Episode 52 – The Devil Emails at Midnight — Transforming Bad Bosses with Mita Mallick

Have you ever had a boss who taught you exactly how not to lead? 

In this episode of The Art of Badassery podcast, host Jenn Cassetta sits down with Mita Mallick, author of The Devil Emails at Midnight: What Good Leaders Can Learn from Bad Bosses. Mita shares how she turned countless rejections into a bestselling book and became a leading voice in diversity and inclusion. Together, Jenn and Mita unpack lessons from difficult bosses, the role of grief in leadership, and practical strategies to navigate tough workplace dynamics. Mita reminds us that true leadership is built on community, storytelling, and the courage to be vulnerable.

Listen to the episode here

Watch the episode here

Introduction

Recently, I had the pleasure of hosting the inspiring author, Mita Mallick, on The Art of Badassery podcast. Known for her transformative work in business and culture, Mita has penned the book “The Devil Emails at Midnight: What Good Leaders Can Learn from Bad Bosses.” During our conversation, we unpacked the trials and triumphs of leadership, offering insights that are invaluable to anyone striving for success in both professional and personal realms.

From Ambition to Accomplishment

Mita’s journey is a testament to perseverance. Her first book, “Reimagine Inclusion,” despite initial hurdles, became a bestseller. Yet her journey to publishing wasn’t straightforward; it was fraught with rejection and obstacles based on narrow industry perceptions. Mita recounts these challenges, emphasizing the resilience required to continue in the face of adversity. Her latest book, already a bestseller, reflects her tenacity and belief in the importance of the narratives she shares.

The Complexities of Bad Bosses

In her latest work, Mita explores the concept that leadership isn’t static—good leaders can become bad bosses under pressure. Various factors, such as market condition shifts, the transition from individual contribution to team leadership, and personal life stresses, can pull leaders into counterproductive behaviors. Mita candidly shares her own experiences with micromanagement and missteps, illustrating the human side of leadership mistakes.

The Power of Empathy and the Mirror Test

Throughout our conversation, Mita emphasized empathy and reflection as crucial components of effective leadership. She introduced the “Mirror Test,” a technique for offering objective feedback during tense interactions. This approach facilitates understanding and resolution, fostering healthier work environments. Mita’s personal stories of dealing with grief underline the necessity of integrating vulnerability and openness in leadership practices.

Conclusion: Lessons in Leadership

Mita Mallick’s insights present a comprehensive guide for navigating the highs and lows of leadership. Her belief in community, continuous learning, and authentic storytelling underscores the value of persistence and empathy in business. The lessons from “The Devil Emails at Midnight” are not limited to traditional corporate settings—they resonate across all facets of life where leadership plays a role.

Takeaways from This Episode:

  1. Understanding Leadership Dynamics: Leadership is not a fixed state; even the most competent leaders can falter under unexpected pressures. By recognizing and acknowledging these dynamics, leaders can mitigate negative behaviors before they escalate.
  2. Building an Authentic Community: The publishing industry highlights the importance of having a dedicated following. Mita’s experience illustrates how nurturing a supportive community can pave the way for personal and professional success.
  3. Empathy as a Leadership Tool: Mita’s personal experiences with grief, along with her mirror test strategy, demonstrate the importance of empathy and open communication in managing teams effectively. Acknowledging and sharing personal challenges can strengthen workplace relationships and overall team morale.

To delve deeper into these ideas, check out Mita’s latest book, “The Devil Emails at Midnight.” You can follow Mita on her personal website or connect on LinkedIn, where she shares more about her journey and ideas. And don’t forget to follow The Art of Badassery podcast for more inspiring stories and conversations.

