Have you ever hit a point where you knew you were meant for more—but couldn’t quite figure out what was holding you back?
In this dynamic episode of The Art of Badassery podcast, host Jenn Cassetta welcomes back powerhouse guest Andrea Owen—global keynote speaker, life coach, and bestselling author. Andrea gets real about navigating setbacks like divorce and grad school rejection, and how those detours revealed unexpected gifts.
Together, they dive into what strong women truly wrestle with: confronting fear head-on, setting unshakeable boundaries, and managing relationships when your personal evolution outpaces those around you. Andrea also gives a sneak peek into her upcoming fourth book, packed with tangible guidance for women committed to continuous growth.
Tune in for an empowering, joy-filled conversation about choosing yourself, protecting your energy, and rising stronger through every season of life.
Listen to the episode here
Watch the episode here
Live Like You Give a Damn With Andrea Owen
Welcome to another inspiring episode of The Art of Badassery podcast, where Jenn Cassetta takes us on a journey with the remarkable Andrea Owen. Known for revolutionizing self-help and personal development, Andrea shares her insights on navigating life’s challenges, transformations, and embracing growth. Here’s a detailed breakdown of this powerful episode.
A Warm Welcome Back
Jenn welcomes back Andrea Owen, a seasoned guest aiming to empower high-achieving women through her work. Andrea, a global keynote speaker and professional life coach, returns to update us on her journey since her last appearance and introduces us to her latest book, “Live Like You Give a Damn: 25 Bold Moves to Get Honest, Face the Hard Stuff, and Show Up for Yourself,” slated for release on December 9th, 2025. Celebrated for her strong stance on key personal development issues, Andrea is a testament to resilience and courage.
From Setbacks to New Beginnings
Andrea shares a deeply personal story about not gaining acceptance into a graduate program, a surprise for her considering her accomplished history. Instead of feeling defeated, Andrea found an unexpected gift in the form of a relationship with someone tied to that very institution. This twist of fate illustrated her belief that sometimes rejections are merely the universe’s way of protecting us, pushing us toward a more suitable path. Her message is clear: life’s curveballs often come with hidden blessings.
Rising Through Personal Turmoil
Navigating her divorce amidst the pandemic and confronting her fears head-on proved to be Andrea’s most challenging life transition. Her ‘longest sunrise’ metaphor beautifully captures her realization that healing doesn’t conform to a timeline. In navigating this period, Andrea emphasizes the importance of acknowledging one’s emotional journey, seeing joy alongside pain, and remaining steadfast when transitions drag on longer than comfort allows.
The Power of Choosing Oneself
Andrea delves into the importance of choosing oneself in the face of inner conflict and societal expectations. Her decision to end a ‘good enough’ marriage underscores a crucial lesson: self-growth may require leaving familiar paths to honor personal needs and dreams. This decision, rooted in honesty and compassion, spotlighted a value misalignment rather than wrongness, paving the way for both partners to pursue fulfillment.
Andrea’s New Book: Back to Basics
“Live Like You Give a Damn” challenges readers to genuinely commit to change rather than merely the idea of it. Andrea emphasizes practical growth concepts—understanding fears, establishing boundaries, and fostering connections—as stepping stones on the journey to self-actualization. By inviting readers to revisit foundational self-help principles, she reinforces the importance of continuous, authentic work over superficial engagement.
Leadership and Human Connection in Modern Times
In the modern workplace, where collective burnout and grief often simmer beneath the surface, Andrea encourages leaders to be transparent and understanding. By naming the struggles and being genuine, leaders can foster deeper trust and connection among their teams, cultivating resilience and motivation in challenging times.
Final Thoughts and Takeaways
As we wrap up this episode, Jenn and Andrea challenge us to reassess our priorities, embrace joy amid chaos, and recognize the value of enduring through life’s darkest moments. Here are three key takeaways from this insightful conversation:
1. Embrace Uncertainty: Life’s rejections and curveballs often lead to unexpected blessings. Keep your heart and mind open to new possibilities when faced with setbacks.
2. Choose Yourself: Identify misalignments in your relationships and have the courage to take paths that prioritize your growth and fulfillment, even if it means leaving a ‘good enough’ situation.
3. Root Yourself in Basics: Navigate your personal development journey by revisiting and reinforcing foundational principles, tuning into your fears, and setting authentic goals aligned with your true self.
Important Links
- Andrea’s website – https://andreaowen.com/
- Andrea’s podcast – Make Some Noise
- Andrea’s New Book – Live Like You Give a Damn
- Subscribe to Jenn’s newsletter so you never miss an episode
- Book Clarity and Connection by Yung Pueblo
- Burnout to Badass
- The 6 Habits Of High Performance With Jenn Cassetta – Past episode
- Art of Badassery Retreat
- Art of Badassery Newsletter
About Andrea Owen
Andrea Owen is an author, global keynote speaker, and professional certified life coach who helps high-achieving women maximize unshakeable confidence, master their mindset, and magnify their courage.
Learn more at https://andreaowen.com/
