I hear you OP, I’m 40 and definitely feel like this. I’ve also moved around quite a bit and have never really climbed the ladder - I don’t want the responsibility. I also feel the pressure that at my age I should have some sort of fancy career behind me, but it never appealed to me.
Actually my favourite time working was on a working holiday visa for 2 years - I did all sorts of temp jobs while I travelled: bar work, cleaner, worked on a farm, but it was always to fund my next adventure. My problem was settling down in my 30’s and feeling like I needed to get a ‘proper’ job. It’s never suited me, but I felt like it’s what I was supposed to do.
I know my family think I’m a bit weird, despite having a good education I’ve never really excelled in any job, the truth is I get bored easily and change jobs/ retrain, I can’t stand the bullshit corporate expectations. I just want to left alone, to travel, to learn new things, I don’t even want a fancy lifestyle, but nowadays even paying for the basics is getting harder.
Maybe it is age thing, at 40 years old we’re far enough into our working lives that the novelty has truly worn off, but still so far away from retirement that it’s a pipe dream.
Also, I have this sense of time running out. My lovely dad died last year, my mum is elderly now and getting frailer - I have this real sense of time ticking on and that I have a limited number of healthy years ahead of me. I don’t want to be wasting them in jobs i don’t care about.
I don’t know what the answer is - I’m currently renting in an expensive city to be near to my mum, but I think when she dies I’ll probably move away to somewhere cheap and just try to live very simply without the need to work much.
Actually I might look into retraining (again) just to give me something interesting to look forward to.