

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

Dec 7, 2020 • 20min
Season 1, Episode 13: Legal Ops Journey - How to Set Yourself on a Path to Success (with Rachita Maker)
Embark on a transformative journey with Rachita Maker, Vice President of Legal Operations and Compliance at Data Communications, in the insightful episode titled "Legal Ops Journey - How to Set Yourself on a Path to Success." Rachita shares her wealth of experience spanning over two decades in the legal services industry, offering invaluable insights into navigating the dynamic landscape of legal operations. Through engaging conversations, she illuminates the strategic role of legal operations in driving organizational efficiency, managing risk, and fostering innovation within legal departments. Join Rachita as she explores essential skills, challenges, and opportunities on the path to success in legal operations, empowering listeners to chart their own course towards professional excellence.
In this captivating episode of "Legal Ops Journey - How to Set Yourself on a Path to Success," Rachita Maker delves into her illustrious career trajectory and shares invaluable wisdom gleaned from her experience as Vice President of Legal Operations and Compliance at Data Communications. Rachita's journey unfolds against the backdrop of the evolving landscape of legal operations, marked by technological advancements, shifting paradigms, and emerging opportunities. Through candid dialogue, she explores the strategic imperatives driving the prominence of legal operations in today's corporate ecosystem, emphasizing the pivotal role of legal operations leaders in driving organizational efficiency and fostering innovation. Rachita navigates through essential skills, challenges, and strategies for success in legal operations, offering listeners actionable insights to propel their professional journey forward.
Learning Outcomes:
Gain profound insights into Rachita Maker's illustrious career trajectory and her role as Vice President of Legal Operations and Compliance at Data Communications.
Explore the strategic significance of legal operations in driving organizational efficiency, managing risk, and fostering innovation within legal departments.
Learn about essential skills, challenges, and opportunities on the path to success in legal operations, including project management, collaboration, negotiation, and process excellence.
Discover actionable strategies for navigating the dynamic landscape of legal operations and charting a course towards professional excellence.
Empower yourself to embark on a transformative journey in legal operations, leveraging Rachita's expertise and insights to set yourself on a path to success.

Nov 30, 2020 • 43min
Season 1, Episode 12: Personal Branding for Lawyers (with Mel Scott)
Embark on a journey of legal innovation and career exploration with Mel Scott on "Counsel: The Podcast." Delve into the dynamic world of in-house counsel life, social media, and personal branding as Mel shares her expertise and insights. Join her in thought-provoking conversations with legal professionals from diverse backgrounds, uncovering the secrets to success in the modern legal landscape. Whether you're a law student, early-career lawyer, or seasoned legal veteran, "Counsel: The Podcast" is your go-to resource for navigating the ever-changing legal terrain.
In this episode, Mel Scott opens up about her experiences leveraging social media to humanize the legal profession. She emphasizes the importance of authenticity and community engagement in shaping her personal brand as an in-house lawyer. Mel discusses the evolution of her online presence and the role of social media in connecting with like-minded individuals within the legal industry. She explores the power of personal branding in creating opportunities and fostering meaningful relationships, both online and offline. Drawing inspiration from her own journey and community feedback, Mel shares valuable insights into content creation, networking, and career development amidst the backdrop of COVID-19. Her father's timeless advice to focus on the journey rather than the destination serves as a guiding principle throughout the conversation, highlighting the importance of enjoying the process of career growth and self-discovery.
Learning Outcomes:
Gain insights into the role of social media in shaping the personal brand and reputation of in-house lawyers.
Understand the significance of authenticity and community engagement in building meaningful connections within the legal industry.
Learn strategies for content creation and leveraging social media platforms to showcase expertise and interests.
Explore the impact of COVID-19 on career development and networking opportunities for legal professionals.
Embrace the importance of enjoying the journey of career growth and exploration, prioritizing personal fulfillment and learning along the way.

