I'm a very late Gen X, my wife is very early Millennial, most of our friend groups are a similar mix... And we're in the same boat as you. I paid off my student loans last year, my mortgage is bearable, I got laid off a little over a year ago but had the savings to bridge the gap until I found a new job (and landed in a better paying position), and just got back from taking my family to Disney World for a week. But I spent most of my 20s and into my 30s eating ramen, saving up to go to maybe 2 concerts a year, asking my parents for gas money, and truly living paycheck to paycheck. Gradually it got better, but I was lucky to not get sick, injured, or addicted and I do acknowledge just how much of my current situation is due to luck, but I also had to put in plenty of hard work.