Joel Oster, a constitutional lawyer turned stand-up comedian, shares how he combined his passion for public speaking with his legal expertise to create a career he loves. From teaching hilarious CLE courses to arguing cases at the U.S. Supreme Court, Joel’s journey is filled with practical advice and laugh-out-loud moments. This episode offers inspiration for lawyers looking to break free from traditional paths and find joy in their work.
LISTEN TO LEARN
WE ALSO DISCUSS
Want to start a podcast?
Save time and create faster with KD Creative. KD Creative offers done-for-you podcasting services by launching podcasts for small business owners and editing podcasts for existing podcasters.
If you’re ready to get your content in the ears of your ideal customers, start working with KD Creative. Visit skiptheboringstuff.com to hire a podcast coach.
Joel Oster is a constitutional lawyer with decades of experience, having argued cases before the U.S. Supreme Court and numerous appellate courts. While his legal career was marked by significant accomplishments, Joel’s true passion for humor and public speaking eventually led him to pursue stand-up comedy. Today, he’s known for making CLEs entertaining and engaging, blending his legal knowledge with his comedic talent.
"I decided to marry the two and start a career doing stand-up comedy for lawyers... I’m shocked and floored that the lights are still on," shares Joel Oster on You Are A Lawyer.
By merging his legal expertise with humor, Joel has carved out a unique niche that allows him to make lawyers laugh while educating them. His work highlights how passion and creativity can transform a traditional career into something extraordinary.
Joel’s decision to attend law school stemmed from a teacher’s comment in junior high school, sparking his interest in legal advocacy. Encouraged by the idea that he’d make a great lawyer, Joel pursued his dream despite the daunting challenges of law school. He credits this early encouragement for helping him push through difficult times, including the rigorous demands of his studies.
"When you are young and someone speaks into your life, the difference that that makes... that carried me through," reflects Joel Oster on Episode 172 of You Are a Lawyer.
Though his law school journey was challenging, Joel’s experience laid the foundation for his career in constitutional law and later as a comedian. His story underscores the importance of following your passion while remaining open to the twists and turns along the way.
Joel Oster believes a law degree equips you with a unique skill set that can be applied in countless ways, from practicing law to building a business. He emphasizes that the ability to think critically, negotiate, and create strategies makes lawyers valuable in almost any field. His own career is proof that a law degree can be leveraged to pursue non-traditional paths like comedy and public speaking
"The JD is extremely valuable... the thought process you brought to law school applies to almost anything and everything that you do," explains Joel Oster, on this episode of You Are a Lawyer.
By thinking outside the box and identifying your strengths, a law degree can open doors to opportunities that align with your passions. Joel’s journey demonstrates how legal training can be the foundation for a career filled with creativity, fulfillment, and impact.
Joel’s career is a testament to the power of side hustles and blending passions with professional expertise. By merging his love for public speaking and humor with his legal background, Joel created a unique business teaching CLEs and performing legal stand-up comedy. He encourages lawyers to explore creative outlets and think beyond traditional career paths.
“What would you do for free? And then is there a way to have that be your career?” shares Joel Oster in Episode 172 of You Are a Lawyer.
Lawyers with side hustles can not only diversify their income but also find new ways to engage with their profession. Joel’s approach shows how stepping outside the norm can lead to fulfilling opportunities that still leverage your legal skills.
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)!
Joel Oster is licensed to practice law in the State of Kansas
Kyla Denanyoh hosts the You Are A Lawyer podcast.
Follow the podcast:
YouTube: youtube.com/@youarealawyer
Instagram: instagram.com/youarealawyer
Twitter: twitter.com/YouAreA_Lawyer
Website: youarealawyer.com
©2025 You Are A Lawyer LLC.
All rights reserved.
