The Free Lawyer

In this episode of "The Free Lawyer," host Gary interviews Ben Glass, co-founder of Ben Glass Law and Great Legal Marketing. Ben shares his journey from traditional legal practice to building a fulfilling, innovative law firm. He discusses the importance of curiosity, collaboration, and values-driven leadership, encouraging lawyers to delegate, focus on client experience, and foster positive firm cultures. Ben also addresses lawyer wellness, advocating for proactive business strategies and personal growth. The episode offers practical advice for lawyers seeking greater satisfaction and success in their careers.Ben Glass is a prominent long-term disability attorney, business leader, and legal marketing expert with over 40 years of experience in representing disabled and injured clients against insurance companies. He is widely recognized for his innovative approach to law and business, making significant contributions to both fields.Ben is a nationally recognized and sought after speaker in the legal industry and has taught and lectured on a variety of legal subjects including direct and cross examination, the use of expert witnesses, conducing effective voir dire and jury selection, maximizing recovery in personal injury cases and effective representation of disabled workers in ERISA long-term disability cases. Ben has been featured prominently in numerous publications and media outlets such as Lawyers Weekly Virginia, The Washington Post, Newsweek, USA Today, and The Wall Street Journal. Ben Glass is not only a successful attorney but also a leading figure in legal marketing. He founded Great Legal Marketing (GLM), an organization dedicated to helping solo and small-firm lawyers refine their marketing strategies and business practices. His expertise has been sought after nationwide, and he is a frequent speaker and author on legal marketing, delivering talks at in-person and virtual conferences for entrepreneurs worldwide.Collaboration vs. Competition in Law (00:06:27Starting Ben Glass Law: Early Challenges (00:07:43)s.Magnetic Marketing and Information-Based Approach (00:09:37) Client Experience and Referral Cultivation (00:12:05) Renegade Lawyer Philosophy (00:14:07) Entrepreneurial Mindset vs. Legal Mindset (00:15:19)Lawyer Wellness and Business Foundations (00:16:16) The Hard Work of Entrepreneurship (00:18:32) .Biggest Misconceptions About Law Practice Success (00:20:17) .Analyzing and Improving Law Firm Systems (00:22:17) Breaking Free from the Prison of Success (00:24:17) Mindset Differences: Stuck vs. Thriving Lawyers (00:26:18) Building a Values-Driven Practice (00:28:34) Lessons from Mistakes: Hiring and Coaching (00:31:12) The Importance of Ongoing Coaching (00:32:39) Controlling Your Environment and Inputs (00:34:23)Advice to Young Ben: Vulnerability and Coaching (00:36:13) .Encouragement for Stuck and Overwhelmed Lawyers (00:38:07) Would you like to learn more about Breaking Free or order your copy? https://www.garymiles.net/break-free Would you like to schedule a complimentary discovery call? You can do so here: https://calendly.com/garymiles-successcoach/one-one-discovery-call

Lawyers face overwhelming pressure in the courtroom. What if the key to showing up with confidence doesn’t come from more prep, but from mental rehearsal? In this episode, we explore how visualization, a strategy used by elite athletes and surgeons, can help lawyers reduce anxiety, improve performance, and bounce back from setbacks. Listen for how picturing your success before trials, client meetings, or even networking events, can create real neural pathways that boost your presence and recall under pressure. Host, Gary Miles shares personal courtroom stories and science backed tips to make this tool part of your daily practice. If self-doubt has ever held you back, this episode will show you how to mentally rehearse your way to resilience. 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

