The Connecticut-based media executive earns close to mid-six figures and no longer worries about paying bills on time. “I have reached a point in my life where if I want to spend $200 on Amazon for no good reason, I can,” Cristobal tells Fortune. 

That’s an impressive feat for a millennial immigrant who moved to the U.S. from the Philippines when she was a toddler. Cristobal makes nearly four times the median U.S. household income of $85,694 for Americans in her age demographic of 35 to 44. Not to mention, she purchased her own home—something only 43% of millennials have managed to do, according to Freddie Mac’s 2021 research. 

Yet while she’s largely been able to overcome some of the obstacles facing her generation—the worst economic downturn in decades, difficult labor markets, stagnant wages, sky-high housing and health care costs—she hasn’t escaped unscathed. 

Courtesy of Gabrielle Cristobal

Seven years after earning her MBA, she still has just over $180,000 in student loan debt. “It doesn’t hurt me, but it’s still a factor in my decision-making,” Cristobal says. “I’ve always had to plan around the student loans.”

And now Cristobal faces new obstacles, including figuring out how to catch up financially after years of being broke early in her career, and learning how to manage her newfound income. Cristobal’s paycheck is taxed in the second-highest tax bracket in the U.S., making careful financial planning more important—and arguably more complicated—than ever before. 

Cristobal is frustrated by her high tax rate—especially when she knows other wealthy Americans have found ways to avoid paying their share.

“I beat this game,” she says. “You told me that I needed to work hard and join affluent America, and I did that—and then you’re gonna punish me for it?”

Climbing the corporate ladder

Cristobal’s family emigrated to New York from the Philippines in 1986. Prior to moving to the U.S., her family was well-off. But Cristobal’s father—a former computer programmer—had to take a job as a freelance truck driver when he got to the U.S. to make ends meet.

After making her way through the New York City public school system, Cristobal landed at Loyola University in New Orleans. “I really didn’t know how to work the American college system. I thought that going to any college would be good,” Cristobal says, adding she regrets not going to an Ivy League school to build better professional connections.  

Her friendships at Loyola did lead to her first job at a sports network in New Orleans. “I feel there are people who have far better networks, and I just got lucky,” Cristobal says. But that luck didn’t hold. Hurricane Katrina hit the city in 2005, sending the then 22-year-old back home to live with her parents. “I didn’t know what to do after a historic catastrophe.”

By 2008, she was working at ESPN as a production assistant. But she still wasn’t earning enough. In fact, when her car needed new tires to the tune of $400, she had to borrow money from her girlfriend at the time; she ultimately picked up a second job at a restaurant to make ends meet. Starting off as a waitress, Cristobal worked her way up to line cook: “It’s probably the hardest job I’ve ever had.” 

“I was broke. I didn’t know what to do—this couldn’t be my life,” Cristobal remembers thinking at the time. And while she eventually moved up the ranks to earn $60,000 at ESPN and could afford to drop the second job, Cristobal felt success was still out of reach. 

On the advice of a friend, she decided to get her MBA to increase her earning potential and score higher-status jobs. It worked. With her first job after graduating from University of Chicago Booth School of Business, she doubled her salary—even though she says she felt unprepared. “For me, the MBA was exceptionally beneficial,” Cristobal says. “I needed that degree to get that job, otherwise there was no way they were going to trust me with it.”

‘I’m now too successful to count’

But the cost of degrees from Loyola and Booth added up. Overall, Cristobal spent about $25,000 for her college degree and close to $200,000 for her MBA. 

Today her student loan balance lingers around $180,000, a mix of federal and private loans. While she’s continued to pay down her private loans during the pandemic, she’s taken advantage of the federal loan pause. But the debt weighs on her.

“Does it suck? Yeah, it sucks,” Cristobal says. “I could buy twice the house—literally twice the house.”

Student loans have impacted not only purchasing decisions but also her dating life. “Thinking of marriage in a very practical and unromantic way, it can really make or break you financially,” says Cristobal, who is currently single. “I don’t have time to focus on someone else’s problems, because she’s probably bringing me her student loans as a dowry.”

But Cristobal is not in a hurry to wipe out her federal loan debt just yet, on the slim hope that the Biden administration launches a forgiveness program. “This is where you start gambling a little bit,” Cristobal says with a chuckle. 

Yet she’s well aware that her chances of getting $50,000 or even $10,000 knocked off her outstanding balance are minimal. “Nothing AOC or Bernie Sanders has put forward will benefit me. I’m now too successful to count,” says Cristobal, who feels like she’s being punished for her success.

She’s also found herself in a strange new financial position: Instead of focusing on keeping her spending minimal and boosting her income to cover her monthly expenses, she’s focused on ways to lower her tax bill. “I pay more taxes than Bezos. I pay more taxes than most people make in a year,” Cristobal says. 

In fact, Cristobal purchased a home in Stamford, Conn., last year for just under $500,000 in an effort to curb some of her tax bill. “I hate owning a house. Anytime there’s a weird sound I’m like, ‘Great. How much is that gonna cost me?’”

But if she hadn’t bought a house, Cristobal says, she feels she’d have been “taxed to death.” 

Beyond trying to tame her taxes, Cristobal says her other big financial obstacle is saving for the future. “I’m woefully behind,” she says, admitting that she hasn’t done a great job of saving for retirement. She liquidated her 401(k) to help pay for her move to Chicago for grad school and has only really been saving for retirement since her mid-30s. 

“I had to make the tradeoff. Am I gonna put [money] into my 401(k)? Or am I gonna have disposable income to pay my student loans?” she says. 

That decision is weighing heavily on Cristobal these days, as she contemplates her career going forward and what retirement may look like. “I don’t know if I can keep this up for 20 years like the boomers did, because that’s exhausting. It’s been a wild ride as an Asian lesbian in corporate America,” she says. 

Since gaining a measure of success, Cristobal says, she’s a bit worried about what she may lose if she makes the wrong choices. “Now I have money,” she says. “But I don’t have wealth, and that’s what I worry about.”