You Are A Lawyer: Take Risks and Change Careers in Law

Tax Attorney Shares When You Really Need Help

Stephen Weisberg is a Detroit-based tax attorney who helps individuals and business owners resolve IRS controversies and tax-debt issues. In this episode, he shares how the 2008 recession launched him from corporate bankruptcy work into tax law, why most people wait too long to seek help, and what every lawyer (and taxpayer) should know before they get that letter from the IRS. What You Can Do With a Law Degree Stephen’s journey proves that a law degree is both a credential and a toolkit. His early work in bankruptcy law introduced him to financial systems and creditor negotiations, while his tax practice taught him how to translate that technical knowledge into advocacy for everyday people. Tax controversy work isn’t glamorous, but it’s vital—and it’s year-round. “People think I’m busiest during tax season, but that’s when the IRS is focused on filing. My work happens the rest of the year," shares Stephen Weisberg on Episode 217 of You Are a Lawyer. He’s built a steady stream of clients through LinkedIn networking, attorney referrals, and partnerships with CPAs, CFOs, and financial planners. The relationships he’s developed prove that collaboration, not competition, sustains a modern law practice. Most of his cases are handled remotely by phone or Zoom, reflecting how legal work has evolved since the pandemic. Did you know that children as young as 10 can be prosecuted as adults in Pennsylvania?  You Are A Lawyer has partnered with YSRP, the Youth Sentencing and Re-Entry Project, to bring awareness to their fight to keep young people out of adult prisons and to advocate for youth lifers.  Visit YSRP.org [http://ysrp.org] to support this cause. Thank you.

Why Authenticity Matters for Lawyers

Sergio Gregorio is a lawyer, podcast host, and creative who’s redefining what it means to have a legal career. In this conversation, he shares how growing up in Brooklyn, studying journalism, and working in federal service shaped his storytelling instincts, and why today’s lawyers must balance visibility, authenticity, and creativity in the digital world. LAWYER SIDE HUSTLES Sergio’s podcast, Frolic & Detour [https://www.frolicanddetourpodcast.com/], showcases the multifaceted lives of lawyers who have stepped outside conventional career paths. Through conversations that blend humour, culture, and creativity, he invites listeners to see law as a foundation, not a limitation. He’s also expanding his creative portfolio with food-review videos, blending his love of storytelling with his natural curiosity about everyday pleasures. “People don’t really get to see the silly side,” Sergio Gregorio admits in Episode 216 of You Are a Lawyer, “The podcast can feel serious, but there’s more to me than that.” By bringing humanity into his work, Sergio embodies the podcast’s core philosophy: lawyers are people first. Thinkers, creators, and dreamers who deserve space to explore beyond the billable hour. His story is a reminder that embracing detours can lead to the most authentic destinations. Did you know that children as young as 10 can be prosecuted as adults in Pennsylvania?  You Are A Lawyer has partnered with YSRP, the Youth Sentencing and Re-Entry Project, to bring awareness to their fight to keep young people out of adult prisons and to advocate for youth lifers.  Visit YSRP.org [http://ysrp.org] to support this cause. Thank you.

Building Confidence and Clarity as a Lawyer (August 2023)

Laura Terrell is an executive coach, general counsel, and former special assistant to the president who has built a career across government, private practice, and nonprofit leadership. In this episode, she shares how coaching helps lawyers advocate for themselves, embrace career pivots, and find clarity in uncertain times. LAWYER SIDE HUSTLES Alongside her legal work, Laura built a thriving executive coaching practice. She now works with clients ranging from law firm associates to government lawyers, helping them prepare for promotions, navigate layoffs, or make strategic pivots. “One of the interesting things about attorneys is we’re really good at advocating for clients. But sometimes attorneys are surprisingly reluctant to advocate for themselves,” shares Laura Terrell in Episode 103 of You Are a Lawyer. Her coaching practice fills that gap, giving lawyers the tools to ask better questions, push beyond comfort zones, and build sustainable, fulfilling careers.

