The Free Lawyer

Gary Miles
  • 5.0 (70)
  • Entrepreneurship
  • Updated Weekly

The Free Lawyer® Podcast is where high-performing attorneys come when success starts to feel like a trap. Hosted by trial lawyer, managing partner, and attorney freedom coach Gary Miles — with over 40 years in practice — this podcast delivers honest conversations and practical tools to help you escape burnout, conquer perfectionism, and build a practice that serves your life, not consumes it. Two episodes every week, built specifically for lawyers who are ready to stop surviving and start thriving. Practice law with purpose. Live life with freedom.

  1. 2d ago

    The Delegation Trap: Why Smart Attorneys Stay Overworked with Gina Cotner #446

    You've hired the associate. Brought on the paralegal. Maybe even added an assistant. And yet you're still the one answering emails at 11 p.m., still the last one making every decision, still the one who can't take a real vacation. Delegation was supposed to fix this. Why hasn't it? In this episode, Gary sits down with Gina Cotner, founder and CEO of Athena Executive Services, to unpack why delegation fails at the leadership level and how attorneys can finally build teams that let them focus on their highest and best use. Gina works just 10 to 15 hours a week running a multimillion-dollar firm, and she shares the mindset shifts, systems, and accountability practices that make it possible for any lawyer to do the same. "World peace is not in the balance here. We're just delegating." — Gina Cotner Key takeaways: Recognize why lawyers are trained to grip control tightly, and learn how to loosen that grip without sacrificing quality or client outcomesAsk "given everything on your plate, when can you have this done?" and watch your team's follow-through transformStop asking "any questions?" and start asking "what questions do you have?" because one assumes questions are goodTrust your team before they've fully earned it, because more often than not people rise to the level of belief you place in themBook a standing golf game, tennis match, or dinner that costs money and involves other people, and let that constraint force your calendar into alignmentIdentify the first task you should offload tomorrow morning to start building real freedom into your practiceGina Cotner is the founder and CEO of Athena Executive Services, one of the top virtual executive assistant firms in the country. Her elite EAs partner with attorneys, executives, and entrepreneurs to take ownership of the work that isn't their highest and best use, freeing leaders to lead. Gina is also a dynamic speaker and workshop facilitator known for her practical approach to delegation, accountability, and building teams rooted in trust. Special for listeners of The Free Lawyer: Receive 5 free hours of service added to your first full month of work with Athena Executive Services, a $275 value. Just mention this offer during your first call. Learn more at athenaexecutiveservices.com. If this episode moved something for you, share it with a colleague who needs to hear it. Subscribe wherever you listen, leave a review, and visit garymiles.net to explore how coaching can help you practice with purpose and live with freedom. You can also reach Gary directly at gary@garymiles.net. TIMESTAMPS [00:00] Introduction and episode preview [01:35] From EA to firm founder [04:31] Better done than perfect [07:08] Why lawyers struggle to let go [09:12] What Athena does differently [14:31] How delegation has evolved [17:09] AI, human EAs, and the future [19:55] The trust and accountability blind spot [28:06] Applying the accountability framework [31:34] One thing to do tomorrow morning GUEST BIO Gina Cotner is the founder and CEO of Athena Executive Services, one of the top virtual executive assistant firms in the United States, specializing in delegation and accountability for high-performing leaders. She serves swamped attorneys, executives, and entrepreneurs by pairing them with elite Executive Assistants who take ownership of the work that isn't their highest and best use. A dynamic speaker and workshop facilitator, Gina spent 25 years leading transformational programs at Landmark before building Athena into the firm it is today. She now runs her business in just 10 to 15 hours a week, spending the rest of her time on tournament pickleball, golf, and life at the California coast. 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-call You can find The Free Lawyer Assessment here- https://www.garymiles.net/the-free-lawyer-assessment

  2. 5d ago

    Sunday Night Dread, Constant Availability, and the Freedom Formula for Overworked Attorneys #445

    Accepting every paying client is a slow subscription to misery in your legal practice. End constant availability and Sunday dread with this episode. In this episode of The Free Lawyer, Gary Miles dismantles the myth that total availability and accepting every paying client are required for professional excellence. He exposes the four hidden fears driving overworked lawyers and reveals how a fear-based practice manufactures the very outcomes attorneys try to avoid.  Gary introduces his Freedom Formula, combining choice, systems, and standards to show how strategic boundaries actually attract higher-quality clients and boost firm growth.  What You’ll Learn in This Episode:  how to apply the Sunday Night Test to diagnose your firm’s health five essential client standards designed to eliminate friction and burnout how to stop feeling like a guest or prisoner in your own career Go to the next level with more from The Free Lawyer episodes: how to navigate difficult client management Listen on Apple Podcasts https://podcasts.apple.com/us/podcast/257-how-can-lawyers-effectively-manage-difficult-clients/id1614507857?i=1000673828638 Or Spotify https://open.spotify.com/episode/6eW6IE3BhtpYETThBKBYAN?si=b98109963c72447d  Take the Free Lawyer Assessment ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠garymiles.net/the-free-lawyer-assessment⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠  Learn more about Breaking Free or order your copy ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.garymiles.net/break-free⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠  Schedule a complimentary discovery call: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://calendly.com/garymiles-successcoach/one-one-discovery-call ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

