Why can’t I get ahead? Is this really how hard life was for our ancestors?

I’m 40, single parent, two boys (16, 23), with a college degree, and 2.5 jobs. I do a ton of side work but I am barely scraping by. <br><br>In less than 10 years my oldest son will be in college, and I’m *terrified* of how I’ll be able to afford it. I’ve tried to save for his college fund, but years ago I had to break into it to pay for a new roof and car repairs just to be able to get back to work (no fmla here). I’ve done everything I’ve been told I’m supposed to do and yet…<br><br>I’ve seen people go from poverty to wealthy in a generation (Oprah, Ryan Coogler, Chris Rock,��이etc.) and I’m starting to feel like I’m just not cut out for this whole “pulling yourself up by your bootstraps” thing.<br><br>Every time I get a *little* ahead (like, I can afford to buy something that’s not beans and rice), something comes along (like a car repair) that knocks me back. I’d love to have a big house and kids in college and a vacation, but right now I feel like I’m just barely scraping by and the magic bullet is evading me. *What did our ancestors do right that I’m doing wrong?*