About this episode

Cassandra Andrews discusses redefining success for high-achieving men over 40 and the importance of emotional freedom over conventional success.

In episode 5 of our Coaching Men series, host Rob Lawrence talks to Cassandra Andrews, author of Unlearning Masculinity: Redefining Success for High Achieving Men over 40 , to explore why so many successful men—CEOs, founders, and elite athletes among them—feel trapped even after ticking every box of conventional success. Cassandra unpacks the identity crises, purpose gaps, and feelings of entrapment that often surface in midlife, tracing them back to an outdated masculine blueprint that prizes stoicism and winning over vulnerability. Rather than rejecting masculinity altogether, she makes the case for relearning what it means to be a man beyond those rigid rules. Her work starts with a vision, rather than goals: a more personal picture of where a client actually wants to be, rather that what they feel expected to chase. The conversation turns to Cassandra's coaching methodology, which draws on NLP, timeline therapy, and motivational mapping to help clients build self-awareness and understand how their motivations have shifted from external validation to internal fulfilment. She also shares the thinking behind her intimate group dinners—safe spaces that give high-achieving men…

People in this episode

Host: Rob Lawrence

Guest: Cassandra Andrews

Topics covered

• redefining success
• masculinity
• midlife crisis
• coaching methodology
• emotional freedom

Keywords

• success
• masculinity
• coaching
• NLP
• emotional freedom
• midlife
• identity crisis

Mentioned in this episode

Books & works: Unlearning Masculinity: Redefining Success for High Achieving Men over 40

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