  3. Aug 6

    Saying No as an Act of Freedom: Ari Tuchman on Building a Boutique Law Firm #444

    Three months ago, Ari Tuchman walked away from Milbank and billion-dollar deals to hang his own shingle. What he's learned about saying no, building a brain trust, and protecting his mornings is a masterclass for any lawyer who feels stuck on someone else's track. In this episode, Gary sits down with Ari Tuchman, founder of Tuchman Law, APC in Beverly Hills. After more than five years working on nine and ten-figure transactions at Milbank, Ari made the leap into solo practice with intention. This is a candid conversation about what it really takes to bet on yourself, why saying no is an act of freedom, and how to build a law firm that serves your life instead of the other way around. Key takeaways: Recognize the difference between external authority (accolades, prestige, the next milestone) and internal authority (confidence built from within your own competence and character).Build your own brain trust of solo practitioners and peers when you leave a big law bench behind.Filter clients through two lenses: the person and the substance. Trust is the foundation of every attorney-client relationship.Understand how AI is reshaping transactional practice, and why boutiques stand to benefit as the middle gets squeezed.Protect the breaks. Some of your best thinking happens when you step away from the desk.Take one concrete step this week: write down ten qualities of the lawyer you want to be, then check whether your practice reflects them.About the guest: Ari Tuchman is the founder of Tuchman Law, APC, a boutique transactional firm in Beverly Hills advising businesses, real estate investors, and family offices. He previously spent over five years at Milbank LLP in New York, where his work included a $700 million casino portfolio sale, a $1.2 billion take-private acquisition, and a $7 billion LNG joint venture. He holds a J.D., cum laude, from Georgetown Law. If this episode moved you, subscribe to The Free Lawyer, leave a review, and pick up a copy of Breaking Free on Amazon. You'll find twelve prisons of the mind and twelve keys to unlock them, including the one Ari names so clearly in this conversation. Learn more at garymiles.net. [00:00] — The accomplished lawyer's trap[01:59] — Deciding to leave Milbank[05:11] — What he left behind[09:35] — Inside a boutique firm[10:53] — Turning work away[13:42] — AI and the road ahead[17:17] — Building his brain trust[26:36] — What freedom looks like[29:19] — One step this week Ari Tuchman is the founder of Tuchman Law, APC, a boutique transactional firm in Beverly Hills advising businesses, real estate investors, and family offices on M&A, joint ventures, real estate transactions, and startup financings. He serves clients who want large-firm capability paired with the responsiveness only a single-principal firm can offer. Before founding his firm, Ari spent over five years at Milbank LLP in New York, where his work included a $700 million casino portfolio sale, a $1.2 billion take-private acquisition, and a $7 billion LNG joint venture. He founded Tuchman Law to build a practice that serves his life rather than the other way around. You can find The Free Lawyer Assessment here- https://www.garymiles.net/the-free-lawyer-assessment 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-call Would you like to learn more about Breaking Free or order your copy? https://www.garymiles.net/break-free Access this free tool to identify your productivity time drains and move to purposeful strategy-  https://upbeat-trailblazer-9238.kit.com/7c3c667ff1 Check out the Elite Lawyer's Productivity System   https://www.garymiles.net/productivity

  4. Aug 3

    A $2.4 Million Dollar Legal Catch and the Time Management System That Did It #443

