

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

Feb 6, 2022 • 24min
Season 4, Episode 3: Outside General Counsel and Alternative Fee Arrangement (with Steven J. Shanker, Esq.)
Welcome to a new episode of Notes to my (Legal) Self, where we dive into the evolving landscape of the legal profession with insights from those at the forefront. Today, we unravel the intricate world of for-hire transportation law and the innovative role of Outside General Counsel with Steven J. Shanker, Esq., a seasoned expert in navigating the turbulent waters of this dynamic industry.
Steven brings over two decades of experience advising companies that have faced the disruptive forces of Transportation Network Companies like Uber and Lyft. His approach has helped these businesses thrive amidst chaos and redefined the traditional client-lawyer relationship through alternative fee arrangements and the strategic role of an Outside General Counsel. This model fosters a partnership that aligns the interests of both parties, leading to more efficient and cost-effective legal services.
In our conversation, Steven illuminates the complexities of for-hire transportation, a field transformed by regulatory challenges and technological disruption. He shares how his entry into this niche area was marked by building robust connections with industry leaders, which he affectionately refers to as the "circle of love." These relationships have been pivotal in maintaining a competitive and healthy industry ecosystem.
Listeners will gain invaluable insights and learning outcomes from this episode:
Understanding the Outside General Counsel Model: Learn how this model can revolutionize the delivery of legal services by aligning lawyer and client interests, reducing costs, and increasing service efficiency.
Navigating Industry Regulations: Discover the critical role of legal expertise in navigating complex regulatory environments, particularly in industries like for-hire transportation that are heavily influenced by local and federal laws.
Adapting to Industry Disruptions: Gain insights into how businesses can adapt legal strategies to thrive in industries disrupted by technology, using the for-hire transportation industry as a key example.
Building Professional Networks: Understand the importance of cultivating strong industry relationships, or the "circle of love," to foster a supportive and collaborative professional environment.
This episode is not just a legal discourse but a masterclass in adaptability and innovation in legal practice. Whether you're a legal professional, business owner, or just curious about the intersection of law and business, a wealth of knowledge is waiting for you. Tune in, ask questions, and be part of the conversation that could redefine your understanding of legal services and their impact on business strategy.

Jan 31, 2022 • 38min
Season 4, Episode 2: Better Contract Content (with Chris Simkins)
Welcome to Notes to My (Legal) Self, where we delve into the intricacies of contract optimization with guest Chris Simkins, Head of Contract Optimisation at Simmons Wavelength. This episode provides a comprehensive look at the art of enhancing contract content, a critical yet often overlooked aspect of contract lifecycle management overshadowed by technology's allure.
Throughout the episode, Chris shares his rich experiences transitioning between big law and in-house roles, applying his deep understanding of the nuances of legal contracts. He introduces the concept of 'legal engineering'—a fusion of law, technology, and process improvement designed to boost the efficiency and effectiveness of legal services. Chris's passion for simplifying the contract process is evident as he discusses strategies for creating modular contracts, utilizing plain English, and preparing documents for automation.
Listeners will leave with actionable insights into improving their contract processes. Learning outcomes include:
Understanding the Importance of Content in Contracts: Recognize the pivotal role clear, balanced, and well-structured contracts play in the lifecycle management process, and how they contribute to more streamlined negotiations and implementations.
Strategies for Contract Simplification: Learn from Chris’s practical tips on drafting modular contracts and using plain language to make contracts more accessible and easier to manage.
Impacts of Contract Optimization: Discover the tangible benefits of optimizing contract content through Chris’s real-world examples, which illustrate reductions in legal spend and negotiation times, ultimately speeding up business processes.
Incorporating Legal Engineering: Gain an appreciation for the interdisciplinary approach of legal engineering and how it can be applied to improve the effectiveness of legal departments and the services they provide.
This episode is essential for anyone involved in contract management, legal innovation, or looking to better understand the intersection of law and technology. Chris's insights offer valuable guidance on making contractual processes less daunting and more efficient, ensuring that the content of contracts aligns with and supports business objectives. Tune in to learn how to optimize your contracts for a clearer, more streamlined future in contracting.

