My dad was a high school grad from the middle of nowhere and was literally raised in a barn (the girls lived in the house—it was too small for all the kids) with no running water (manual-pump well). His dad was a small-acreage farmer and slightly-successful rodeo rider. Birth year puts him in the early part of the Boomer generation.
He puttered around with not-quite-successful-but-not-quite-failure blue collar sole-proprietor small businesses for most of his 20s, then got a low-level railroad job, worked his way up and spent his last ~15 years in middle management there before being forced into early retirement. Recall, just a high school diploma. He couldn't handle middle-school math (by more recent standards) when I was learning it, and could barely use a computer. But he could run a train yard. Go figure.
My mom quit work when they married in her late 20s, and never worked again. She had a junior college degree and just made enough to get by before that. Lived in a trailer when she was single.
They retired very well and paid my way through college in the early '00s. We never wanted for money at all when I was a kid—which is how they were able to drop four figures on a first computer (good ol' Tandy) for me, just in case that led to something. A big week-and-change road trip every year, sometimes flights instead, plenty of time off and travel around the holidays. We lived in some pretty damn nice houses (at times—there's only so much available when the railroad moves you to some podunk town and you want to buy on short notice).
On one income. In a pretty mundane, middling-pay career.
Union pensions and 20th century union health plans were magical. As were housing costs.