This Legal Life: Lessons Learned from a Life in Legal

In this episode of This Legal Life, host Ben Chiriboga sits down with Gary Miles — former trial lawyer turned wellness coach — to explore the mind traps that hold legal professionals back. Drawing on 40+ years of experience and a powerful personal transformation, Gary opens up about the silent challenges many lawyers face, including perfectionism, isolation, and burnout. From his journey into sobriety to launching a podcast at 66, Gary’s story is a testament to resilience, reinvention, and the importance of redefining success on your own terms. He also shares practical insights on coaching, mindset shifts, and building a legal career that’s both meaningful and sustainable.

Meet Our Guest:

Gary Miles, a seasoned law practitioner for over four decades, has dedicated his career to litigation and, more recently, family law. As the managing member of Huesman, Jones, and Miles in Maryland for over three decades and now of counsel to the firm, his diverse experience includes being a trial lawyer, managing partner, author, leader, podcaster, coach, and entrepreneur.

His true passion lies in helping people solve their problems and guiding them toward liberation from the prisons that hold them back. Having experienced the pressures inherent in the legal profession, Gary is deeply committed to helping his clients find fulfillment in their practice. He equips them with practical tools to overcome obstacles, thereby enabling them to achieve the success and freedom they aspire to. He loves supporting lawyers and lifting the legal profession.

He enjoys his Pinehurst, NC, home with his wife, Brenda, and their two beautiful English Goldens. They have five children and six grandchildren (so far!).

Learn more: www.garymiles.net

In this episode of This Legal Life, host Ben Chiriboga sits down with Rachel Clar, founder of Interconnected Us, to explore how women in Big Law are transforming their careers through the power of community. Rachel shares her personal journey—leaving law, building a career in real estate, discovering peer learning, and ultimately returning to law to create space for women lawyers to connect, collaborate, and thrive.

Rooted in a philosophy of non-binary thinking and spiritual leadership, Rachel’s work is redefining professional growth—not through competition, but through connection. From early struggles with belonging to launching cohort-based programs that drive real economic and career impact, this episode is a powerful conversation about creating change from the inside out.

Guest Bio:

Rachel Clar, Esq. is a strategic networking and confidence-building expert and the Founder of Interconnected Us, where BigLaw women lawyers gain the clarity they need to land the clients they deserve. Result? Clout.

Through her three-part framework, Rachel guides women lawyers in mastering strategic networking, communicating with power, and using their unique qualities to confidently win more business. Interconnected Us members skip the guesswork by gaining access to shortcut knowledge from successful women rainmakers who’ve done it before. Additionally, private conversations with peers, regular office hours, and private coaching empower members to land high-value clients that grow their pay, put them in control over their careers, and grow their influence.

Before founding Interconnected Us, Rachel built a career in business strategy and persuasive communication by developing affordable housing, urban infill neighborhoods and commercial-scale solar arrays in the real estate and clean energy sectors. Working in male-dominated fields, Rachel honed her strategic networking and influence building skills until they became razor sharp. Now, she guides powerful women lawyers to understand and leverage their unique strengths to grow their book of business - supporting them in confidently being their full selves is her edge.

Rachel is dedicated to shifting the status quo in BigLaw by building generational wealth and influence within a new tranche of women lawyers, calling herself a “compassionate disruptor.” In 2022, in furtherance of her mission to empower 1000 BigLaw women to grow their pay and influence (so that they can lift up others), she joined the ABA Law Practice Division’s Women Rainmakers Committee, where she has served ever since.

Connect with Rachel through LinkedIn at http://www.linkedin.com/in/rachelclar/

Subscribe to the newsletter at https://www.interconnectedus.com/newsletter.

Learn more about how Interconnected Us is helping BigLaw women rise at https://www.interconnectedus.com/inner circles.

In this episode of This Legal Life, host Ben Chiriboga speaks with Karina DuQuesne—lawyer, investor, operator, and now legal tech founder—about her extraordinary career journey from Goldman Sachs to Big Law, and ultimately to launching a legal tech startup designed to empower underserved entrepreneurs. Karina opens up about the challenges of navigating motherhood in a demanding legal career, the mindset shift from employee to founder, and why she believes general counsel roles are on a natural trajectory toward CEO. Her story is an inspiring blueprint for redefining success in the modern legal landscape.

