6 in 10 People Regret Their Careers — and This Legendary Investor Spent a Decade Finding the Fix
Entrepreneur
by Dan BovaFebruary 19, 2026
AI-Generated Deep Dive Summary
Bill Gurley, the renowned venture capitalist behind successful startups like Uber and Zillow, has spent years researching why so many people regret their career choices. His findings reveal that nearly 60% of individuals wish they had taken different paths, with regrets often stemming from missed opportunities rather than mistakes. Drawing on Daniel Pink’s research, Gurley highlights the emotional weight of "boldness regrets"—the things we didn’t try—especially as we age. He cites Jeff Bezos’ regret minimization framework, encouraging people to envision their 80-year-old selves and ask if they’d wish they had tried something new. This mindset inspired Bert “Tito” Beverage to create Tito’s Vodka after unconventional career shifts, proving it’s never too late to pursue bold ideas.
For those seeking mentorship, Gurley advises against fixating on elusive figures like Warren Buffett. Instead, he suggests identifying "aspirational mentors" through their work and "pragmatic mentors" who are accessible and willing to guide. This approach is particularly valuable for entrepreneurs and startup founders, who often need both inspiration and practical advice to navigate uncharted territory. By leveraging these relationships, individuals can build confidence and clarity in their career paths.
Gurley’s insights are especially relevant for startups, where boldness and innovation are key to success. His emphasis on taking action—whether by pursuing unconventional opportunities or seeking mentorship—aligns with the risk-taking culture of early-stage ventures. By addressing the fear of regret head-on, entrepreneurs can make more intentional decisions, turning potential career regrets into stepping stones for growth and fulfillment. Gurley’s message is a reminder that the best careers
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Originally published on Entrepreneur on 2/19/2026