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

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 to support this cause. Thank you.

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, 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 to support this cause. Thank you.

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.

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, 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, which was written while she was still fully employed. She also established The Humble Rising podcast 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 to support this cause. Thank you.

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 to support this cause. Thank you.

Rob Levine is the founder of a multi-state law firm and an advocate for operational efficiency in legal practices. In this episode, he breaks down the vital role of case managers in improving law firm operations, building better client relationships, and increasing profitability. Whether you're a solo attorney or managing a growing team, this conversation will change how you think about delegation and workflow.

LAWYER SIDE HUSTLES

Rob's "side hustle" is more like a second empire. In addition to his legal practice, he also runs businesses in medical records, call centers, and more. But everything he does is connected by a single goal: improving operational efficiency. His passion is not just practicing law, it's optimizing it.

"I'm always looking at what we do and how we can do it better," Rob Levine shares in Episode 212 of You Are a Lawyer.

For lawyers who feel stuck or overwhelmed, Rob Levine's story is a reminder that entrepreneurship doesn't have to look like leaving law. You can innovate inside the legal industry by shifting your mindset and creating systems that support your bigger goals.

LISTEN TO LEARN

• Why case managers are essential for scaling a law firm
• How to increase client satisfaction through structured case management
• Ways to improve productivity and reduce attorney burnout

WE ALSO DISCUSS

• Rob's transition from military service to entrepreneurship
• The systems behind running a high-volume personal injury firm
• The mindset shift lawyers need to run their firms like businesses

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Interact with You Are A Lawyer

Kyla Denanyoh hosts the You Are A Lawyer podcast.

Follow the podcast:

YouTube: https://www.youtube.com/@youarealawyer

Website: https://www.youarealawyer.com

Debra Whitson is a New York-based attorney, former prosecutor, family law mediator, and author of Divorce Like a Pro. In this conversation, she shares how mediation offers a healthier alternative to courtroom battles—and why divorce doesn't have to destroy families. With decades of experience, Debra helps clients find clarity, peace, and dignity in even the most difficult transitions.

LAWYER SIDE HUSTLES

Debra's side hustle became a calling: she wrote Divorce Like a Pro to provide an accessible, empowering guide for anyone going through separation or family breakdown. The book distills her real-world experience into practical advice and it's a resource she wishes more people had earlier.

"I wrote the book because I found myself saying the same things over and over again to clients… there are better ways.," shares Debra Whitson in Episode 75 of You Are a Lawyer.

When she's not running her practice or writing, Debra is a global advocate for women's rights through Zonta International. Her passion for service, travel, and equity informs her entire professional ethos, from her client relationships to her vision of justice.

LISTEN TO LEARN

• Why courtroom litigation often makes family issues worse, not better
• How mediation can lead to reconciliation
• The biggest myths Debra wants to debunk about divorce and conflict

WE ALSO DISCUSS

• Debra's early career as a prosecutor and what pushed her to shift paths
• Her book Divorce Like a Pro and why she felt called to write it
• How international travel and service work shaped her career and values

Elise Holtzman left Big Law to raise her children, without a clear roadmap for what came next. Now she's a leadership coach and founder of The Lawyer's Edge, helping lawyers build confidence, develop business skills, and grow professionally. In this episode, Elise shares the mindset shifts that led her from practicing law to coaching those still in the field.

LAWYER SIDE HUSTLES

What began as a curiosity became a calling. Elise explored executive coaching and soon realized she could use her background in law to serve other lawyers. That side interest eventually became The Lawyer's Edge, which she now runs full-time, offering coaching programs, firm-wide trainings, and a popular podcast.

"I didn't set out to start a business. I set out to help people," Elise Holtzman shares in Episode 210 of You Are a Lawyer.

Elise's story shows how side projects can evolve into full-fledged careers. By paying attention to what energized her, and what drained her, she built a business that supports both her clients and her life. She encourages other lawyers to give themselves permission to try something new, even if it starts small.

