The Free Lawyer

In this episode of "The Free Lawyer" podcast, host Gary interviews guest Ana Juneja, an IP lawyer and entrepreneur. They discuss Ana’s journey from law firm associate to media company owner. Ana shares how she sold her media business to focus on law and explains how AI has revolutionized her firm’s transactional work, enabling a small team to serve clients efficiently. She offers insights on trademark protection, debunks common IP myths, and highlights the importance of early trademark registration. The episode highlights the importance of innovation, transparency, and leveraging AI and social media to empower lawyers and improve client service.As an award-winning intellectual property attorney and the founder of Ana Law®, Ana Juneja is redefining how attorneys leverage AI to create impactful social media content.She empowers celebrities, athletes, influencers, start-ups, entrepreneurs, and corporations to not only protect their brands and ideas but also amplify them across digital platforms using cutting-edge AI-driven strategies.Ana Law® is the first and only law firm offering flat-fee, 100% guaranteed patent, trademark, and copyright services, with Ana maintaining a 100% success rate.Beyond traditional legal work, she speaks widely on the intersection of AI, law, and social media, helping professionals understand how emerging technologies can safeguard and scale their influence.AI’s Impact on Legal Practice (00:03:04)Scope of IP and Transactional Work (00:04:20)Scaling with AI (00:05:47)Lawyers’ Resistance to AI (00:06:42)AI in Transactional vs. Litigation Work (00:07:37)Best Uses of AI in Litigation (00:09:23)Lawyer Hesitancy and AI Psychosis (00:10:26)Big Law Firms and AI Adoption (00:11:41)Prompt Engineering and Lawyer Skillsets (00:14:10)Ana’s Background at USPTO (00:16:02)IP Protection for Businesses (00:17:09)]Basic IP Protections for Businesses (00:19:06)Automating Client Communication with AI (00:21:39)Common IP Misconceptions (00:23:25)Client Types and Fee Structure (00:24:11)Service Guarantees in Legal Practice (00:26:02)Advice for Lawyers New to AI (00:26:54)Personal Freedom and Business Systems (00:27:49)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-callWould you like to learn more about Breaking Free or order your copy? https://www.garymiles.net/break-free

In this episode, Gary Miles introduces a powerful 10-minute assessment designed to help lawyers find out what’s truly standing between them and professional freedom. Traditional success metrics—billable hours, income, and case wins—often hide deeper struggles like burnout, self-doubt, and misalignment. Gary breaks down the three dimensions that determine whether you’re thriving or merely surviving in your practice: Internal Authority, Sustainable Excellence, and Authentic Practice. Even high-achieving attorneys can feel trapped by their own success. Listen for how to identify which area is holding you back and how small shifts can create lasting change. Take the assessment here: https://www.garymiles.net/the-free-lawyer-assessment

In this episode of The Free Lawyer podcast, host Gary interviews Jessie Brown, a former attorney turned career and executive coach. Jessie shares her journey from big law to coaching, discussing her experiences with burnout and how she found balance by aligning her work with her values. The conversation explores redefining success, managing stress, and practical strategies like energy audits, mindfulness, and setting boundaries. Jesse offers insights on overcoming financial fears, reconnecting with authenticity, and prioritizing well-being, providing valuable guidance for lawyers seeking fulfillment and sustainable careers without burnout.Jessie Brown practiced law for 15 years, primarily in Big Law, before becoming a career and executive coach for lawyers. She specializes in helping attorneys navigate career decisions and transitions and learn how to succeed on their own terms without burnout. Before becoming a coach, Jessie navigated balancing a demanding career as a litigator while raising young kids. She created the balance she sought as a Senior Counsel in Big Law, while working a reduced billable hour schedule, before deciding to resign from the law to focus exclusively on coaching. Jessie also leads transformational women's retreats and is a certified meditation teacher and forest bathing guide and has a deep love for nature, reading, and spirituality. Jessie’s Legal Background & Strengths Assessment (00:01:11) Transitioning Legal Practice Areas (00:04:27)Hospice Work & Mentoring Associates (00:06:25) Becoming a Career Coach (00:07:56) Recognizing and Experiencing Burnout (00:08:47) Finding Balance & Reducing Hours (00:09:53) JFinancial Fears & Career Transition Fund (00:10:50) Aligning Work with Values (00:12:28) Energy Audit & Burnout Prevention (00:13:43) Impact of Early Loss & Mortality Perspective (00:15:20) Mortality in Coaching & Future Visualization (00:16:51) Defining Success Beyond External Metrics (00:18:18) Rediscovering Authenticity (00:22:23) Mindfulness & Forest Bathing Explained (00:24:28) Practical Self-Care for Burned-Out Lawyers (00:28:04) Work-Life Balance & Boundaries (00:30:10) Creating Personal Freedom & Focus (00:32:57) Advice to Her Younger Self (00:35:15) 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-callWould you like to learn more about Breaking Free or order your copy? https://www.garymiles.net/break-free

