Stop Waiting for Permission | Preston Cherry & Jenny Wood on Owning Your Choices

In this episode of *Just Press Record*, Matt Zeigler brings together Dr. Preston Cherry, author of *Wealth in the Key of Life*, and Jenny Wood, former Google exec and author of *Wild Courage*. They dive into the power of rejection, the value of “weird,” the courage to stand out, and why nobody likes to be “should on.” This conversation blends psychology, storytelling, and practical lessons on living boldly and authentically.

### Topics Covered

* Why rejection is often just the first step toward success

* Jenny’s “wild courage” story of meeting her husband on the subway

* The role of fear—failure, judgment, and uncertainty—in holding us back

* How to embrace “weird” as a strength in work and life

* Reframing “manipulative” into the courage to influence for good

* The balance between seeking permission and trusting yourself

* The importance of stage of life, self-audits, and giving yourself grace

* Session work, entrepreneurship myths, and the underrated power of enthusiasm

* Practical frameworks like Preston’s “6 As” and Jenny’s “WINN” and “FLIP” tools