I was fortunate to grow up relatively (lower?) middle-class, but even then, we weren't exactly financially secure, and I still remember how bad things were during the Great Recession, even though I wasn't working at the time. My wife grew up in poverty, and even though we're both doing decently in our careers, I don't know if she'd ever truly be able to get rid of the worry and anxiety that something might happen and we'd end up homeless. Even if we suddenly won the lottery and ended up with $500 million, that fear would probably still be there at least a little bit. And like you said, that fear makes enjoying/being comfortable with unemployment impossible.
DUDE!!
Im older than you and I grew up poor.
Between my husband and I we have a little under half a million dollars in easily accessible liquid assets. I also have enough in my retirement accounts that I could definitely retire at 65 comfortably if I stopped contributing today (CoastFIRE).
I am just barely starting to feel like I'm financially secure.. like I don't feel it, but I logically tell myself that I am. I feel like I'm finally starting to believe myself.
now i am not exactly well off either. but i never felt i was financially insecure even when i was low on money. that safety net is always there, and having experienced it, i am comfortable trusting it.
Same, although I'm not sure it's always a privilege thing, but also one's background. I've done pretty well for myself these last few years, and financially speaking it would not be the end of the world if I lost my job tomorrow. But I come from a working class family, and grew up with nothing.
I was raised and surrounded by family members who work a lot harder than I do for a lot less pay. They sacrificed a lot for me to go to school and get a good job, so if I were to lose it, the last thing I'd want to do is just chill for 2yrs even if I could afford to.