Several times in my consultation sessions as well as among friends and acquaintances have I encountered guys being stuck between two worlds. On the one hand, they would like to keep dating (or sleeping) around, or pursuing their hobbies, or make more money, but on the other they also realize that they have been, abstractly speaking, running in place. Essentially, their life is the same it was a few years ago. They got older and surely also have a bit more money in the bank but, by and large, they are the same person they used to be.
I think that after a certain age big changes in your life are rare. For instance, early in your career you have the highest potential for moving up, relatively speaking. You may even double your salary within a few years. In contrast, ten years into your career, meaningful promotions will be hard to get buy, primarily because you are stuck in an organizational pyramid where there are only so many positions available, and even if you manage to move up one more rung, many others will not be able to, based on simple arithmetic. Of course, I do not want to say that you have to lose all ambition but, realistically speaking, you will probably have topped out in your career in your mid-to-late 30s, if there are no strong signs that you are on an upward trajectory.
As I do not want anybody to misinterpret this article as being defeatist, I would like to qualify the message of the preceding paragraph. Yes, you can have breakout success later in your career, but this is simply not common. Also, we cannot all be winners. That being said, I have seen some rather impressive examples of guys turning their life around. There is one guy I know who used to work as a software developer for about ten years. Then he got a promotion to manager and he stayed in this position, at the same company, for a staggering 15 years. He looked as if he had given up on life. For him, things changed only after his wife divorced him and kicked him out of their (his!) apartment. This gave him the push to see what he can achieve in the last third of his career. A year later, he got a CTO position at a smaller company, and four years later he became a director at a pretty large company. This can happen, but it is not very common. Also, I bet that if he had not gotten divorced, he would still have his first manager job.
Now I have talked enough about careers and return to the issue of not wanting to settle even if you think you do want to settle. Those guys tend to waver back and forth. They date some woman for a year or two, then things do not work out and they look for another woman. As those guys are in good-enough shape and pretty well-established, they normally have little difficulty finding a girlfriend; ONS are a lot harder for them, though. I have seen several of those guys going through a string of women and none was ever really good enough. Some seem to be waiting for a chick who is somehow clearly much more attractive or smarter or more fun to be around than the caliber of woman they are getting, but oftentimes this is a bit delusional. You will get women of a certain caliber, with a bit of variation around the mean, but if some guy only ever gets 6s or 7s, he is not likely to one day get a 9.
It is not clear to me what those men want to achieve with their meandering. In my view, they should decide if they really want to settle down, which, in my opinion, boils down to the question of whether they want to have children. If they do want children then it is clear what they need to do. This does not mean that they have to take the first girl who comes along, but they surely no longer need to date a chick for a few years to find out that she is not the right one. You can figure this out a lot sooner. Also, if you do not want to have children, then embrace this decision as well and then do not waste your 30s or 40s still dating women you have no real interest in. I know a guy in this category. In my opinion, he would be a lot happier just banging whores and having the occasional fuck buddy. Instead, he has been telling me for about a decade that the chick he is currently dating could be a good match, but he only ends up talking himself out of it. I bet that deep down he knows that he does not want to have children but he just cannot admit this to himself. Instead, he feels pressure to pretend to be well-adjusted and have a token girlfriend. Also, in his case, a compounding factor is that hobnobbing is part of his job and he feels pressure to bring a girl along, at least often enough.
There is another analogy to the working world, which I only realized after I had to vet CVs for a job opening. Some guys show a clear progression. They went from working at a small company to a somewhat bigger one, or they ended up doing more and more meaningful work. This is a good sign. In contrast, a lot of guys have completely bizarre CVs, with a string of stints ranging from 1.5 to 3 years in length. Their job title does not change, their responsibilities seem to be comparable, and the companies they work at you have never heard of. When I ask them about a summary of their CV, they just rattle down their positions without presenting a coherent story. I think they just got bored and decided that they will just do the same job at a similar company, without putting all that much effort into it. I think guys who just go through the motions when dating some chick do the very same. They have one mediocre-looking chick after another. Perhaps, the reason that kind of man does not commit to a job for long, or to the same woman, is that this would be an admission that they, in fact, cannot do any better.