At this point in my life I'd say I'm less successful on both fronts. Professionally, only time will tell, but financially I don't know that I'll ever be as successful. My parents are boomers. They don't realize how high the cost of living is and they didn't have to deal with student debt. They don't understand that even though I make decent money now and I tend to be frugal, my bills take up over half of my net pay. When my parents were my age they had enough money to buy a house on one income (and pay it off in 22 years), they felt comfortable starting a family, adopting, starting college funds for us, etc. My mom always asks me why I'm wasting money on rent when I could "just go buy a house," like I'm just buying a pair of shoes I like or something. She doesn't understand that a down-payment on a house in my city costs $30-$40K, and that's the low end. I can't even imagine planning a wedding or starting a family at this point in my life, and I don't know how others in similar financial situations do the same.