SideBar Advisors

Send us a textBefore AI, commercial space exploration, or 3D printing became mainstream, James Wolff was already deep in the weeds - founding startups in college and chasing cutting-edge ideas long before they hit the headlines.In this episode, James shares how his lifelong passion for technology continues to shape the way he practices law, advises clients, and builds his reputation in the industry. We explore the winding path that led him from engineering and entrepreneurship to law, and how his side projects —whether speaking on stage, writing books, or serving on forward-thinking boards— help position him as a thought leader in fast-evolving spaces. This one’s a little geeky, a little strategic, and packed with insight for anyone looking to future-proof their career.

Send us a textGail 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.

Send us a textIn this episode, we sit down with Andrea D’Ambra, Partner and Global Executive Committee Member at Norton Rose Fulbright. Andrea shares her remarkable journey from leaving a major firm to pursue a true partnership track, to navigating Big Law while raising five kids and ultimately rising to leadership at one of the world’s largest law firms.We talk about her role co-chairing the firm’s Women’s Initiative (WiN), her influential work with The Sedona Conference, where she helps shape best practices for the responsible use of AI in legal settings,  and how she balances the intensity of law firm leadership with personal time ( including video games to decompress). This conversation is honest, inspiring, and packed with insights for attorneys navigating their own careers and values.

Ian Murray, a Certified Financial Planner and Student Loan Professional, shares his expertise on financial planning for attorneys. He discusses the unique challenges high-earning lawyers face with student loans and the importance of tailored repayment strategies. Ian explores the balance between loan repayment and long-term financial goals, including homeownership and retirement. He also delves into recent changes in student loan legislation and the intricacies of income-driven repayment plans, offering valuable insights for professionals navigating their financial futures.

Send us a textIn this episode, we sit down with Emily Logan Stedman, attorney at Husch Blackwell, to explore her unconventional path to Big Law and the powerful personal brand she’s built along the way. Emily shares how she began her career as a teacher before making the leap to law, and how writing and blogging helped her find her voice in a demanding profession. We dive into how her current firm has supported her passion for authenticity—whether that’s speaking openly about mental health, posting from the lake, or leveraging AI to streamline her work. Emily offers a candid look at how she balances high performance with well-being, and why the idea that Big Law and work-life balance can’t coexist is more myth than reality. We also discuss her journey to 21,000+ LinkedIn followers, her evolving approach to business development (with the help of a coach), and how she’s positioning herself for long-term leadership as she works toward equity partnership. Whether you're navigating a legal career or just curious about how to build a brand that aligns with your values, this conversation with Emily is one you won’t want to miss.

Send us a text🎙 On this episode of the SideBar Advisors Podcast, we’re joined by Derek Brainard, CFP®, Director of Financial Education at AccessLex Institute—the nation’s largest nonprofit dedicated to supporting law students and legal education.We cover:The top resources AccessLex offers for law students and recent gradsHow practicing attorneys with student loans should approach repayment plans—especially with ongoing policy shiftsWhy it’s crucial to leave all your options open in an unpredictable loan environmentHow law school alumni can bring AccessLex’s tools and support back to their alma matersWhether you’re just a few years out of law school or advising the next generation, this episode is packed with practical insights on education, access, and long-term financial well-being.🎧 Referenced Resource: AccessConnex by AccessLex – a free financial coaching service for law students and attorneys. Learn more at https://www.accesslex.org/accessconnex

Send us a textFrom skateboarding teen to leading one of the top environmental law practices in the country — meet Justin Savage, partner at Sidley Austin.Justin shares his journey from the DOJ, where he helped try what was then the largest environmental settlement in U.S. history, to his current role advising major companies on high-stakes regulatory and litigation matters.But his story goes way beyond the courtroom. A high school teacher inspired him to pursue college, a debate team flyer led him to his future wife, and together they navigated law school while raising a newborn — sometimes literally bringing the baby to class.It’s a story about grit, purpose, and building a meaningful career without losing sight of what matters most.

Send us a textIn this episode of the Sidebar Advisors Podcast, we're joined by Stacy Phillips—renowned family law attorney and partner at Blank Rome LLP.With nearly four decades of experience, Stacy has represented some of the most high-profile names in entertainment, business, and beyond. From complex divorces to custody battles, she brings unmatched insight and grace to some of life’s toughest transitions.We dive into her experiences working on cases involving public figures like Britney Spears and Bobbi Brown, her leadership in philanthropy, and her ongoing mission to create more space for women in law through mentorship and firm-wide initiatives like the Women’s Leadership Summit.This conversation is a must-listen for anyone curious about what it really takes to build a powerful, purpose-driven legal career.

Send us a textWomen attorneys face unique challenges when it comes to growing and scaling their firms—something Davina Frederick knows firsthand. As a lawyer, law firm growth strategist, and founder of Wealthy Woman Lawyer®, Davina has built a career helping women attorneys overcome business hurdles, set boundaries, and create sustainable success.In this episode, she shares how she went from running her own practice to coaching women lawyers on business development, mindset shifts, and the systems that make firm growth possible.

Send us a textIn this episode, we sit down with Breeana J. Somers, a litigation associate at Ballard Spahr, who shares her incredible story of resilience and success. From being a teen mom relying on government assistance to working multiple jobs while attending law school at night—Breeana defied the odds to break into Big Law. She opens up about hiding her motherhood from her firm, the challenges of balancing it all, and how embracing her authenticity changed everything. Breeana also discusses her journey with ADHD, from a misdiagnosis to sharing her experience publicly—leading to women reaching out to her for support and even driving new business her way. Tune in for an inspiring conversation on perseverance, breaking barriers, and the power of owning your story.