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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 Timestamps 00:00 – Introduction 03:55 – Jenny’s subway story & the psychology of courage 07:44 – Fear of “no,” rejection, and the lessons it teaches 11:32 – Shamelessness, rejection, and confidence 13:40 – Preston’s 6 A’s framework & honest self-audits 19:00 – Overcoming limiting beliefs and self-perception 20:00 – Why being “weird” is a strength 23:45 – Permission, reckless courage, and taking action 28:00 – Fear, paradox of choice, and making bold moves 30:20 – FLIP framework for change 31:40 – Preston’s 5 P’s framework for prosperity 33:00 – WINN: What I Need Now 34:18 – Session work, career building, and enthusiasm 38:13 – Redefining “manipulative” as influence and connection 43:03 – Nobody likes to be “should on” 46:32 – Why Jenny and Preston were paired together Watch every Just Press Record ever here: • Just Press Record Is your attention span too short for full episodes? Try some shorts here: • Cultish Creative Shorts And if the written word is more your thing, sign up for my mailing list and you can grow your network of ideas and people alongside me: https://cultishcreative.com/ AND - CHECK OUT @DrPrestonCherry and @itsjennywood on YouTube too!