This is an interesting topic to me. I can follow my paternal lineage back quite a way and find very stark differences from generation to generation. My great-grandfather was one of 29 kids. He was dirt poor, and basically clawed his way into the lower middle class, eventually putting 3 out of his 4 kids through college by farming 70 acres. My family still has the land, and a cousin of mine still lives in the modest ~1200 square foot home with 7' ceilings(!) that he built himself in the 1940s.
My grandfather grew up during the Depression. He was born in a log cabin and knew what it was like to have no running water or electricity until he was a teenager. He knew what it was like to not have food on the table unless you grew it or butchered it yourself. He went to college got a good government job, and married a woman who was raised under similar conditions. Their difficult early lives gave them a work ethic and frugal habits that served them well. They retired in their mid-50s as millionaires (despite never being particularly high income-earners), and they both have healthy pensions.
My grandparents raised three incredibly successful children (including my father). All of them went on to college, and 2 out of 3 earned Master's Degrees. All three have had great work ethics and wonderful careers. My dad recently retired in his early 50s with a government pension, although he still works part-time. However, the funny thing is that, although my dad has a great pension that will see him comfortably through retirement, unlike my grandparents, he saved very little on the side. Especially considering his salary during the last few years of his employment, which was at least twice what I ever expect to earn. Part of the problem was my mom, who, though I love her very much, was always a bit of a spendthrift (and she is now in assisted living with Alheimer's unfortunately, which also doesn't help with my Dad's savings). But I've also notice that my grandparents' frugality didn't well translate to the next generation. My dad hasn't lived "paycheck to paycheck", but his lifestyle inflation was pretty huge as his pay went up during the last decade or so of his working career.
When I entered the working world in 2008 (what a great time to be a new college grad!), I started off following my Dad's footsteps. I got a nice government job and chose the pension plan, rather than the defined contribution plan, because as far as I knew, your employer was responsible for your retirement. My Dad also kind of pushed me that way. I bought a house with a 100% loan and a healthy PMI payment, because that's what you do when you start working, right? And housing always goes up anyway, right? You can see where this is leading...I lost my ass and a half on the house when I moved. I didn't get to keep any of the employer contributions when I left my first job because I was on the pension plan instead of the defined contribution plan. I also married a lovely woman who had $36,000 in student loans that would be forgiven if only she worked 4 years as a teacher in South Carolina...but I couldn't find a decent job in South Carolina, so we had to pay the loans back ourselves. And then, to top it all off, we had a child with multiple birth defects who will require lifelong medical care.
But the funny thing is, I'm very thankful that we have been forced into frugality due to the difficult circumstances that we've faced. We are now debt-free except for the mortgage, we already have a decent investment portfolio started, and we are saving like mad for financial independence (probably about 10 years off). I could complain about the difficulties we've faced or I could look at my granddad, who grew up in far worse circumstances than I did and accomplished so much. Or I could look at my great-granddad, who worked his butt off until he could no longer work but was still (materially) behind where we are today. In short, I really don't give a rat's ass whether I am better or worse off than my parents, but I am happy to be where I am, and I'm even happier with where I am headed.
