

The Free Lawyer
Gary Miles
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!
Episodes
Mentioned books

Dec 11, 2025 • 33min
Are You Paying a "Soul Toll" in Your Legal Career? #376
In this episode of "The Free Lawyer" podcast, host Gary interviews Anusia Gillespie, a lawyer-turned-novelist and yoga instructor. Anusia shares her journey from high-pressure legal roles to writing her debut novel "Soul Toll," which explores the personal costs of professional success. The conversation delves into legal innovation, leadership, and the importance of integrating joy, purpose, and authenticity into legal careers. Anusia offers practical advice on self-awareness, values alignment, and using coaching or mindfulness to create a more fulfilling path, encouraging lawyers to redefine success on their own terms.Anusia Gillespie is a lawyer-turned-novelist and RYT-200 certified yoga instructor whose debut contemporary fantasy, Soul Toll, blends corporate ambition with personal awakening. Her writing is shaped by a career at global law firms, legal tech companies, and Harvard Law School Executive Education—offering a sharp, insider perspective on high-performance culture and the personal cost of chasing success.Well known in the legal industry for her insight on leadership and transformation, Anusia now channels those themes into fiction that invites readers to question the lives they’ve been told to want. In Soul Toll, a high-achieving attorney’s search for clarity pulls her into a hidden world, and a battle for something far more meaningful than success.Anusia holds a JD and MBA from Boston College and a BS in Management from Tulane University. She lives north of Boston with her husband, young son, and old dog.Defining Moment for Writing "Soul Toll" (00:01:20) Meaning of "Soul Toll" (00:02:35) Anusia’s Personal Soul Toll Experience (00:04:25) Transitioning Careers and Lessons Learned (00:06:18) High Achievers and the Cost of Success (00:08:16) Common Tolls Lawyers Pay (00:08:32) Skepticism Toward Meaning and Fulfillment (00:10:04) Anusia’s Approach to Legal Transformation (00:11:36) Integrating Joy and Seriousness in Law (00:12:46) Importance of Coaching for Lawyers (00:15:02) How Coaching Shifts Lawyers’ Focus (00:16:55) Recent and Future Changes in Legal Profession (00:18:26) Technology, Boundaries, and Lawyer Well-being (00:20:35) Patterns of Lawyers Who Build Soul (00:23:38) Message and Purpose of "Soul Toll" (00:25:08) Finding Personal Fulfillment in Law (00:27:23) Advice for Miserable but Successful Lawyers (00:29:08) Advice to Her Younger Self (00:31:30) 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-callYou can find The Free Lawyer Assessment here- https://www.garymiles.net/the-free-lawyer-assessmentWould you like to learn more about Breaking Free or order your copy? https://www.garymiles.net/break-free

Dec 8, 2025 • 17min
Overthinking: the Ability to Live in Tomorrow’s Problems #375
Lawyers are excellent at thinking ahead, but when that instinct turns into constant worst-case rehearsing, it becomes a trap rather than a strength. In this episode of The Free Lawyer, Gary Miles shares why the same mental habits that make lawyers really good at their jobs also make them miserable after hours. The true cost of overthinking ranges from sleep disruption to strained relationships. Listen to this episode for the ten actionable tools designed specifically for lawyers to interrupt worry loops, return to the present, and regain control of their minds. Learn to distinguish solving from suffering, use grounding to shut off “awfulizing,” create a worry window, run a probability check, and take the next right action when anxiety tries to steal your focus.Get the Values Alignment Guide https://upbeat-trailblazer-9238.kit.com/1604bbf4cbTake the Free Lawyer Assessment garymiles.net/the-free-lawyer-assessment Learn more about Breaking Free or order your copy https://www.garymiles.net/break-freeSchedule a complimentary discovery call: https://calendly.com/garymiles-successcoach/one-one-discovery-call Watch this episode on YouTube: https://www.youtube.com/channel/UCqcfaTWo17uxmYS9hfAdiaQ