Guest Bio:

Karina DuQuesne is the CEO and Co-Founder of Encore, a first-of-its-kind legal intelligence platform built specifically for entrepreneurs. Drawing from her deep experience in both high-stakes corporate law and tech innovation, Karina has steered Encore to deliver legal solutions that are timely, efficient, and cost-effective—helping founders stay focused on building their businesses instead of wrestling with outdated legal processes.

Before co-founding Encore, Karina practiced at top-tier law firms, including Saul Ewing and DLA Piper LLP, advising fast-growth tech companies and investment funds on mergers, acquisitions, and strategic transactions. She later established the Technology and Innovation Practice at Caldera Law, shaping legal strategies for venture-backed startups, and remains a Partner there, guiding founders from seed to scale.

Karina’s passion for high-impact ventures led her to serve as Chief People Officer, General Counsel, and Interim GM (U.S.) at Ironhack, a global edtech company where she championed rapid expansion and nurtured the next generation of tech leaders. She also played a pivotal role on the executive team of a global enterprise SaaS firm, driving a merger of equals that spanned six countries. Over the course of her career, she has been involved in more than 15 leveraged buyout transactions worth over $2 billion across multiple sectors.

A Miami native who began her career as an analyst at Goldman Sachs in New York, Karina returned to her hometown to blend her expertise in finance, law, and technology. Committed to elevating underrepresented voices in the tech sector, she founded the Ironhack Women in Tech Collective and actively invests in diverse early-stage founders.

Karina earned her Bachelor of Science in Economics from the Wharton School and her Juris Doctor from Benjamin N. Cardozo School of Law, along with a Certificate in Dispute Resolution. Recognized as “Counsel on the Rise” by the Daily Business Review, she continues to shape a more inclusive, forward-thinking startup community—one founder at a time.

In this episode of This Legal Life, host Ben Chiriboga sits down with Hannah Beko — lawyer, coach, author, and mental health advocate — to explore her journey from commercial real estate partner to a purpose-driven legal entrepreneur. Hannah shares how a life-altering moment with her father’s health catalyzed her pivot toward coaching, wellness, and redefining success in law. With honesty and warmth, she unpacks the challenges of running multiple businesses, confronting imposter syndrome, and building a legal life anchored in authenticity. This episode is a powerful look at the intersection of legal leadership, resilience, and humanity.

Guest Bio:

Hannah Beko is a trauma-informed coach, commercial real estate lawyer, and founder of Authentically Speaking, a coaching and training consultancy supporting legal professionals in creating more sustainable, fulfilling careers.

Drawing on her own experience as a practicing lawyer, business owner, and parent, Hannah understands the unique pressures faced by those in the legal profession—constant demands, high stakes, and the challenge of maintaining personal wellbeing in a high-performance culture.

Since 2016, she’s been helping legal professionals across the world move beyond burnout and disconnection. Her nervous system-aware approach combines coaching, mentoring, and practical tools to support clients in reconnecting with themselves, navigating stress, and realigning their professional lives with their personal values.

Whether working with firm leaders, junior or senior lawyers, or legal entrepreneurs, Hannah creates a compassionate space for reflection, growth, and meaningful change. Her work is grounded in the belief that law doesn't have to come at the cost of health, family, or authenticity.

Links:

www.authenticallyspeaking.co.uk

https://www.amazon.co.uk/Authentic-Lawyer-Hannah-Beko-ebook/dp/B0B1JPNRTS

https://www.linkedin.com/in/hannahbeko/

In this episode of This Legal Life, host Ben Chiriboga sits down with Shane Percival — a lawyer, engineer, and partner at NOD Law. Shane shares his unique journey from an engineering career during the dot-com era to becoming a leader in intellectual property law. They explore how his technical background and project management skills influenced his legal practice, his path from associate to partner, and the development of a dynamic, hybrid work culture. Shane also discusses the future of boutique law firms, the integration of AI, and how building meaningful client relationships remains central to success.

