Most entrepreneurs talk about risk as a calculated equation, weighing the cost of stability against the potential for innovation. For Dara Woo, the leap wasn’t from one startup to another, but from coding for Lyft to performing eight shows a week on Broadway in The Picture of Dorian Gray.
Speaking with Ginni Saraswati on The Ginni Show, Woo revealed a career arc that reads like a study in both strategic focus and fearless reinvention. Raised in Silicon Valley by tech executive parents, she followed a predictable path: computer science at the University of Michigan, internships at EA and Salesforce, then a software engineering role at Lyft. But a lunchtime audition, just a block from the office, set her on a collision course with an entirely different life.
“I’ve been coding for ten years,” Woo said, “but I wanted to challenge myself in a way that made me feel brave.”
1. Optimize for Your Peak Hours, Not Someone Else’s
In a world that glorifies the 5 a.m. club, Woo thrives as a night owl, writing code after 10 p.m. and sending 50 emails after dinner. Her takeaway for founders? It’s not about conforming to productivity clichés; it’s about protecting and amplifying the hours when your brain is at its best.
2. Make Risk Less Risky Through Incremental Action
Before her Broadway debut, Woo spent years preparing for a creative pivot, guided by her “one thing a day” rule, a small, intentional action toward her goal, whether filming a self-tape, attending an audition, or updating her acting reel. “Could be as small as an email or as big as an audition,” she said. “I’ve done it every day for the last five years.” For entrepreneurs, that’s a masterclass in consistency compounding into opportunity.
3. Diversify Your “Fishing Lines”
Woo borrows a lesson from her fisherman father: always have multiple lines in the water. In her case, that meant balancing auditioning with tech work, not just for financial security, but for mental resilience when rejection inevitably came. Founders can adopt the same mindset: don’t rely solely on one lead, one client, or one investor.
4. Focus on Fewer Things to Win Bigger
Echoing Warren Buffett’s philosophy, Woo doesn’t chase every shiny object. “Right now, my intention is to get really good at acting,” she explained. That means no splitting focus between producing, writing, and performing — yet. Entrepreneurs often fall into the trap of doing too much too soon; Woo’s story is a reminder that mastery is often the fastest route to expansion.
5. Redefine Representation Without Stereotypes
As a third- or fourth-generation Asian American, Woo is passionate about roles where ethnicity is part of the character’s identity but not the plot’s entire premise. It’s a subtle but important lesson for business leaders: true inclusion integrates diversity naturally rather than tokenizing it.
For founders staring down a career pivot, whether from one industry to another or from the boardroom to the creative stage, Woo’s journey is proof that brave transitions are built on long-term intentionality, not sudden leaps. Her advice is simple but potent: know what you don’t want, follow what you do naturally, and keep at least one fishing line in the water.
Because sometimes, the life-changing bite comes during your lunch break.
Spencer Hulse is the Editorial Director at Grit Daily. He is responsible for overseeing other editors and writers, day-to-day operations, and covering breaking news.
