322. The Best Approach to Law: Embracing "Feel Good Lawyering"

Jun 5, 2025

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In this episode of "The Free Lawyer," host Gary converses with Lani Medina, a corporate and M&A attorney, Air Force veteran, and founder of Lani Law LLC. Lani shares her journey from a senior associate at a law firm to starting her own practice. She discusses the challenges of this transition, her philosophy of "feel good lawyering," and the importance of aligning one's practice with personal values. Lani also highlights her cultural background, military experience, and the role of technology in her practice. The episode emphasizes finding joy and fulfillment in the legal profession through compassion and integrity.

Lani Medina is a corporate and M&A attorney, Air Force veteran, and founder of Lani Law PLLC—a boutique law firm that delivers high-level legal counsel with a human touch. A Bronx native and proud Puerto Rican, Lani helps entrepreneurs and mission-driven companies navigate complex deals with clarity, compassion, and confidence.

She brings 15+ years of experience, including Big Law and in-house roles, and is building a network to support socially conscious startups through accessible, feel-good lawyering.

Challenges at the Law Firm (00:01:55)
Fear and Anxiety in Transition (00:03:10)
Cultural Background's Influence (00:04:24)
Lessons from Military Service (00:05:44)
Seeking Coaching (00:06:38)
Breakthrough Moments in Coaching (00:07:51)
Business Planning Process (00:08:32)
Overcoming Fear of Leaving (00:09:27)
Feel Good Lawyering Philosophy (00:10:54)
Human Side of M&A Transactions (00:11:50)
Advice for Stuck Lawyers (00:12:44)
Mindset Shift to Business Owner (00:14:15)
Using AI in Legal Practice (00:14:57)
Redefining Success (00:16:07)
Promoting Feel Good Lawyering (00:17:41)
Investing in Yourself (00:19:41)
Mindset Over Environment (00:20:39)
Surprises in Coaching Relationship (00:21:27)
Impact of Lani Law on Personal Life (00:22:20)
Future Aspirations for Lani Law (00:23:28)

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