I compare myself to my parents when they were my age, and this is what I see:
Financially, I do not expect to ever be as successful as my parents. My dad got a good idea and found himself in the right place/right time and as a result my parents denied themselves nothing until dad died.
Me? I make 1/3 of what my parents did in 1981. That's raw dollars, not adjusted for inflation.
In other avenues, I am more successful. Unlike my dad, for instance, I graduated college, I never used illicit drugs, I've never been arrested, I didn't get knocked up/knock someone up in high school, I didn't turn 27 years old with two failed marriages, a third that was on its way to failing, and a court order to stay away from my two young, angry children. My dad, for all his financial success, cannot say the same for any of those. Thank god that by the time I came along he had mostly snapped out of it. I'm told that when he was younger he was an insufferable asshole, but by the time I was born he had reformed into an extremely charming and likeable asshole lol.
My mom had no failed marriages but she did do the teen pregnancy and drug use thing, and pretty much stumbled aimlessly through her young adulthood until she met my (significantly older) dad and let him support her financially and run her life for her. To her credit though, she did run her own manicure shop in her mid-twenties, before she sold it to raise my sister and I. I'm yet to discover the entrepreneurial acumen to own my own business. So for that she definitely trumps me.
So on those counts, I'm mostly more successful than the both of them so far. Hope it sticks.