Kalena Masching’s life is a nonlinear path. After graduating from Paly in 2004, Masching has worked in retail and real estate while playing the bass in her band, the Doll Parts, and recreational softball in her spare time.

Recently returning to school to obtain a degree in sociology with a minor in education and a master’s in school counseling, she said she has always embraced the values of resilience and adaptability.

Due to financial instability growing up, Masching said she struggled to connect with her peers while attending Paly.

“People were not nice,” Masching said. “I used to call Palo Alto ‘Shallow Alto.’ I didn’t grow up with the same income level that a lot of the other kids did … It can be really isolating when you’re not in the honors classes and you don’t necessarily have the money to do the things they’re doing.”

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Masching also said she felt an overwhelming pressure to excel academically during her time at Paly.

“Wherever you are, teachers and parents have a lot of influence on what kind of classes you take,” Masching said. “Honors classes weren’t weighted back then, but there was this stigma that if you weren’t in them, then you were doing it wrong.”

She also said the school’s college-centered culture hasn’t changed much since she was a student, with students sometimes prioritizing academics above all else.

“As long as on paper you were doing fine, then there was a lot of free reign,” Masching said. “A lot of people are getting absolutely stoned on the weekends, but they’re getting straight As, and they’re working in labs.”

Despite these challenges, Masching graduated with a schedule filled with softball, student council and nearly every music ensemble offered — jazz, pep, concert and symphonic band. However, hidden behind these activities, she said she struggled with undiagnosed attention-deficit hyperactivity disorder.

“Having ADHD means there’s so many things you want to do, and Paly has such amazing offerings,” Masching said. “It’s hard to pick all of them.”

After high school, Masching decided to attend community college while working in retail.

“By the time I was 19, I was the manager of a retail store — the youngest manager in company history,” Masching said.

Eventually, Masching moved to real estate — one of the few jobs that didn’t require a college degree. However, the transition wasn’t easy.

“My first five years, the best year I had, I made $900,” Masching said. “That’s not a lot of money.”

Eventually, though, she turned it around. By 2024, Masching ranked among the top 10% of realtors in California. But Masching said the stress of real estate and 70 to 80 hour work weeks drove her to seek change.

“You have to live to work, not work to live,” Masching said. “I was working really hard, and we were able to do all those things, but if you’re not happy, and if you’re stressed all the time, are you really living? So I went back to school, and I didn’t tell anyone.”

Masching now attends the University of California, Berkeley, in pursuit of a sociology degree. She said she wants to continue focusing on her personal well-being while becoming a secondary school counselor to support students in finding career paths after graduation.

“I went to Paly,” Masching said. “I know what it feels like to not be the one going to the four-year college. My life is awesome.

Masching said students should take time to find their passions before committing to a career instead of feeling pressured to pursue a path defined by external expectations.

“I think there’s value in going to college when you know what you want to do,” Masching said. “For me, community college was great for figuring out what I wanted.”

Similarly, in her own life, Masching continues to adjust her career path to align with her personal values.

“I’m still going to sell real estate because I want to, but I don’t want to be stressed out all the time,” Masching said. “The life I want has a stable retirement, time for travel, time for my family and helping people.”

Ultimately, Masching said students should embrace failure and focus on their own interests.

“Sometimes there’s value in looking at what you are learning in the activities that you like versus just doing things because they look good for an application,” Masching said. “There are very few mistakes that are irreversible … as long as you’re still alive and functioning, you can basically reinvent yourself over and over again.”