Guest Bio:

A problem-solver by nature, Shane frequently organizes cross-disciplinary actions in providing clients innovative legal solutions. As a former project manager tasked with the timely resolution of client issues while operating independently within a client location, Shane translates those previously honed organizational and managerial skills to apply intricate legal frameworks to cutting-edge technology and novel business models. Whether he is providing a client with patent, trademark, transactional due diligence, litigation support, or licensing/commercial agreement work, Shane ensures all firm work product is aligned with the client’s vision and needs. As an engineer, Shane was previously based in London, UK, and frequently worked with customers while stationed in Hong Kong. He is now able to rely on the skills honed during this time when managing clients’ global legal issues to fortify their market position and secure their commercial success.

In this episode of This Legal Life, host Ben Chiriboga sits down with Gwen Griggs — lawyer, co-founder, entrepreneur, consultant , and passionate advocate for reinventing the legal profession. Gwen shares her deeply personal and professional journey from the early spark of inspiration rooted in justice to building a law firm and consultancy grounded in purpose, innovation, and value. She reflects on leaving behind the billable hour, embracing design thinking, and creating systems that center client experience, well-being, and impact. This conversation is a masterclass in courageously aligning professional life with personal values — and designing legal services that truly matter.

Guest Bio:

Gwen Griggs, co-founder of ADVOS legal and ADVOS Pro, has a background in Big Law and C-suite roles. In ADVOS legal, she and her partner built a new model, that – instead of hours - measures what matters to the client, team, and owner. (Click here for more about Gwen's legal experience.) The innovative approach - solving a problem worth solving, the sustained success, and the impact on the community, earned ADVOS legal recognition by GrowFL as a Florida Company to Watch.

Built from the lessons learned in business and ADVOS legal, ADVOS Pro’s created training, coaching and a community helping law firm owners build practices they love that love them back.

Gwen is passionate about the world-changing impact of entrepreneurs - especially when those entrepreneurs lead law firms. She has been honored to serve on boards of organizations supporting entrepreneurs and is a frequent speaker on leadership, innovation, and alternative business and pricing models.

Links:

Website: https://advospro.com

PROmance Scorecard: https://advospro.com/promance-scorecard/

LinkedIn: https://www.linkedin.com/in/gwengriggs/

Instagram: https://www.instagram.com/griggsgwen/

Schedule a call: https://calendly.com/gwen-griggs/virtual-coffee

In this episode of This Legal Life, host Ben Chiriboga sits down with Tess Blair, former litigation and eDiscovery pioneer at Morgan Lewis, to discuss her journey of building a groundbreaking legal practice and transitioning into a thriving post-retirement career as an artist. From the early challenges of navigating technology in the legal field to leading a transformative practice, Tess reflects on the evolution of law, the creative parallels between legal innovation and art, and the importance of knowing when to pivot. This episode is a testament to the power of reinvention, resilience, and embracing creativity in all its forms.

Guest Bio:

Tess Blair is a litigator and legal entrepreneur who has practiced at the intersection of law, technology, and design for more than two decades. Tess is the founder and leader of Morgan Lewis’s eData practice, a data-driven practice that combines great lawyering with technology and design to enhance the delivery of legal services. A proven leader with a unique combination of skills: 20+ years of practice at an AmLaw 50 firm, Masters in Law Firm Management, undergraduate studies in Industrial Design. Author, Speaker, Visionary focused on reimagining the delivery of legal services.

In this insightful episode of This Legal Life, host Ben Chiriboga sits down with Robert Flint, a lawyer, entrepreneur, and now author of Working with Strangers: Building Your Career and Growing Your Business Through Referrals. They discuss the evolving nature of professional networking in an AI-driven world, the overlooked power of referrals in business development, and the role of technology as a facilitator rather than a replacement for human connection. Robert shares his personal journey—starting in law, navigating political upheaval, and ultimately founding Adviserly, a global referral network for boutique law firms. Through this engaging conversation, listeners gain actionable insights on operationalizing referrals, building collaborative legal networks, and preserving authentic relationships in the digital era.

In this episode of This Legal Life, host Ben Chiriboga talks with lawyer-turned-coach and TEDx speaker Lora Cheadle about overcoming burnout and redefining success in the legal industry. Lora shares her journey through career transitions, the pressures of law, and the importance of setting realistic expectations. Together, they explore strategies for finding balance, maintaining well-being, and building a fulfilling legal career.