In this episode, Gary Miles reveals why the confidence so many lawyers chase through case wins, titles, and recognition is actually built in the everyday moments with their clients. Genuine, empathetic client relationships can transform your professional confidence from something fragile to something unshakable. Gary breaks down how preparation, clear communication, and authentic care create a positive feedback loop that strengthens both your client’s trust and your own self-assurance. He shares how even difficult cases and setbacks can become confidence builders when approached with honesty and collaboration. Confidence isn’t earned in the courtroom, it’s cultivated through consistent service and meaningful connection. By the end, you’ll understand how every client interaction can reinforce your purpose, validate your professional worth, and create lasting fulfillment in your practice.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" podcast, host Gary interviews Casita Simpson, founder of Simpson Associates LLC and expert in law firm systems and automation. Casita shares her journey from paralegal to operations consultant, highlighting common inefficiencies in law firms and the transformative impact of centralized systems and automation. They discuss how to choose the right case management tools, overcome resistance to change, and implement practical steps to streamline operations, improve client experience, and boost profitability. Casita encourages firms to start small, embrace technology, and continuously improve their processes.The Problem: Disorganization in Law Firms (00:03:22) The Solution: Implementing Systems & Automation (00:06:10) Pushback & Cost of Inefficiency (00:09:04) Common Inefficiencies in Law Firms (00:10:39) Why Lawyers Resist Automation (00:12:38) Choosing the Right Case Management System (00:14:34) Mistakes in Implementing New Systems (00:17:43) Process of Working with Casita (00:20:03) Quick Wins Without New Technology (00:22:36)First Steps for Firms Getting Organized (00:23:41) .How Systems & Automation Enable Scaling (00:25:14) Measuring Success of Implemented Systems (00:26:39) How Quickly Results Are Seen (00:28:06) Overcoming Fear of Change (00:29:04) Personal Example of Trying Something New (00:32:42) Casita Simpson, featured in Legal Management Magazine, is a sought-after speaker, CRM Consultant, and the founder of Simpson & Associates LLC, a virtual operations hub. Casita is a Systems and Automations Queen who helps service-based businesses (law firms, doctors, real estate agencies, financial practices, nonprofits, and more.) patch the leaks in their operations, untangle disorganized processes, and eliminate time-sucking manual tasks. By streamlining internal systems and automating daily operations across marketing, sales, HR, and administration, she closes costly gaps from a lead's first touchpoint to client delivery, that drain time, money, and team morale so businesses can scale efficiently and confidently.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-callWould you like to learn more about Breaking Free or order your copy? https://www.garymiles.net/break-free

Intuition, decision paralysis, decision fatigue, decision-making, and self-doubt. These are the hidden forces that quietly derail even the most capable lawyers. So many attorneys freeze when it’s time to act and this episode is your answer as to why. Perfectionism and overanalysis undermine confidence and slow progress. Gary Miles shares how to shift from hesitation to action by trusting your professional instincts and using structured methods that reduce mental overload. Gary introduces the 80% rule, showing why waiting for total certainty leads to missed opportunities, and explains how to rank decisions by strategy, tactics, and execution for clarity under pressure. Listen to this episode to learn how to set decision deadlines, use the impact–urgency–cost–reversibility framework, and track choices in a decision journal to strengthen judgment. 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 podcast, host Gary interviews Cecilia Ju, a Washington-based family law attorney. Cecilia shares her journey from immigrating to the U.S. to founding her own successful law firm, highlighting challenges faced by Asian immigrant families and clients in the tech industry. She discusses the emotional toll of family law, the importance of mentorship, and strategies for work-life balance. Cecilia and Gary explore the value of community, resilience, and cultural understanding in legal practice, offering practical advice for attorneys seeking fulfillment and support in their careers.Cecilia’s Upbringing and Values (00:02:18) Immigration Journey and Law School Challenges (00:04:24) Decision to Start Her Own Law Firm (00:06:58)Early Challenges and Successes as a Firm Owner (00:08:41) Emotional Demands of Family Law (00:11:11) Work-Life Balance and Self-Care (00:13:12) Serving Asian Immigrant Families (00:16:16) CNavigating Cultural Differences in Family Law (00:18:49) High-Tech Industry Divorce Considerations (00:20:29) Handling Custody Fears and Client Emotions (00:22:19) Mentorship and Career Clarity (00:25:24)Benefits of Coaching and Overcoming Solo Practice Challenges (00:30:30) Mindset Shifts and Personal Growth (00:33:09) Advice for Family Lawyers: Support and Passion (00:35:51) 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-callWould you like to learn more about Breaking Free or order your copy? https://www.garymiles.net/break-free

