What would change if you stopped waiting to be chosen, stopped settling for “good enough,” and started being bold about what you actually want? In this episode, Jenn sits down with Jen Cohen, four-time bestselling author, serial entrepreneur, keynote speaker, and host of the Habits and Hustle podcast, for a conversation about ambition, resilience, confidence, relationships, and the habits that help us create a life we actually want. Jen shares how fitness became the foundation for her discipline and mental strength, why resilience matters more than avoiding failure, and why boldness is a skill you can build through small, consistent actions. Jenn and Jen also get into the deeper side of success—including what happens when your drive and ambition start affecting your relationships, why connection is something neither of them is willing to sacrifice, and the importance of knowing your worth personally and professionally. They also talk about dating, self-abandonment, rejection versus regret, taking control of your own life, and why “you have to start” even when you don't feel ready. Jen's advice? Build the muscle of boldness, make the ask, take the risk, and keep going. If you’re ambitious, stuck in “what if,” afraid of rejection, or simply ready to stop playing small, this conversation will challenge you to get out of your own way—and start creating the life you actually want. Follow Jen Cohen: Instagram: @therealjencohen Website: https://www.jennifercohen.com SUBSCRIBE TO MY CHANNEL Healthy relationships don't happen by accident. They happen through awareness, intention, and practice. Subscribe for weekly insights on relationships, attachment, emotional wellness, communication, intimacy, and building lasting connection. https://www.youtube.com/@jennpinkerton Take the FREE Pinkerton Relational Health Index Quiz Now: https://pinkertonrelationalhealthindex.scoreapp.com CONNECT WITH JENN: Website: www.jennpinkerton.com Instagram: @Jennbpinkerton Facebook: Jennifer Pinkerton Twitter: @redheadreveal TikTok: @redheadreveal Connection Cards: Shop Here: https://linktr.ee/jennbpinkerton?utm_source=ig&utm_medium=social&utm_content=link_in_bio Purchase one of Jenn's course here: https://jennifer-pinkerton.mykajabi.com/to-do-before-i-do Click here to work with Jenn and her transformational 30 day program: https://jennpinkerton.com/