

Notes to My Legal Self®
Olga V. Mack
Notes to My Legal Self® is a podcast for lawyers who want to think better, lead better, and practice with judgment, not just knowledge.
Hosted by Olga V. Mack, the show explores the real decisions lawyers face but rarely talk about openly. The gray areas. The tradeoffs. The moments where legal advice shapes business outcomes and trust.
Each episode blends candid reflection and conversations with experienced legal leaders who share what actually works in practice.
This is not about memorizing rules. It is about developing legal judgment, clarity, and confidence over time.
Hosted by Olga V. Mack, the show explores the real decisions lawyers face but rarely talk about openly. The gray areas. The tradeoffs. The moments where legal advice shapes business outcomes and trust.
Each episode blends candid reflection and conversations with experienced legal leaders who share what actually works in practice.
This is not about memorizing rules. It is about developing legal judgment, clarity, and confidence over time.
Episodes
Mentioned books

Sep 7, 2021 • 31min
Season 3, Episode 3: GC Leading the Social Responsibility Initiatives (with Christine Uri)
Dive into the nexus of legal acumen and corporate sustainability with this enlightening episode of Notes to my (Legal) Self, where we delve into the role of in-house legal departments in spearheading sustainable initiatives within their organizations. Join us as we unpack the journey of Christine Uri, Chief Sustainability and Legal Officer at ENGIE Impact. With a rich career trajectory from Corporate Counsel to her current dual-executive role, Christine shares her transformative insights from leading legal and sustainability strategies globally.
In this episode, Christine discusses the evolving responsibilities of corporate counsel, emphasizing the significant shift from traditional legal roles to dynamic, purpose-driven positions within enterprises. She explains how her career decisions, initially sparked by an introspective period after years in a law firm, guided her toward a role where legal expertise meets corporate sustainability. Her narrative is a compelling account of personal growth intertwined with professional evolution, where the pursuit of meaningful, impactful work takes center stage.
You will understand how legal professionals can be at the forefront of corporate sustainability efforts, transforming their roles into pivotal positions within their companies. Christine's story is not just about career development but also about the broader implications of embedding sustainability into the core strategic functions of a business.
Learning outcomes from this episode include:
Navigating Career Transitions: Insights into transitioning from traditional legal roles to positions that merge legal oversight with corporate sustainability, offering a blueprint for lawyers looking to pivot their careers towards more purpose-driven paths.
Role of In-House Counsel in Sustainability: Understanding the critical role that in-house counsel can play in shaping and driving their companies' sustainability strategies, highlighting the potential for legal departments to lead in corporate environmental initiatives.
Strategic Development and Implementation: Practical advice on developing and implementing sustainability strategies within a corporate structure, based on Christine's firsthand experiences integrating these initiatives into her role at ENGIE Impact.
Personal Growth and Professional Impact: Lessons on balancing personal values with professional responsibilities, enabling you to foster a career that meets corporate objectives and personal and societal contributions.
Join us to explore how you can be part of this vital shift towards a more sustainable future, gaining actionable insights on integrating sustainability into your legal practice and aligning your career with your values for a more fulfilling professional journey.

Sep 7, 2021 • 32min
Season 3, Episode 2: Adventures of a Silicon Valley General Counsel (with Sangeetha Raghunathan)
Join us on a riveting journey through the high-stakes world of Silicon Valley with one of its top legal minds, Sangeetha Raghunathan, in the latest episode of "Notes to My (Legal) Self." As General Counsel, CCO, and Head of Government Relations for the financial services powerhouse Earnin, Sangeetha has carved a niche in the intricate labyrinth of technology law and startup dynamics. With a career that spans heavyweights like Indiegogo, Squaretrade, Disney Interactive, and Visa, her experience is as vast as it is fascinating.
In this episode, Sangeetha delves into her legal odyssey, beginning with her formative years handling antitrust litigation and evolving into a privacy and fintech specialist. Discover how the litigation skills acquired in her early career are relevant and crucial in navigating the legal challenges of large corporations and startups alike. She shares her insights on the allure of fintech—a sector known for its rapid innovation and regulatory puzzles.
Sangeetha also unfolds her strategic approach to assembling a top-tier legal team, emphasizing the importance of recruiting individuals who are not only skilled but also fit the unique culture of a startup. She discusses the art of aligning legal strategies with business goals to fuel growth and scalability, and the importance of fostering trust and camaraderie among team members to build a resilient organizational structure.
Listeners will gain invaluable lessons on:
The seamless integration of complex litigation experiences to manage and lead in tech-driven environments.
Strategies for building and managing effective legal teams in the fast-paced startup ecosystem.
Methods for aligning legal functions with broader business objectives to facilitate sustainable growth.
Techniques for cultivating strong, trust-based relationships within professional settings.
This episode is a treasure trove of insights for anyone intrigued by the convergence of law, technology, and business strategy. Whether you're a legal professional, a tech enthusiast, or just curious about the inner workings of Silicon Valley's legal battles, there's something here for you. Dive into the strategic mind of Sangeetha Raghunathan and discover how legal expertise shapes the world of tech and startups. Join us for an enlightening session on the front lines of legal innovation!