    A solid productivity system is not only about relieving overwhelm and burnout. It can be the difference between spotting a $2.4 million dollar loophole in the fine print... or not.  In this episode, Gary Miles shares why the most expensive mistakes in a law practice are often the ones attorneys never find out about. Together, we examine two versions of the exact same morning and how a $2.4 million settlement agreement was reviewed. Gary reveals how practice architecture, not talent or effort, dictates legal output.  What You’ll Learn in This Episode:  why trying to out-effort a broken practice design leads directly to burnout, exhaustion, and dangerous blind spots in critical documents. the transformative strategy of protecting your first 90 minutes of the day for high-level thinking how structural changes to your daily schedule can protect your clients Go to the next level with more from The Free Lawyer episodes: Gary Miles' signature Triangle System for productive lawyers Listen on Apple Podcasts https://podcasts.apple.com/us/podcast/a-3-part-productivity-system-for-lawyers-to-reclaim/id1614507857?i=1000771667568  Or Spotify https://open.spotify.com/episode/0ZbFkNdnNVW7IgCr4sVXRc?si=9c8d74f2c0214aa7  Resources Mentioned in This Episode: Get the Values Alignment Guide ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://upbeat-trailblazer-9238.kit.com/1604bbf4cb⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠  Use this free diagnostic tool to help you identify your specific time drains and move from reactive chaos to purposeful strategy. ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://upbeat-trailblazer-9238.kit.com/7c3c667ff1⁠⁠⁠⁠⁠⁠⁠⁠ ⁠ Learn more about Breaking Free (the book) and order your copy ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.garymiles.net/break-free⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

  5. Jul 30

    Finding Your Why and Your Happy Place in Law with Sara Naheedy #442

    A lot of lawyers hit every milestone they thought they wanted, only to feel a quiet resistance to the work they built their career on. In this conversation, one attorney explains what she did when that resistance became impossible to ignore. Gary sits down with real estate attorney and broker Sara Naheedy to unpack what it looks like to redesign a legal practice around who you actually are. After more than a decade in litigation, Sara walked away and built her own firm centered on mediation, empathy, and living on her own terms. It's a candid look at what it takes to bet on yourself and reclaim your career from the inside out. Key takeaways: Recognize the resistance you feel toward daily work as valuable information, not weaknessGet clear on your why before making any move so intentional action can replace exhausting motivationReframe client relationships as long-term investments rather than one-off transactionsPosition yourself as a legal advisor who listens first, not just another attorney who talks at clientsAnticipate that rebranding an established reputation takes more work than building one from scratchInvest in coaching and honest outside perspective to see what you cannot see in yourselfBuild a financial safety net before you leap so courage is grounded in real preparationAbout the guest: Sara Naheedy is a California real estate attorney and licensed broker with over 15 years of experience. As founder of Sara Naheedy Law APC, she has built a practice around mediation, empathy, and efficient resolution instead of litigation. She is also the author of Stack the Legal Odds in Your Favor. If this conversation resonated, subscribe to The Free Lawyer wherever you listen and leave a quick review so more attorneys can find the show. When you are ready to design a practice built around your own why, visit garymiles.net or reach out to Gary directly at gary@garymiles.net. TIMESTAMPS [00:00] Opening reflection on the profession [02:31] Sara's defining moment to launch [06:18] Choosing empathy over aggression [08:13] What sets Sara apart [10:21] Fears of starting from scratch [13:24] Advice for the stuck lawyer [16:10] How client expectations are shifting [18:44] The role of coaching and networking [23:17] Can lawyers actually be happy [25:52] The first step to your own terms GUEST BIO Sara Naheedy is a California real estate attorney and licensed broker with more than 15 years of experience helping landlords, tenants, buyers, and sellers navigate transactions, mediation, and dispute resolution. As founder of Sara Naheedy Law APC, she has built her practice around a simple conviction: most real estate conflicts can be resolved efficiently, humanely, and without ever setting foot in a courtroom. She is the author of Stack the Legal Odds in Your Favor, a legal self-help resource with a foreword by Dr. Ron Paul. When she is not working with clients, she is likely outside with her dogs, on a pickleball court, or on a yoga mat, exactly the life she built her practice to protect. 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-call Access this free tool to identify your productivity time drains and move to purposeful strategy-  https://upbeat-trailblazer-9238.kit.com/7c3c667ff1 Check out the Elite Lawyer's Productivity System   https://www.garymiles.net/productivity You can find The Free Lawyer Assessment here- https://www.garymiles.net/the-free-lawyer-assessment Would you like to learn more about Breaking Free or order your copy? https://www.garymiles.net/break-free

