Liz Weeks listened to her parents. Go to college, they said. Then get a good job, save for a down payment and buy a home. That was how they achieved financial success.

So she followed their playbook. She borrowed more than $165,000 to attend the University of Rochester, and then law school at Syracuse University. Now 32, she is a regulatory attorney in Seattle.

But things haven’t gone as planned. Ms. Weeks still owes more than $140,000 on her student loans despite making monthly payments over the past decade. Home prices in Seattle have soared as the economy has boomed. In 1989, the median home price there was $77,300, or $163,773 in today’s dollars, according to the National Association of Realtors. Today it’s $542,700.

“I have been stressed about money since I was 11,” Ms. Weeks said. “There was always this overarching sense of dread. The debt I have now colors so many of the decisions I make.”

For Ms. Weeks and her peers, the rules have changed. Americans entering the workforce in the decade since the financial crisis face a starkly different landscape than their parents did at the same age. They often have far higher student loan debt. Housing eats up a bigger chunk of each paycheck. And young households have lower incomes and fewer assets than previous generations did at the same ages.