Redefining Success and Alignment in Law

Arivee Vargas is a first-generation Latina lawyer who went from Big Law litigation to in-house corporate leadership, all before pivoting to become an author, executive coach, and speaker. She shares the raw story of her identity crisis after having her first child and how that led her to develop the framework for her book, Your Time to Rise [https://www.amazon.com/Your-Time-Rise-Unlearn-Limiting/dp/B0D7FNPHS2], focusing on aligning your career with your deepest values. This conversation is essential for any high-achieving lawyer ready to stop checking boxes and start building a life of true purpose. LAWYER SIDE HUSTLES Arivee Vargas has successfully layered multiple non-traditional ventures alongside her demanding corporate career, demonstrating how a side hustle can evolve into a full-time business. While working full-time in high-level corporate roles, she became a certified coach and simultaneously cultivated her writing and speaking business. Her specific "hustle" involved writing her book, Your Time to Rise [https://www.amazon.com/Your-Time-Rise-Unlearn-Limiting/dp/B0D7FNPHS2], which was written while she was still fully employed. She also established The Humble Rising podcast [https://humblerising.libsyn.com/] in 2021 as a platform to test and experiment with her ideas and voice before making the full-time jump. “I started to realize, oh, I love coaching. I love, you know, doing this type of work,” Arivee Vargas shares in Episode 214 of You Are a Lawyer. Her current full-time business is built around executive coaching, speaking, and authoring, all centered on the theme of alignment, the process of ensuring what clients truly believe inside matches what they pursue on the outside. Arivee's focus with her clients is on "transformation from the inside out," working primarily with high-achieving lawyers and leaders who are looking for executive-level life coaching to navigate a career pivot and better align their professional achievements with their personal happiness. LISTEN TO LEARN * How to separate your self-worth from your professional titles * Why focusing on the next right step eliminates career anxiety * How to apply law school grit to internal transformation WE ALSO DISCUSS * Why lawyers struggle with compartmentalization in personal life * Deconstructing cultural beliefs about sacrifice and hustle * Choosing "Work-Life Harmony" over the balance trap Partnership: Did you know that children as young as 10 can be prosecuted as adults in Pennsylvania?  You Are A Lawyer has partnered with YSRP, the Youth Sentencing and Re-Entry Project, to bring awareness to their fight to keep young people out of adult prisons and to advocate for youth lifers.  Visit YSRP.org [http://ysrp.org] to support this cause. Thank you.

Solo Firm Autonomy: Escaping the Partnership Trap

Yladrea Drummond went from being “team no care about the law" to becoming a highly successful trial attorney and solo firm owner in Maryland and DC. She openly shares the grit required to get barred after a seven-year journey, how she transitioned her practice from family law to dominating criminal defense, and the non-negotiable value of complete autonomy that running her own firm provides. This conversation is a raw, honest look at the transition from legal disappointment to becoming a respected "big dog in court" who is truly building a legacy LAWYER SIDE HUSTLES While Yladrea is a self-proclaimed "workhorse" focused on the rapid expansion and day-to-day operations of her successful trial firm, she also acknowledges the importance of creative outlets that serve as a side interest and a form of therapy. Her personal hustle is in the realm of writing, specifically fiction, which is a powerful creative counterbalance to the high-stress demands of her criminal defense practice. “I love to write,” Yladrea Drummond shares in Episode 213 of You Are a Lawyer. Although the fiction novel was ultimately shelved, Yladrea recognizes her love for writing remains strong. She notes that if she were to pursue a writing project now, after achieving success in her firm, she would aim to share her professional expertise in a non-traditional format. LISTEN TO LEARN * How to protect your peace and stay grounded in high-pressure legal roles * What it looks like to lead authentically, even in corporate settings * Why saying “yes” to rest is essential for longevity in the legal field WE ALSO DISCUSS * The pressures of overachievement and burnout in law * Black joy, healing, and the power of community * Redefining success beyond titles and traditional career paths Partnership: Did you know that children as young as 10 can be prosecuted as adults in Pennsylvania?  You Are A Lawyer has partnered with YSRP, the Youth Sentencing and Re-Entry Project, to bring awareness to their fight to keep young people out of adult prisons and to advocate for youth lifers.  Visit YSRP.org [http://ysrp.org] to support this cause. Thank you.