In this episode of "The Free Lawyer," host Gary Miles interviews Alexandra "Sasha" Berkowitz, discussing Sasha’s journey from contract lawyer to founding her intellectual property firm, Iconic Inc. Sasha shares insights on overcoming fears, embracing entrepreneurship, and prioritizing personal well-being. She highlights the value of flexibility, meaningful client relationships, and cost-effective legal services. The conversation offers practical advice for lawyers seeking independence and fulfillment, emphasizing the importance of aligning career choices with personal values and goals. Sasha’s story inspires listeners to pursue professional growth and personal freedom within the legal field.Sasha first developed a love of intellectual property during a trip to the World Intellectual Property Organization headquarters in Geneva, Switzerland as an undergraduate student. After a brief stint as an IP paralegal, Sasha attended law school at the University of San Diego School of Law in San Diego, California, where she concentrated on intellectual property law. Following her tenure as Senior Partner at a World Trademark Reporter-rated firm, Sasha launched Iconic Inc.Sasha has over a decade of experience assisting small and medium businesses in all industries with securing and protecting their intellectual property rights. She provides advice and counsel to clients nationwide, and is dedicated to helping them protect their intangible assets in a way that is accessible and affordable.Decision to Start Her Own Firm (00:04:36) Managing Mindset and Overcoming Fears (00:05:10) Early Success and Client Work (00:06:04) Benefits of Independence (00:06:25) Dealing with Doubts and Work-Life Balance (00:06:46) Advice for Lawyers Considering Entrepreneurship (00:07:34)Personal Growth and Lessons Learned (00:08:26) Marketing and Business Development Strategies (00:09:30) Biggest Challenges in Running a Firm (00:10:20) Balancing Cost-Effective Services and Profitability (00:10:49) Client Collaboration and Proactive Legal Solutions (00:11:51) Building Strong Client Relationships (00:12:53)Professional Development and Differentiation (00:13:48) Fee Structures: Flat Fees vs. Hourly Billing (00:14:27) Problems with Hourly Billing and Benefits of Alternatives (00:14:59) Attorney Burnout: Causes and Solutions (00:16:50) Advice on Facing Fears and Finding Mentors (00:17:34) Advice to Her Younger Self and Career Reflections (00:19:02) Greatest Joys of Founding Iconic Inc. (00:20:08) Final Advice for Unhappy Lawyers (00:20:42) Would you like to learn more about Breaking Free or order your copy? https://www.garymiles.net/break-free Would you like to schedule a complimentary discovery call? You can do so here: https://calendly.com/garymiles-successcoach/one-one-discovery-call

In this episode, Gary Miles covers the emotional toll of a courtroom loss and how perfectionism can distort a lawyer’s sense of self-worth. He reveals why even top attorneys fall into the trap of harsh self-talk and a fixed mindset after failure. But instead of spiraling, you can reframe setbacks as powerful catalysts for growth. Listen for a three-stage recovery strategy that transforms professional disappointments into personal development tools. You'll learn how to shift your self-talk, replace perfectionism with progress, and build a resilient legal mindset rooted in the growth mindset. 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

In this episode of "The Free Lawyer," host Gary interviews Ben Chiriboga, a former maritime litigator turned legal tech executive and co-founder of Nexl. Ben shares his journey from traditional law to legal technology, discussing the challenges of overcoming fear and imposter syndrome. Together, they explore the importance of authenticity, redefining success beyond financial gain, and building meaningful client relationships. The conversation highlights how technology, personal growth, and connection can help lawyers find fulfillment and adapt to the evolving legal industry.Ben is a former practicing lawyer turned legal tech executive. He is the founding team member of Nexl, one of the fastest growing companies in APAC (Financial Times). He is also the host of This Legal Life, where he interviews legal professionals on how they built their careers.Ben’s Legal Career and Hero’s Journey (00:02:24) Maritime Law Practice (00:03:06) Stirring for Change and Discovery of Legal Tech (00:05:12) Transition to Legal Tech and Nexl (00:07:16) What is Nexl? (00:09:13) EHow Nexl Works (00:10:39) AI, Automation, and Data Accuracy (00:12:26) First-Party vs. Third-Party Data (00:13:30) CTransition Challenges: Imposter Syndrome (00:15:55) Transferable Skills and Leadership (00:16:28) Leadership Traits and Inner Work (00:20:31) Fear, Authenticity, and Lawyer Challenges (00:22:38) Managing Uncertainty and Mindset (00:23:51) Traits of Fulfilled Lawyers (00:26:14) Redefining Success and the Hero’s Journey (00:29:18) Values-Based Practice and Intentionality (00:31:45) Trends in Legal Careers and Fulfillment (00:32:56) Connection and Combating Isolation (00:36:26) Advice to Younger Self: Risk and Instinct (00:37:15)Would you like to learn more about Breaking Free or order your copy? https://www.garymiles.net/break-free Would you like to schedule a complimentary discovery call? You can do so here: https://calendly.com/garymiles-successcoach/one-one-discovery-call 

