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Sidebar Advisors
A podcast exploring the careers, choices and strategies shaping today’s legal landscape.
Hosted by Niraj Chhabra, each episode explores the intersection of law, career growth, and financial decision-making. Through conversations on leadership, professional development and business building, we unpack the moments that define success.
For those thinking about what’s next or looking to grow and feel more fulfilled in their current role, these conversations offer a thoughtful look at building a meaningful and successful career in and around the legal world.
Sidebar Advisors
Gail Cummings: From Big Law to Therapist and Executive Coach
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Gail Cummings began her legal career to meet expectations, but the deeper truth was harder to ignore. After more than a decade in Big Law, with a thriving practice and two young children at home, she made the bold decision to pursue her long-standing dream of becoming a psychotherapist.
In this episode, Gail shares her path from lawyer to licensed therapist and executive coach, the emotional and practical hurdles she faced, and why so many attorneys find themselves questioning the career they worked so hard to build.
We also explore the mental health themes that come up repeatedly in her work with attorneys and the growing demand from law firms and bar associations for her expertise.
Whether you're thinking of leaving the law or trying to make peace with staying, Gail offers compassionate, actionable guidance on how attorneys can build happier, more authentic careers.