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Building a Values Aligned Legal Career feat. John Lopez
John Lopez is the Legal Director of the Youth Sentencing and Reentry Project, where he supports children charged as adults across Pennsylvania. In this episode, John shares how combining law and social work allowed him to practice in alignment with his values, and why treating people as people is central to meaningful legal advocacy.
1 day ago3 min read


When Being a Lawyer No Longer Fits feat. Casey Berman
Casey Berman is the founder of Leave Law Behind and a former in-house lawyer who helps attorneys transition into careers that better align with their skills, values, and lives. In this episode, Casey shares how he left traditional legal practice, built a remote business from Hawaii, and helps lawyers rethink identity, risk, and what fulfillment can look like after law.
Feb 43 min read


What Justice Looks Like When You Start With People feat. Bianca Van Heydoorn
Kyla Denanyoh interviews Bianca Van Heydoorn about juvenile life sentences, reentry, and centering dignity in criminal justice work.
Jan 283 min read


A Law Degree That Travels With You (October 2021) feat. Michelle Words
Michelle Words is a business law professor and licensed attorney who has spent the last seven years living and teaching abroad in the Middle East. In this episode, Michelle shares how her law degree became a tool for freedom, travel, and reinvention.
Jan 213 min read


Soft Skills Every Lawyer Needs feat. David Sclar
Kyla Denanyoh interviews David Sclar is a technology lawyer and the author of Workplace Strategies for Technology Lawyers. In this episode, David explains why soft skills are essential for modern legal careers, how he found his place in law after early uncertainty, and what lawyers can do to build careers that align with how they actually work.
Jan 143 min read


When Advocacy Becomes the Career feat. Mary Ellen O'Connor
Kyla Denanyoh interviews Mary Ellen O’Connor to discuss workers’ compensation and Social Security disability law.
Jan 83 min read


Choosing a Different Kind of Legal Career feat. Akshay Verma
Kyla Denanyoh interviews Akshay Verma, Chief Operating Officer at SpotDraft and a former environmental lawyer whose career spans law firms, legal operations, and executive leadership in tech. In this episode, Akshay shares what it felt like to leave firm life, take a financial risk for his family, and build a career that better aligned with how he wanted to live and work.
Jan 13 min read


Healing Lawyer Burnout Through Boundaries and Self-Advocacy feat. Lora Cheadle
Kyla Denanyoh interviews Lora Cheadle is a former insurance defense attorney who traded burnout for a career built on wellness, boundaries, and helping high achievers navigate betrayal in both personal and professional life. In this episode, she explains why many lawyers mislabel their exhaustion as burnout when it is actually the rupture of unmet expectations, unmanaged stress, and years of self-neglect.
Dec 25, 20253 min read


Why the Hourly Billing Model Is Broken feat. Stephen Caldelmo
Stephen Candelmo is a corporate lawyer turned tech founder who has spent nearly thirty years advising emerging companies and building his own ventures. In this episode, he explains how a recession, a machine learning experiment, and a desire for fairness inspired him to create Paralex, a legal platform that delivers fixed-fee, AI-powered legal services for small businesses and startups. He also shares why he believes the legal profession is on the edge of a major transformati
Dec 11, 20253 min read


What’s Harder: Law School or a PhD? feat. Daria Levina
Kyla Denanyoh interviews Daria Levina is a lawyer, academic, and business owner whose path spans Russia, the United States, Italy, and now Berlin. With two law degrees, a PhD in law, and a thriving admissions-advising business, Daria brings a global perspective to legal education and career design. In this episode, she shares what makes a PhD different from a JD, how stand-up comedy transformed her thinking, and why she believes education should be accessible to everyone.
Dec 4, 20253 min read


How Solo Practice Gives Lawyers More Freedom feat. Edward Cohn
Kyla Denanyoh interviews Edward Cohn is a criminal defense attorney who has spent 23 years running his own solo practice across three states. In this episode, he shares why opening his own firm right out of law school gave him the freedom he always wanted, how a background in music shaped his confidence and creativity, and why some lawyers thrive when they build their practice on their own terms.
Nov 27, 20253 min read


Reinventing Your Legal Career After 40 (August 2023)
Kyla Denanyoh interviews Anne Hamer is a top-rated family lawyer based in Nashville, Tennessee, whose path to success was anything but traditional. After years in corporate and plaintiff work, and even a decade as a stay-at-home mom, Anne returned to the courtroom with a new sense of purpose. In this episode, she shares how to change your legal career at any age, how her own divorce reshaped her understanding of family law, and why it’s never too late to find work you love.
Nov 20, 20253 min read


Authenticity Is Your Strategy: Marketing Lessons for Lawyers with Chelsea Jones
Kyla Denanyoh interviews Chelsea Jones is the founder of Chelsea Anne Media, a social media marketing agency that helps lawyers build personal brands that feel genuine, not forced. In this episode, she shares how one Upwork client turned into a thriving niche, why Instagram remains the most powerful platform for lawyers, and how authenticity can turn online visibility into real relationships.
Nov 13, 20253 min read


Tax Attorney Shares When You Really Need Help feat. Stephen Weisberg
Kyla Denanyoh interviews 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.
Nov 6, 20253 min read


Why Authenticity Matters for Lawyers feat. Sergio Gregorio
Kyla Denanyoh interviews 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.
Oct 30, 20253 min read


Building Confidence and Clarity as a Lawyer feat. Laura Terrell (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.
Oct 23, 20253 min read


Redefining Success and Alignment in Law feat. Arivee Vargas
Kyla Denanyoh interviews lawyer and coach Arivee Vargas shares her journey from Big Law to coaching, writing, and alignment, showing how to create a career that fits your life.
Oct 16, 20254 min read


Solo Firm Autonomy: Escaping the Partnership Trap feat. Yladrea Drummond
Kyla Denanyoh interviews 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.
Oct 9, 20254 min read


How Hiring a Case Manager Will Transform Your Law Practice feat. Rob Levine
Kyla Denanyoh interviews Rob Levine and discussed how case managers can transform your law firm’s operations. Attorney Rob Levine shares three ways case managers improve workflow, client experience, and firm scalability.
Oct 2, 20253 min read


Save Your Relationships with Mediation or Divorce Like a Pro feat. Debra Whitson (February 2023)
Kyla Denanyoh interviewsfFormer prosecutor turned mediator Debra Whitson shares how mediation can save relationships, even during divorce. Learn how she helps families navigate separation with less conflict and more compassion.
Sep 25, 20253 min read
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