The experience of the “bottom falling out” in a person’s life is common enough on the spiritual journey that some people speak of it as a part of the path. I would not say that’s universal, any more than a period of no-self is. I have awake friends who have not lost any of their outward trappings. Perhaps because they were able to detach without having to let go overtly. They could see and release the internal bindings. They became more deeply OK with what is, as it is.
If there are subtle attachments or perhaps an even more subtle ‘sense of self’ derived from ones occupation, relationships, or possessions, that can be the place where some letting go must happen. When a spiritual journey comes to revolve around life changes, it can be a large transition.
This doesn’t mean a person is “less evolved” or something if they have an overt set of endings in their lives. We all have different obligations and journeys. Also, people who are “sensitives” or empaths tend to take on qualities of their environment. These easily lead to identification if such lines are not internally clear. Put another way, someone more “connected” may struggle more with the shift into detachment. There are also compensators, people trying to fill gaps in self with things outside of them. These “fillers” can seem to us like self so are not so easily detached. And then of course the run of the mill insecurity and craving that leads to binding.
Letting go is a good practice but you really know you’re doing well when it’s pretty much automatic. It becomes the natural habit. It is how you are responding to much of life. Then, it doesn’t really matter what happens, what shows up or what falls way: it’s all OK. It may be frustrating or annoying. But it’s OK.
It’s much easier to be happy when it’s OK. Even easier when you go deeply enough into OKness to be happiness itself.