How Jenny Became a Pilot

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

Get full show notes and links at https://GoodWorkShow.com.

Watch the episode on YouTube: https://www.youtube.com/@barrettabrooks.

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