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Episode 2198: Megan Hellerer exposes the "achievement lie" of how we think about our careers and lives

Directional Living: A transformational Guide to Fulfillment in Work and Life

Working on Sheryl Sandberg’s team at Google, Megan Hellerer - who had just graduated top of her Stanford class - was on the fast track to become a young Silicon Valley superstar. A few years later, however, she had a breakdown and quit. Describing herself as an “underfulfilled overachiever”, she writes about this traumatic experience in her new book, Directional Living. Hellerer - who now runs her own career coach consultancy and includes Representative Alexandria Ocasio-Cortez as a client - confesses that at Google she wasn’t living her life and thus was miserable. Her answer to what she calls the traditional “destinational thinking” of career development is in “directional living” - a concept that replaces the “achievement lie” with a more authentic and less quantifiable path to personal fulfillment.


Megan Hellerer is a career coach and the founder of Coaching for Underfulfilled Overachievers. She has led hundreds of women, including Representative Alexandria Ocasio-Cortez, to transform their lives by transforming their careers. After checking all the traditional boxes of success—graduating at the top of her class from Stanford University and spending eight years as a Google executive—and still deeply unhappy, she quit her great-on-paper job with no plan. Now her mission is to provide others with the support and guidance that she needed when she herself was struggling. Megan has been featured in New York, Vogue, The Wall Street Journal, CNBC, and The Times. She lives with her husband and daughter in the Hudson Valley, New York.


Named as one of the "100 most connected men" by GQ magazine, Andrew Keen is amongst the world's best known broadcasters and commentators. In addition to presenting KEEN ON, he is the host of the long-running How To Fix Democracy show. He is also the author of four prescient books about digital technology: CULT OF THE AMATEUR, DIGITAL VERTIGO, THE INTERNET IS NOT THE ANSWER and HOW TO FIX THE FUTURE. Andrew lives in San Francisco, is married to Cassandra Knight, Google's VP of Litigation & Discovery, and has two grown children.

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Keen On
Keen On
Nobody asks sharper or more impertinent questions than Andrew Keen. In KEEN ON, Andrew cross-examines the world’s smartest people on politics, economics, history, the environment, and tech. If you want to make sense of our complex world, check out the daily questions and the answers on KEEN ON.
Named as one of the "100 most connected men" by GQ magazine, Andrew Keen is amongst the world's best-known technology and politics broadcasters and commentators. In addition to presenting KEEN ON, he is the host of the long-running show How To Fix Democracy and the author of four critically acclaimed books about the future, including the international bestselling CULT OF THE AMATEUR.
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