Healing the Success Wound: Enneagram 3, Work Addiction, and the Path to Aligned Ambition with Brooke Taylor (S09-047)

 
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What happens when the very thing that makes you successful is slowly hollowing you out?

That's the question at the heart of this conversation — and it’s one of the most honest and penetrating descriptions of the Enneagram Three's inner world I've heard on this show in years.

Today’s guest is Brooke Taylor, an Enneagram Three, career coach, and author of the new book Healing the Success Wound. Brooke grew up in Silicon Valley where worth was measured in gold stars, landed at Google by her early twenties, and found herself drowning in a success she couldn't feel. We talk about the success wound which, as Brooke describes it, is the pain that comes from mistaking productivity and achievement for self-worth — the deeply installed belief that the more you produce and achieve, the more worthy of love and belonging you become..

This wound isn't just for Enneagram Threes. It's a human condition — and it shows up differently depending on your type, your culture, your family system, and what "success" looks like in your particular world.

We talk through Brooke's five types of unfulfilled achievers — the grinder, the hider, the seeker, the work-hard-play-hard, and the pleaser — and I couldn't help mapping those to the Enneagram types in real time. We also get into the distinction between the true self, the wounded self, and the socialized (or protector) self — a framework rooted in Internal Family Systems and gestalt psychology that I think will resonate deeply with longtime Typology listeners.

What I found most striking, and what I want you to sit with, is Brooke's observation that fulfillment comes from how we work — not what we do for work. She says 60% of the clients who come to her convinced their job is the problem end up staying in that job once they fix their relationship with success. That's not a small thing.

And at the end of the day, Brooke and I both kept circling back to: the deepest answer to the success wound is spiritual. Non-duality. Abundance. Faith. Letting something larger than your fear define what's enough. Easy to say. A lifetime to practice.

Whether you're a Three or you love one, this episode is for you. The success wound doesn't ask for your Enneagram type before it takes up residence. It just needs an open door. 

About Brooke Taylor

Brooke Taylor is a Career Coach, speaker, workshop facilitator, and former Marketing Lead at Google. In the crowded space of career coaching, she is distinguished as an expert in helping transform the lives and careers of over 5,000 high-achieving female leaders at companies like Google, Uber, Coinbase, McKinsey, Goldman Sachs, and Salesforce through healing their success wound. While other thought leaders have talked around the insatiable need for success and validation, she is the first to package it and name it as the “Success Wound.” She is a regular spokesperson in the international media across US, UK, Australia and Canada, featured in and contributed to Forbes, Entrepreneur, Hip & Healthy, Business Insider NASDAQ, and The Australian Financial Review. She is a regular keynote speaker at women in business summits including Women@Google Global Summit and have been invited to speak with organizations including the Australian Government, BBC, Google, Uber, General Assembly and many more.

 
 
 

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Spirituality, Internal Family Systems, Leadership, Type 3Ian Cronenneagram, spirituality, self-awareness, LeadershipComment