LISTEN TO LEARN

• How to overcome the fear of leaving traditional law practice
• What lawyers actually need when it comes to leadership and business development
• How to build a coaching business tailored to legal professionals

WE ALSO DISCUSS

• The identity crisis many lawyers face when stepping away from the profession
• Why law school doesn't prepare you to be a leader or entrepreneur
• How to balance motherhood and career reinvention

Join the FREE mailing list!

Get behind-the-scenes content from You Are A Lawyer.

1) Visit www.youarealawyer.com

2) Add your email address to the Subscribe pop-up box OR

3) Enter your email address on the right side of the screen

4) Get emails from me (I won't fill your inbox with junk)!

Interact with You Are A Lawyer

Kyla Denanyoh hosts the You Are A Lawyer podcast.

Follow the podcast:

YouTube: https://www.youtube.com/@youarealawyer

Website: https://www.youarealawyer.com

Lamia Rahman is a Forbes 30 Under 30 honoree, TEDx speaker, and co-founder of SEEKR, a tech startup creating wearable AI devices for the blind. In this inspiring episode, Lamia shares her journey from law school in Hong Kong to the front lines of legal tech, accessibility, and advocacy.

LAWYER SIDE HUSTLES

SEEKR began as a passion project and has since grown into a globally recognized AI startup. The company develops wearable devices that help blind and visually impaired users navigate the world more independently. Lamia co-founded SEEKR during her law degree, blending her passion for tech with her desire to serve.

"It was a small idea at first. Now we're building something that's used across countries. That's wild," Lamia Rahman shares in Episode 209 of You Are a LawyerMore than a "side hustle," SEEKR is a mission-driven business, fueled by Lamia's belief that tech should be inclusive and empathetic. In the episode, she shares what it's like to build a team, pitch to investors, and develop AI that solves real-world problems, all while still figuring out what comes next in her legal career.

LISTEN TO LEARN

• How Lamia co-founded an AI startup that creates wearable tools for the blind
• Why legal knowledge helps entrepreneurs navigate business growth
• How public speaking and networking open unexpected career doors

WE ALSO DISCUSS

• Her experience studying law in Hong Kong as an international student
• How being a woman of color in tech and law shaped her journey
• Ways to combine social justice, accessibility, and innovation

Join the FREE mailing list!

Get behind-the-scenes content from You Are A Lawyer.

1) Visit www.youarealawyer.com

2) Add your email address to the Subscribe pop-up box OR

3) Enter your email address on the right side of the screen

4) Get emails from me (I won't fill your inbox with junk)!

Interact with You Are A Lawyer

Kyla Denanyoh hosts the You Are A Lawyer podcast.

Follow the podcast:

YouTube: https://www.youtube.com/@youarealawyer

Website: https://www.youarealawyer.com

Daniel Rosenberg is a former prosecutor and defense attorney turned novelist who's turning real-life courtroom experience into gripping legal thrillers. In this episode, he shares how his background in acting and law helped him build a successful writing career, why COVID was the creative catalyst he needed, and how his novels teach readers about the legal system, without getting lost in legalese.

LAWYER SIDE HUSTLES

Daniel's side hustle as an author didn't just stem from a love of books—it came from lived experience. Drawing from real cases he prosecuted and defended, he built compelling plots that read like fiction but are grounded in courtroom realism. He even test-ran his early manuscripts with a jury of trusted friends and lawyers for feedback.

"Write what you know… because I can spot right away someone who's never been in a courtroom," Daniel Rosenberg shares in Episode 208 of You Are a Lawyer

He also manages his own publishing relationships and book marketing, blending legal savvy with entrepreneurial spirit. From book signings to readings to podcast interviews, Daniel shows that you can take a legal career and build something entirely new, without leaving your skills behind.

LISTEN TO LEARN

• How courtroom experience can shape compelling legal thrillers
• Why creative skills are valuable assets in a legal career
• How to write fiction that's both entertaining and educational

WE ALSO DISCUSS

• The role of performance and storytelling in trial work
• How Daniel's background in acting helped him excel in law and writing
• Practical advice for lawyers who want to write books or pursue creative paths