I used to think it was all about having a job. If you have a job, there's a good chance of getting the necessities of life.
Later my thinking moved beyond the "get a job" idea to "get an income." Income might come from a job, but it could be from self-employment, investments, royalties, rents -whatever. (choosing the right ancestors and inheriting -nice if you have that going for you.)
Now I'm not even so much concerned about having an income. Instead, I like to think about having a life. What does it take to live? What are the trade offs? Would you rather work hard so you can buy all the things you need, or would you rather reduce your needs, produce things for yourself, and work "for the man" a whole lot less.
Does working in your garden make you happier than working in a cubicle? Are you happy to ride to ride a bike rather work hard to keep a car on the road? Would you rather spend your days fishing than fighting traffic?
How important is freedom to you? What is your time worth to yourself? Time is life. How do you want to spend it?
Personally, I'd rather find ways of living on my shrinking income than search for more work, but that's just me. Others can make their own choices.
You are making a choice, aren't you? It's not just a matter of automatically keeping up with the Joneses? The dream you are pursuing is your own, not someone else's?
I'm not saying to avoid getting a job -if that's what you like. I myself, once had a job I loved, and the schedule was flexible. It was good for me at that time in my life, but I wouldn't go back now if I could. Life moves on. Priorities change.
It can be eye opening to examine the assumptions we live our lives by -even things as basic as getting a job.