For years, I believed perfectionism was the key to being a great lawyer. I triple-checked every brief, obsessed over every detail, and beat myself up over the smallest mistakes. But instead of making me better, it left me anxious, second-guessing myself, and disconnected from my purpose. In this episode of The Free Lawyer, I share what finally helped me break free from perfectionism and embrace a mindset rooted in excellence, not flawlessness. You'll hear courtroom stories, the reframing techniques that shifted my perspective, and how choosing imperfection over performance led to more authentic advocacy. We’ll also explore why self-compassion is essential for success and how authenticity builds deeper client trust.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

In this episode of "The Free Lawyer," host Gary interviews Katie Mickelson, a prominent family law attorney in Illinois. Katie shares her journey from public relations to becoming an equity partner in her law firm. She emphasizes the importance of emotional intelligence in family law, effective communication, and maintaining client relationships post-divorce. Katie discusses her leadership philosophy, which focuses on humility, teamwork, and creating a supportive work environment. She advises lawyers to find joy in their work and explore new opportunities if they feel stagnant. The episode concludes with insights on the future of legal practice and the importance of client-centered resolutions.Known for her thoughtful and straightforward approach to family law, Kathryn Homburger Mickelson has distinguished herself among her peers by identifying her individual client’s goals and then drawing on her extensive courtroom and mediation experience to bring strategic and empowering representation to each case. By looking at family law issues pragmatically, Ms. Mickelson will craft strategies that will result in resolution that is efficient, expeditious and drama-free. Ms. Mickelson understands and appreciates that no client is the same and that long after family law matters are resolved, the individual and their family remain. It is this understanding that has driven Ms. Mickelson to ensure that her clients are treated with respect, their needs are met, and they emerge from family law conflict feeling empowered and whole. Ms. Mickelson represents her clients and their complex financial estates and sensitive family matters with the utmost discretion and confidentiality. From business owners and professional athletes to entertainment executives and influential rain makers, Ms. Mickelson’s clients come to her for her reputation among colleagues and judges as prepared, responsive, and attentive to the smallest of details, and for her no-nonsense approach to the practice of family law. Ms. Mickelson treats every case as an opportunity to educate her clients and promote financial and emotional dignity.Emotional Navigation in Family Law (00:04:05)Career Progression and Loyalty (00:06:55)Mentoring Younger Attorneys (00:08:01)Setting Realistic Client Expectations (00:11:29)Importance of Listening (00:15:53)Post-Divorce Client Relationships (00:16:39)Maintaining Work-Life Balance (00:20:23)Leadership in a Law Firm (00:24:10)Letting Go of Ego (00:24:46)The Role of Management in Law (00:26:40)Finding Joy in Law (00:27:12)Feeling Overwhelmed in Law (00:28:34)Creating Boundaries (00:30:01)Career Redirection (00:32:00)Options for Career Change (00:32:53)Future of Legal Practice (00:36:32)Would you like to learn more about Breaking Free or order your copy? https://www.garymiles.net/break-free Would you like to schedule a complimentary discovery call? You can do so here: https://calendly.com/garymiles-successcoach/one-one-discovery-call