Aug 8, 2021 • 26min
Season 3, Episode 1: Exploring a Change to the Mindset of IT Contracting (with Robin Meyer)
In the latest episode of Notes to my (Legal) Self, delve into the intricate world of IT contracting with Robin Meyer, General Counsel for TokenEx. This enlightening discussion unveils the layers and complexities of tech contracts, showcasing the need for a pivotal shift in how these contracts are crafted and understood.
Robin, with her extensive experience in tech contracting from a buyer's perspective and now a legal leader at TokenEx, shares her insights on the necessity of data tokenization for securing sensitive data. Throughout the episode, she and Olga explore aggressive contract terms and the strategic scattering of obligations across documents—a common tactic that complicates transparency and fairness in business dealings.
Listeners will gain crucial knowledge on several fronts:
Understanding Contract Complexity: Learn how to identify and interpret aggressive and misleading language in tech contracts.
Advocacy for Transparency: Recognize the importance of clear and fair contract terms and how they influence trust between tech providers and clients.
Strategic Negotiation Techniques: Discover effective strategies for negotiating contracts that protect your interests and promote a healthy, long-term business relationship.
This episode is a must-listen for legal professionals, tech industry insiders, and anyone interested in the intersection of technology and law. It offers practical advice on navigating and negotiating the often opaque world of tech contracts. Tune in for a compelling conversation that educates and empowers listeners to demand and drive change toward more transparent and fair contracting practices.

Aug 1, 2021 • 38min
Season 2, Episode 20: Legal Design (with Marty Finestone)
In this riveting episode of Notes to my (Legal) Self, we delve into the innovative world of legal design with Marty Finestone, a seasoned professional who is not just a lawyer but also an artist, DJ, and legal designer. With a rich background spanning over 15 years in private practice, in-house roles, and government, Marty now leads Legal Adjacency, his boutique consultancy. This episode explores how legal professionals can transcend traditional boundaries and become stellar advisors through creative thinking and legal design.
Marty discusses the evolving role of in-house counsel, emphasizing that the true value they bring to an organization lies not just in legal expertise but in how creatively and effectively they solve business problems with legal dimensions. By viewing legal challenges through the lens of legal design—an approach that prioritizes the internal client's needs, interests, and constraints—Marty illustrates how legal professionals can enhance their advisory role and influence within their organizations.
Listeners will gain insights into legal design principles and learn practical strategies for applying creativity to legal operations and documentation. Marty shares compelling examples from his career, where legal solutions tailored to clients' specific communication styles and business objectives led to more successful outcomes. This episode is a must-listen for anyone interested in elevating their role from a traditional legal advisor to a pivotal business strategist.
By the end of this episode, you will learn:
How to adopt a legal design mindset to enhance problem-solving capabilities.
Ways to integrate creativity into legal practices to support and advance business objectives.
Strategies for transforming the role of in-house counsel to become a more effective advisor and business partner.
Tune in to discover how to break free from conventional legal constraints and bring innovative solutions to complex business challenges.

Jul 25, 2021 • 30min
Season 2, Episode 19: Selecting a Mediator (with Winter Wheeler)
Dive into the fascinating world of mediation with our latest episode of Notes to My (Legal) Self, featuring the exceptionally skilled mediator Winter Wheeler. Winter, a former top civil litigator and now a devoted mediator, shares her unique approach to resolving conflicts, which she has honed through years of experience and cultural insight. Join us as we explore her innovative "Four Cornerstones of Mediation™," a methodology designed to enhance understanding and empathy in all forms of human interaction.
In this enlightening discussion, Winter reveals how transitioning from litigation to mediation ignited her passion for helping people communicate more effectively and compassionately. Her approach caters to the needs of a diverse clientele, including Spanish-speaking communities, and addresses the broader challenge of making the mediation process more inclusive and representative of the changing American demographic.
Listeners will gain invaluable insights into developing emotional intelligence, leveraging cultural knowledge, and the importance of genuine empathy. Winter's strategies are applicable in legal settings and everyday life, promoting better understanding and cooperation among people from all walks of life.
Learning Outcomes:
Embrace Emotional Intelligence: Learn to develop a deeper awareness of your own emotions and those of others, which can enhance interactions and reduce conflicts.
Cultural Proficiency: Gain insights into the importance of cultural knowledge and immersion and learn strategies for adapting communication styles to diverse groups.
Applying Mediation Principles in Everyday Life: Discover how mediation skills can improve personal and professional relationships, ensuring more productive and empathetic engagements.
By the end of this episode, you will learn how to apply these principles to improve your professional and personal relationships and understand why embracing mediation as a lifestyle rather than just a conflict resolution tool can lead to more meaningful and effective interactions. Tune in to discover how to transform how you communicate and connect with others.