Nov 23, 2020 • 38min
Season 1, Episode 11: How We Regulate One of Our Most Crucial Resources – Energy (with James Strange)
Join us as we explore the dynamic world of energy law and policy with James Strange, Associate General Counsel at a Southern California-based nonprofit specializing in energy advisory services. From his unconventional path starting with an art degree to navigating the complexities of energy regulation, James shares insights into the challenges and opportunities in shaping the future of energy.
In this enlightening conversation, James Strange shares his journey from an art graduate to an Associate General Counsel deeply entrenched in energy law and policy. Starting in a solar company during the economic downturn of 2008, Strange's curiosity about energy policy led him to pursue law school with a focus on energy and administrative law. His studies at the University of Hawaii, amidst the state's renewable energy debates, provided a rich foundation in understanding energy regulation and community engagement. Strange highlights key challenges in energy policy, including transitioning to renewable energy sources, managing surplus electricity, and updating aging infrastructure. Despite the complexities, he remains optimistic about the possibilities and emphasizes the importance of continued momentum and targeted policymaking. For aspiring energy lawyers, Strange offers valuable advice, including focusing on environmental and administrative law courses, seeking internships at utilities or public utilities commissions, and engaging with nonprofit organizations working on energy issues.
Learning Outcomes:
Gain insights into the unconventional career path of a lawyer specializing in energy law and policy.
Understand the challenges and opportunities in shaping the future of energy regulation and policy.
Explore key issues such as transitioning to renewable energy sources, managing surplus electricity, and updating aging infrastructure.
Learn valuable advice for aspiring energy lawyers, including educational focus areas, internship opportunities, and community engagement strategies.
Gain a deeper appreciation for the role of law and policy in driving sustainable energy practices and fostering community involvement in energy decision-making.

Nov 16, 2020 • 39min
Season 1, Episode 10: Creativity and Innovation for In-House Lawyers (with Catherine McGregor)
Explore the dynamic intersection of law and business with Catherine McGregor, a consultant, content creator, and trainer in the legal profession. Catherine shares insights from her extensive experience in law and academia, offering a fresh perspective on how in-house lawyers can drive innovation, collaboration, and creativity within their organizations. From discussing the evolving role of in-house legal teams to exploring the importance of business skills for lawyers, this podcast delves into practical strategies and real-life examples to inspire legal professionals to embrace change and lead with impact.
In this engaging podcast, Catherine McGregor discusses the dynamic landscape of the legal profession, particularly focusing on the role of in-house lawyers in driving innovation and change. Catherine draws from her diverse background in law, publishing, academia, and the creative arts to offer unique insights into the evolving nature of legal practice. The conversation covers topics such as the importance of business skills for in-house lawyers, the power of creativity and collaboration, and the transformative potential of purpose-driven legal departments. Through compelling anecdotes and practical advice, Catherine highlights the ways in which legal professionals can leverage their skills to become strategic business partners and catalysts for positive change within their organizations.
Learning Outcomes:
Gain an understanding of the evolving role of in-house lawyers in today's business landscape.
Explore the intersection of law and business, and the importance of business skills for legal professionals.
Learn practical strategies for fostering innovation, creativity, and collaboration within legal departments.
Discover real-life examples of successful legal teams that have embraced change and driven organizational growth.
Reflect on the broader implications of purpose-driven lawyering and its impact on the future of the legal profession.

Nov 9, 2020 • 32min
Season 1, Episode 9: The Intersection of Art and Law (with Sarah Feingold)
Sarah Feingold, a co-founder of The Fourth Floor, an organization dedicated to empowering women in board positions and helping startups thrive, is also an Engelberg Center fellow at NYU Law School. As a lawyer, she made iconic contributions as Etsy's first lawyer and Vroom's first lawyer. Sarah's passion for art, particularly jewelry and metalsmithing, has been a lifelong pursuit. She intertwines her legal expertise with her creative pursuits, recognizing the synergy between law and art in fostering personal growth and professional development.
In her conversation, Sarah shares insights into the intersection of law, art, and coping mechanisms during challenging times like the COVID-19 pandemic. She discusses her project, Legal Madness, which aims to bring to light the untold stories of in-house counsel through theater. Through her experiences and reflections, Sarah offers valuable lessons on authenticity, dealing with imposter syndrome, and the power of storytelling in both legal practice and artistic expression.
Learning outcomes:
Understanding the intersection of law and art: Sarah Feingold demonstrates how her legal background complements her artistic pursuits, highlighting the transferable skills and personal growth opportunities that arise from engaging in both fields.
Coping mechanisms during challenging times: Sarah shares her journey of navigating the COVID-19 pandemic, offering insights into dealing with feelings of guilt, shame, and imposter syndrome, and finding inspiration through creative outlets.
The importance of storytelling in law and art: Through her project, Legal Madness, Sarah emphasizes the significance of storytelling in legal practice and its potential to foster empathy, learning, and connection within the legal community and beyond.