Dec 5, 2025 • 32min
How Can Law Firms Transform Their Marketing Strategy for Sustainable Growth? #374
In this episode of "The Free Lawyer," host Gary interviews Eric Ritter, CEO of Digital Neighbor and digital marketing professor, about law firm growth through effective SEO and branding. Eric shares his journey into legal marketing, the importance of defining an ideal client, and how law firms can stand out in a crowded market. They discuss AI’s impact on legal marketing, the value of continuous learning and coaching, and practical strategies for work-life balance. Eric emphasizes building authentic brands and sustainable marketing systems, offering actionable advice for lawyers seeking fulfillment and long-term success.Eric Ritter is the CEO & Founder of Digital Neighbor, a nationally recognized SEO and digital marketing agency specializing in law firm growth. With over a decade of experience, Eric is a leading authority in legal marketing and AI-driven client acquisition. Known as "The SEO Sommelier," he simplifies complex digital strategies to drive growth for law firms.Eric is an adjunct professor at the University of South Florida, teaching digital marketing. He has also been featured in Authority Magazine, Search Engine Watch, and Porch. He hosts The Search Bar Podcast and leads Sip & Search, a networking series for attorneys.In addition to his professional work, Eric is actively involved in the community, serving on multiple nonprofit boards in the Tampa Bay area.Eric’s Journey into Legal Marketing (00:02:10) The SEO Sommelier Concept (00:03:07) Myth 1: The Ideal Client Profile (00:04:28)SEO Focus and Resource Allocation (00:06:11)Standing Out in a Crowded Market (00:06:56) Myth 2: All Cases Are the Same (00:09:08) Consistency and Lawyer Involvement in Marketing (00:10:48) Digital Neighbor’s Differentiation (00:12:44) Teaching and Staying Current (00:13:46) AI’s Impact on Digital Marketing (00:15:06) The Future of Digital Marketing (00:16:58) Answer Engine Optimization (00:20:17) Sustained Law Firm Growth vs. Burnout (00:21:15) The Value of Coaching and Professional Development (00:22:44) Lawyer Fulfillment and Avoiding Burnout (00:24:19) First Steps for Established Law Firms (00:25:04) Work-Life Balance and Delegation (00:26:16) Recharging and Hobbies (00:28:02) Transformation Through Marketing (00:29:44)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-callWould you like to learn more about Breaking Free or order your copy? https://www.garymiles.net/break-freeYou can find The Free Lawyer Assessment here- https://www.garymiles.net/the-free-lawyer-assessment

Dec 1, 2025 • 16min
Why Being a High Achiever Doesn’t Protect You From Internal Pain #373
In this solo episode of The Free Lawyer, Gary Miles shares the story he’s never fully told. Despite all of his outward success, there was an internal suffering that winning couldn't fix. Outward success often hides deep internal struggle. So many elite attorneys feel trapped even at the height of their careers. There are a few foundational pillars that helped Gary move out of perfectionism and isolation: internal authority, sustainable excellence, and professional freedom. Listen to this episode for your invitation to stop struggling alone.Take the Free Lawyer Assessment to findout which pillar you should start working on first and how: garymiles.net/the-free-lawyer-assessment Get the Values Alignment Guide https://upbeat-trailblazer-9238.kit.com/1604bbf4cbLearn more about Breaking Free or order your copy https://www.garymiles.net/break-freeSchedule a complimentary discovery call: https://calendly.com/garymiles-successcoach/one-one-discovery-call Watch this episode on YouTube: https://www.youtube.com/channel/UCqcfaTWo17uxmYS9hfAdiaQ

