What’s Stopping You From Taking the Risk That Could Change Everything?
Mar 26, 2025
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Jenny Wood, author of Wild Courage and a former Google executive, dives into the power of overcoming fear in this engaging conversation. She shares personal stories of career shifts and the significance of embracing one's so-called negative traits like shamelessness. Listeners will learn how reframing fears can lead to personal growth and what 'fearscaping' means in the context of overcoming self-doubt. Jenny emphasizes the beauty of vulnerability, resilience, and even obsession as tools for success, encouraging everyone to take bold actions towards their dreams.
Jenny Wood emphasizes transforming fear into action through the practice of separating exaggerated fears from verifiable truths.
The podcast encourages redefining perceived negative traits, like being 'shameless,' as potential strengths that can enhance personal and professional growth.
Listeners are reminded that developing courage is a gradual process, where even small steps can significantly impact one's life and career.
Deep dives
Overcoming the Fear of Change
The discussion highlights the personal journey of making a significant career decision, specifically leaving a comfortable position at a major tech company to pursue writing. The speaker reflects on the fears that clouded this decision, such as the fear of financial instability and being too old to find new employment. By separating tales from truths—identifying exaggerated fears versus verifiable facts—the speaker emphasizes the importance of recognizing genuine strengths, like having savings and the ability to prioritize family time. This realization ultimately helps in overcoming the fear of change and taking necessary risks.
The Journey to Wild Courage
Courage is portrayed as a crucial trait that everyone can develop, regardless of their personality type. The podcast emphasizes that living with wild courage means pushing past fear and acting despite uncertainty. Listeners are reminded that they do not need to fully conquer their fears; even a slight increase in courage can lead to significant actions, whether that means stepping out of one’s comfort zone or attempting to connect with new opportunities. The conversation underscores actionable strategies for cultivating this courage in everyday life.
Embracing Your Unique Traits
The episode introduces a concept of embracing uniquely perceived negative traits, such as being 'nosy' or 'shameless,' as potential strengths. These traits can assist individuals in achieving their goals by encouraging them to connect with others and advocate for their needs. The speaker articulates that fear of judgment often suppresses these traits, hindering personal growth and connection. By redefining these characteristics, one can approach relationships and opportunities with a more assertive and confident mindset.
Transforming Fear into Action
The podcast emphasizes the critical role of transforming fear into practical actions. A framework is introduced to categorize fears into truths and tales, allowing individuals to confront what is genuinely holding them back. This process involves writing down these fears and reframing negative narratives into more neutral or positive perspectives. The application of this strategy helps in making informed decisions and encourages continuous personal growth by pushing individuals to work through their discomfort.
Lessons from Grandma Lila
A personal anecdote about Grandma Lila illustrates the importance of resilience and finding compromise in the face of challenges. At 88, she shares her wisdom, teaching the value of persistence despite setbacks, exemplified when her grandson faces job insecurity. Her mantra, 'no is just an opening offer,' reflects a mindset that promotes negotiation and resourcefulness. This story serves as a reminder that embracing discomfort and pushing through fears can lead to unexpected opportunities and success.
In this episode, Jenny Wood shares how to overcome fear and take bold action.
Jenny spent 18 years rising from entry-level to executive at Google, where she founded one of the company’s largest career programs. Now, she’s the author of Wild Courage, a book that flips the script on success by reclaiming nine so-called “negative” traits—like being reckless, nosy, or shameless—and showing how they can fuel massive growth.
We get into what it really takes to break through fear, bounce back from rejection, and build the kind of courage that moves your life and career forward. Jenny holds nothing back—sharing wins, stumbles, and the surprising moment she chased her now-husband off a subway car.
Some highlights we explore:
The email rejection that made her lose sleep—and what she did next
Why separating “truths from tales” is a life-changing tool for fear
How to reframe being “shameless” as a leadership superpower
What it means to be obsessed... in the healthiest, most productive way
Enjoy!
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