saw how I have spent my time untill now. Though I had been perfectly content, stress and care-free, from the outside my contentedness looked more like despair or depression, and the force of sympathy caused my idea of their disapproval to be elevated to an impression of disapproval in myself.
So for the last two months I have been initiating huge changes in my life, including applying to go back to school. From my point of view, this was not a positive thing. My motivation was the anxiety and unhappiness that was threatening to undo me. I was pushed into action by a desperate need to find some relief from it. I conceived my life for the last 10 years, and when I looked ahead and imagined spending the next 30 to 40 in the same manner I thought that simply ending myself would be preferable. (Not because it would be unbearable, but that it would be so boring and uneventful.) It was funny to me then when my parents asked me what caused me to have my "epiphany."
I tried to explain but it fell on deaf ears. They saw me leaping into action, in their mind I was motivated, driven by desire, out to conquer the world. Ridiculous. And yet once again sympathy caused me to conceive of their idea of me, and to view it in a stronger light, and the idea of how they saw me was elevated to the impression of how I saw myself.
Yet then my anxiety was greatly diminished, as well as my motivation, and I once again languish. Nothing is there to push me foward but what is left of that initial impulse, and the arrangements I have already made. That will only carry me so far.
I was kind of at a stand still, but this thread has made me think about it more deeply. Now I conclude that my motivation for leaving behind what is comfortable to me, to struggle through doubt and uncertainty to achieve my goals, is the approbation of others. As they view my actions, they will conceive of them in a positive light, on account of the esteem they place in the dedication and courage it has taken to pursue them. They will imagine me to be happy, and then by sympathizing with their view, I will be.
It seems to me that those who find themselves in a less comfortable position, and take strong measures to enact changes in their lives out of necessity, still receive this approbation and receive the idea of their own happiness through sympathy with others, without having to specifically
seek it out or even understand what it is.
About your situation. I am certain of at least one thing, that you are not and cannot be responsible for your son's happiness. It sounds like you did the best that you could raising him. There is then nothing to regret, although it is natural that you should be sad if he seems unhappy. The only thing you can do, that I can imagine, is to let him know it makes you sad to see how he is living his life, and why. And to let him know what sort of things he could do that would make you happy for him.