The Free Lawyer

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/3Nfkne3Jen’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 MatterTake 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 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-free

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/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

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-assessmentWould 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-free

The "badge of honor" culture in the legal profession actually equates exhaustion with dedication. In this episode, Gary Miles shares why constant availability isn't a leadership trait, rather a form of martyrdom that creates bottlenecks and fuels psychological distress. Listen for the 4 Pillars of Boundary Leadership—a framework designed to help managing partners and senior associates regain control of their time without losing clients. Setting strategic boundaries actually enhances your authority and improves work quality, when done the right way. This episode helps lawyers transition from a practice that "owns you" to one that operates on professional systems and sustainable excellence. 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

In this episode of "The Free Lawyer" podcast, host Gary interviews M&A advisor David Shavzin about how lawyers can prepare their firms for sale or transition. David explains the importance of reducing owner dependency, improving productivity, and building sustainable marketing systems to increase a law firm’s value. They discuss strategies for gradual exits, the emotional challenges of leaving a practice, and the need for early planning. David also highlights the value of revenue diversification and assembling a trusted advisory team. The episode offers practical advice for lawyers seeking freedom while preserving their professional legacy.David is an M&A Advisor and Exit Strategist who truly understands what business owners go through when they start thinking about their exit strategy and the real value of what they have built.What makes David stand out is his rare combination of deep M&A transaction experience, strategic planning expertise, and business valuation knowledge. He founded The Value Track to help owners understand and grow their company’s value — whether they are planning to exit in two years or ten.He does not just focus on the sale - he helps owners look 3–5 years ahead and build value systematically. It is a practical, forward-looking perspective that most business owners will benefit from, whether or not they are actively thinking about an exit.David’s Background and Human Element in Exits (00:01:07) Learning the Importance of Personal Conversations (00:02:27) What Makes a Law Firm Sellable? (00:04:50) Myths vs. Reality of Selling a Law Firm (00:08:12) Optimizing Value and Owner Irrelevance (00:09:40)Productivity, Process, and Marketing Systems (00:12:31)Building a Marketing Machine (00:13:35) The Buyer’s Perspective and Value Multipliers (00:15:05) Team Quality and Internal Dynamics (00:17:31) TPersonal Goodwill vs. Enterprise Goodwill (00:20:08) Deal Structures for Gradual Transition (00:22:12) When to Start Exit Planning (00:23:53) Cost of Waiting Too Long (00:25:18) Navigating Post-Sale Identity Crisis (00:26:11) Strategic Exit Planning for Freedom (00:28:12) Most Overlooked Value Creation Strategy (00:29:37) First Steps for Lawyers Considering Exit (00:31:58) 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 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-free

While meticulousness may have earned you early success, it eventually becomes a liability that fuels anxiety and drains your energy.In this episode, Gary Miles addresses the cost of the perfectionism that many attorneys rely on to build their careers. He breaks down the critical distinction between excellence, which stems from competence, and perfectionism, which is rooted in fear and the need to manage uncertainty. Learn a practical five-step framework to transition from being a perfectionist to a powerful practitioner who operates with confidence. Plus, three immediate practices to help you set strategic standards and stop the cycle of endless document revisions. 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

In this episode of "The Free Lawyer" podcast, host Gary interviews LinkedIn ghostwriter Victoria Michaels. Victoria shares her journey from running a marketing agency to helping lawyers and professionals build authentic LinkedIn brands. She discusses the importance of consistent, genuine content, the power of engagement, and how to overcome fears of posting online. Victoria offers practical tips for optimizing profiles, creating compelling posts, and building meaningful connections. The episode highlights how lawyers can use LinkedIn strategically to boost visibility, attract opportunities, and showcase their expertise while maintaining authenticity in an AI-driven digital world.Victoria Michaels is a LinkedIn ghostwriter who works with CEOs, lawyers, and legal professionals to build a consistent and credible presence online. She captures each client’s natural voice and translates their experiences into content that attracts top talent, clients, and new opportunities. She began her career building and scaling a marketing agency, eventually selling the business and turning to LinkedIn to explore new opportunities. After being coached on personal branding, her content quickly gained traction; leading her to help high-level executives develop their own thought leadership and online presence.She has written for clients across a wide range of industries and enjoys helping professionals understand how to use LinkedIn strategically.She also serves as a writing expert for one of LinkedIn’s top creators, where she continually sharpens her copywriting skills, studies user psychology, and stays up-to-date with algorithm shifts and emerging content trends.Early LinkedIn Experiences (00:02:52) First Viral Post & Lessons Learned (00:03:52) Transition to Personal Branding Coach (00:05:16) Overcoming Resistance to Posting (00:06:56) Impact of Consistent LinkedIn Posting (00:08:19) Importance of Consistency & Long-Term Strategy (00:10:19) Authenticity in Branding (00:12:01) Active vs. Passive Networks (00:14:37) Unique Branding Challenges for Lawyers (00:16:03) Voice Capture & Authenticity in Ghostwriting (00:17:48) Why Content Fails on LinkedIn (00:19:45) Hooks and Their Importance (00:22:03) Recent LinkedIn Trends & Algorithm Shifts (00:24:00) Evolving Authenticity with AI & Ghostwriting (00:25:43) Victoria’s Process Working with Attorneys (00:27:06) Defining Success Beyond Metrics (00:29:25) Outbound vs. Inbound Engagement (00:30:50) Getting Started on LinkedIn for Busy Lawyers (00:31:40) Helping Lawyers Get Seen on LinkedIn (00:33:53) Results and Impact for Clients (00:35:11) 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