An experience that revealed how the greatest battle for most lawyers isn’t fought in the courtroom, but in their own minds. Despite years of achievement, Gary Miles realized that self-doubt and over-preparation often rob attorneys of the confidence they’ve already earned. Gary unpacks the difference between faking confidence and building it authentically through preparation, presence, and belief in oneself. From body posture and eye contact to pacing and tone, listen for practical tips that help lawyers project calm authority and earn trust. Beyond trial work, these same habits strengthen client relationships, improve decision-making, and reduce burnout. By learning to shift from fear to curiosity, lawyers can turn pressure into clarity and perform at their best. Ultimately, this episode is a masterclass in transforming anxiety into authentic confidence.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 podcast, Gary interviews Brianna Beski, a Certified Divorce Financial Analyst at Raymond James. Brianna shares how her parents’ divorce inspired her career and discusses the financial complexities of divorce, including common misunderstandings about retirement accounts and asset valuation. She explains the critical role of financial clarity, collaboration with attorneys, and tailored support for high net worth individuals and business owners. Brianna emphasizes empowering clients to make informed decisions, reduce stress, and confidently rebuild their financial futures after divorce.Brianna’s not just a Certified Divorce Financial Analyst (CDFA®)— she’s someone who truly understands the emotional weight of divorce and how it impacts every area of life. Her unique backgroundallows her to:✔️ Provide financial clarity in emotionally charged situations, helping clients avoid fear-driven decisions they’ll regret later.✔️ Help high-achieving professionals maintain control over their financial future, especially when assets, businesses, and long-term planning are at stake.✔️ Act as a calm, strategic advocate—helping clients navigate complex financial decisions while prioritizing their well-being and their family’s future.Brianna’s Personal Divorce Experience (00:02:11)Career Path and Olympic Aspirations (00:04:14) BEmotional Impact of Divorce (00:05:27) Common Retirement Account Mistakes (00:05:44) Valuing Pensions and Retirement Assets (00:07:44) When to Use a CDFA (00:09:39) Case Example: Settlement Misconceptions (00:11:26) Role of CDFA in Divorce Process (00:13:37) Client Support and Financial Clarity (00:16:05)Unique Challenges for High Net Worth and Business Owners (00:18:55) Transformation Through Financial Clarity (00:22:16)Advice for Lawyers Hesitant to Use Financial Experts (00:24:13)Maintaining Self-Worth After Asset Division (00:26:31) Finding Personal Freedom After Divorce (00:29:48) Advice for Lawyers Going Through Divorce (00:30:49) Financial Planning for Married Couples (00:32:41) Advice to Her Younger Self (00:35:10)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-callWould you like to learn more about Breaking Free or order your copy? https://www.garymiles.net/break-free

On the surface, many lawyers appear to have it all: partnerships, accolades, case wins, and financial security. Yet behind the polished exterior lies exhaustion, anxiety, and an unshakable sense of emptiness. In this episode, Gary Miles explores what he calls the success paradox: how the very drive and perfectionism that fuel achievement often become the source of stress, burnout, and self-doubt. He shares candid stories from his own career, including the hidden costs of chasing external validation and the personal turning point that reshaped his perspective on law and life. Through vulnerability and hard-earned wisdom, Gary shows how perfectionism can be transformed into sustainable excellence, and how redefining success leads to both professional mastery and personal fulfillment. Practical strategies from his Free Lawyer framework highlight the power of setting boundaries, embracing internal authority, and building a practice that truly serves one’s life. 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