92: Success Starts where the Comfort Zone Ends | Alicia Jessop

How can you push your organization—and yourself—past the status quo?  

In this insightful episode of The Learn-It-All Leader Podcast, attorney, journalist, and tenured professor Alicia Jessop shares powerful insights from her career that highlight the importance of stepping out of comfort zones, refining your leadership skills, and driving true growth.  

Learnit CEO Damon Lembi sits down with Alicia Jessop to discuss the evolution of her career, from attorney to sports journalist and professor, and the lessons she's learned about leadership, risk-taking, and storytelling along the way. Alicia left behind a comfortable law career to pursue a passion in sports media and offers listeners a fresh perspective on success. Business leaders will learn how embracing discomfort and focusing on disciplined growth can unlock their full potential, while storytelling and active listening are critical tools for connection and impact. 

This Episode Covers: 

• Why leaving your comfort zone is essential for long-term growth and success. 
• How business leaders can apply lessons from top athletes about discipline and peak performance. 
• The power of storytelling in leadership and how to become a better storyteller. 
• Practical tips for fostering trust and openness in your team through active listening. 
• Insights into the evolving landscape of women's sports and leadership opportunities in that space. 
• Strategies for leaders to support their teams' growth by asking the right questions. 
• Alicia's personal journey and what it reveals about defining success on your own terms. 

Episode Highlights:  

(00:00) Introduction to Alicia Jessop – Damon introduces Alicia Jessop, attorney, sports journalist, and founder of Ruling Sports, setting the stage for a conversation on pursuing purpose. 

(01:20) Embracing Risk for True Growth – Alicia shares her decision to leave a comfortable corporate job to follow her passion for sports media. 

(05:58) Defining Success on Your Own Terms – Alicia explains why true success means growing as a person, challenging comfort, and making intentional choices. 

(08:45) The Power of Discipline and Role Models – Alicia reflects on lessons from elite athletes and why discipline is key to success. 

(10:55) Building Trust Through Listening – Alicia shares tips for building trust as a leader and interviewer by truly listening and creating safe spaces for others to open up. 

(14:45) Memorable Interviews and Earning Trust – Alicia recalls her challenging interview with Mike Tyson and how she gained his trust to uncover deeper insights. 

(20:30) Storytelling as a Tool for Connection – Alicia explains the importance of storytelling in connecting with people and shares how leaders can improve their storytelling skills. 

(24:00) Supporting Athletes Beyond the Game – Alicia discusses her work at Ruling Sports, helping athletes transition from their sports careers to entrepreneurial endeavors. 

(32:00) The Evolution of Women’s Sports – Alicia offers her perspective on the growth of women’s sports and the need for continued investment and equity. 

(48:00) Finding Your Life’s Purpose – Alicia encourages listeners to reflect on their legacy and take small steps toward fulfilling their true calling. 

About Alicia: 

Alicia Jessop is a tenured professor, sports law attorney, and media entrepreneur focused on leadership, athlete well-being, and career transitions. As the founder of Ruling Sports, she empowers athletes and business leaders through storytelling, legal expertise, and tailored career strategies. She has been a prominent voice in sports media, covering major events such