Use this productivity guide to find more time in the day for billable hours. This is your opportunity to overhaul your approach to work and life. Constant busyness and burnout hold lawyers back from both personal fulfillment and professional efficiency. Host, Gary Miles, introduces his proven Triangle System—a simple 3-phase productivity method designed to help attorneys work with greater focus, intention, and purpose. Learn how to eliminate distractions, document time effectively, and plan your day to maximize productivity. Register for the July Masterclass — From Overwhelmed to Outstanding: https://us02web.zoom.us/meeting/register/xRkgcV0VRpO7G8zIWaOuRgGet the Values Alignment Guide ⁠⁠⁠⁠⁠⁠https://upbeat-trailblazer-9238.kit.com/1604bbf4cb⁠⁠⁠⁠⁠⁠Would you like to learn more about Breaking Free or order your copy? ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.garymiles.net/break-free⁠⁠⁠⁠⁠⁠⁠⁠⁠Would you like to schedule a complimentary discovery call? You can do so here: ⁠⁠⁠⁠⁠⁠⁠⁠⁠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 converses with Tony Smith, an experienced attorney specializing in small business advising, intellectual property, and emerging technologies like cryptocurrency and blockchain. Tony shares his professional journey from working at Stryker to founding his own law firm. He discusses his fascination with Bitcoin, the importance of legal foundations for startups, and strategies for managing imposter syndrome and control in the legal profession. The episode offers valuable insights for lawyers on navigating stress, achieving balance, and embracing resilience in their practice.Tony's Professional Journey (00:01:36)Discovery of Bitcoin (00:02:17)Understanding Bitcoin and Blockchain (00:03:16)Bitcoin Network Security (00:05:31)Mining Bitcoin and Energy Use (00:08:13)Transition to His Own Law Firm (00:10:20)Reputation in Cryptocurrency (00:10:48)Current Law Practice (00:14:05)Supporting Startups (00:14:39)Foundational Legal Documents (00:15:51)Managing Imposter Syndrome (00:16:33)Letting Go of Control (00:18:06)Master of My Own Domain (00:20:37)Managing Urgency and Importance (00:21:22)Living in the Present (00:22:26)Resilience Through Medical Challenges (00:23:17)Dealing with Health Scares (00:24:10)Bouncing Back from Setbacks (00:28:56)Finding Work-Life Balance (00:31:05)Tony Smith is a seasoned attorney with deep expertise in intellectual property law, blockchain strategy, and emerging technologies. As General Counsel at Zuber Lawler, Tony provides critical legal guidance at the intersection of innovation, compliance, and corporate growth. With nearly two decades of legal experience—including senior roles at firms like Xsolla and Stryker—he brings a pragmatic, future-forward approach to legal strategy.Tony is especially focused on helping companies leverage blockchain and smart contracts to streamline operations and protect digital assets. His legal acumen and tech fluency make him a go-to resource for businesses navigating the evolving regulatory landscape of cryptocurrency, decentralized technologies, and intellectual property law.Would you like to learn more about Breaking Free or order your copy? https://www.garymiles.net/break-free Would you like to schedule a complimentary discovery call? You can do so here: https://calendly.com/garymiles-successcoach/one-one-discovery-call

Negative thoughts silently sabotage lawyers’ confidence, performance, and long-term career satisfaction. This episode reveals the three most damaging mental habits that plague even the most accomplished attorneys: self-doubt, perfectionism, and comparison. Gary Miles shares personal stories and real-world examples to highlight how inner criticism can be more damaging than any opposing counsel. Learn practical, evidence-based strategies to reframe self-talk, build resilience, and approach high-stakes situations with clarity and confidence. External success doesn't erase internal doubt — taking control of your mindset is essential to thriving in your legal career. Whether you're a new attorney or a seasoned litigator, this episode offers the tools to reclaim your self-worth and transform your professional experience. Get the Values Alignment Guide ⁠⁠⁠⁠⁠⁠https://upbeat-trailblazer-9238.kit.com/1604bbf4cb⁠⁠⁠⁠⁠⁠Would you like to learn more about Breaking Free or order your copy? ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.garymiles.net/break-free⁠⁠⁠⁠⁠⁠⁠⁠⁠Would you like to schedule a complimentary discovery call? You can do so here: ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://calendly.com/garymiles-successcoach/one-one-discovery-call⁠⁠⁠⁠ ⁠⁠⁠⁠Watch this episode on YouTube: https://www.youtube.com/channel/UCqcfaTWo17uxmYS9hfAdiaQ