The Free Lawyer

Gary Miles
  • 5.0 (66)
  • ENTREPRENEURSHIP
  • UPDATED WEEKLY

The Free Lawyer Podcast is designed for the lawyer, entrepreneur or professional who is in some way unfulfilled, stressed or stuck and looking for something better. We will discuss various blocks that limit us from achieving the personal freedom we all desire but have not yet fully experienced. Are you looking to achieve a new level of success? If so, this podcast is for you!

  1. 2D AGO

    Are You Accidentally Training Your Associates to Quit? #395

    The invisible curriculum: the powerful, unintended lessons law firm partners teach their associates through behavior rather than words. Gary Miles illustrates how elite attorneys accidentally model burnout, perfectionism, and the "external authority trap." He breaks down the five destructive lessons that drive top talent to leave the profession and explains why tying your identity to being indispensable hinders your firm's growth. Listen for the difference between external and internal authority and receive three actionable shifts to create a sustainable, high-performing firm culture. Get the Values Alignment Guide ⁠⁠⁠⁠⁠⁠⁠https://upbeat-trailblazer-9238.kit.com/1604bbf4cb⁠⁠⁠⁠⁠⁠⁠ Take the Free Lawyer Assessment ⁠garymiles.net/the-free-lawyer-assessment⁠ Learn more about Breaking Free or order your copy ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.garymiles.net/break-free⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Schedule a complimentary discovery call: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://calendly.com/garymiles-successcoach/one-one-discovery-call⁠⁠⁠⁠⁠ ⁠⁠⁠⁠ Watch this episode on YouTube: ⁠https://www.youtube.com/channel/UCqcfaTWo17uxmYS9hfAdiaQ

    15 min

  2. 6D AGO

    The Best Strategies for Lawyers to Set Healthy Boundaries #394

    In this episode of "The Free Lawyer," host Gary interviews Yeve Chitiga, a former lawyer turned certified executive and leadership coach. Yeve shares her journey from big law and in-house roles to launching her own coaching practice. Together, they discuss the challenges lawyers face with people-pleasing, boundary-setting, and aligning career success with personal fulfillment. Yeve offers insights on overcoming burnout, reconnecting with inner values, and supporting women in law. The episode highlights the transformative power of coaching for lawyers seeking greater joy, confidence, and authenticity in their professional and personal lives. Yeve leads Yevedzo Coaching and Consulting, an executive and leadership coaching and consulting practice that supports high-achieving women and senior leaders who want to lead with clarity, confidence, and alignment. A lawyer with Big Law and in-house counsel experience and a former financial institution internal auditor in both the US and UK, Yeve brings deep corporate experience to her coaching. As an ICF Professional Certified Coach she blends empathy and strategy to help clients elevate their leadership, strengthen their presence, and align their work with their values and vision. The Power of Coaching (00:03:33) Personal Trainer for the Heart, Mind, and Soul (00:06:11) Redefining Success: Internal vs. External Validation (00:09:04) Listening as a Superpower (00:11:41) Challenges for Women Lawyers and Leaders (00:16:28) People Pleasing and Burnout (00:21:11) Setting and Maintaining Boundaries (00:24:42) Reconnecting with Inner Wisdom (00:28:43) Achieving Alignment, Not Just Success  You can find The Free Lawyer Assessment here- https://www.garymiles.net/the-free-lawyer-assessment Would you like to learn what it looks like to become a truly Free Lawyer? You can schedule a complimentary call here: https://calendly.com/garymiles-successcoach/one-one-discovery-call Would you like to learn more about Breaking Free or order your copy? https://www.garymiles.net/break-free

    37 min

  3. FEB 9

    3 Reasons Your Boundaries Collapse Every Time #393

    In this episode, Gary Miles challenges the common belief that high-achieving attorneys struggle with boundaries because they lack discipline. The real issue is the "External Authority Trap," where lawyers tie their self-worth to constant availability and others' perceptions. This trains family, teams, and lawyers themselves that their personal needs do not matter. To break this cycle, Gary introduces the concept of "Internal Authority," where professional confidence is rooted in competence and preparation rather than response time. This is your 30-day protocol centered on maintaining a single, frequent boundary to rebuild trust in yourself. Get the Values Alignment Guide ⁠⁠⁠⁠⁠⁠⁠https://upbeat-trailblazer-9238.kit.com/1604bbf4cb⁠⁠⁠⁠⁠⁠⁠ Take the Free Lawyer Assessment ⁠garymiles.net/the-free-lawyer-assessment⁠ Learn more about Breaking Free or order your copy ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.garymiles.net/break-free⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Schedule a complimentary discovery call: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://calendly.com/garymiles-successcoach/one-one-discovery-call⁠⁠⁠⁠⁠ ⁠⁠⁠⁠