Important Links

About Mita Mallick

Mita Mallick is a Wall Street Journal, USA Today, LA Times Best Selling Author. She’s on a mission to fix what’s broken in our workplaces. She’s a corporate change maker with a track record of transforming businesses. She’s a highly sought-after speaker who has advised Fortune 500 companies and start-ups alike. She is a LinkedIn Top Voice, a contributor to Harvard Business Review, Fast Company, Adweek, and Entrepreneur. Learn more at https://www.mitamallick.com/

We’re Almost There! How to Finish the Year Strong (A Pep Talk)

Feeling ready to finish 2025 strong—or wondering how to get there? In this solo episode of The Art of Badassery podcast, Chief Badassery Officer Jenn Cassetta shares a roadmap for surviving the year and stepping into 2026 with confidence. Drawing from her martial arts experience, Jenn introduces “White Belt Month”—a reset to strip away titles, revisit the basics, and reconnect with your inner strength.

She guides listeners through creating a “Greatest Sh*ts List” to honor tough lessons, uncovering secret weapons built through adversity, and building a “Greatest Hits List” to celebrate wins and joyful moments.

This episode is your guide to ending the year grounded, empowered, and ready to tackle the next chapter with clarity and courage.

Listen to the episode here

Watch the episode here

Introduction

Welcome to a special edition of The Art of Badassery Podcast blog, where we dive deep into the art of surviving and thriving as we approach the upcoming year. This solo episode with Jenn Cassetta, your Chief Bad Assery Officer, is all about harnessing the power within you to finish 2025 strong and step into 2026 with renewed energy and confidence.

Back to Basics: The White Belt Month

In the world of martial arts, humility and foundation are keys to mastery. Jenn shares the concept of “white belt month,” where practitioners of all ranks embrace beginner’s lessons to reinforce their skills. This exercise isn’t just about martial arts; it’s about shedding accomplishments and societal labels, and focusing on foundational strengths to rebuild a stronger self.

Embrace the Suck

One of the key lessons Jenn shares is the idea of embracing the suck. Life is rife with unavoidable challenges. Fires in LA, overwhelming news cycles, and personal hardships have all tested us in 2025. Instead of resisting, embracing these hardships allows us to grow stronger, more resilient, and ultimately more prepared for whatever comes next.

Your Greatest Shits List

Jenn encourages us to identify the challenging, unavoidable situations (or “greatest shits”) of the year. Recognizing these allows us to then discover our secret weapons developed as a result. Just as martial artists hone their unique skills, we too have emotional and mental strengths that evolve through adversity—grit, empathy, and resilience are just a few examples.

Discover Secret Weapons

The power of our secret weapons comes from the adversities we’ve faced. Jenn emphasizes that perseverance, patience, and empathy are gifts, honed under life’s pressures. They serve us as we tackle future challenges. She urges us to identify these personal strengths and cherish them as essential tools for the future.

Celebrating Achievements with Your Greatest Hits List

Once we’ve embraced our challenges and discovered our secret weapons, it’s time to celebrate wins—both big and small. Jenn speaks about the importance of compiling a “greatest hits list” of our accomplishments and joyful moments from 2025. Reflecting on our successes boosts our confidence, reminding us that we’ve made significant strides this year.

Visualizing the Future

Jenn highlights the importance of visualization and mindful goal setting for overcoming chaos and creating a positive future. Through exercises like vision boarding, we can shape our subconscious to guide us toward our aspirations. As 2026 approaches, embodying calm, confidence, and clarity becomes crucial to navigating a world that may yet be turbulent.

Conclusion

To thrive in the coming year, Jenn leaves us with the reminder to focus on creating joy and raising our vibration. This mindset ripples through our interactions and community, creating a positive impact beyond what we see. Moving forward, let us embrace each day with the spirit of a renewed sensei, ready for transformation and growth.

3 Takeaways from This Episode:

Celebrate and Visualize: Compile a list of your achievements and thrilling moments. Visualize an empowered future to keep you grounded and focused on the positive amid uncertainty.

Embrace the Basics: By stepping back to the basics, we strip away ego and rebuild our core strengths. Remember, foundational skills are often the most powerful.

Find Your Secret Weapons: Reflect on the past year’s challenges and recognize the hidden strengths you’ve developed. These secret weapons will serve you as you face future trials.

Important Links