Jan 24, 2022 • 37min
Season 4, Episode 1: Better Contract Design (with Stefania Passera and Paula Doyle)
In the latest episode of Notes to my (Legal) Self, the conversation with Stefania Passera and Paula Doyle illuminates the transformative power of user-centered contract design. Stefania, hailing from Finland with a rich background in contract simplification, and Paula, a veteran innovator in legal frameworks, unpack the complexities and outdated conventions that plague traditional contracts. They offer a compelling narrative on how contracts can evolve beyond mere legal obligations into dynamic, effective tools that support and streamline business operations.
Throughout this enlightening discussion, listeners will gain a clear understanding of several key learning outcomes:
The Importance of Simplicity: The episode delves into why simplifying contracts can lead to increased efficiency and understanding among all parties involved, emphasizing that simplicity does not compromise legal rigor but enhances it.
User-Centric Design Principles: Stefania and Paula explain the principles of user-centric design—where the focus shifts from legal jargon to clear, navigable information that aids decision-making and reduces barriers to agreement.
Strategic Communication: The conversation highlights how contracts can serve as a communication tool, not just a legal requirement, aligning stakeholders' needs and expectations to foster better relationships and outcomes.
Practical Steps for Implementation: The experts share actionable advice for listeners on how to start integrating these design principles into their own contract practices, encouraging a shift towards more accessible and engaging contracts.
This episode is essential for anyone looking to transform the mundane task of contract negotiation into a strategic component of business success. It encourages legal professionals and business leaders alike to rethink how contracts are drafted and utilized, making them easier to understand and more effective in achieving business goals.

Jan 16, 2022 • 42min
Season 3, Episode 20: The Fear of Letting Go - A Journey to Self (with Niti Nadarajah and Lisa Lang)
Embark on an enlightening journey in this episode as we explore the often-unspoken challenges faced by legal professionals in their pursuit of perfection and fear of failure. This candid conversation features Niti Nadarajah, a seasoned corporate lawyer and head of legal at Philip Morris in Australia, alongside Lisa Lang, whose legal career spans from insurance defense to serving as General Counsel for a regional public university.
Through their narratives, Niti and Lisa discuss the pressures of maintaining an invisible armor in the legal profession—meticulously dotting every "i" and crossing every "t." They share heartfelt stories of personal and professional crises that forced them to confront and eventually shed this armor, revealing the vulnerability beneath. This episode illuminates the transformative moments that compel legal professionals to embrace their authentic selves amid intense professional demands.
Listeners will gain a multitude of learning outcomes from this engaging discussion:
Understanding Vulnerability in Professional Life: Discover the importance of embracing vulnerability as a strength, rather than a weakness, in high-stress environments.
Balancing Personal and Professional Identity: Learn strategies for maintaining authenticity while managing the demands of a legal career, and how this balance can lead to improved mental health and job satisfaction.
Advocacy for Mental Health and Inclusion: Gain insights into advocating for mental health, diversity, equity, and inclusion within the workplace, and the positive impacts these efforts can have on organizational culture and personal well-being.
This episode provides practical advice for legal professionals and inspires anyone grappling with the pressures of perfectionism in their careers. Tune in to discover how letting go of fear can reconnect you with your true self and potentially transform your professional identity in empowering ways.

Jan 9, 2022 • 29min
Season 3, Episode 19: Calling All Aspiring GCs (with David Hamm)
In this episode of Notes to My (Legal) Self, we delve into the strategic insights and personal narratives that shape the journey to becoming a general counsel. David Hamm, our guest, and a seasoned corporate counsel, shares his experiences and the foundational decisions that have defined his career trajectory. Here are the key learning outcomes from our discussion:
Strategic Networking and Vocalizing Ambitions: David emphasizes the significance of networking and the importance of openly discussing career goals. He illustrates how unexpected opportunities often arise from intentional connections and being vocal about one's ambitions within professional circles. This serves as a practical guide for listeners on the importance of building and utilizing a professional network effectively.
Diverse Career Pathways: Through David's recount of his own path and the stories from his podcast, "Conversations with GCs," listeners learn that there is no singular route to becoming a general counsel. The discussion highlights the varied backgrounds of general counsels, from corporate law to litigation, revealing that career flexibility and adaptability are crucial in reaching executive legal roles.
Importance of Skill Development: This episode underlines the critical skills necessary for a general counsel, with a focus on high-level communication and understanding corporate governance deeply. David discusses how aspiring general counsels can develop these skills through specific roles and responsibilities in their current positions, thereby preparing for the complexities of the general counsel role.
Mentorship and Continuous Learning: The conversation brings to light the role of mentorship and continuous learning in achieving significant career milestones. David shares how his educational pursuits, like obtaining an LLM in securities at Georgetown, and informal learning from mentors, have shaped his professional development, offering a blueprint for listeners to follow in their educational and professional endeavors.
Listeners are encouraged to approach their career development intentionally, embracing both the structured aspects of educational advancement and the unstructured opportunities that arise from professional interactions and mentorships. This episode not only provides a glimpse into the life of a senior corporate counsel but also serves as an educational tool for those aiming to navigate their careers toward the role of a general counsel.

