In this episode of Clocking Out, we dive into the inspiring journey of Robert Markowitz. Once a criminal lawyer, now a children’s musician, author, and performer whose story proves it’s never too late to choose joy.

Robert spent years chasing a traditional definition of success: Duke Law, criminal trials, and the prestige of a respected profession. But behind the courtroom victories, he felt trapped, weighed down by family expectations, office walls, and a career that didn’t fit his temperament. After just a few years in practice, he walked away, leaving behind a decade of preparation and a stable paycheck for what many dismissed as unrealistic: performing for children.

The leap wasn’t easy. Friends drifted away, family questioned his choices, and doors slammed in his face. But Robert persisted, first as “Bobo the Clown,” then as a musician singing to toddlers in libraries and schools across New York. What began as a radical pivot turned into a decades-long career rooted in joy, presence, and connection. Along the way, he also embraced writing, publishing essays in The New York Times and most recently his novel Clown Shoes, now adapted into a stage play.

In this conversation, Robert reflects on ego, family pressure, reinvention, and the messy but meaningful journey of leaving behind a life that looks right on paper for one that feels right in your heart. If you’ve ever wondered what might happen if you truly followed your bliss, this episode is for you.

Connect with Robert at:

• Free Substack blog: https://markowitz.substack.com/
• ‘Clowns Shoes’ on Amazon: https://www.amazon.com/Clown-Shoes-Robert-Markowitz/dp/1956474307 
• ‘Clown Shoes, The Musical’: https://clownshoesthemusical.my.canva.site/ 
• Facebook: https://www.facebook.com/robert.markowitz.77 

Follow Careerminds: 

• LinkedIn: https://www.linkedin.com/company/careerminds
• Instagram: https://www.instagram.com/careerminds/
• Facebook: https://www.facebook.com/Careerminds
• Youtube: https://www.youtube.com/@Careerminds

Follow Raymond: 

• LinkedIn: https://www.linkedin.com/in/raymondmlee/
• Instagram: https://www.instagram.com/raymondlee.co
• Tiktok: https://www.tiktok.com/@clockingoutpod
• X: http://twitter.com/hrentrepreneur
• Youtube: https://www.youtube.com/@clockingoutwithraymondlee/videos
• Visit Raymond’s website: https://www.raymondlee.co/
• Order Clocking Out: A Stress-Free Guide to Career Transitions: https://www.amazon.com/Clocking-Out-Stress-Free-Career-Transitions/dp/1586446541 

Become a guest on Clocking Out