Jul 18, 2021 • 26min
Season 2, Episode 18: Diversity Metrics 3.0 - Correlation and Automation (with David Cunningham and Ashley Clingo)
Welcome to a revolutionary episode of the Notes to my (Legal) Self podcast, where we dive deep into the cutting-edge world of Diversity Metrics 3.0. This episode, titled "Diversity Metrics 3.0 - Correlation and Automation," features David Cunningham, founder of Legal Metrics and CIO of Winston & Strawn, alongside Ashley Clingo, a licensed attorney who's pivotal in bringing Legal Metrics to life through innovative dashboards.
Today, we explore the evolution of diversity metrics in the legal field, moving from simple headcounts to complex analyses correlating diversity with client satisfaction, matter outcomes, and more. David and Ashley share their journey in automating these metrics to save time and enhance accuracy and relevance in diversity reporting.
Listeners will gain insights into how technology can transform the measurement of diversity from a burden into a powerful tool for change. Discover the potential impacts of automated, nuanced diversity metrics on law firms' decision-making processes, client relationships, and overall business success. This discussion is not just about the what and the how of diversity metrics but also delves into the why—highlighting the importance of a diverse legal team in achieving superior outcomes and client satisfaction.
Learning Outcomes:
Understand the technological advancements in diversity metrics from basic tracking to sophisticated correlation and automation.
Learn about the challenges of maintaining data privacy and compliance in the context of global diversity metrics.
Explore how automated diversity metrics can lead to better decision-making within law firms and improved client satisfaction.
By the end of this episode, you'll be equipped with a richer understanding of the evolving landscape of diversity metrics in the legal profession. Whether you're a legal professional, a tech enthusiast, or someone passionate about diversity and inclusion, this episode promises to enlighten and inspire actionable changes in your approach to diversity metrics.

Jul 12, 2021 • 34min
Season 2, Episode 17: Why I’m Trading Contracts for Code (with Ryan Finn)
Welcome to a riveting episode of Notes to my (Legal) Self, where we delve into the evolving intersection of law, technology, and business. In this installment, titled "Why I’m Trading Contracts for Code," we join Ryan Finn, a seasoned attorney turned technologist, discussing his transformative journey from legal expert to tech enthusiast.
Ryan, who currently spearheads Contracts & Risk Management at Boeing, shares insights from his extensive experience negotiating commercial agreements and implementing no-code solutions for contract management. His work exemplifies a shift towards a more efficient, tech-driven approach to legal processes, advocating for integrating software tools to enhance contract administration and risk assessment.
Throughout the conversation, we explore the concept of "contracts as code"—a revolutionary idea suggesting that contracts can be automated and managed through software, which speeds up the process and reduces the potential for human error. Ryan illustrates how adopting tech solutions in legal practices supports strategic business growth and aligns legal outputs with broader organizational objectives.
Listeners will glean valuable insights on the benefits of merging legal expertise with technological acumen. Ryan’s narrative is a compelling call to action for legal professionals to embrace technological advancements to stay relevant and efficient in a rapidly changing professional landscape. This episode enlightens and inspires legal practitioners to consider how technology can significantly transform their roles and the nature of legal work itself.
Learning Outcomes:
Understanding Contracts as Code: Learn how contracts can be transformed into automated, software-managed processes that enhance efficiency and accuracy.
Strategic Integration of Tech in Legal Work: Gain insights into how integrating technology into legal practices can align legal strategies with business goals and improve overall risk management.
Embracing Technological Change: Be inspired to consider how learning and integrating new technologies can fundamentally enhance law practice, from contract negotiation to compliance and governance.
Join us as we navigate this intriguing dialogue on the future of law, where coding and contract management converge to create a dynamic new realm of possibilities for legal professionals worldwide.

