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

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Written By damon lembi

Alicia Jessop, Tenured Professor, Sports Law Attorney, and Founder of Ruling Sports, left behind a traditional legal career to build a platform that empowers athletes and leaders through storytelling, legal insight, and entrepreneurial strategy. In this episode, host Damon Lembi sits down with Alicia to unpack the bold decisions and disciplined mindset that have shaped her unconventional path.

Read the full breakdown of Alicia Jessop’s episode on Learnit.

Key Leadership Lessons from Alicia Jessop’s Journey:

  • Comfort is the enemy of growth. Alicia shares how stepping away from a stable legal career unlocked purpose-driven leadership and creative impact.

  • Discipline isn’t just for athletes. Leaders can learn peak performance habits from elite sports figures - and apply them in business.

  • Storytelling builds trust. From interviewing Mike Tyson to mentoring athletes, Alicia explains why great leaders are great listeners and storytellers.

Connect with Alicia Jessop:

Alicia’s insights have appeared in Forbes, The Washington Post, and The Athletic. She is a passionate advocate for leadership, athlete well-being, and redefining success on your own terms.

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damon lembi
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93: | He Went From Pro Athlete To Leading Sales Expert With This Mindset | Charles Thompson
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91: 4 BOLD Moves to Reinvent Yourself as a Leader | Kayla Logue