Intro

This chapter features insights from a former Google leader who debunks common misconceptions about career success. It emphasizes the significance of overcoming fear, embracing authenticity, and a program designed to aid individuals in career advancement.

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In today’s episode, we’re joined by Jenny Wood—career coach, former Google executive, and author of Wild Courage. Over 18 years at Google, Jenny rose from entry-level to executive and created one of the company’s largest career development programs. Her work focuses on breaking the myths of professional success and teaching high performers how to reclaim “taboo” traits—like being shameless, weird, or even manipulative—to build authentic relationships, increase visibility, and take control of their careers.

Introduction

Join us for a bold and insightful conversation with Jenny Wood as she reveals why playing it safe is holding you back—and how to reclaim traits like weird, shameless, and even manipulative to fuel career growth. Jenny shares hard-earned lessons from her rise to executive at Google, the power of strategic visibility, and why soft skills are your ultimate edge in the AI era.

What to Listen For

Introduction – 00:00:00

What separates high performers who rise from those who stagnate in their careers?
What soft skills do tens of thousands of high performers crave—despite excelling technically?

Visibility, Influence, and Strategic Self-Promotion – 00:05:21

Why managing your boss isn't enough—and what it means to “manage higher” and “manage diagonally”
How to get noticed before a promotion cycle even begins.
What’s the right way to brag—and how do you do it without sounding arrogant?

Reclaiming “Taboo” Traits – 00:17:31

What are the nine negative traits Jenny says you must reclaim—and why are they the key to getting ahead?
How do bold, assertive actions (like chasing someone off a subway) illustrate professional courage?
Why being manipulative might actually make you a better leader

Frameworks That Help You Win – 00:34:27

How to use the “WIN” framework to advocate for your needs without guilt
Why saying “yes” to everything might be sabotaging your career
What is the “SAFE” framework for giving clear, kind, and honest feedback?

Is It Time to Leave? – 00:48:01

What’s the FLIP framework—and how can it help you decide whether to stay or go?
How to know when your manager is holding you back—and when it’s time to make your move

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