Jul 4, 2021 • 21min
Season 2, Episode 16: Unicorns Do Exist (with Sarah Stogner)
In this enlightening episode of Notes to my (Legal) Self, guest expert Sarah Stogner explores the surprising parallels between the oil and gas industries and the emerging cannabis sector. With over a decade of experience in risk management and legal advisory, particularly within energy-related businesses, Sarah deeply understands how traditional legal frameworks can adapt to new, fast-evolving markets.
Throughout the episode, Sarah discusses her journey from conventional energy law to the innovative frontier of cannabis legislation. She outlines how methodologies for mitigating risks, allocating liabilities, and drafting contracts in oil and gas can be effectively translated to the cannabis industry. This cross-industry perspective is particularly timely as federal decriminalization of cannabis looms, promising rapid sector growth and new legal challenges.
Learning Outcomes:
Cross-Industry Application of Legal Strategies: Listeners will learn how oil and gas risk management and contractual strategies can apply to the cannabis industry, offering insights into cross-industry adaptability.
Navigating Federal Ambiguity: The episode illuminates the complexities of operating within an industry still federally unrecognized, including banking challenges and interstate commerce issues.
Regulatory Evolution and Compliance: Understand the vital role of smart contracts and blockchain in enhancing transparency and compliance and grasp the shifting regulatory landscape as states move towards legalization.
This episode is designed for legal professionals, business strategists, and anyone interested in how seasoned industries can legally inform emerging markets. Whether you're exploring the legal intricacies of the cannabis industry or curious about innovative applications of traditional legal principles, Sarah's expert insights provide a rich educational experience. Join us for a deep dive into the legal dynamics in two surprisingly interconnected sectors.

Jun 27, 2021 • 30min
Season 2, Episode 15: Limitless Mindsets to Elevate Your Legal Career (with Charlotte Smith)
Embark on a journey to elevate your legal career with Charlotte Smith, a former lawyer turned leadership coach, in this transformative episode of Notes to my (Legal) Self. Charlotte, a pioneer in coaching lawyer leaders, shares her insights on how legal professionals can break through the barriers of conventional mindsets to unlock their true potential. This episode is a must-listen for anyone in the legal field feeling stifled by traditional paths and looking to craft a career that resonates deeply with their personal and professional aspirations.
Charlotte discusses the common mental challenges lawyers face, such as imposter syndrome and perfectionism, and offers effective strategies to overcome these issues. She highlights the importance of shifting from a catabolic energy that drains to an anabolic energy that uplifts and energizes. Through engaging stories and actionable advice, Charlotte illustrates how lawyers can transform their thinking to enhance not only their careers but also their personal satisfaction and leadership capabilities.
Listeners will gain valuable insights into:
Overcoming Mental Barriers: Techniques to combat imposter syndrome and perfectionism, empowering lawyers to feel more confident and competent.
Mindset Shifts for Enhanced Performance: How to adopt an anabolic mindset to foster positivity and opportunity in legal practices.
Leadership and Personal Growth: Strategies for personal development that align with professional goals, enhancing individual and team performance.
Join Charlotte Smith in this enlightening episode to explore how you can leverage a limitless mindset to advance your career and enrich your life. Discover the power of mindset in shaping your path to becoming a more effective and fulfilled legal professional. Tune in to transform your approach and become the leader you are meant to be in the legal world.

Jun 6, 2021 • 30min
Season 2, Episode 14: After Getting the Seat at the Table (with Yilin Chen)
In this riveting episode of Note to my (Legal) Self, we delve into the nuanced journey of Yilin Chen, General Counsel at Hearth, a fintech SaaS company revolutionizing financial tools for contractors. Transitioning from her initial law firm environment to the pinnacle of in-house counsel, Yilin brings a unique blend of legal acumen and strategic business insight. She shares the pivotal moments that shaped her into a formidable leader, underscoring the importance of asserting one's voice within traditionally male-dominated spaces.
Throughout the conversation, Yilin articulates the challenges and triumphs of finding her place at the leadership table as an Asian American woman in fintech. She candidly discusses the often-overlooked nuances of post-seat acquisition at the table—how to assert influence, foster effective communication, and navigate the complexities of corporate dynamics as a minority female voice. Her experiences reveal the critical balance between humility, confidence, and the strategic navigation of being a lone minority in high-stakes environments.
Listeners will glean valuable insights on empowering oneself through self-reflection, effective communication strategies, and the importance of empathetic leadership. The learning outcomes from this episode are particularly impactful, offering strategies to:
Enhance personal and professional self-awareness to navigate leadership roles better.
Employ effective communication techniques that assert one’s position while fostering collaborative and respectful environments.
Develop strategies for building and leading diverse teams with empathy and confidence.
Yilin's journey offers profound lessons on leveraging one's unique perspectives to foster business growth and mitigate risks. It provides a masterclass in transforming obstacles into opportunities for advocacy and leadership within the legal and business realms. This episode is a must-listen for anyone aspiring to elevate their professional impact in the face of systemic challenges.


