In a candid conversation, Julia Stiles, now a prominent figure in both acting and directing, reminisced about her early days in the entertainment industry. During an episode of the PEOPLE in the '90s podcast, she shared memorable encounters with fellow actors and the challenges she faced as a young actress. Stiles vividly recalled feeling starstruck upon meeting Natalie Portman, who was already a rising star at the time. This encounter left a lasting impression on her, highlighting the competitive nature of the industry. Stiles also discussed her experiences attending a performing arts school, where she crossed paths with other future celebrities. Over the years, her interactions with peers evolved from nervous auditions to genuine friendships on set. Today, Stiles has shifted her focus to directing while occasionally returning to acting, most recently starring in Chosen Family and premiering her directorial debut, Wish You Were Here.

Back in 1999, when Stiles was just 18, she found herself navigating the bustling world of New York City auditions. It was during this period that she encountered several established and emerging stars. One such moment stood out: bumping into Natalie Portman. "I remember seeing her and thinking, 'Oh, I’m never going to get this job,' " Stiles said, acknowledging Portman's already significant fame. Despite these moments of self-doubt, Stiles persevered, eventually landing roles that would define her career. She appeared on the cover of Teen PEOPLE as one of the '21 Hottest Stars Under 21,' alongside other notable names like Justin Timberlake and Katie Holmes.

Stiles' journey through high school was equally transformative. In her final year, she switched to a performing arts school, where she met Christina Ricci. These formative years laid the foundation for her growing network of famous friends. As she transitioned from auditions to actual film sets, Stiles noticed a shift in her relationships with co-stars. "Once you actually have the job and you’re on location, not only are you sort of forced to hang out with everybody and you quickly become friends, but you have the confidence of, I’ve already got the job," she explained. This newfound camaraderie enriched her experience and helped build lasting connections within the industry.

In recent years, Stiles has taken a more behind-the-scenes approach, focusing on directing. However, her acting roots remain strong, particularly through her iconic role as Kat Stratford in 10 Things I Hate About You. At the premiere of her directorial debut, Stiles reflected on how playing Kat resonated deeply with her. "Kat Stratford was like this feisty outspoken girl who did not care what people thought about her," Stiles said. The character provided her with a sense of empowerment and validation during a time when she often felt pressured by external expectations. Stiles expressed gratitude for the continued impact of this role, noting its enduring relevance to audiences.

Through her evolving career, Julia Stiles has navigated the highs and lows of Hollywood, transforming from a young actress facing industry pressures to a respected director and occasional performer. Her reflections offer valuable insights into the challenges and rewards of building a lasting career in entertainment. Stiles' journey underscores the importance of resilience and adaptability in an ever-changing industry, while celebrating the milestones that have shaped her path.