Nov 2, 2020 • 37min
Season 1, Episode 8: LinkedIn for Lawyers (with Neil Greenbaum)
Embark on a journey into the dynamic world of LinkedIn with Neil Greenbaum, a distinguished transactional attorney and strategic consultant based in Florida and New York. In this episode of "Notes to My Legal Self," Neil shares his expertise in corporate and commercial real estate transactions and contracts while offering invaluable insights into leveraging LinkedIn effectively as a legal professional.
In this illuminating conversation, Neil explores the dichotomy between practicing law in-house and in private practice, providing listeners with a comprehensive understanding of the unique challenges and opportunities associated with each setting. From navigating corporate boardrooms to drafting complex contracts, Neil's firsthand experiences offer a compelling glimpse into the multifaceted nature of the legal profession.
But the heart of the discussion lies in the transformative potential of LinkedIn for lawyers. As a platform that transcends geographical boundaries and fosters meaningful connections, LinkedIn has emerged as a powerful tool for legal professionals seeking to enhance their professional presence and expand their networks. Neil shares actionable strategies for optimizing LinkedIn profiles, engaging with relevant content, and cultivating a strong personal brand that resonates with peers and potential clients alike.
Learning Outcomes:
Understand the nuanced differences between practicing law in-house and in private practice, and gain insights into the distinct challenges and opportunities in each domain.
Learn practical tips for leveraging LinkedIn effectively as a legal professional, including optimizing profiles, engaging with content, and building a compelling personal brand.
Discover how LinkedIn can serve as a catalyst for career growth and business development, enabling lawyers to establish thought leadership, explore new opportunities, and expand their professional networks.
Gain a deeper appreciation for the role of digital platforms in shaping the future of the legal profession, and learn how to harness the power of LinkedIn to thrive in an increasingly interconnected world.
Join us on "Unlocking LinkedIn: A Lawyer's Guide with Neil Greenbaum" and unlock the secrets to maximizing your professional potential in the digital age.

Oct 25, 2020 • 31min
Season 1, Episode 7: The Culture of Recognition (with Lauren Zajac)
Join Lauren Zajac, Chief Legal Officer of WorkHuman and Chair of the Board of LeaderMom, in a captivating conversation as she delves into the transformative power of recognition in legal leadership. Discover how Lauren's accidental journey led her to a company aligned with her values, and how recognition became a cornerstone of her leadership style. Gain valuable insights into the ripple effects of recognition on team dynamics, innovation, and strategic partnerships within an organization.
Explore the intersection of legal leadership and recognition with Lauren Zajac, who shares her unique career trajectory and the profound impact of recognition on her team at WorkHuman. From initial skepticism to transformative leadership, Lauren recounts the journey of integrating recognition into the fabric of her legal department, fostering collaboration, innovation, and a positive culture. Discover practical strategies for leveraging recognition to empower legal leaders and drive organizational success.
Learning Outcomes:
Gain insights into the role of recognition in fostering a positive culture and enhancing team dynamics within a legal department.
Understand the transformative effects of recognition on individual confidence, innovation, and risk-taking among legal professionals.
Learn practical approaches for integrating recognition into daily workflows and leadership practices to drive organizational impact.
Explore the strategic benefits of recognition in strengthening cross-functional partnerships and building a cohesive company culture.
Discover how legal leaders can leverage recognition as a proactive tool to drive engagement, productivity, and strategic alignment within their organizations.

Oct 20, 2020 • 28min
Season 1, Episode 6: Finding Your First Legal Job in a Bad Economy (with Ken Ito)
Embark on a journey of resilience and adaptability with Ken Ito, General Counsel of Green Solar, as he recounts his unconventional path to becoming a legal leader. From humble beginnings in commercial real estate to honing his litigation skills as an auto insurance defense attorney, Ken's story is a testament to perseverance and resourcefulness. Discover the pivotal moments and strategic decisions that shaped his career, including the transition to in-house counsel at Green Solar. With practical advice and candid reflections, Ken offers valuable insights for aspiring legal professionals navigating the complexities of today's job market.
Join Ken Ito as he shares his compelling career journey from law school graduate to seasoned legal professional. Gain valuable insights into building a diverse skill set, overcoming obstacles, and thriving in an ever-evolving legal landscape. With practical advice and candid reflections, Ken offers valuable insights for aspiring legal professionals navigating the complexities of today's job market.
Learning Outcomes:
Understand the importance of building a diverse skill set and seizing opportunities for professional growth.
Explore strategies for overcoming challenges and leveraging personal connections to advance your career.
Gain insights into the dynamic role of in-house counsel and the multifaceted responsibilities involved in supporting a complex business.
Learn how to navigate career pivots and adapt to changing market conditions with resilience and determination.
Discover practical tips for job seekers, including the value of internships, pro bono work, and networking in securing employment opportunities.

