The Free Lawyer Are You a Successful Lawyer but Still Unfulfilled? #390
In this episode of "The Free Lawyer," host Gary welcomes Jen Gillman, founder of Gillman Strategic Group, to discuss the disconnect many lawyers feel between external success and personal fulfillment. Jen shares her journey from practicing attorney to legal recruiter focused on helping rainmakers find the right firm fit. She introduces her “Six Pillars to Becoming a Happy Rainmaker” framework, emphasizing self-care, boundaries, and legacy. The conversation explores practical strategies for lawyers to achieve both professional success and personal happiness, highlighting the importance of intentional career choices, coaching, and redefining success on one’s own terms.
Jen Gillman is the founder of Gillman Strategic Group, where she helps rainmakers find their exact right, perfect-fit firm and law firm owners navigate strategic mergers. As a former practicing attorney herself, Jen understands that professional success doesn’t always equal fulfillment—and she’s on a mission to change that.
After earning her J.D. from NYU School of Law and B.A. from Brandeis University, Jen practiced law for 12 years before transitioning to legal recruiting.
Unlike traditional recruiters who find lawyers for firms, Jen finds firms for lawyers. She helps partners identify what they truly need to be fulfilled, whether that’s better resources, growth opportunities, or work-life balance, and then matches them with firms where they can thrive.
Jen is the creator of the “6 Pillars to Be(coming) a Happy Rainmaker” framework and author of the forthcoming The Happy Rainmaker: A Little Tale About a Lawyer Who Found Success and Happiness Too. She shows up for her clients as part agent, part therapist, and part cheerleader, because successful lawyers deserve to be happy too. Learn more at happyrainmakers.com.
You can purchase The Happy Rainmaker here: https://amzn.to/3Nfkne3
Jen’s Career Transition Story (00:03:32)
The Candidate-Focused Recruiting Model (00:05:33)
Holistic Support for Lawyers (00:07:01)
Difference from Traditional Recruiting (00:09:23)
Honesty and Advising Against Moving (00:10:58)
Why Successful Lawyers Feel Unfulfilled (00:13:02)
Six Pillars to Becoming a Happy Rainmaker (00:16:08)
Deep Dive: Defining Boundaries (00:21:12)
Deep Dive: Designing a Legacy (00:24:31)
The Future of Legal Practice (00:27:21)
The Value of Coaching and Outside Guidance (00:29:08)
Where to Find the Six Pillars & The Happy Rainmaker Book (00:30:28)
About The Happy Rainmaker Book (00:30:45)
Implementing the Six Pillars at Any Career Stage (00:32:22)
First Steps for Unfulfilled Lawyers (00:34:00)
Final Advice: Small Steps Matter
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