My First Million Bill Gurley: 6 Out of 10 People Are Making This Mistake
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Mar 9, 2026 
Bill Gurley, veteran venture capitalist and longtime partner who advises founders, shares how to avoid the biggest mistake in your career. He discusses finding fascination over grit, practical experiments to test paths, the power of peer groups, learning leadership, and using flexibility and AI to multiply your options. Short, tactical ideas woven through stories and career rules.
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Most People Regret Inaction Not Mistakes
- Six out of ten people would restart their careers because they regret inaction rather than action.
- Bill Gurley cites Wharton People Analytics and Gallup data showing widespread disengagement and life-long "what if" regret patterns.
Ask If You'd Do It For Thirty More Years
- Use a long-horizon test: ask whether you want to still be doing this 30 years from now to reveal true fit.
- Gurley also recommends Bezos' regret-minimization: imagine your 80-year-old self to cut through short-term fear.
Battle Card Multiple Career Paths
- Battle-card multiple career paths by imagining 2–5 trajectories and simulating outcomes over two years.
- Treat early experiments as reversible: try things, learn, and quit if they don't work rather than locking in.
