The Free Lawyer

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

In this episode of "The Free Lawyer," host Gary interviews neuro coach and Neuro Savvy founder Keshawn Hughes. Drawing from her own experience with burnout, Keshawn shares how neuroscience-based coaching can help lawyers and other professionals manage stress, improve leadership, and foster healthier workplace cultures. The conversation covers practical tools like the SCARF model, breathwork, and visualization, emphasizing self-awareness, intentional breaks, and connection. Keshawn encourages listeners to find fulfillment beyond competition and perfectionism, while Gary highlights the importance of collaboration and self-care for a more rewarding legal career.Keshawn Hughes, M.S. is a NeuroLeadership Strategist, Executive Coach, and Founder of NeuroSavvy® Leadership, a Women's Business Enterprise National Council (WBENC)- and Women-Owned Small Business-certified firm transforming workplaces through brain science and authentic leadership. With two decades of experience guiding global brands, Keshawn integrates neuroscience, communication, and business strategy to help corporations improve employee productivity, retention, and engagement.Known for her ability to make complex brain science deeply practical, Keshawn equips HR and Tech leaders with proven strategies to enhance well-being, fuel performance, and develop cultures of high-impact leadership. She is certified by the International Coaching Federation (ICF) and actively involved with the Society for Human Resource Management (SHRM) and the Association for Talent Development (ATD).Based in Atlanta, Georgia, Keshawn lives with her husband and daughter, and brings heart, clarity, and bold insights to every stage she steps on.Here is her free Breakout from Burnout Guide- https://keshawnhughes.com/breakout-from-burnout-guideKeshawn’s Background and Burnout Journey (00:00:54)What is Neuro Coaching? (00:04:16).Neuroscience for Managing Lawyer Stress (00:06:24)Keshawn’s Personal Burnout Story (00:10:00)Why Lawyers Struggle with Communication and Leadership (00:13:14)The SCARF Model and the “SCARF Trap” (00:16:43)SCARF in Law Firms: Competition and Perfectionism (00:17:57)Threat Detection and Decision-Making Under Stress (00:22:19)Applying Neuroscience to Difficult Interactions (00:23:51)Practical Tools: Nature, Breathwork, and Box Breathing (00:26:38)Visualization and the Brain (00:29:42)Connect Before You Correct: Feedback and Delegation (00:31:40)Building Trust and Overcoming Micromanagement (00:34:27)Finding Fulfillment and Mindfulness Practices (00:37:13)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

Host Gary Miles shares his personal journey from being a bullied, perfectionist kid to a successful trial lawyer who still battled self-doubt and an unforgiving inner critic. Despite graduating first in his class, clerking for a federal judge, and winning countless cases, he discovered that external success never silences internal struggles. Through stories of career choices, courtroom victories and defeats, and the guidance of mentors who modeled humility and courage, this episode reveals how authenticity becomes a lawyer’s greatest strength. Listen for a roadmap for moving beyond perfectionism, silencing the inner critic, and practicing law with confidence, fulfillment, and presence. More than a story of resilience, this conversation redefines success in the legal profession as something deeper than billable hours and courtroom wins.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 Joel Chorny, a veteran criminal defense attorney and former public defender now running a solo practice in Tucson. Joel discusses his transition to solo work, the emotional toll of public defense, and the challenges of building a client base. He shares insights on self-care, mental health, setting boundaries, and the value of coaching and community. Joel also highlights the importance of culturally informed advocacy and honest client communication, offering practical advice for lawyers seeking a more fulfilling and sustainable legal career.Joel Chorny is a veteran criminal defense attorney and former public defender who has spent over a decade standing up for individuals caught in the harshest corners of the criminal system. Fluent in Spanish and committed to culturally informed advocacy, he now runs a thriving solo practice in Tucson. Joel also teaches trial advocacy at the University of Arizona’s James E. Rogers College of Law, where he trains future lawyers in the art of compelling courtroom storytelling. Outside of his legal work, he’s a devoted husband and father, an avid cyclist, and a student of improv comedy—skills that sharpen both his presence in the courtroom and his perspective on life.Joel’s Background and Transition Catalyst (00:01:06)Emotional Toll and Decision to Leave (00:03:06)Mentorship and Planning the Transition (00:05:01)Accelerated Transition and Office Opportunity (00:06:11)Starting Without Clients and Early Advice (00:07:36)Building a Caseload and Court Appointments (00:08:29)Cultural Background and Language Skills (00:09:42)Managing Emotional Weight and Self-Care (00:11:00)Accepting Limits and Caseload Realities (00:13:12)Choosing Clients and Setting Boundaries (00:14:19)Control, Outcomes, and Client Expectations (00:16:14)Challenges of Attracting Clients and Marketing (00:19:49)Doubts, Optimization, and Imposter Syndrome (00:21:12)Dealing with Career Anxiety and Support (00:22:07)Work-Life Balance and Transition Rituals (00:24:41)Quality Time and Family Anchors (00:26:54)Teaching Trial Advocacy (00:27:52)Value of Coaching and Seeking Support (00:31:08)Breakthroughs from Coaching (00:33:42)Advice for Lawyers: Support and Community (00:39:27)Giving Back and Building Community  (00:41:57)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 exposes what he calls the success paradox. This is the surprising reality that more wins, recognition, and achievements often intensify imposter syndrome rather than cure it. Gary shares how perfectionism and the constant chase for external validation leave even the most accomplished lawyers feeling like frauds. His Free Lawyer Framework is a model built on internal authority, clear boundaries, and value alignment, designed to help attorneys reclaim their freedom and joy in practice. He explains how shifting the focus from outcomes to effort, preparation, and authenticity transforms both professional performance and personal well-being. Listen for practical steps to set client boundaries, reduce stress, and cultivate sustainable excellence without burnout. 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