Guest Bio:

Lora Cheadle, JD, CHt, is a leadership wellness coach, TEDx speaker, and bestselling author specializing in burnout and betrayal recovery. As a former attorney who walked away from a high-stress legal career, she understands the toll of exhaustion, overwork, and the hidden betrayals that drain passion and purpose. Through her signature Life Choreography® and Fuel Up Burnout Recovery Method, she empowers individuals and organizations to break free from burnout, reclaim their vitality, and step fully into their power.

A recognized authority in emotional resilience, self-trust, and holistic self-expression, Lora helps women heal from infidelity, self-betrayal, and limiting beliefs, guiding them to rebuild confidence and create a life they love—on their own terms. Her work blends mind-body practices, somatic healing, and actionable mindset tools, ensuring that both personal and professional transformations are deep, lasting, and fulfilling.

As the author of It’s Not Burnout; It’s Betrayal: 5 Tools to FUEL UP & Thrive and the award-winning FLAUNT! Drop Your Cover and Reveal Your Smart, Sexy & Spiritual Self, Lora delivers practical, inspiring strategies for overcoming life’s challenges with grace, resilience, and authenticity. She also leads Step into Your Moxie® Speak Up & Influence corporate workshops, teaching professionals how to advocate confidently for themselves, their careers, and their ideas.

With a background in law, trauma-informed coaching, clinical hypnotherapy, somatic attachment therapy, and energy healing, Lora’s unique approach bridges science, spirituality, and self-discovery. She hosts the top-rated podcast, FLAUNT! Create a Life You Love After Infidelity and Betrayal, and speaks globally on burnout recovery, self-worth, and authentic empowerment.

Lora is licensed to practice law in California and Colorado and holds multiple certifications in wellness and personal development. When she’s not coaching or speaking, she loves travel, adventure, and curling up with a great book.

Links:

Download BURNOUT UNCOVERED: Fostering Candid Conversations for Thriving Teams at www.BurnoutOrBetrayal.com

Learn more at www.workplace-burnout.com

In this episode of This Legal Life, host Ben Chiriboga interviews Patricia Gannon, an accomplished lawyer, founder, and digital nomad, as she shares her transformative journey from establishing a pioneering law firm in the Balkans to launching Platform 9, a groundbreaking social audio app for lawyers. Patricia opens up about navigating personal and professional transitions, the challenges of entering the legal tech space, and her mission to build global legal communities. This episode is a compelling look at resilience, innovation, and redefining what it means to thrive in the legal profession.

Guest Bio:

Patricia is a qualified Irish Solicitor with over 30 years experience in the legal profession. She has worked in leading Irish and European corporate law firms, NGO’s, Inhouse legal and the European Commission. Patricia has gained broad and varied experience working in multiple practice areas, teams and cultures within the legal field.

In 1995 she established a full-service law firm and today, Karanovic & Partners is the largest regional law firm in the Balkans. Her experience gained as a law firm founder to the development of a 200 strong cross border firm is unique and specific to building a firm in the ever- changing legal landscape. She founded the Serbian Private Equity Association, served as Board member of the American Chamber of Commerce and was a Board Member of Impact Hub in Serbia where she advised and mentored early stage startups. She developed the WE Angel network of female angels in Serbia.

Having exited the firm in 2020, she tapped into that experience and built Gannon Advisory, a boutique advisory consultancy for law firms. Her particular focus is leadership development and strategic growth.

She has been active in the International Bar Association for over 20 years and held senior leadership roles there including Co -Chair of the European Regional Forum. She is a committed advocate of building law firm networks and personal brands within those networks.

These various careers within the legal profession resulted in astute observance of the disconnect between lawyers locationally, generationally and cross-sectorally. There is a strong need to improve communication and connectivity in a world where physical travel will be less of an option.

As a result, she established Platforum9 which is a B2B social audio platform connecting lawyers globally. It was established to create live interactive forums for conversation, learning and business generation.

Important links:

Google Play: https://play.google.com/store/apps/details?id=com.platforum9&hl=en_IE&pli=1

App Store: https://apps.apple.com/ie/app/platforum9/id6497323190