Nov 28, 2025 • 39min
Are You Stuck in the Golden Handcuffs of Law? #372
In this episode of "The Free Lawyer," host Gary Miles interviews Casey Berman, founder of Leave Law Behind. Casey shares his journey from burned-out attorney to career coach, detailing how he helps lawyers transition into fulfilling non-legal roles. They discuss overcoming the "golden handcuffs" of legal careers, identifying transferable skills, and taking small, practical steps toward change. Casey emphasizes the importance of self-awareness, actionable coaching, and redefining personal success. The episode offers hope, resources, and concrete advice for attorneys seeking more meaningful, aligned careers outside the law.Casey Berman is the founder of Leave Law Behind (www.leavelawbehind.com), a nationally recognized coaching and content platform that helps unhappy attorneys leave the legal field and transition into non-law careers they love. Leave Law Behind has been featured in or covered by the Wall Street Journal, The Washington Post, The Atlantic, The Guardian, among other publications. A former attorney himself, Casey launched Leave Law Behind over a decade ago to help lawyers overcome fear, rediscover their transferable skills, and find roles that align with their strengths, values, and lifestyle goals. He’s helped hundreds of attorneys break free from burnout and self-doubt and take confident steps toward more fulfilling, sustainable careers.Casey is a speaker, writer, and entrepreneur based in Maui, where he lives with his wife and two children. He brings a thoughtful, down-to-earth perspective to conversations about career change, entrepreneurship, mindset, emotional resilience, and building a life that works for you.Casey’s Defining Moments Leaving Law (00:02:46) Transitioning Out of Law (00:05:44) Transferable Skills & Golden Handcuffs (00:07:31)Overcoming Feeling Stuck (00:11:19) Incremental Steps to Change (00:12:30) What Sets Leave Law Behind Apart (00:15:11) Unique Genius Framework (00:16:29) Who Leave Law Behind Serves (00:17:28) Paralysis by Analysis & Perfectionism (00:18:22)Changes in Lawyers’ Motivations & Opportunities (00:21:05) Ripple Effect of Career Fulfillment (00:23:39) TPractical First Steps for Dissatisfied Lawyers (00:25:12) Importance of Coaching & External Support (00:27:48) Redefining Success & Authenticity (00:31:40) Transforming Your Current Practice (00:33:23) Magic Wand: More Options & Less Feeling Stuck (00:35:39) 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-callTake The Free Lawyer Assessment (10 minutes, completely free):https://www.garymiles.net/the-free-lawyer-assessmentWhat 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

Nov 24, 2025 • 26min
3 Reasons Your Work Feels Heavy #371
Here's the real reason your work feels heavier than it should and why it has nothing to do with the number of cases on your desk. There are subtle ways lawyers hand over their emotional power to clients, outcomes, and external expectations without even realizing it. You’ll hear how constantly seeking validation creates pressure that builds silently in the background, making even routine work feel overwhelming. Learn how to reclaim your sense of stability, confidence, and control. Get the Values Alignment Guide https://upbeat-trailblazer-9238.kit.com/1604bbf4cbTake the Free Lawyer Assessment garymiles.net/the-free-lawyer-assessment Learn more about Breaking Free or order your copy https://www.garymiles.net/break-freeSchedule a complimentary discovery call: https://calendly.com/garymiles-successcoach/one-one-discovery-call Watch this episode on YouTube: https://www.youtube.com/channel/UCqcfaTWo17uxmYS9hfAdiaQ

Nov 20, 2025 • 34min
Are You a Successful Lawyer Feeling Empty Inside? #370
In this episode of "The Free Lawyer" podcast, host Gary interviews Susan Filan, a former legal analyst and prosecutor turned transformational speaker. Susan shares how a near-fatal accident forced her to reevaluate her life and redefine success beyond external achievements. Together, they discuss the pressures lawyers face, the dangers of burnout, and the importance of authenticity and self-care. Susan introduces her "Wake Up Call Method" for finding fulfillment and encourages listeners to embrace vulnerability, gratitude, and proactive change. The episode offers hope and practical advice for lawyers seeking greater clarity, purpose, and joy in their personal and professional lives.Susan F. Filan, Esq. is a former MSNBC Senior Legal Analyst, prosecutor, and trial lawyer who reinvented herself as a transformational speaker and life strategist. After nearly 30 years in the legal world, a near-death accident became her wake-up call, forcing her to confront what true success really means. Today, she helps lawyers and high-achieving professionals who appear accomplished on the outside but are collapsing inside. Through her signature Wake-Up Call Method, Susan guides clients from burnout and disconnection to clarity, vitality, and fulfillment. Known as the Architect of Reinvention, she is on a mission to revolutionize how lawyers and high-achievers live, love, and lead.Susan Filan’s Background & Accident (00:01:01) Early Career Choices & Legal “Off Ramps” (00:02:31)The Accident Experience (00:04:25) Rehabilitation & New Perspective (00:05:52) Shifting from Achievement to Presence (00:08:14) Life After the Accident (00:10:08) Practicing Law & Academic Transition (00:11:16) External Success vs. Internal Fulfillment (00:12:11) Ignoring Inner Signals (00:14:33) The Wake Up Call Method (00:15:29)Lawyer Well-being & Cultural Change (00:18:18)Escaping vs. Authentic Alignment (00:20:04) Facing Fear & First Steps to Change (00:21:44) Role of Coaching for Lawyers (00:22:38) Lawyers’ Resistance to Coaching (00:24:11) First Shift for Transformation (00:26:04) Aligning with True Purpose & Values (00:27:23)Susan’s Legacy & Message (00:29:24) Advice for Stuck Lawyers (00:30:23)Would you like to learn what it looks like to become a truly Free Lawyer? You can schedule a courtesy call here: https://calendly.com/garymiles-successcoach/one-one-discovery-callYou can find The Free Lawyer Assessment here- https://www.garymiles.net/the-free-lawyer-assessmentWould you like to learn more about Breaking Free or order your copy? https://www.garymiles.net/break-free

