This week, I talk with Jenny Wood, who spent 18 years at Google, rising through the ranks and building global programs used by tens of thousands of employees. From the outside, Jenny had the kind of career many people aspire to—prestige, influence, and steady advancement inside one of the world’s most admired companies. But over time, she began to realize that the very habits that fueled her success—relentless drive, constant striving, and an obsession with achievement—were also taking a personal toll. In this conversation, we talk about ambition and when it becomes a trap, the pressure to keep chasing the next milestone, and the challenge of celebrating wins along the way. We also explore money, identity, imposter syndrome, motherhood, and the fear that comes with walking away from something impressive to build a life that feels more aligned with who you truly want to become. Let’s get to it!
In this episode:
- (00:00) – Intro
- (00:44) – How Jenny became a pilot—and what flying gives her
- (02:59) – What flying represents in Jenny’s life
- (04:25) – The importance of finding an escape
- (06:57) – Optimizing for leisure versus optimizing for productivity
- (14:06) – Jenny’s early interest in psychology
- (19:15) – Packaging compelling ideas without losing what’s true
- (22:09) – When obsession helps—and when it starts holding you back
- (25:54) – Jenny’s years inside Google
- (28:54) – Anticipatory grief and the psychology of impact bias
- (34:19) – Balancing career, health, family, and the leap into
- entrepreneurship
- (41:29) – Leaving the comfort zone and taking a leap of faith
- (44:06) – The moment Jenny decided to leave Google
- (52:00) – Jenny’s journey into parenthood and being a career mom
- (56:29) – How slowing down changed Jenny’s relationship with her kids
- (01:01:47) – Chasing the New York Times bestseller list
- (01:07:32) – How this conversation between Barrett and Jenny came to be
- (01:12:33) – How Jenny is making a living today—and what’s next
- (01:15:05) – Jenny’s ambitious family travel plans
- (01:17:31) – Building a business that supports a life of travel
- (01:20:37) – Trusting that stepping away for a year will work out
- (01:26:11) – What makes Jenny world-class?
- (01:26:54) – The change Jenny hopes to create through her work
- (01:28:40) – Who Jenny is becoming
Key Takeaways
- Ambition Is a Powerful Tool—but a Dangerous Master: The same ambition that drives achievement can quietly become destructive if it goes unchecked. Jenny reflects on how high performers often build their identity around success, promotions, and external validation. Over time, this can lead to burnout or misalignment with what truly matters. Ambition works best when it is guided by values rather than allowed to run the show.
- Security Can Become the Biggest Barrier to Growth: One of the hardest decisions in a successful career is walking away from something that looks objectively “good.” Jenny explains that comfortable roles—especially prestigious ones—can become traps that prevent people from pursuing work that actually aligns with their deeper goals. Growth often requires leaving behind the safety of what already works.
- Your Relationship With Money Shapes Your Career Choices: Many professionals stay in jobs they no longer enjoy because of the lifestyle those jobs support. Jenny emphasizes that understanding your financial needs—and separating them from your ego or status—can unlock freedom. When you reduce the pressure that money exerts on your decisions, you gain the flexibility to pursue work that feels meaningful.
- Life Transitions Force You to Reevaluate What Success Means: Major life events—like becoming a parent—can fundamentally change how you think about work, time, and ambition. Jenny shares how motherhood shifted her priorities and forced her to reconsider what kind of life she wanted to build. These transitions can feel disruptive, but they often reveal what matters most.
- Reinvention Requires Courage and Self-Honesty: Leaving a successful career path or redefining your professional identity is rarely comfortable. Jenny’s story illustrates that reinvention requires confronting fear, uncertainty, and the possibility of failure. But the alternative—continuing down a path that no longer fits—can ultimately be far more costly.
Quotes
“Wild courage is about pushing past three fears: fear of failure, fear of uncertainty, and fear of judgment by others.” ~ Jenny Wood
“I was struggling so hard to push past my own fears, and yet had I stayed at Google, I would’ve been a total fraud because how can I tell a story about wild courage if I’m just going to stay in the same job for 18 more years?” ~ Jenny Wood
“The people who hired you have a lot of experience hiring. Who are you to be so arrogant to think that they made a mistake?” ~ Jenny Wood
“By the time your kids go to college, you will have spent 90% of the time with them that you will ever spend with them.” ~ Jenny Wood
“If I was able to do this and build something from nothing, having no experience as an entrepreneur, having no experience as a writer, having no experience as a keynote speaker and be this successful this quickly — then it doesn’t serve me for a single second to live in fear that I won’t be able to replicate this again.” ~ Jenny Wood
Links
- Wild Courage by Jenny Wood: https://wildcouragebook.com/
- University of Michigan: https://umich.edu/
- Hemingwrite: https://hemingwrite.com/
- Wild Courage by Jenny Wood: https://wildcouragebook.com/
- Google: https://google.com
- Harvard Business School: https://www.hbs.edu/
- Vanessa Van Edwards: https://www.scienceofpeople.com/
- Why Real Relationships Are the Secret to Growing Your Business with Mo Bunnell: https://barrettbrooks.com/podcast/why-real-relationships-are-the-secret-to-growing-your-business-with-mo-bunnell/
- The Power of Regret by Dan Pink: https://www.danpink.com/the-power-of-regret/
- The Secret Ingredient to a Dream Career and Life | Jenny Wood: https://www.goodlifeproject.com/podcast/nine-traits-of-a-good-life-jenny-wood/
Connect with Jenny
- Website: https://itsjennywood.com/
- Instagram: https://www.instagram.com/itsjennywood/
- LinkedIn: https://www.linkedin.com/in/jennyilles/
- Jenny’s newsletter: https://itsjennywood.com/newsletter
Connect with Barrett
- Barrett’s newsletter: https://BarrettBrooks.com
- X / Twitter: https://twitter.com/barrettabrooks
- Instagram: https://www.instagram.com/barrettabrooks
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