Jan 6, 2022 • 30min
Season 3, Episode 18: The Future of Law (with Electra Japonas)
Dive into a riveting exploration of the legal landscape as we uncover the innovative strides in contract law with special guest Electra Japonas, co-founder of oneNDA and CEO of tlb. This episode promises to unravel the complexities of contracts and breathe new life into how legal professionals approach documentation.
Electra brings over a decade of experience from her tenure in commercial legal roles across various large organizations. Her journey from legal practitioner to revolutionary leader in legal design illuminates her passion for transformative change within the industry. The discussion kicks off with Electra's professional origins, tracing her path to founding oneNDA, a pioneering community-led initiative aimed at standardizing non-disclosure agreements universally. As we delve into why Electra sees contracts not just as documents but as crucial data sets, listeners will gain an intimate understanding of her vision for a streamlined, efficient legal process.
Throughout the episode, we tackle some of the most pressing questions facing today's legal professionals. How quickly can one truly understand their agreements? What drove Electra to initiate the oneNDA project, and why are some contract dilemmas better addressed on an industry-wide scale rather than individually? Her insights are backed by the impressive traction oneNDA has gained since its inception, with over 1,000 legal enthusiasts joining the cause, creating a vibrant community eager to drive change.
You will walk away with key learning outcomes, including:
An appreciation of legal design and its impact on simplifying complex processes.
Strategies for viewing and managing contracts as dynamic data rather than static paperwork.
Understanding the importance of community and collaborative efforts in achieving widespread industry reform.
This episode is not just for legal professionals but for anyone intrigued by the intersection of innovation, law, and technology. Join us as we dissect how shifting perspectives can lead to significant improvements in how legal services are delivered and experienced. Whether you're drafting your next agreement or simply curious about the future of law, this conversation with Electra Japonas is an essential listen.

Dec 13, 2021 • 43min
Season 3, Episode 17: Creating the New Conscious Legal System (with J Kim Wright)
Welcome to the latest episode of the Notes to My (Legal) Self podcast, where we dive deep into the evolving world of law with pioneers at the forefront of change. Today, we're exploring the transformative realm of Integrative Law with guest J Kim Wright, a trailblazer who's dedicated over two decades to redefining the legal landscape.
In this thought-provoking discussion, Kim shares her journey from practicing traditional law to advocating for a holistic approach that encompasses restorative justice, non-violent communication, and collaborative law, among others. These methods aim to humanize the legal process and align with a broader vision of creating a legal system that is conscious, inclusive, and attuned to the real human needs of those it serves.
You will gain invaluable insights into how Integrative Law can serve as a catalyst for creating more compassionate and effective legal frameworks. Key takeaways include understanding the importance of reflective practices for lawyers, the power of aligning legal practice with core personal and community values, and the transformative potential of conscious contracts that prioritize human relationships over rigid legal frameworks.
Learning Outcomes:
Reflective Practice: Understand the significance of self-reflection and mindfulness in legal practice, enhancing empathy and effectiveness in legal proceedings.
Values-Based Law Practice: Learn how integrating personal and community values into legal work can reshape priorities and outcomes, leading to more fulfilling and impactful legal careers.
Conscious Contracts: Explore the concept and application of conscious contracts to foster cooperative and positive relationships between parties, reducing conflicts and litigation.
This episode is not just a conversation but an invitation to think differently about the role of law and lawyers in society. It challenges traditional perceptions and encourages legal professionals and laypeople alike to envision a legal system that contributes to healing and unity rather than division. Join us to discover how you can be part of this crucial shift toward a more equitable and holistic legal future.

Dec 8, 2021 • 23min
Season 3, Episode 16: Freelance Paralegals (with Berlinda Bernard)
In this engaging episode of Notes to My Legal Self, we explore the transformative role of freelance paralegals in modern legal practice with expert guest Berlinda Bernard, founder of Quintessential Pillar Paralegal Consulting, LLC. With over a decade of experience across diverse legal settings, Berlinda offers a comprehensive look into how freelance paralegals can significantly enhance the efficiency and productivity of legal departments.
Throughout the discussion, listeners are introduced to the benefits of integrating freelance paralegals into their teams. Berlinda outlines how these professionals help manage and streamline extensive legal tasks, allowing lawyers to focus on more complex aspects of their cases. This shift optimizes operational efficiency and results in substantial cost savings, as freelance paralegals can be engaged on an as-needed basis without the overhead associated with full-time staff.
Key learning outcomes from this episode include:
Strategic Utilization: Understand how to strategically employ freelance paralegals for project-specific work or during peak workload periods, which can lead to better management of resources and reduced legal expenses.
Effective Collaboration: Learn the best practices for forming and maintaining productive partnerships with freelance paralegals, ensuring that they become a seamless extension of the in-house team.
Budgeting Insights: Gain insights into planning and budgeting for freelance paralegal services with practical tips on how to achieve cost-effective solutions without compromising on the quality of legal support.
Berlinda also shares her personal journey to becoming a freelance paralegal, reflecting on how her diverse background has equipped her to offer high-quality, adaptable support to various legal professionals. Her commitment to ongoing education and professional development is particularly inspiring, emphasizing the importance of continuous improvement in raising the standard of paralegal practice.
Tune in to enrich your understanding of how freelance paralegals can be a game-changer in the legal industry, offering flexible, efficient, and cost-effective legal support. Whether you are looking to streamline your legal operations or are a paralegal aiming to expand your career opportunities, this episode delivers essential advice and key strategies to leverage the unique skills of freelance paralegals effectively.

