From Almost Quitting Law School to Google Legal Director | Finding Purpose in Your Career

Make your next 30 minutes count with new episodes delivered to your inbox. Click here: https://karen-gilhooly.kit.com/makeminutesmatter1 In this episode of Make Minutes Matter, Karen Gilhooly sits down with Darryl Chiang, Director in Google’s Legal Department, for an honest and thought-provoking conversation about career fulfillment, pivots, and purpose. Darryl shares his unconventional journey from nearly walking away from law school to building a meaningful career in corporate law, unpacking the realities behind prestigious titles and the internal questions many professionals are afraid to ask. Together, they explore imposter syndrome, the gap between expectations and reality in big law, and the courage it takes to admit when something isn’t working. Darryl reflects on formative moments that shaped his path from clerking for a federal judge to realizing that loving the idea of a career isn’t the same as loving the day-to-day work. He discusses the power of mentors who teach lessons no textbook ever could, why understanding business context often matters more than legal clauses, and how a simple mindset shift “you just gotta ask” can change the trajectory of a career. The conversation also touches on becoming a parent later in life, staying relevant in a fast-changing world, and defining success on your own terms. This episode is a must-listen for law students, young professionals, and anyone navigating a career transition or questioning whether the path they’re on is truly aligned. Be sure to subscribe and tune in for Part 2, where the conversation goes even deeper. About Darryl Chang Darryl Chiang is a Director in Google’s Legal Department, where he focuses on AI policy and regulation. His career spans federal clerkships, big law, and in-house counsel roles, giving him a rare and well-rounded perspective on the legal profession and what it takes to find the right professional fit. Connect with Darryl on LinkedIN: https://www.linkedin.com/in/darryl-chiang-63524/ This podcast was Produced by Rainbow Creative with Executive Producers Matthew "MoJo" Jones, and Editors Anthony Parisi and Yuval Yosha of Big Fable. Graphic Design by Mohamed Naser. Filmed at Wolff Studios in Brooklyn, NYC 0:00 - Cold Open: The Business Questions Story 0:36 - Welcome & Introduction to Darryl Chiang 2:38 - Being a Dad at 50 & Working in AI at Google 4:02 - Why Law? The Five Professions 10:55 - The Fork in the Road: Almost Quitting Harvard Law 16:39 - Big Law Burnout: Wearing a Mask at Work 21:32 - Serendipity: Landing the In-House Job 24:37 - Working with Real People & Street Smart Mentors 26:00 - The Lesson: Business Context Matters More Than Legal Documents 27:40 - "You Just Gotta Ask" - The Power of Negotiation Learn more about your ad choices. Visit megaphone.fm/adchoices