    14 min

  4. FEB 5

    Are You Leaving Money on the Table in Your Law Practice? #392

    In this episode of The Free Lawyer podcast, host Gary interviews Danielle Hendon, founder of Four Corners CFO. Danielle shares her journey from corporate finance to helping law firms achieve financial clarity and balance. The discussion covers common financial challenges lawyers face, such as overreliance on billable hours, the importance of understanding profit margins, and the need for sustainable business practices. Danielle introduces her six-part financial framework and emphasizes building teams, leveraging technology, and prioritizing personal fulfillment. The episode offers practical strategies for lawyers to create profitable, purpose-driven practices that support both their professional and personal lives. Danielle Hendon is the founder and owner of 4 Corners CFO, where she helps small business owners and law firms bring clarity and confidence to their finances. After spending more than a decade in corporate finance and accounting, Danielle left the long hours and burnout behind to build a business grounded in balance and purpose. Today, she combines big-business expertise with a passion for helping lawyers and other service-based entrepreneurs transform financial stress into strategic growth. Her mission is simple: to help firm owners build profitable, sustainable practices that support the lives they want to live. Why Focus on Law Firms? (00:04:18)  Law Firm Financial Challenges (00:05:38)  What Makes Four Corners CFO Different? (00:07:08)  Why Successful Lawyers Struggle Financially (00:08:45)  The Three Profit Levers (00:09:09)  From Bookkeeping to Budgets and Cash Flow (00:11:20)  Common Financial Blind Spots (00:14:04) I Shifting Mindset from Revenue to Profit (00:16:18)  Owner as CEO: Achieving Balance (00:18:16)  Building Profitable and Sustainable Practices (00:19:51)  Trends in Law Firm Operations (00:21:11)  Future Challenges: AI and Technology (00:23:04)  The Value of Coaching and Mentorship (00:24:30)  Why Lawyers Hesitate to Seek Financial Help (00:26:26)  First Steps for Lawyers Not Paying Themselves (00:28:20)  Aligning Practice with Personal Fulfillment (00:29:28)  Building a Team and Delegating (00:32:23)  Would you like to learn what it looks like to become a truly Free Lawyer? You can schedule a complimentary call here: https://calendly.com/garymiles-successcoach/one-one-discovery-call Would you like to learn more about Breaking Free or order your copy? https://www.garymiles.net/break-free You can find The Free Lawyer Assessment here- https://www.garymiles.net/the-free-lawyer-assessment

    36 min

  5. FEB 2

    Is Your Dedication to the Law Actually Martyrdom? #391

    The legal profession has a "dirty little secret." The toxic culture of martyrdom that equates suffering with success. In this episode, Gary Miles shares his journey from professional excellence to internal collapse. This episode challenges the industry standard of the 80 hour work week and explores why the most "dedicated" attorneys are often the most trapped. Listen for the vital difference between external validation and internal authority, and why strategic rest is actually a professional tool rather than a weakness. It's time for attorneys to choose personal freedom without compromising our professional standards. Gary provides a roadmap for moving from martyrdom to mastery, proving that you can serve your clients with excellence while still being present for your family. Get the Values Alignment Guide ⁠⁠⁠⁠⁠⁠https://upbeat-trailblazer-9238.kit.com/1604bbf4cb⁠⁠⁠⁠⁠⁠ Take the Free Lawyer Assessment garymiles.net/the-free-lawyer-assessment Learn more about Breaking Free or order your copy ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.garymiles.net/break-free⁠⁠⁠⁠⁠⁠⁠⁠⁠ Schedule a complimentary discovery call: ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://calendly.com/garymiles-successcoach/one-one-discovery-call⁠⁠⁠⁠ ⁠⁠⁠⁠ Watch this episode on YouTube: https://www.youtube.com/channel/UCqcfaTWo17uxmYS9hfAdiaQ