Nov 22, 2021 • 41min
Season 3, Episode 15: Storytelling for Thought Leaders (with Jay Harrington)
In this enlightening episode of Notes to my (Legal) Self, we delve into the transformative power of storytelling with Jay Harrington, President of Harrington Communications. Known for his expertise in thought-leadership marketing, particularly in the legal sector, Jay unpacks the essential role of storytelling in enhancing business communication. His insights illuminate how stories deeply influence decisions by connecting ideas to emotions, vital for persuasion and engagement in any professional context.
Throughout this episode, you will gain valuable strategies on constructing compelling narratives that resonate with their audience. Jay introduces practical frameworks for crafting stories that align personal or brand identities with the needs and interests of the audience, ensuring that the content is not only engaging but also strategically effective. He also discusses the importance of authenticity in storytelling, providing techniques for legal professionals to narrate their experiences in ways that build trust and establish authority in their fields.
Learning outcomes from this episode include:
Understanding the Psychological Impact of Storytelling: Learn why storytelling is a powerful method for making emotional connections and how it can drive decision-making processes in business and law.
Frameworks for Effective Storytelling: Discover specific storytelling frameworks that help professionals package their expertise and personal journeys into engaging narratives that appeal to clients, colleagues, and broader audiences.
Strategies for Personal Branding: Gain insights on using storytelling to enhance personal branding, particularly for legal professionals, by conveying expertise and values in a way that builds trust and fosters professional relationships.
Application in Professional Settings: Learn how to apply storytelling techniques across various professional scenarios, from LinkedIn posts to courtroom presentations, to enhance persuasion and influence.
Join us for a journey into the power of storytelling, where logic meets emotion, and learn how to craft narratives that are not only heard but felt and remembered. Whether you're in private practice or a corporate environment, this episode is packed with actionable insights that can transform how you communicate your expertise and personal brand in the legal world.

Nov 15, 2021 • 38min
Season 3, Episode 14: Mental Illness (with Emma Sharma)
In this enlightening episode of Notes to my (Legal) Self, explore the intersection of mental health and professional leadership with Emma Sharma, Chief Administrative Officer and General Counsel of Valiant Integrated Services. Emma, a seasoned business executive known for her empathetic leadership and advocacy for workplace mental wellness, shares her insights and personal experiences, particularly her own struggles with PTSD.
Throughout the episode, Emma discusses the critical need for mental health awareness in the corporate world, especially post-pandemic. She shares her approach to building supportive environments that foster open discussions about mental health challenges. Her personal narrative underscores the importance of empathy, support networks, and proactive mental health initiatives in overcoming the stigmas that often silence those in need.
Listeners will walk away with several key learning outcomes:
Understanding the Impact of Mental Health in High-Pressure Roles: Learn about the nuances of mental health challenges faced by professionals, especially in leadership and high-stress environments.
Strategies for Fostering Empathetic Leadership: Gain actionable tips on how to cultivate an empathetic approach in leadership that can help break down barriers to mental health discussions at work.
Navigating Personal Mental Health: Emma provides practical advice on managing personal mental health issues, advocating for oneself, and utilizing available resources to seek help.
Creating Supportive Work Environments: Discover how to implement organizational changes that promote mental health awareness, reduce stigma, and support recovery and well-being among employees.
This episode is an essential listen for anyone looking to understand more about mental health in the legal and business sectors, offering guidance on both personal and organizational levels. Emma’s message of hope and empowerment will inspire you to advocate for change and support within your own spheres, paving the way for a healthier, more inclusive professional environment. Tune in to hear how embracing vulnerability and fostering open conversations can lead to transformative outcomes in both personal and professional realms.