Nov 17, 2025 • 20min
Are You Letting Your Clients Control Your Happiness? #369
In this episode, Gary breaks down a hard truth many lawyers quietly live with: their happiness rises and falls based on client reactions, case outcomes, and external praise. He shares why this constant emotional roller coaster leaves even high-performing attorneys exhausted, anxious, and feeling like their career is controlling them instead of the other way around. Through stories from his own four decades in litigation, Gary explains how tying your well-being to factors you can’t control actually diminishes your clarity, confidence, and long-term fulfillment. Instead, he reveals the three pillars that allow lawyers to build happiness from the inside out.Get the Values Alignment Guide https://upbeat-trailblazer-9238.kit.com/1604bbf4cbTake the Free Lawyer Assessment garymiles.net/the-free-lawyer-assessment Learn more about Breaking Free or order your copy https://www.garymiles.net/break-freeSchedule a complimentary discovery call: https://calendly.com/garymiles-successcoach/one-one-discovery-call Watch this episode on YouTube: https://www.youtube.com/channel/UCqcfaTWo17uxmYS9hfAdiaQ

Nov 13, 2025 • 46min
How Can Lawyers Build Resilience and Mental Fitness in a High-Stress Profession? #368
In this episode of "The Free Lawyer," host Gary interviews Jonathan Cohen—attorney, speaker, and former IDF soldier—about mental fitness, resilience, and burnout in the legal profession. Jonathan shares his journey from military service to law, highlighting lessons on overcoming self-doubt, managing stress, and building purposeful routines. Together, they discuss practical strategies for active recovery, combating self-sabotage, and creating a holistic “stress management ecosystem.” The episode emphasizes self-awareness, setting boundaries, and developing a clear vision to help lawyers thrive, not just survive, in their careers and personal lives.Jonathan Z. Cohen is an attorney, speaker, podcaster, and philanthropist. Jonathan’s background includes 5 years of public service in 2 different countries as a Bronx Special Victims Division Criminal Prosecutor and IDF Infantry Combat Soldier. With over 1,000 legal and business professionals trained, Jonathan educates, inspires, and shares actionable insights to help thousands of ambitious professionals lead a purpose-driven life through stories, frameworks, and systems.Jonathan’s Background and Pivotal Moments (00:01:00) Defining Mental Fitness and Transformation (00:02:08) Military and Legal Service: Lessons in Resilience (00:06:31) Resilience vs. Mental Fitness, Strength, and Toughness (00:11:06) Speed to Recovery and Burnout in Law (00:13:06) Root Causes and Elements of Burnout (00:14:05) Early Warning Signs of Burnout (00:20:33)Active Recovery for Lawyers (00:23:27) Self-Sabotage: Recognition and Frameworks (00:28:26) Stress Management Ecosystem (00:34:34) Mindset Shift: From Surviving to Thriving (00:39:14) Crafting a Vision and First Steps to Mental Fitness (00:43:05) Take The Free Lawyer Assessment (10 minutes, completely free):https://www.garymiles.net/the-free-lawyer-assessmentWhat 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 weekWould you like to learn what it looks like to become a truly Free Lawyer? You can schedule a courtesy call here: https://calendly.com/garymiles-successcoach/one-one-discovery-call

13 snips
Nov 10, 2025 • 27min
Reclaim the 30%, 8 Productivity Tools Every Lawyer Should Know #367
Discover how to reclaim 30% of your lost time with eight essential productivity tools tailored for legal professionals. Uncover the value of a personal time audit to highlight inefficiencies and optimize billable hours. Learn the power of strategic time blocking to enhance focus and productivity. Explore the importance of setting clear boundaries and strategic communication to reduce interruptions. Finally, prioritize mental and physical health to sustain your performance and redefine your approach to work.


