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Sidebar Advisors
Sidebar Advisors Attorney Podcast explores the career moves, risks, and decisions that shape a life in law.
Hosted by Niraj Chhabra, financial planner and founder of Sidebar Advisors, the show features candid conversations with attorneys, legal leaders, and professionals connected to the legal industry.
Guests share how they navigated firm changes, leadership, business growth, career pivots, and the moments that pushed them to bet on themselves.
Each episode offers a practical look at the professional, personal, and financial choices attorneys face as their careers evolve.
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.