  6. Jul 27

    3 Productivity Drains Stealing Billable Hours Every Single Day #441

    There is a painful gap between the long, exhausting hours attorneys work and the low billable output that actually makes it onto our timesheets.  Many high-performing attorneys assume a thin timesheet is a personal failure of discipline or willpower, but Gary Miles explains why trying to outwork this problem is the most expensive wrong answer in a legal practice. Through the example of an experienced attorney named Marcus, the episode highlights the three productivity drains that erode focus. To combat these drains, Gary introduces a practice shift that supports Marcus’ transformation of his daily output from 4–5 billable hours to 10.3 captured hours while finishing the day with calm, clarity, and zero burnout.  What You’ll Learn in This Episode: The first 90 minute focus strategy The 3 small interruptions that you call productivity, but actually are consistent setbacks How one lawyer went from a daily output of 4–5 billable hours to 10.3 captured hours Go to the next level with more from The Free Lawyer episodes: recover more of your hours without adding more time to the clock Listen on Apple Podcasts https://podcasts.apple.com/us/podcast/the-five-figure-leak-how-to-recover-billable-hours/id1614507857?i=1000762377833  Or Spotify https://open.spotify.com/episode/41MFYpdAmiP5ipObf72qIC?si=f881c727b1d54454  Use this free diagnostic tool to help you identify your specific time drains and move from reactive chaos to purposeful strategy. ⁠⁠⁠⁠⁠⁠⁠⁠https://upbeat-trailblazer-9238.kit.com/7c3c667ff1⁠⁠⁠⁠⁠⁠⁠ ⁠ Learn more about Breaking Free (the book) and order your copy ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.garymiles.net/break-free⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

  7. Jul 23

    The Business of Health Law, Managing Client Relationships, and Scaling Your Law Firm Without The Billable Hour #440

    First-generation attorney, Jamaal Jones shares how to succeed in health law, manage client relationships, and scale a law firm without the billable hour. This episode of The Free Lawyer, host Gary Miles speaks with Jamaal Jones, founder of Jones Health Law, about what it takes to transition from an entry-level attorney doing document review to running a successful health law practice. Jamaal shares candid stories about the realities of launching a firm with no initial network, transitioning away from the traditional billable hour, and protecting the business of medicine. Jamaal outlines key strategies for delegating effectively, maintaining firm culture through rigorous hiring, and seeking out mentorship regardless of how long you've been practicing. Listen to this episode for: How to leverage limited resources and temporary income streams to build a client base from scratch. Insights into defending providers long before appeals are filed. How fixed pricing creates income predictability, aligns attorney-client goals, and prevents bill shock. Implementing strict response timelines with your team and clients to build long-term trust. Practical guidance on establishing intentional calendar boundaries so your business serves your life instead of consuming it. To learn more about Jamaal Jones and his firm, visit Jones Health Law. Connect with Gary Miles: Use this free diagnostic tool to help you identify your specific time drains and move from reactive chaos to purposeful strategy. ⁠⁠⁠⁠⁠⁠⁠⁠https://upbeat-trailblazer-9238.kit.com/7c3c667ff1⁠⁠⁠⁠⁠⁠⁠ ⁠ Learn more about Breaking Free (the book) and order your copy ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.garymiles.net/break-free⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠

  8. Jul 20

    3 Daily Habits High Performing Lawyers Use to Reclaim Professional Confidence #439

    Corner offices and impressive incomes, yet there is a deep dread that keeps surfacing on Sunday nights.  Gary Miles details why traditional metrics of legal success frequently lead to burnout and empty victories for high performing lawyers. Perfectionism, constant availability, and relying on external validation create what Gary calls “golden handcuffs." Handcuffs that keep accomplished lawyers feeling trapped in the very success they built.  What You’ll Learn in This Episode: The 3 core pillars you need to transition into internal authority and personal validation. Take action on practical daily habits that don’t require more time from your day. And resources to build the roadmap to unlock the cage of unsustainable success. Go to the next level with more from The Free Lawyer episodes: defining internal authority and what it looks like in action. Listen on Apple Podcasts https://podcasts.apple.com/us/podcast/whats-your-freedom-score-find-out-in-10-minutes-363/id1614507857?i=1000733678200  Or Spotify https://open.spotify.com/episode/7Bm5Joo1904Sk18CuFVIhR?si=c41f7460c63d4525  Use this free diagnostic tool to help you identify your specific time drains and move from reactive chaos to purposeful strategy. ⁠⁠⁠⁠⁠⁠⁠⁠https://upbeat-trailblazer-9238.kit.com/7c3c667ff1⁠⁠⁠⁠⁠⁠⁠ ⁠ Learn more about Breaking Free (the book) and order your copy ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.garymiles.net/break-free⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

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5
out of 5
70 Ratings

About

The Free Lawyer® Podcast is where high-performing attorneys come when success starts to feel like a trap. Hosted by trial lawyer, managing partner, and attorney freedom coach Gary Miles — with over 40 years in practice — this podcast delivers honest conversations and practical tools to help you escape burnout, conquer perfectionism, and build a practice that serves your life, not consumes it. Two episodes every week, built specifically for lawyers who are ready to stop surviving and start thriving. Practice law with purpose. Live life with freedom.

Information

  • Creator
    Gary Miles
  • Years Active
    2022 - 2026
  • Episodes
    446
  • Rating
    Explicit
  • Copyright
    © Gary Miles
  • Show Website
    The Free Lawyer

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