In this conversation with Jenny Wood, a former Google executive and author of Wild Courage, she challenges the perception of traits like selfishness and bossiness as negatives. Jenny reveals how these qualities can be powerful tools for self-advocacy and growth. She shares personal anecdotes about her corporate journey, the necessity of embracing one’s fears, and the importance of prioritizing big aspirations. Through her insights, listeners are encouraged to redefine courage and unlock their true potential.
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question_answer ANECDOTE
Subway Courage Anecdote
Jenny Wood shared a personal story of chasing a man off the subway propelled by "wild courage."
She reframes traits like boldness and recklessness as powerful assets rather than flaws.
insights INSIGHT
Regret Outweighs Failure
Regret of inaction often weighs heavier than failure itself.
Leaving unhealthy situations late is still better than enduring prolonged unhappiness.
volunteer_activism ADVICE
Say Yes To Big Things
Say yes to big impactful tasks and no to small, non-promotable work.
Prioritize work that moves the business to advance your career.
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In this episode of A Productive Conversation, I'm joined by Jenny Wood — author of the book Wild Courage: Go After What You Want and Get It. Jenny and I dive deep into the nine supposedly “negative” traits she reclaims as powerful tools for getting what you want in work and life.
From her 18-year journey at Google, rising from entry-level to executive, to launching the company’s massive Own Your Career program, Jenny shares stories that challenge the conventional wisdom around being “too much.” Whether it’s being nosy, selfish, or bossy — Jenny reframes these traits as strengths that fuel progress, self-awareness, and courageous action.
Six Discussion Points
Why Jenny reclaims words like selfish, bossy, and reckless — and what they actually mean.
How Wild Courage was born from a homework assignment… and a subway love story.
The role of nuance and reframing in personal development and leadership.
Lessons from Google on prioritization: “Say yes to the big, say no to the small.”
When obsession is a strength — and when it turns into burnout.
Permission slips, spotlight effects, and overcoming fear of judgment.
Jenny doesn’t just write about boldness — she lives it. This conversation will nudge you to reexamine how you show up, reframe what’s holding you back, and redefine what courage looks like in your life and work. If you’ve ever felt like you had to shrink to succeed, this episode offers another path — one rooted in wild, unapologetic courage.
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A Productive Conversation 