    15 min

  6. JAN 29

    Are You a Successful Lawyer but Still Unfulfilled? #390

    In this episode of "The Free Lawyer," host Gary welcomes Jen Gillman, founder of Gillman Strategic Group, to discuss the disconnect many lawyers feel between external success and personal fulfillment. Jen shares her journey from practicing attorney to legal recruiter focused on helping rainmakers find the right firm fit. She introduces her “Six Pillars to Becoming a Happy Rainmaker” framework, emphasizing self-care, boundaries, and legacy. The conversation explores practical strategies for lawyers to achieve both professional success and personal happiness, highlighting the importance of intentional career choices, coaching, and redefining success on one’s own terms. Jen Gillman is the founder of Gillman Strategic Group, where she helps rainmakers find their exact right, perfect-fit firm and law firm owners navigate strategic mergers. As a former practicing attorney herself, Jen understands that professional success doesn’t always equal fulfillment—and she’s on a mission to change that. After earning her J.D. from NYU School of Law and B.A. from Brandeis University, Jen practiced law for 12 years before transitioning to legal recruiting. Unlike traditional recruiters who find lawyers for firms, Jen finds firms for lawyers. She helps partners identify what they truly need to be fulfilled, whether that’s better resources, growth opportunities, or work-life balance, and then matches them with firms where they can thrive. Jen is the creator of the “6 Pillars to Be(coming) a Happy Rainmaker” framework and author of the forthcoming The Happy Rainmaker: A Little Tale About a Lawyer Who Found Success and Happiness Too. She shows up for her clients as part agent, part therapist, and part cheerleader, because successful lawyers deserve to be happy too. Learn more at happyrainmakers.com. You can purchase The Happy Rainmaker here: https://amzn.to/3Nfkne3 Jen’s Career Transition Story (00:03:32)  The Candidate-Focused Recruiting Model (00:05:33) Holistic Support for Lawyers (00:07:01)  Difference from Traditional Recruiting (00:09:23)  Honesty and Advising Against Moving (00:10:58)  Why Successful Lawyers Feel Unfulfilled (00:13:02)  Six Pillars to Becoming a Happy Rainmaker (00:16:08)  Deep Dive: Defining Boundaries (00:21:12)  Deep Dive: Designing a Legacy (00:24:31)  The Future of Legal Practice (00:27:21)  The Value of Coaching and Outside Guidance (00:29:08)  Where to Find the Six Pillars & The Happy Rainmaker Book (00:30:28)  About The Happy Rainmaker Book (00:30:45)  Implementing the Six Pillars at Any Career Stage (00:32:22)  First Steps for Unfulfilled Lawyers (00:34:00)  Final Advice: Small Steps Matter Take The Free Lawyer Assessment (10 minutes, completely free): https://www.garymiles.net/the-free-lawyer-assessment What you'll get immediately: ✓ Your Professional Freedom Score (out of 300 points) ✓ Breakdown across Internal Authority, Sustainable Excellence, and Authentic Practice ✓ Personalized action plan in your inbox ✓ Specific steps you can take this week Would you like to learn what it looks like to become a truly Free Lawyer? You can schedule a complimentary call here: https://calendly.com/garymiles-successcoach/one-one-discovery-call Would you like to learn more about Breaking Free or order your copy? https://www.garymiles.net/break-free

    38 min

  7. JAN 26

    3 Pillars of High-Performance Integration for Elite Attorneys #389

    Our industry holds a toxic myth: that professional excellence requires the sacrifice of your personal life. This episode reveals how constant availability actually creates fragility in a practice rather than preventing disaster. There are three pillars of high-performance integration for attorneys: strategic systems design, the power of being present, and the integration of one’s authentic identity. Gary Miles shares personal stories of recovery and success—from managing a high-stakes federal trucking case to achieving a major verdict through collaboration—to prove that personal strength and professional effectiveness are collaborative partners. Listen for practical strategies for setting client boundaries, delegating effectively, and implementing transition rituals to ensure you are fully present for your family. Get the Values Alignment Guide ⁠⁠⁠⁠⁠⁠https://upbeat-trailblazer-9238.kit.com/1604bbf4cb⁠⁠⁠⁠⁠⁠ Take the Free Lawyer Assessment garymiles.net/the-free-lawyer-assessment Learn more about Breaking Free or order your copy ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.garymiles.net/break-free⁠⁠⁠⁠⁠⁠⁠⁠⁠ Schedule a complimentary discovery call: ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://calendly.com/garymiles-successcoach/one-one-discovery-call⁠⁠⁠⁠ ⁠⁠⁠⁠ Watch this episode on YouTube: https://www.youtube.com/channel/UCqcfaTWo17uxmYS9hfAdiaQ