A roadmap for legal professionals to move from being "owned" by their practice to owning their lives. Gary Miles shares four transformative lessons that supported The Free Lawyer community most in 2025. Covering the power of mental presence, building resilience after devastating losses, using AI as a tool for liberation rather than a threat, and jury psychology. Learn practical techniques like focus methods and the "three R's" for maintaining client trust during setbacks. Together, we challenge the outdated notion that professional excellence requires sacrificing personal freedom. By mastering these four lessons, attorneys can achieve high-level success while still making it home for dinner with their families.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

In this episode of "The Free Lawyer," host Gary interviews Bo Royal, a former Fortune 500 marketing executive who successfully transitioned to legal marketing. Bo shares how he quadrupled online case volume at a major Philadelphia injury law firm by implementing data-driven strategies and shifting focus from traditional to digital channels. He discusses the importance of tracking, intake systems, and operational readiness for law firms, and explains how his company, Pareto Legal, helps firms build robust case pipelines. The episode offers practical insights for maximizing marketing efficiency and leveraging digital tools to drive sustainable law firm growth.Bo Royal is a former Fortune 500 agency exec who spent over a decade scaling online revenues for iconic brands like Calvin Klein, GNC, Sallie Mae, and Kate Spade New York. After leaving the corporate grind, he took the helm at a top Philadelphia injury law firm, supercharging its online case volume by fourfold through data-driven decisions and relentless focus. His journey from high-stakes agency work to legal marketing quickly established him as an industry expert with a knack for results.Now, as an advisory board member at that very firm—thriving with eight-figure revenues and 12 office locations across Pennsylvania—Bo drives innovation at Pareto Legal. His team empowers small and medium-sized law firms to secure seven- to eight-figure case pipelines by leveraging real-world experience and smart digital strategies. When he’s not optimizing campaigns, Bo shares his marketing insights on podcasts and uses his success to give back to the community.Bo’s Transition from Corporate to Legal Marketing (00:02:05) Initial Surprises in Legal Marketing (00:03:59) Diagnosing and Transforming the Law Firm’s Marketing (00:05:49) Shifting from Traditional to Digital Marketing (00:08:35)Earned vs. Unearned Case Pipeline (00:10:41) OTT and Modern Advertising Explained (00:12:13) Importance of Data-Driven Decision Making (00:13:19)Implementing a Culture of Data and Change (00:15:45) Pareto Legal’s Differentiated Approach (00:18:22) Assessing Firm Readiness for Digital Marketing (00:22:06) Vanity Metrics vs. Real Results (00:25:39) Holistic Marketing Efficiency and Attribution (00:27:52) The Hawthorne Effect and Tracking Benefits (00:32:06) Current Trends and AI in Legal Marketing (00:33:49)You can find The Free Lawyer Assessment here- https://www.garymiles.net/the-free-lawyer-assessmentWould 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-free

Status, income, respect, yet something still feels off. In this episode, Gary explains why so many successful lawyers feel anxious, dissatisfied, or burned out despite “winning,” and why the problem isn’t our mindset, rather it’s our outdated mental operating system. There are four law school programs still running in our brain and they cost us our health, relationships, and performance. Listen for how perfectionism, external validation, scarcity thinking, and binary decision-making quietly sabotage sustainable success for lawyers. 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 ⁠⁠⁠⁠