Richard Holloway

I help people rethinking their career path explore meaningful work beyond traditional employment

Book a session

For more than 30 years, I've helped people navigate important education, career, business, and professional decisions. I currently serve as Dean of Criminal Justice and Homeland Security Programs for a multi-university system and previously practiced law for 10 years, representing individuals and small businesses in a wide range of matters. My experience also includes owning my own law practice, co-owning a specialty retail business, developing academic programs, mentoring students and professionals, and helping people evaluate career changes, graduate school, law school, and business opportunities. I also co-host and producer of the podcast Raw and Refined: The Gentlemen's Hour, where we discuss leadership, culture, personal growth, and current events. Whether you're considering a new career, educational path, business venture, or major professional decision, I provide practical perspective based on real-world experience. I offer guidance and insight, not legal advice.

Chicagoland
Career Coaching & Counseling

Services

1:1 Video Call

Book a private video call to get personalized advice and guidance.

30 min$100.00
Clarity Session

A structured conversation designed to help you evaluate options, identify obstacles, and leave with a practical action plan.

1 hour$150.00