In my early twenties, I had a business mostly on autopilot that let me work maybe an hour a day. I mostly spent my time writing poetry, hiking, making friends, etc. It was great. It was not sustainable, but it was perfect for a twenty something exploring the joys and freedoms of youth.
Now, I work much harder, have kids, and responsibilities. That being said, I know the work I do is meaningful, and serves many people. We have significant savings. Though living in a big city means we can't retire early. That's beside the point though: I motivate myself to work because it is meaningful. The same with kids: I don't do things because I enjoy them, I do them in the service of my kids and my family. Reading the story in the OP, I get the sense that the OP hasn't made that transition to thinking about work in terms of serving others. A happy life is not a life of retirement, its a life of meaning. What was meaningful once (aiming for retirement), loses its meaning once it has been attained. You have to keep moving forward. This is not about "Keeping Up," but about stepping outside of oneself, and learning to put others ahead, even if it requires personal suffering. (Something parents of young children know very well.)
Now, I work much harder, have kids, and responsibilities. That being said, I know the work I do is meaningful, and serves many people. We have significant savings. Though living in a big city means we can't retire early. That's beside the point though: I motivate myself to work because it is meaningful. The same with kids: I don't do things because I enjoy them, I do them in the service of my kids and my family. Reading the story in the OP, I get the sense that the OP hasn't made that transition to thinking about work in terms of serving others. A happy life is not a life of retirement, its a life of meaning. What was meaningful once (aiming for retirement), loses its meaning once it has been attained. You have to keep moving forward. This is not about "Keeping Up," but about stepping outside of oneself, and learning to put others ahead, even if it requires personal suffering. (Something parents of young children know very well.)