I grew up with My dad making a ton of money. Then when he left my mom when I was 13, he also decided to do the happiness over money thing, respectfully and change his career slightly. He was definitely still making plenty for us to be comfortable though.
Once I started college though my parents did the whole "youre kicked out of the nest, time to fly" thing, I was all on my own. Luckily I paid for everything on scholarship including rent and all my bills so the money I made from my part time job paid for any extra stuff.
I wasn't poor til I graduated and found a job, got a place, then had to leave it and was screwed. It was only about a month-long period, but I was sleeping at different people's houses and eating like a bird.