Oct 12, 2020 • 35min
Season 1, Episode 5: Building The Legal Department of The Future (with Laurie Ehrlich)
Step into the future of legal operations with Laurie Ehrlich, Chief Counsel - Sales and Alliances at Datadog. In this thought-provoking podcast, Laurie shares her journey of innovation and transformation in legal services, from pioneering the legal operations function at Cognizant to driving strategic initiatives at Datadog. Gain valuable insights into leveraging technology, fostering cross-functional collaboration, and redefining the role of in-house counsel in the digital age.
Join Laurie Ehrlich as she delves into the evolution of legal departments and the key strategies for building a future-ready legal operation. Drawing from her experience at Cognizant and Datadog, Laurie emphasizes the importance of embracing technology, data analytics, and collaborative approaches to enhance legal services and mitigate risks. From side projects to financial knowledge, discover the essential elements for shaping the legal department of tomorrow.
Learning Outcomes:
Explore innovative approaches to legal operations and the role of technology in driving efficiency and effectiveness.
Understand the significance of cross-functional collaboration and intradepartmental synergy in delivering value-added legal services.
Gain insights into the evolving role of in-house counsel and the importance of business acumen in strategic decision-making.
Learn about the integration of data analytics and common-sense solutions in optimizing legal service delivery.
Discover practical strategies for transforming legal departments into agile, proactive, and future-proof entities.

Oct 5, 2020 • 50min
Season 1, Episode 4: The Changing Future of Contracts (with Jeanette Nyden)
Join Jeanette Nyden, a leading authority on contract negotiation and governance, as she shares her expertise in navigating complex agreements. Gain invaluable insights into the strategic use of legal tools, the importance of tribal knowledge in governance, and the power of intentional negotiation to achieve mutual gain and drive performance-based outcomes.
Jeanette Nyden's extensive experience in contract negotiation and governance offers a wealth of knowledge for professionals seeking to optimize their contracting processes. From her background as a former litigator to her passion for teaching clients how to negotiate agreements, Jeanette emphasizes the transformative potential of understanding contracts as instruments for mutual gain and sustainable relationships.
In her discussions, Jeanette explores the evolution of her career from traditional legal practice to empowering clients to negotiate agreements proactively. She highlights the critical role of governance in mitigating risks and solving complex problems before they escalate. By sharing real-world examples and practical strategies, Jeanette illuminates the importance of fostering tribal knowledge within organizations to ensure effective collaboration and problem-solving.
Jeanette's approach emphasizes the intentional use of legal tools, such as indemnities and limits of liability, to align contractual terms with the desired outcomes and value propositions. Rather than relying solely on legal remedies, she advocates for a holistic approach that integrates legal, operational, and strategic considerations to drive performance and achieve mutual success.
Learning Outcomes:
Strategic Negotiation: Gain insights into Jeanette Nyden's journey from litigation to proactive negotiation, and learn how to leverage contracts as instruments for mutual gain and sustainable relationships.
Governance Best Practices: Understand the importance of documented governance structures in mitigating risks and solving complex problems proactively, and learn how to foster tribal knowledge within organizations to enhance collaboration and decision-making.
Intentional Use of Legal Tools: Discover how to use legal tools such as indemnities and limits of liability intentionally to align contractual terms with desired outcomes and value propositions, ensuring a holistic approach to contract negotiation and management.
Performance-Based Contracting: Explore the principles of performance-based contracting and outcome-based agreements, and learn how to structure contracts to drive performance and achieve mutually beneficial outcomes.
Practical Strategies: Gain practical strategies for optimizing contract negotiation processes, including risk profiling, governance documentation, and intentional use of legal tools, to enhance value creation and minimize disputes.
Embark on a transformative journey with Jeanette Nyden as she shares her insights and expertise in mastering contract negotiation, empowering you to navigate complex agreements with confidence and achieve sustainable success.