    23 min

  8. JAN 22

    How Can Lawyers Find Joy and Fulfillment in Their Careers? #388

    In this episode, host Gary interviews Ariana Tadler, a renowned lawyer and leader, about finding fulfillment and balance in the legal profession. Ariana shares insights from her 33-year career, discussing leadership, the impact of technology, and the importance of rituals for well-being. She emphasizes compassion, candor, and adaptability, especially for younger lawyers navigating blurred work-life boundaries. The conversation highlights practical strategies for managing stress, setting boundaries, and leading with empathy. Ariana and Gary encourage legal professionals to align their careers with personal values, prioritize presence, and pursue joy and purpose both in and out of the office. Ariana is the founding partner of Tadler Law LLP, a WBENC-certified, women-owned boutique law firm and Of Counsel to Kaplan, Fox & Kilsheimer LLP. With 33 years’ experience advocating for consumers, employees, investors, and businesses through negotiation, arbitration, and litigation, Ariana is one of our nation’s leading women lawyers. Ranked by Chambers and Partners, Ariana is also a global ”STAR” in e-Discovery (the use of data for litigation) – she is the first woman to receive this distinction and one of only three people ever to have achieved this distinction. Beyond the courtroom, Ariana is the founder of Ariana Speaks LLC, a thought leadership platform where she shares her voice as an author, entrepreneur, emcee, and keynote speaker. Drawing from decades of real-world experience, she speaks powerfully on leadership, resilience, innovation, and what it takes to thrive in today’s fast-moving world. Her message resonates deeply with Millennials, Gen Z, and women of all ages—those seeking to confidently and joyfully design a life that is both highly effective and deeply fulfilling. A proud member of National Speakers Association’s New York City Chapter, Ariana speaks nationwide about resilience and grit; and work-life integration, built on her curated formula for living a happy, highly effective life. Her mission? To empower and mentor the next generation of leaders—giving them tools not just to succeed, but to lead boldly and live fully. Optimizing Life & Career Choices (00:02:12) Launching a Boutique Firm: Lessons in Leadership (00:05:13)  E-Discovery and Star Distinction Explained (00:07:37)  The Human Edge in a Tech-Driven Legal World (00:09:29)  Listening as a Core Legal Skill (00:11:43)  Risk, Litigation, and Core Values (00:13:54)  Leading with Candor & Difficult Conversations (00:15:09)  Learning from Junior Team Members (00:17:40)  Flex and Pivot: Adapting to Change in Law (00:19:16)  Gen Z, Millennials, and Evolving Legal Culture (00:21:57)  Boundaries, Joy, and Work-Life Balance (00:23:49)  Rituals for Happiness and Success (00:24:49)  Presence and Avoiding Burnout (00:26:55)  Personal Story: The Cost of Not Being Present (00:27:35)  Non-Negotiable Rituals for Wellbeing (00:29:39)  Transition Rituals and Sleep (00:34:00)  Ariana Speaks: Mentoring and Impact (00:35:35)  The Power of Coaching and Mentorship (00:38:22)  Empowering the Next Generation (00:41:44) You can find The Free Lawyer Assessment here- https://www.garymiles.net/the-free-lawyer-assessment Would you like to learn what it looks like to become a truly Free Lawyer? You can schedule a complimentary call here: https://calendly.com/garymiles-successcoach/one-one-discovery-call Would you like to learn more about Breaking Free or order your copy? https://www.garymiles.net/break-free

    47 min
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About

The Free Lawyer Podcast is designed for the lawyer, entrepreneur or professional who is in some way unfulfilled, stressed or stuck and looking for something better. We will discuss various blocks that limit us from achieving the personal freedom we all desire but have not yet fully experienced. Are you looking to achieve a new level of success? If so, this podcast is for you!

Information

  • Creator
    Gary Miles
  • Years Active
    2022 - 2026
  • Episodes
    395
  • Rating
    Clean
  • Copyright
    © Gary Miles
  • Show Website
    The Free Lawyer