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.

Three Connection Points

• Read Wild Courage: Go After What You Want and Get It
• Jenny's website
• Read How to Decide When to Say "No"

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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