303: Letting Go of Winning: What It Really Means to Redefine Success After 40 with Cassandra Andrews

2026-07-13

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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the identity crises, purpose gaps, and feelings of entrapment that often surface in midlife, tracing them back to an outdated masculine blueprint that prizes stoicism and winning over vulnerability.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 vis...

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the identity crises, purpose gaps, and feelings of entrapment that often surface in midlife, tracing them back to an outdated masculine blueprint that prizes stoicism and winning over vulnerability.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 permission to open up honestly with peers, often for the first time. Rob and Cassandra close on what she sees as the real prize of this work: not more success, but emotional freedom, autonomy, and choice.

You will learn:

· Winning isn't the same as fulfilment: many high-achieving men over 40 are feeling trapped despite external success.

· Self-awareness, including understanding shifting motivations is key to creating the life a client really wants, rather than what he thinks he should want.

· How Cassandra's work helps men find emotional freedom, autonomy and choice.

"When a woman tells a coach, "I've never told anyone this before," she means apart from her mother, her sister, her best friend. When a man says it, those words have never left his lips."

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For the episode resources and guest bio, please visit:

https://www.associationforcoaching.com/page/dl-hub_podcast-channel-coaching-men-unlearning-masculinity-high-achievers

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